5+ Bedroom Vacation Rentals In Siesta Key, FL

$2625.92

NEW LISTING! The Village Breeze 8BR with heated Pool, near Beach, 250ft to Siesta Key Village!

Siesta Key, Florida, United States

The Village Breeze 8BR (REMODELED '25). No car required! Four side by side 2BR Siesta Key vacation rental units near shopping dining and attractions, with heated Pool, near Beach, but just 250ft to the world famous Siesta Key Village. A true favorite of initiated guests, and sure to provide a combination of fun and rejuvenation you won't find in other getaways. *NEW LISTING!! Please read the other Gertrude Rentals reviews. We are very proud of them!brbrWhat Guests Lovebr∙ The Village – 1-min walk to 25 restaurants in world famous Siesta Villagebr∙ The Fun – steps to live music, daiquiris, oysters, stone crab, craft beer, ice cream & donutsbr∙ Space - 4 separate private units (8BR total) perfect for larger groups who enjoy spacebr∙ Decor – beautifully remodeled thru-out in May 2025br∙ Sunsets – 8-min walk to Siesta Key's best sunsets & 300-degree Gulf viewsbr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ Activities - kayak, bike, paddleboard, scooter, golf cart rentals nearby br∙ No Car Required - you're already where everyone on Siesta Key wants to be:)br∙ The Memories - one of a kind Siesta Key experience, the favorite of initiated visitorsbrbrThe LocationbrThe possibilities are endless! Enjoy the best Beaches, Seafood, Drinks, Ice-Cream, Shopping, Oysters, Live-Entertainment, fresh-Donuts, Daiquiris, big-Breakfast, and the Coldest-Beer on the Island. Rare secluded street in the heart of Siesta Keys world famous Village. Just a short walk to two of the best beaches on the planet and only 250 feet to all the best of the Village. One of only four units in this building. The beaches at this location are the widest and have panoramic views of the gulf to the North-West-and-South and are the top spot in North America for viewing sunsets. You can swim or “often” wade to Sand Dollar Island, a naturally occurring white sand cay popular with dolphin's sand-dollars and “occasionally” giant-conch. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. This is the only Siesta neighborhood where you can go from the water to lunch or dinner and back to the sand without putting on your shirt and shoes. brbrProperty TruthsbrOur front is residential but the back is alley access for stores. This is the heart of Siesta Village with many nearby shops restaurants stores and attractions. It won't be noisy, makes shopping and other activities convenient, but we want you to be aware.brbrPossible Siesta Key ItinerarybrWakeup, decide if you will wear shoes today, then head to Sun Garden Café for a Crab Cake Benedict. Theirs is the best and they serve breakfast til 12 so there's no rush. Eat there Al Fresco, return to the pool, or walk over to the beach and look for dolphins, swim, bike, or just or just go back to sleep. This is a special spot so exploring a little will be worth your while. I like wading out to the sand bar at low tide. Bike rides on the beach are also amazing. Bike south to check out Point of Rocks or north and east to Big Pass. I usually skip lunch and have a 3PM happy hour meal at SKOB or the Hub, after drinking my fill I grab a real dinner, then walk back down to the beach to watch the sunset and digest. The sunsets are amazing, it's what leaf season in the north would be like if it happened every day, and if they had dolphins and great weather there. Now it's dark and you can go out or go to bed, but you have to make a decision. While deciding consider my grandmothers advice “Life is a string of pearls and you never know how many you have left.”- GVLJbrbrBedroom DetailsbrThis is four ground floor 2BR units (8BR total, sleeps 24). Each unit has a king bedroom, a queen bedroom, and a queen sleeper sofa in the living room. If you need more space, I can get an additional unit nearby. brbrBeach GearbrThis vacation rental comes with beach towels and beach chairs at every location, umbrellas and carts. Correction for Air-b-n-b listings, we do not provide snorkeling gear at any locations. Sorry for the confusion. Snorkeling gear can be rented or purchased nearby.brbrSupport Post BookingbrI understand vacation time is precious and I will make sure you get the most out of it. My number is the only contact information you need. My units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. Check-in any day of the week at any time using your private door-code. No requirement ever at checkout. Free early check-in when possible. Never hidden fees or solicitations. Every unit including this one is available for instant booking. brbrEventsbrMany of our properties are wonderful locations for gatherings, unfortunately this unit cannot allow gatherings involving third party vendors or visitors outside your occupancy limit.brbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. brbrTravel InsurancebrIf you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.

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Bath

Sleeps

$1427.64

/ Nightly

Private Vacation Home

The Lookout - 891 “Siesta Key’

Siesta Key, Florida, United States

KEEP READING BELOW. THIS IS NOT JUST A BASIC DESCRIPTION OF THE HOME. THERE IS VERY USEFUL INFORMATION THAT YOU WON’T WANT TO MISS!!brbrPremier local manager, Destination Paradise welcomes you to “The Lookout”… a beautiful, grand vacation home on a magnificent waterfront area of the bay with an awesome outdoor lounge and heated pool area! This 4 level home sleeps up to 13. It is located on the ultra-premium North end of the island in a super private neighborhood and is just minutes from world famous Siesta Key Beach and Siesta Key Village.brbrIndulge in unbeatable waterfront living in this breathtaking Siesta Key vacation rental, nestled on the serene waters of a luxury peninsula. Marvel at beautiful sunsets from your very own private pool area or from the charming terraces that adorn the third and fourth levels of this enchanting Siesta Key vacation rental. Spanning an expansive 6,300 square feet, this vacation home rental in Siesta Key offers a lavish retreat where even large families can relish in absolute privacy. brbrEntertain in style within the sprawling outdoor spaces, complete with a delightful grill area for hosting a family cookout and a refreshing pool and luxurious hot tub for ultimate relaxation. Discover cozy and inviting outdoor patios on each of the three levels, featuring a fire pit on the first and a fireplace on the second floor, perfect for unwinding under the beautiful Siesta Key sky. brbrThis Siesta Key rental spoils you with amenities, including a street-legal golf cart powered by lithium batteries, accommodating up to six passengers, provided by The Toy Barn. Explore the island’s treasures effortlessly for just $75/day, exclusively available to guests of this exquisite Siesta Key vacation home rental. Immerse yourself in leisure within the game room boasting pool and skeeball tables, or ascend to the rooftop crow's nest for unbeatable panoramic views of Siesta Key. Unwind in the full bar/movie room, ensuring endless entertainment options. brbrNestled on the North end of The Key, this Siesta Key rental offers a strategic location, minimizing your encounters with traffic. Embark on leisurely rides to The Village or the world-renowned Siesta Beach. Venture on over the North bridge to discover key destinations such as Southside Village, Selby Gardens, UTC, and downtown, all within easy reach by car. The possibilities are endless in this idyllic paradise, waiting to welcome you. Your next trip to paradise is closer than you imagine– book your well-deserved escape to Siesta Key today!brbrwww.vacationDP .(c o m)brbr“The Lookout” can accommodate up to 13 guests with a bedding configuration as follows:br• Bedroom #1, 1st Floor: King Bed (1) - Sleeps: 2br• Bedroom #2, 2nd Floor: King Bed (1) - Sleeps: 2br• Bedroom #3, 2nd Floor: King Bed (1) - Sleeps: 2br• Bedroom #4, 3rd Floor: Bunk/Trundle Bed (2), Floor Mattresses (2) - Sleeps: 5br• Bedroom #5, 3rd Floor: King Bed (1) - Sleeps 2brbrbr***PLEASE NOTE***brbrCOFFEE MAKER: Combo Coffee maker (both drip and K-cups)brbrPOOL HEATER RULES:brPool heat temp is set at 83º and runs each day from 7 AM until 7 PM from October 15-April 15. Outside of these dates, the Florida weather should naturally heat the pool. Pool temps are not guaranteed. This pool is heated by a heat pump and is only capable of heating to around 20-25 degrees warmer than the ambient temperature. (If the high for the day is 55, the pool may only be able to reach 75).brThe spa has a timer of 3 hours, once turned on and can be run at any time and will heat to 100ºbrbrPET POLICY: This home has a $25/pet/day fee. Aggressive breeds (ie. pitbulls, etc) may not be allowed and will need to be approved by management prior to your stay. If you bring your pet without claiming them on the reservation or by trying to avoid paying the pet fee, a minimum fine of $500/pet will be collected. By making this reservation, you agree to this policy. DOGS ONLY. CATS ARE NOT ALLOWED.brbrThe boat dock is not allowed to be used for docking personal or rented boats unless you get approval from management! Using without approval is subject to a minimum $2,500 fine.brbrA SIGNED DESTINATION PARADISE RENTAL AGREEMENT AND ID WILL BE REQUIRED FOR ALL RESERVATIONS.brbrVR Certificate #VR22-00113brbrAREA INFORMATION:brbrExperience the serenity of our world class beaches where you can swim, sunbathe, surf, paddle board, and fish. Take a morning walk down to the soft white sand of Siesta Key Beach or to little Shell Beach to find sand dollars and an assortment of other sea shells. Head to the South side of Siesta key to check out Turtle Beach; a more secluded beach with less people and great surf fishing on the south end.brbrVisit one of the centerpieces of Siesta Key, the AMI City Pier where there is great fishing and plenty of restaurants to choose from. Take a stroll down the Coquina Baywalk and Leffis Key to find a small nature walk with peaceful walking trails.brbrTake the provided bicycles all around the island and search for the 6 beaches that AMI has to offer (can you find them all ); Coquina Beach, Manatee Beach, Bradenton Beach, Holmes Beach, Cortez Beach and Anna Maria Beach (with Bean Point being part of that).brbrOur favorite Anna Maria Island Restaurants:br•Beach House Waterfront (Excellent Seafood)br•Ugly Grouper (Bar/Pub Style Food)br•Waterfront Restaurant (High End Seafood and Steak, Great ambiance)br•Hurricane Hanks (Bar/Burgers)brbrOur favorite Bradenton/Sarasota restaurants:br•KOJO (My personal favorite - High end Asian Fusion)br•Selva Grill (Amazing ceviches and high end courses-Try the KOJO sushi roll and Wagyu Skirt Steak!)br•Owen’s Fish Camp (Unique atmosphere, great seafood)br•Baker and Wife (American, great food)br•SKOB - Siesta Key Oyster Barn (Great happy house and oysters)br•Hyde Park Prime Steakhouse (High end steakhouse)brbrOur favorite Tampa/St Pete restaurants:br•Rococo Steakhouse (High end steakhouse)br•Texas De Brazil (All-you-can-eat Brazilian Steakhouse)br•Bern’s Steakhouse (If you can get a table-amazingly unique eating experience - WORLD FAMOUS)br•Ulele (Local Cuisine, Brew Pub, Michelin Star rated)br•Ocean Prime (High end Seafood)brbrOur favorite Casey Key/Venice restaurants:br•Pop’s Sunset Grill (Ma & Pa style bar and grill)br•Casasariano Italian Eatery (Italian)br•The Breakfast Cottage (Breakfast/Brunch)

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$1846.09

/ Nightly

Private Vacation Home

Gertrude's Siesta | 4-min Walk to Beach & Village, Tropical & 100% Private!

Siesta Key, Florida, United States

Casa Van Lopikbr100% Private 6BR duplex in the Siesta Key Village, 4-min walk to best beaches shopping dining and entertainment on the island. Leave the car behind and walk to white-sand cays, 20 bars and restaurants, quartz-sand beach with calm water, ice-cream, shopping, daiquiris, live music, craft beer, fresh oysters and seafood. Enjoy tropical patios tiki-bar and alfresco dining area. Free bikes and paddleboards. Sure to provide a combination of fun and relaxation you can't get in other vacations so book a special getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiestabr brbrWhat Guests Lovebr∙ Beaches – 4-min walk to award-winning beachesbr∙ The Village – 4-min walk to shopping dining and entertainment world famous Siesta Villagebr∙ Relaxing – tropical patios tiki-bar and alfresco diningbr∙ Sunsets – 4-min walk to best sunsets in America & 300-degree Gulf viewsbr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ Activities – bikes and paddleboards provided, scooter and golf cart rentals nearby br∙ Island Trolleys - you're already where you want to be, but they're free:)br∙ The Memories – walk to all siesta key is top attractions and guaranteed fun for allbrbrThe BeachbrOur beach is the widest, has panoramic views of the gulf to the North-West-and-South, and is the top spot in North America for sunsets. You can swim or wade to Sand Dollar Island, a naturally occurring white sand cay popular with dolphin sand-dollars and “occasionally” manatee and giant-conch. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. You can go from the water to lunch or dinner and back to the sand without putting on your shoes.brbrThe HomebrLarge 3BR x 3BR duplex home, 100% private, with king beds in both master bedrooms. Out-door grilling and dining (shared), open floor plan perfect for bigger groups, surrounded by palms. Deeded access to the Grand Canal across the street. Set in the Village just 4-min walk to the best fresh oysters, seafood, tropical drinks, ice cream, entertainment, and even gourmet donuts on the island.brbrBedroom Detailsbr100% Private 6BR duplex with living spaces on the second and third floors. Each unit has two king BRs, one bunked BR containing 2 full over queen beds, a large 120' sofa in the living room, and one or two tempur-pedic rollaway beds. Sleeps up to 24. If you need more space, I can get an additional unit nearby. brbrBeach Gear ProvidedbrWe provide beach towels, chairs, carts, umbrellas, and a few bikes and paddleboards. If you don't have what you need, just reach out and we can usually get it for you. Correction for Air-b-n-b listings this location doesn't provide snorkeling gear but this and anything you need can be rented or purchased nearby.brbrCasa Van Lopikbr100% Private 6BR duplex in the Siesta Key Village, 4-min walk to best beaches shopping dining and entertainment on the island. Leave the car behind and walk to white-sand cays, 20 bars and restaurants, quartz-sand beach with calm water, ice-cream, shopping, daiquiris, live music, craft beer, fresh oysters and seafood. Enjoy tropical patios tiki-bar and alfresco dining area. Free bikes and paddleboards. Sure to provide a combination of fun and relaxation you can t get in other vacations so book a special getaway now!brbrWhat Guests Lovebr∙ Beaches 4-min walk to award-winning beachesbr∙ The Village 4-min walk to shopping dining and entertainment world famous Siesta Villagebr∙ Relaxing tropical patios tiki-bar and alfresco diningbr∙ Sunsets 4-min walk to best sunsets in America 300-degree Gulf viewsbr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ Activities bikes and paddleboards provided, scooter and golf cart rentals nearbybr∙ Island Trolleys - you re already where you want to be, but they re free:)br∙ The Memories walk to all siesta key is top attractions and guaranteed fun for allbrbrThe BeachbrOur beach is the widest, has panoramic views of the gulf to the North-West-and-South, and is the top spot in North America for sunsets. You can swim or wade to Sand Dollar Island, a naturally occurring white sand cay popular with dolphin sand-dollars and manatee and giant-conch. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. You can go from the water to lunch or dinner and back to the sand without putting on your shoes.brbrThe HomebrLarge 3BR x 3BR duplex home, 100% private, with king beds in both master bedrooms. Out-door grilling and dining (shared), open floor plan perfect for bigger groups, surrounded by palms. Deeded access to the Grand Canal across the street. Set in the Village just 4-min walk to the best fresh oysters, seafood, tropical drinks, ice cream, entertainment, and even gourmet donuts on the island.brbrBedroom Detailsbr100% Private 6BR duplex with living spaces on the second and third floors. Each unit has two king BRs, one bunked BR containing 2 full over queen beds, a large 120 sofa in the living room, and one or two tempur-pedic rollaway beds. Sleeps up to 24. If you need more space, I can get an additional unit nearby.brbrProperty TruthsbrThe unit is advertised as “100% private,” and in almost all cases it will be. On rare occasions, however, a brief staff visit may be necessary. These visits are unlikely and typically do not occur. If one is required, it will be limited to exterior or storage areas, take only a few minutes, and occur during daytime hours.brbrBeach Gear ProvidedbrWe provide beach towels, chairs, carts, umbrellas, and a few bikes and paddleboards. If you don t have what you need, just reach out and we can usually get it for you. Correction for Air-b-n-b listings this location doesn t provide snorkeling gear but this and anything you need can be rented or purchased nearby.brbrHousehold Items ProvidedbrWe provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.brbrWhat to BringbrIt s a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.brbrPost Booking SupportbrWe understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time.brbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.brbrTravel InsurancebrIf you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.brbrHousehold Items ProvidedbrWe provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.brbrWhat to BringbrIt's a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.brbrPost Booking SupportbrWe understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time. brbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.brbrTravel InsurancebrIf you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.

6

Bed

4

Bath

22

Sleeps

$2466.08

/ Nightly

Private Vacation Home

Pool, Spa & Rooftop Fire Pit • Steps to Beach

Siesta Key, Florida, United States

Summary:brbrVunique Vacations was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result Unmatched value for travelers who expect more from their getaway.brbrbrbrThe Space:brbrWelcome to Vantage Point, a standout Siesta Key retreat designed for elevated group getaways just moments from the beach. With 6 bedrooms, 6 full bathrooms, and 2 half baths, the home comfortably sleeps up to 18 guests and is thoughtfully designed so everyone can gather without feeling crowded. From a resort-style pool with a sun shelf, waterslide, and heated spa to ping pong, poolside basketball hoop, putt putt, corn hole, rooftop fire pit, and multiple outdoor gathering spaces, the home is built around fun, connection, and easy downtime. Inside and out, every level offers something memorable—from relaxed mornings by the pool to evenings spent together under the open sky. Come experience Vantage Point, where the house itself becomes part of the vacation! brbrbrbrFloor Plan Description (by level): brbrGround Level: brbrbrbrThis level includes a 2-car garage with an EV charger, along with driveway parking for 4 additional vehicles, plus elevator and stair access to all levels of the home, including the rooftop. Through the foyer you’ll make your way into a covered pool area with a resort-style pool featuring a sun shelf, waterslide, and heated spa, and a putt putt course located directly next to the waterslide. The covered pool area offers generous space to gather, with plenty of seating for your whole group, additional bar-height dining, 3 HD TV's and soft seating arranged throughout the space. A natural gas grill is set up nearby for easy poolside cooking. There is also a pink pong table and a corn hole set up so nobody in your group will be bored. brbrbrbrFirst Level of Living (Main Living Level): brbrThis level brings everyone together indoors with an open, inviting layout centered around a chef’s kitchen designed for group stays. The kitchen features double ovens, a large island with seating for 5, and a butler’s pantry equipped with a beverage fridge with ice maker and a microwave drawer. The main dining table seats 12, and the living room opens to a spacious balcony with dining for 10, with stairs leading directly down to the pool area for easy indoor-outdoor flow. This floor also includes a half bath and 2 bedrooms. Master Bedroom 1 features a king bed, an en suite bathroom with a freestanding tub, walk-in shower, and single vanity with 2 faucets, along with balcony access with seating for 2 overlooking the pool area. Bedroom 4 offers a king bed and an en suite bathroom with a single-sink vanity and walk-in shower. A dedicated laundry room on this level includes a utility sink, 2 stackable washer and dryer units, and a clothes hanging rod with shelving. brbrbrbrSecond Level of Living: brbrThe second living level is designed for entertainment and private retreats. A dedicated club room features an media centre with 85-inch TV w/surround sound, two theater-style sofas with seating for 7, Nintendo Switch gaming console, a built-in media wall with 2 workstations, and a beverage refrigerator with ice maker. Sliding doors open to a balcony with soft seating for 8, which is also accessible from Master Bedroom 3 and Bedroom 5. This level includes 4 bedrooms. Both Master Bedroom 3 has a king size bed, built in work station, walk-in closet, balcony access with Gulf Views and a en suite bath with both shower and soaking tub. Master Bedroom 2 also includes balcony access with soft seating for 2 overlooking the pool area. Bedroom 5 has a king size bed, en suite bathroom with shower and access to the balcony shared with the Club Room and Master Bedroom 3. Bedroom 6 serves as the bunk room and includes 2 full-over-full bunk beds, a bathroom with a walk-in shower, one sink with 2 faucets, and an additional sink located just outside the bathroom for added convenience. brbrbrbrRooftop Deck: brbrThe rooftop at Vantage Point offers a relaxed escape above it all, with elevator access, a half bath, and sweeping Gulf views. A covered rooftop lounge features 2 HDTVs, soft seating, bar height dining and a bar area with a beverage fridge with ice maker, creating a comfortable spot to gather and unwind. There is also an outdoor fire put with seating and multiple chaise lounges provided for you to enjoy the sunshine, coastal breeze, and Gulf views stretching out toward the water. Whether you’re spending time together during the day or enjoying a quiet moment at sunset, the rooftop offers a memorable setting that feels elevated without being overdone.brbrbrbrGetting Around:brbrThis home is located just across the street from the north entrance to the public Siesta Key Beach. Siesta Key Village and all the restaurants, entertainment, shopping, grocers, and more on the Key can be accessed by bike, golf cart, car, or free trolley. If you want to explore further, without the hassle of driving, you’ll find multiple stops nearby for the free trolley that provides transportation service to the entirety of Siesta Key. You’re also just a quick drive or Uber/Lyft (10-15 minutes) to downtown Sarasota for access to the amazing Sarasota Performing Arts scene, and numerous fantastic restaurants, shops, marinas, bars and entertainment, and more. And, day trips to Lido Key and Anna Maria Island are just 30 minutes away, as well as the amazing theme parks of Tampa and Orlando that are all just 1-2 hours away!brbrbrbrOther Things to Note:brbrThis Siesta Key luxury vacation rental features Smart TVs with cable and streaming services, as well as Free Wi-Fi throughout the property - including the outside areas for complete coverage for all your work or personal needs. TVs in all bedrooms. brbr brbrAccessibility - in addition to the home’s elevator access to all levels, most doorways and walkways are 30 inches or larger and walk-in showers featured in most bathrooms. Please see the Photos, 3D Tour, & Video for this home for exact information. brbr brbr*Don't forget to check out our Matterport 3D Tour for this home* And, if you still have any questions concerning our homes, rates, availability calendar, amenities, policies, or otherwise, please contact our team of professional reservationists and we will be happy to assist you. We want you to fully understand what you are booking, and yes, an actual human team member is available to help! You are just a couple of clicks away from paradise!brbrbrbrInteraction with Guests:brbrPersonal service and attention to detail define the Vunique Difference. We want your vacation to fit your schedule, which is why we offer flexible bookings starting at just 3 nights for most of the year and any-day arrivals. Our homes are spacious and thoughtfully designed, made for connection as much as comfort. Here, luxury isn’t an upgrade – it’s the standard. Within our portfolio of branded residences, you have every amenity that you need for an unforgettable stay - waterslides, movie rooms, resort-style pools, sport courts, golf simulators, climbing walls, putt-putt courses, zip lines, gaming systems, rooftop decks, biked and beach equipment and more. Our proactive maintenance team ensures everything is in top shape before your arrival, and each property has a dedicated manager who welcomes you personally and stays available throughout your stay should you need anything. Transparency is at the core of everything we do. What you see is what you pay – no hidden fees for pool heat (up to 86 degrees), bikes, propane, or any of the extras that should already be included. Why settle, when you can stay somewhere extraordinary

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$1521.94

/ Nightly

Private Vacation Home

Private Beach Access/Pool Volleyball/Rock Climbing

Siesta Key, Florida, United States

Summary:brbrVunique Vacations was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result Unmatched value for travelers who expect more from their getaway.brbrbrbrThe Space:brbrPeople love beach volleyball here, so we designed a heated saltwater pool and spa with a volleyball theme! The pool volleyball area is nearly 20 feet by 30 feet, and it’s separated by a wall and landscaping from the remainder of the pool area and covered patio, so the effects of the volleyball game don’t extend beyond the court! The pool also has a waterslide, and a large sun shelf with seating, bubblers, lights, and staircase that leads to the pool. At the backside of the pool, you’ll find a turfed area with putt-putt golf. Adjacent to the pool is the covered patio area that features 3 smart TVs, outdoor grill (natural gas), and plenty of covered seating and dining. These spaces are all within the fenced backyard for privacy and security making it family friendly and perfect for the home’s pet friendly policy (fees and restrictions apply).brbrbrbrThis nearly 3,600 square foot home provides views and balconies on all levels, including the rooftop deck that is over 50 feet above the ground. This home has an elevator with service to all floors (except the rooftop). This home provides 5 bedrooms (all with en suite baths and balcony access) and there is a rock-climbing wall in the bunk room! There are 4 king beds and 2 custom full over full bunk beds; and 5 full baths and 2 half baths. The home comfortably sleeps 14 people in beds. The great room is family friendly and includes the kitchen, living, dining areas, and balcony. The kitchen is fully stocked, and we mean that because we know how important it is to you, our valued guests! Not only is it stocked, but it’s also stocked with the products and manufacturers you trust. This home also has a club room or secondary living space with multiple games, wet bar that supports this space, and the balcony that provides access to the home’s 50-foot-high rooftop deck!brbrbrbrFloor Plan Description (by level):brbrbrbrGround Level:brbrFree parking for up to 4 vehicles. The fully fenced pool and backyard area (pet friendly – fees and restrictions apply), includes the covered patio space and pool that was previously described and there are ceiling fans throughout. The home’s ping pong table, corn hole boards, poolside basketball hoop, outdoor connect 4, bocce ball and beach equipment can be found here that includes 2 beach wagons, 2 coolers, 10 beach chairs, and 4 bikes. We include a full refrigerator and deep freezer nearby for easy storage of food, drinks, and ice, so your beach prep and breakdown are that much easier. These appliances can also be used to support your pool days and time at home. You’ll also access the home’s main entrance foyer with elevator and stair access to the home's three (3) living levels and rooftop deck above.brbrbrbrThe First Level of Living (2nd Floor):brbrThe great room has a fully stocked kitchen with a large pantry, cooktop with hood vent, double ovens (2), full sized refrigerator (with ice maker) and freezer, 2 trash/recycling pull-outs, 2 dishwashers, microwave, toaster, coffee maker, and is very well appointed with cookware, bakeware, dishware, cutlery, and specialty items like crockpots, blenders, and more. If you have any questions on kitchen supplies, our reservationists would be happy to provide more details. The living area is very comfortable with balcony access and the dining area seats 13 people comfortably via an 8-person dining table, 5-person kitchen island bar top. Master bedroom 2 has double ‘Juliet balconies’ accessed from the bedroom and bath, a king bed, and an en suite bathroom with double faucet vanity and walk-in shower. There is a half bath on this floor.brbrbrbrThe Second Level of Living (3rd Floor): brbrBedrooms 3 and 4 both have balcony access, a king bed, and an en suite bath with double faucet vanity and walk-in shower. Bedroom 5 has a rock-climbing wall built into the room that every child is going to love, a seating area with smart TV, balcony access (with parental safety features) and, 2 full over full bunk beds, and an en suite bathroom with vanity and shower/bathtub combination. There is also an oversized laundry room on this level with utility sink and 2 stackable washer/dryer units.brbrbrbrThe Third Level of Living & Rooftop Deck (4th Floor):brbrMaster bedroom 1 has Gulf views, balcony access, walk in closet, and a large en suite bathroom with 2 vanities, walk-in double shower, freestanding bathtub, and private water closet. The club room has a wet bar, seating, workspace area, and games including Nintendo Switch gaming console and shuffleboard in this room. The wet bar has a sink, beverage and wine refrigerators, ice maker, and trash pull-out. It also has a half bath, and a balcony and stair access to the roof top deck (both with Gulf views). The rooftop deck is perfect for enjoying sunrise over Siesta and greater Sarasota, or sunset over the Gulf of Mexico. So, be sure to grab a book, a coffee or cocktail, and enjoy the sea breeze and Florida sun from this amazing elevated outdoor living space that overlooks all of Siesta Key. These are great indoor and outdoor entertainment spaces! brbrbrbrGetting Around:brbrPrivate beach! This amazing home is a few steps from the sands of the world-famous Siesta Key Beach and the private section of it that is just for those on this private street! It’s centrally located to the North and South Siesta village entertainment districts and all the restaurants, entertainment, shopping, grocers, and more on the Key. Everything can be accessed by bike, golf cart, car, or free trolley. If you want to explore further, without the hassle of driving, you’ll find multiple stops nearby for the free trolley that provides transportation service to the entirety of Siesta Key. You’re also just a quick drive or Uber/Lyft (10-15 minutes) to downtown Sarasota for access to the amazing Sarasota Performing Arts scene, and numerous fantastic restaurants, shops, marinas, bars and entertainment, and more. And, day trips to Lido Key and Anna Maria Island are just 30 minutes away, as well as the amazing theme parks of Tampa and Orlando that are all just 1-2 hours away!brbrbrbrOther Things to Note:brbrThis home provides private beach access. Access to the private beach is controlled. Please accurately list the number of travelers associated with your reservation, and our team will contact you and walk you through the easy to follow private beach rules.brbrbrbrThis Siesta Key luxury vacation rental features Smart TVs with cable and streaming services, as well as Free Wi-Fi throughout the property - including the outside areas for complete coverage for all your work or personal needs. TVs in all bedrooms.brbrbrbrAccessibility - in addition to the home’s elevator access to all levels, most doorways and walkways are 30 inches or larger and walk-in showers featured in most bathrooms. Please see the Photos, 3D Tour, & Video for this home for exact information.brbrbrbr*Don't forget to check out our Matterport 3D Tour for this home* And, if you still have any questions concerning our homes, rates, availability calendar, amenities, policies, or otherwise, please contact our team of professional reservationists and we will be happy to assist you. We want you to fully understand what you are booking, and yes, an actual human team member is available to help! You are just a couple of clicks away from paradise!brbrbrbrInteraction with Guests:brbrPersonal service and attention to detail define the Vunique Difference. We want your vacation to fit your schedule, which is why we offer flexible bookings starting at just 3 nights for most of the year and any-day arrivals. Our homes are spacious and thoughtfully designed, made for connection as much as comfort. Here, luxury isn’t an upgrade – it’s the standard. Within our portfolio of branded residences, you have every amenity that you need for an unforgettable stay - waterslides, movie rooms, resort-style pools, sport courts, golf simulators, climbing walls, putt-putt courses, zip lines, gaming systems, rooftop decks, biked and beach equipment and more. Our proactive maintenance team ensures everything is in top shape before your arrival, and each property has a dedicated manager who welcomes you personally and stays available throughout your stay should you need anything. Transparency is at the core of everything we do. What you see is what you pay – no hidden fees for pool heat (up to 86 degrees), bikes, propane, or any of the extras that should already be included. Why settle, when you can stay somewhere extraordinary

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$795.46

/ Nightly

Private Vacation Home

Pineapple Palms: Pool+Hot Tub, 5 min to Beach

Siesta Key, Florida, United States

Welcome to Pineapple Palms, your tropical getaway in beautiful Siesta Key. With space for up to 10 guests, this 4-bedroom home features an open layout made for gathering, a private heated pool, hot tub, and inviting indoor spaces where everyone can unwind after a day in the sun.brbrJust minutes from the powdery white sands of Siesta Beach, this cozy, updated space is perfect for a laid-back getaway. Comfort, island vibes, and the perfect location—everything you need for a memorable stay.brbrThe Spacebr• Sleeps up to 10 guestsbr• 4 bedrooms, 2 bathroomsbr• Spacious one-level layoutbr• Private heated poolbr• Hot tubbr• Cozy movie roombr• Large family dining roombr• Open kitchen perfect for entertainingbr• Propane grillbr• Smart TVsbr• High-speed Wi-FibrbrWhere You'll Sleepbr• 2 King bedsbr• 2 Queen bedsbr• Additional sofa bed in the movie roombrThe primary king suite is a peaceful retreat featuring a large walk-in shower and soaking bathtub, perfect for unwinding after a day at the beach.brbrFully Equipped KitchenbrWhether you’re preparing breakfast before the beach or dinner for the group, the kitchen is stocked with essentials and ready for your stay.brbrIncluded for guest use:brPots and pans, cooking utensils, plates, cups, and dining essentials, cooking range with oven, microwave, dishwasher, toaster, blender, coffee maker, and Keurig machine with coffee pods providedbrbrPrime LocationbrLocated just 5 minutes from Siesta Beach and Siesta Village, you’ll be close to world-famous white sand beaches, restaurants, shops, nightlife, and island activities.brbrDog Friendlybr• No cats allowed due to property restrictionsbr• Must be disclosed at the time of bookingbr• $100 pet fee per dog, per staybr• Maximum of 2 dogs unless approved in advancebrbrGood to Knowbr• Quiet hours begin at 10 PMbr• This is a residential neighborhood, so we ask guests to be respectful of neighborsbr• Routine pool or lawn maintenance may occasionally occur during your staybrbrYour Siesta Key Escape AwaitsbrSpend your days at the beach, your evenings by the pool, and your nights relaxing with family and friends. Whether you’re here for adventure or downtime, Pineapple Palms is the perfect home base for your Siesta Key vacation.brbrBook your stay today and start making memories.

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Sleeps

$1396.92

/ Nightly

Private Vacation Home

Siesta Key Home, Heated Pool, Spa, near the beach! - Talk To The Sand

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$984.67

/ Nightly

Private Vacation Home

Dog-friendly gated spacious Siesta Key Getaway — Pool, Spa, & Mancave.

Siesta Key, Florida, United States

Discover your perfect getaway on the prestigious North End of Siesta Key, where coastal sophistication meets relaxed island living. This meticulously maintained and gated four-bedroom, 3.5-bath residence offers every modern comfort in Sarasota’s most desirable locations.brbrStep through the private gated entrance into a fully turfed, low-maintenance paradise featuring a two-car garage and resort-style outdoor living. Enjoy a sparkling pool and spa, complete with a fully equipped outdoor kitchen, privacy wall, and lounge area ideal for entertaining or unwinding after a day at the beach.brbrInside, you’ll find a gourmet chef’s kitchen with high-end appliances, a spacious master suite with a spa-inspired bath, and a large bonus media room/mancave with five TVs—perfect for sports fans or family movie nights. The second-floor balcony offers a tranquil retreat for morning coffee or evening cocktails beneath the Siesta Key sunset.brbrJust a short stroll to Shell Road Beach, minutes from the vibrant Siesta Key Village and Downtown Sarasota, and steps from the BREEZE line public bus transportation, this home provides the perfect balance of privacy and proximity to the island’s best dining, nightlife, and attractions. brbrThoughtful extras include kayaks, a paddleboard, beach chairs, lots of toys, and a basketball hoop, ensuring fun for all ages. And yes, your furry friends are welcome—we’re dog-friendly (for an added fee)!brbrIf traveling with kids, Mote Marine, Sarasota Children's Garden, Selby Garden, and Selby Library are minutes away.brbr**There are no newer reviews because we moved back into the home for 4 years and have since decided to rent again.

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Sleeps

$1077.29

/ Nightly

Private Vacation Home

Isla Amor | Escape to a Luxury Waterfront Home with Heated Pool & Stunning Views in Siesta Key

Siesta Key, Florida, United States

Isla Amor | Waterfront Oasis + 0.3 Miles to Siesta Key Beachbrbr Why You'll Love This HomebrImagine waking up to serene canal views, stepping out onto your private balcony, and spending your day basking in the sun by a resort-style heated pool. Isla Amor delivers an unforgettable escape—romantic, family-ready, and infused with island charm. With five thoughtfully appointed bedrooms, stylish open-concept interiors, and outdoor living spaces made for memory-making, this Siesta Key gem is a tranquil paradise tucked in the sought-after Palm Island enclave.brbr ‍ ‍ Perfect ForbrFamilies, couples, and adult groups looking for a peaceful waterfront home near Siesta Key Beach—ideal for extended stays, celebrations, or a quiet, luxurious reset.brbr ️ Imagine ThisbrBegin your day with coffee on the main floor balcony, the canal glistening below and palms swaying in the breeze. Head inside to the gourmet kitchen to whip up breakfast, or grab your beach gear—just a 7-minute stroll (0.3 miles) and you're on Siesta Key Beach's iconic powder-white sand. Spend the afternoon lounging by the heated pool or enjoying drinks at the outdoor wet bar with a mini fridge. As the sun sets, gather around the table-top fire pit or dine al fresco in the screened-in porch. Whether you're sharing laughs at the indoor bar or winding down in your plush king suite, Isla Amor wraps every moment in warmth and comfort.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Ensuite, Main Floor, TVbr• Bedroom 2: King Bed, Shared Bath, Upper Floor, TVbr• Bedroom 3: King Bed, Shared Bath, Upper Floor, TVbr• Bedroom 4: 2 Twin Beds, Shared Bath, Upper Floor, TVbr• Bedroom 5: 3 Twin Modular Beds, Shared Bath, Upper Floor, TVbrbr Explore the Areabr• 0.3 Miles to Siesta Key Beach – A 7-Minute Walk to the Soft Quartz Sand and Turquoise Waterbr• 1.2 Miles to South Siesta Key Village – Boutique Shopping, Dining, and Live Musicbr• Canal-Front Living With Peaceful Coastal Ambiancebr• Quick Access to Kayaking, Paddle Boarding, and Local Excursionsbr• Quiet Palm Island Neighborhood With Minimal Through-Trafficbrbr⌛ Don't wait—this home books fast. Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection.brbr Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Free high-speed WiFi throughout. This pool is heated between November 15 – April 15. If any guest has difficulty with stairs, please contact us for alternative accommodations.

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$487.15

/ Nightly

Private Vacation Home

Sunshine on Siesta - Refreshed Duplex!

Siesta Key, Florida, United States

Sunshine on Siesta – by Siesta Key Luxury Rental PropertiesbrbrWelcome to Sunshine on Siesta, a recently refreshed four-bedroom, two-bath Super Unit designed for families and groups who want to vacation together while enjoying space, comfort, and an unbeatable Siesta Key location. By combining both the Sunrise and Sunset residences, this home offers a unique opportunity to book the entire property at once, making it ideal for multi-generational families or friends traveling as a group.brbrLocated just steps from the Gulf, Sunshine on Siesta provides private beach access and a relaxed coastal setting close to Siesta Key Village, local dining, and shopping. This thoughtfully arranged home allows guests to enjoy shared experiences while still having room to spread out and unwind.brbrHighlightsbr• Private beach access – 5 minute walkbr• 4 Bedrooms / 2 Bathroomsbr• 2 King beds and 4 Twin bedsbr• Recently refreshed homebr• Shared pool with neighboring condominium – 2 minute walk br• Beach chairs and beach cartbr• Shared firepitbr• Washer and dryerbr• Pets allowed with host approval br• 2 Parking spotsbr• Convenient Siesta Key location near dining and shoppingbrbrSunshine on Siesta offers convenient access to shared amenities designed for relaxed island living. The shared pool is located just a two-minute walk from the home at the Calini Beach Club, which also provides private beach access about five minutes away. A shared laundry area sits between the two duplex residences, making it easy for guests booking the full Super Unit to use. The shared backyard includes a BBQ grill and a cozy firepit seating area, perfect for unwinding after a day at the beach.brbrThe Super Unit features two comfortable living areas, making it easy for larger groups to relax without feeling crowded. Each side of the home includes inviting seating and a television, perfect for movie nights or quiet evenings in. The kitchens are equipped for everyday cooking, making it easy to prepare meals, snacks, or beach-day essentials while enjoying time together indoors.brbrEach side of the home includes a primary bedroom with a king bed, offering a calm and comfortable retreat at the end of the day. The additional bedrooms feature twin beds, making them ideal for children or additional guests. Bathrooms are conveniently located and feature walk-in showers, providing easy access for everyone in the group.brbrRoom Detailsbr• Primary Bedroom 1: King bedbr• Primary Bedroom 2: King bedbr• Bedroom 3: Two twin bedsbr• Bedroom 4: Two twin bedsbrbrSunshine on Siesta by Siesta Key Luxury Rental Properties delivers the space of a private compound with the ease of private beach access and shared outdoor amenities. Whether you are planning a family reunion or a group getaway, this Super Unit offers comfort, location, and a true Siesta Key experience. Secure your dates today and start planning your coastal escape.brbr-brThis home is managed by Siesta Key Luxury Rental Properties. brbrWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Siesta Key Luxury Rental Properties Rental Policies for full details. brbr2 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

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$1951.83

/ Nightly

Private Vacation Home

#1 Rooftop Deck w/ Gulf Views - Steps to Beach

Siesta Key, Florida, United States

Summary:brbrVunique Vacations was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result Unmatched value for travelers who expect more from their getaway.brbrbrbrThe Space:brbrThis house is spectacular, and the rooftop deck (elevator access) is unreal with what it offers and the 360-degree views that it provides! With an outdoor kitchen area that includes ice maker, beverage refrigerators, and grill (natural gas), there is no better view for the chef on all of Siesta Key. There are multiple dining options including a banquet table for 12. There are also sunning and lounging chairs overlooking the Gulf, and a rear turf space with all sorts of games, seating, and a large TV for movies on the lawn'. It's really a remarkable space! The heated saltwater pool and spa features a waterslide, two sun-shelf areas perfect for lounging or for the kids to play, and two water curtains that rain down from the ceiling into the pool and create a wonderful ambiance. The covered patio space includes 2 large smart TVs, multiple seating and dining options, ping pong and putt putt! These spaces are all within the fenced backyard for privacy and security making it family friendly and perfect for the home's pet friendly policy (fees and restrictions apply). As you go up in this home, you'll find multiple balconies with seating and amazing views on all levels, ending at the gigantic roof top deck that features wide open Gulf of Mexico and Siesta Key views.This nearly 4,000 square foot home has soaring 10-foot ceilings, so it feels open and spacious throughout! The floor plan is so inviting for a family or travel group. There are great views and balconies on all levels. This home has an elevator with service to all floors, including the rooftop deck. This home provides 6 bedrooms (6 with en suite baths), and 6 full baths. There are 5 king beds and a custom full-over queen bunk bed. It comfortably sleeps 14 people in beds. The great room is on the top floor and that provides the best views for everyone to enjoy. It is set up as the perfect gathering space that includes the kitchen, living, and dining areas of the home with access to a balcony with great views. The kitchen is fully stocked, and we mean that because we know how important it is to you, our valued guests! Not only is it stocked, but it's also stocked with the products and manufacturers you trust. This home also offers a club room or secondary living space. The club room is on the first living level.This Siesta Key luxury vacation rental features Smart TVs with cable and streaming services, as well as Free Wi-Fi throughout the property - including the outside areas for complete coverage for all of your work or personal needs. TVs in all bedrooms.Accessibility - in addition to the home's elevator access to all levels, most doorways and walkways are 30 inches or larger, and walk-in showers in Baths 1-5. Please see the Photos, 3D Tour, & Video for this home.brbrbrbrFloor Plan Description (by level):brbrbrbrGround Level:brbrFree parking for up to 6 vehicles (2 covered spaces, and 4 spaces in the driveway). On this ground level you'll find the fully fenced pool and backyard area (pet friendly - fees and restrictions apply), including the covered patio space and putt putt. As we already shared, the pool and covered patio areas are great spaces! In addition to all the details already shared, there are ceiling fans throughout the space for added comfort and an outdoor grill (natural gas). The home's beach equipment can be found here, which includes 2 beach wagons, 2 coolers, 6 beach chairs, and 4 bikes. We include a full refrigerator and freezer (with ice maker) here as well so your beach prep and breakdown, and your use of the home and pool is that much easier. These appliances can also be used to support your pool days and time at home as well. You'll also access the home's main entrance foyer with elevator and stair access to the home's two (2) living levels and rooftop deck above.brbrbrbrThe First Level of Living (2nd Floor):brbrFeatures a club room with a living area with large TV, Nintendo Switch gaming console and a balcony. There are 4 Bedrooms including the home's luxurious master bedroom on this floor. The master bedroom features balcony access, king bed, large walk-in closet, and an en suite bathroom with double vanity, oversized soaking tub and walk-in shower. Bedroom 2 features a set of custom full over queen bunk beds, a workspace, and an en suite bathroom with vanity and shower/bathtub combination. Bedroom 3 & 4 both feature a king bed, and an en suite bath with an oversized vanity (double vanity in bathroom 4) and walk-in shower. Bedroom 3's bathroom is also accessed from the hallway and supports the club room space. There is a stackable washer/dryer on this level.brbrbrbrThe Second Level of Living (3rd Floor):brbrThis level features a great room with the fully stocked kitchen that includes a full range and cooktop with hood vent, full sized refrigerator (with ice maker) and freezer, double trash and recycling storage, double dishwasher, microwave, toaster, coffee maker, and is very well appointed with cookware, bakeware, dish ware, cutlery, and specialty items like crockpots, blenders, and more. If you have any questions on kitchen supplies, our reservationists would be happy to provide more details. The living area is very comfortably appointed with smart TV and Gulf views. The dining area here seats 19 people comfortably via a 10-person dining table, 5-person kitchen island bar top, and 4 additional high top bar seats. The main balcony off the great room has additional seating, and sunset and Gulf views. There are 2 bedrooms on this floor. Bedroom 5 & 6 both feature a king bed, and an en suite bath with an oversized vanity (double vanity in bathroom 6) and walk-in shower. Bedroom 5's bathroom is also accessed from the hallway and supports the living room space. There is a half bath and stackable washer/dryer on this level.brbrbrbrThe Rooftop Deck:brbrThis rooftop space is an elevated outdoor living space that really can't be rivaled! As we shared, the outdoor kitchen, dining and seating options, and turf area with games and TV are incredible. The sunrise and sunset experience here is supported so well by the amenities of the space, and trust us, you'll want to be up here throughout the day too. It is perfect for enjoying sunrise over Siesta and greater Sarasota, or sunset over the Gulf of Mexico. So, be sure to grab a book, a coffee or cocktail, and enjoy the sea breeze and Florida sun from this amazing elevated outdoor living space that overlooks all of Siesta Key.brbrbrbrGetting Around:brbrThis home is located about a 5min walk from the Siesta Key Village. South Siesta village entertainment districts and all the restaurants, entertainment, shopping, grocers, and more on the Key can be accessed by bike, golf cart, car, or free trolley. If you want to explore further, without the hassle of driving, you’ll find multiple stops nearby for the free trolley that provides transportation service to the entirety of Siesta Key. You’re also just a quick drive or Uber/Lyft (10-15 minutes) to downtown Sarasota for access to the amazing Sarasota Performing Arts scene, and numerous fantastic restaurants, shops, marinas, bars and entertainment, and more. And, day trips to Lido Key and Anna Maria Island are just 30 minutes away, as well as the amazing theme parks of Tampa and Orlando that are all just 1-2 hours away!brbrbrbrOther Things to Note:brbrThis Siesta Key luxury vacation rental features Smart TVs with cable and streaming services, as well as Free Wi-Fi throughout the property - including the outside areas for complete coverage for all your work or personal needs. TVs in all bedrooms.brbrbrbrAccessibility - in addition to the home’s elevator access to all levels, most doorways and walkways are 30 inches or larger and walk-in showers featured in most bathrooms. Please see the Photos, 3D Tour, & Video for this home for exact information.brbrbrbr*Don't forget to check out our Matterport 3D Tour for this home* And, if you still have any questions concerning our homes, rates, availability calendar, amenities, policies, or otherwise, please contact our team of professional reservationists and we will be happy to assist you. We want you to fully understand what you are booking, and yes, an actual human team member is available to help! You are just a couple of clicks away from paradise!brbrbrbrInteraction with Guests:brbrPersonal service and attention to detail define the Vunique Difference. We want your vacation to fit your schedule, which is why we offer flexible bookings starting at just 3 nights for most of the year and any-day arrivals. Our homes are spacious and thoughtfully designed, made for connection as much as comfort. Here, luxury isn’t an upgrade – it’s the standard. Within our portfolio of branded residences, you have every amenity that you need for an unforgettable stay - waterslides, movie rooms, resort-style pools, sport courts, golf simulators, climbing walls, putt-putt courses, zip lines, gaming systems, rooftop decks, biked and beach equipment and more. Our proactive maintenance team ensures everything is in top shape before your arrival, and each property has a dedicated manager who welcomes you personally and stays available throughout your stay should you need anything. Transparency is at the core of everything we do. What you see is what you pay – no hidden fees for pool heat (up to 86 degrees), bikes, propane, or any of the extras that should already be included. Why settle, when you can stay somewhere extraordinary

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$889.37

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Private Vacation Home

Walkable to Siesta Key Village and Beaches, Family Friendly - Cypress Cottage

Siesta Key, Florida, United States

Welcome to the Cypress Cottage! brThe perfect beach getaway - just minutes from the amazing Siesta Key Village and powder sand Siesta Beaches! This house is perfect for families, couples and group trips! This property is ready for you to make memories - with 5 bedrooms, a fully equipped kitchen and spacious living room.brbrThe secluded backyard is perfect for lounging in a hammock, using the outdoor shower, or your kids playing in the tree house! brbrSpending the day at the beach, or on the pickleball/tennis courts We have everything you could need! Beach wagons, chairs, umbrella, beach tent, towels, beach toys, pickleball paddles, etc! brbrWhether you decide to hit the night life in the vibrant Siesta Key Village, or spend a night in playing board games - Twister, Monopoly, etc. This property is ready for all your needs!

5

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2

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12

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$1171.67

/ Nightly

Private Vacation Home

Siesta Key 6Br Beachfront Suites Retreat, Gulfview

Siesta Key, Florida, United States

Beachfront Suites Compound: Surfside, Serenity, and Dreamview Condos on Siesta KeybrbrWelcome to your ultimate beachfront retreat on Siesta Key, where the serene beauty of the Gulf of Mexico meets unparalleled comfort in our exclusive Beachfront Suites compound. Comprising three distinct condos - Surfside, Serenity, and Dreamview - each offering unique features and amenities, this stand-alone triplex delivers a personalized beach getaway experience directly on the world-famous Siesta Key Beach. Whether you seek a family adventure, a tranquil escape, or a romantic rendezvous, our Beachfront Suites cater to every desire.brbrProperty Features:brbr-Surfside Condo (1st Floor): A family-friendly 3-bedroom haven with immediate beach access, a newly renovated bathroom, and a private patio. It's perfect for beach days or relaxing with a book in the large shared backyard.br• Primary Bedroom: King Bedbr• Guest Bedroom 1: Queen Bedbr• Guest Bedroom 2: Twin BedsbrbrSerenity Condo (2nd Floor): Offers a peaceful 2-bedroom escape with stunning Gulf views from a private balcony. Its calming aesthetic and fully stocked kitchen provide a zen-like atmosphere for a truly serene vacation.br• Primary Bedroom: King Bedbr• Guest Bedroom: Queen Bedbr• Pull Out SofabrbrDreamview Condo (3rd Floor): This 1-bedroom suite boasts the best views on Siesta Key, featuring a large Jacuzzi bathtub, plush king bed, and private balcony for unforgettable sunsets. Ideal for romantic getaways or small families.br• Primary Bedroom: King Bedbr• Futon SofabrbrShared Amenities for All Guests:br- Immediate access to Siesta Key Beachbr- Breathtaking views of the Gulf of Mexicobr- HD Smart TVs, outdoor firepit, picnic area, propane & charcoal grillbr- Outdoor and board games, beach suppliesbr- Large shared backyard for ultimate relaxation and funbrbrPet Policy: Each condo welcomes your furry friends with a pet-friendly policy for dogs up to 50 lbs or two dogs with a combined weight of 50 lbs, ensuring no family member is left behind.brbrLocal Area:br- Just .25 miles to Siesta Key Public Beach and .5 miles to Siesta Key Village for dining, shopping, and entertainment. Downtown Sarasota is a short drive away, offering cultural attractions and more.brbrExclusive Compound Advantage:brRenting the Beachfront Suites compound provides an exclusive beachside experience for larger groups or families, offering a blend of privacy, luxury, and shared outdoor spaces. It's an ideal setting for creating lasting memories together on Siesta Key.brbrExperience the best of Siesta Key in one of our beachfront condos, where every stay is tailored to your preferences, whether it's soaking up the sun on the beach, enjoying backyard barbecues, or simply unwinding to the soothing sound of the waves.

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$905.98

/ Nightly

Private Vacation Home

Waterfront KEY home w/ Pool, HotTub, mins to beach

Siesta Key, Florida, United States

Minutes from the beach, marina, and village center, your tropical paradise awaits you at this bright, 5 bedroom 3 bathroom vacation rental house. This property boasts a private pool with jacuzzi tub. There’s even a putting green on site to polish your golf skills. Families can decide between enjoying the private pool, nearby beach, charter boats, eco tours, or shopping and dining. Challenge your guests to some friendly competition via the arcade Pac Man or Golden Tee Golf games located right in the lower level!brbrBRAND NEW 6 SEAT GOLF CART AVAILABLE FOR RENT!brStreet legal 6 seater cart with a 4+2 Seat cart configuration featuring Apple Car Play, rear camera, premium sound system, head/tail lights, turn signals, back seat folds down to hold beach chairs, groceries, etc. It has a 60-mile range and max speed of 25 mph.brbrRental rates are:br$700 /weekbr$1800 /monthbrPlease inquire to reserve for your stay!brbrUpstairs:brBedroom 1- King BedbrBedroom 2- King BedbrBedroom 3- Two Twin BedsbrDownstairs:brBedroom 4- King BedbrBedroom 5- Two Twin XL over Queen Bunk Bedsbr2 Living Rooms! (2 Rollaway single beds available for use)brbrWeather Disclaimer: Pool temperatures may not fully reach the temperature the heater is set to if the outside air temperature is below 70 degrees.brbrHouse is located blocks from the Out of Doors Academy. Approximately 1 mile from the village area of Siesta Key and about 1 mile from the closest beach access.brbrAs you step into this lovely home, you feel refreshed as you gaze up toward the open-air cathedral ceilings. Enter the living room to a plush new sofa and comfy loveseat set in front of a large flat-screen TV. For your viewing pleasure, watch your favorite movies, enjoy complimentary Youtube TV or local channel programming on Roku. Past the living area, you`ll find a beautifully appointed dining table with seating for 8 guests to enjoy a delicious meal.brbrThe fully equipped kitchen offers ample granite countertop space for preparing a home-cooked meal while your travel companions join you. Enjoy the feast at the nearby dining table, while taking in the views of the natural setting as you dine. The chef in your group will appreciate the newly updated stainless-steel appliances.brbrBask in the sun when you head out to the open and airy patio to take a refreshing swim in the sparkling, heated pool. Let your spa treatment continue as you progress into the soothing hot tub. Then dry off under the warm Florida sun as you soak up the rays on the plush chaise lounge chairs. Outdoor living at its best!brbrWhen hunger strikes, cookout on the gas grill and enjoy your lunch at the nearby patio table. Want a large family meal Make use of the Crock Pot Slow Cooker. Brew your morning coffee using the provided Keurig coffee maker.brbrAfter a fun-filled day, retreat to one of the cozy bedrooms for a peaceful slumber. The master has a king bed, second bedroom a king, third bedroom a king, fourth has two twin beds, and the fifth has 2 Twin XL over Queen Bunk Beds. Room for everybody! What’s more, two twin rollaway beds are also provided featuring super comfy memory foam!brbrYour family can tour the key on the 5 provided “Beach Cruiser” bicycles parked in the garage awaiting your adventure. Beach chairs, beach umbrella, beach toys, beach wagon, pool toys, etc. are also included.brbrPack lightly when you travel to this lovely home, as you`ll be able to refresh your laundry in the washer and dryer. No need to fumble with keys and lock boxes as this rental is equipped with quick & easy keyless entry.brbrOutside:brbrThe home is set back from the street with a deep, palm-filled front yard. Behind the house are a shady pool, hot tub, and putting green! The house is at the end of a private canal and driveway parking.brbrbrInside:brbrThe updated, top-of-the-line, windowed kitchen is fitted with stainless steel appliances, Keurig and all useful gadgets, and terrific cooking and eating counter space. The kitchen storage exceeds any renter`s needs!brbrThe kitchen is open to the dining/living room, with large dining area, TV, working fireplace, and pool views. The entire living room opens through sliding doors to the balcony above the patio with a lovely view of the canal, with another roomy dining table and separate seating area. Proximity to the living room is ideal for entertaining: opening the sliding door brings the outside into the whole living space, and island breezes fill the porch all evening. Off the porch, back stairs lead directly to the pool area.brbrThis newly renovated upper-level home has been meticulously updated and appointed to highlight its open layout and airy entertaining space. A vacation-ready Siesta Key pool & canal residence, the house is elevated on a corner waterfront lot in a prime, quiet neighborhood minute from the beach.brbrSiesta Beach continues to rank highly on the “Top Beach” lists curated by worldwide travelers and renowned coastal experts. Its nearly 100% quartz-crystal sand, dubbed the “world’s finest, whitest sand”, never gets hot under the Gulf Coast sun and tropical weather.brbrSiesta Key Beach named by TripAdvisor as the top beach in the U.S.!br$25 Pet fee per pet, per nightbrbrAdditional $200 per week or $500 per month to heat pool to the optimal and desired temperature of 88 degrees!brbr24-hour outdoor camera and remote security team monitoring not actively monitoredbrNoise detection sensors installed in property – These devices monitor decibel levels inside the property 24 hours a day and automatically notify us if noise levels are too high.

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$1947.38

/ Nightly

Private Vacation Home

Sugar Sand Cottage – Gulf-View Siesta Key Escape

Siesta Key, Florida, United States

Summary:brbrSugar Sand Cottage is a 5BR/3.5BA Siesta Key retreat directly across from the Gulf . Just a 2-minute walk to the beach and moments from Siesta Key Village, this home offers Gulf views, a private pool, and a wraparound patio perfect for sunset lounging. With a split floor plan, bunk rooms, and plenty of space to gather, it’s ideal for families and groups ☀️ ️.brbrbrbrThe Space:brbr ️ Sugar Sand Cottage – Gulf-View Siesta Key Escape brbrbrbrWelcome to Sugar Sand Cottage, a bright and breezy 5-bedroom, 3.5-bath coastal retreat directly across the street from the Gulf of Mexico . Just steps from the powdery white sands of Siesta Key Beach and moments from the lively Siesta Key Village, this home offers the perfect blend of location, comfort, and relaxation. Enjoy non-stop Gulf views, a private pool, and a stunning wraparound patio designed for soaking up the island sunshine ☀️.brbrbrbrSpend your days at the beach, then retreat to your peaceful backyard oasis to cool off in the sparkling pool or unwind on the deluxe outdoor seating with Gulf breezes and sunset views . With shops, restaurants, and nightlife just minutes away, you’ll have everything you need for an unforgettable island getaway.brbrbrbrInside, the open living space is warm and inviting, featuring cozy seating, a large TV, and coastal touches throughout . The gorgeous kitchen is a dream for entertaining, equipped with stainless steel appliances, stylish tile work, and plenty of storage. Gather around the dining table or bar-top seating for meals, game nights, or morning coffee.brbrbrbrDesigned with a split floor plan, Sugar Sand Cottage offers privacy and flexibility for families and groups. A second living area provides extra space to spread out, while sleeper sofas add even more sleeping options for guests.brbrbrbr✨ Highlights ✨brbrbrbr• ️ 2-minute walk to Siesta Key Beach (across the street)brbr• ️ 5 Bedrooms / 3.5 Bathroomsbrbr• Gulf views from wraparound patiobrbr• Private poolbrbr• ️ Walk to restaurants, shops & Siesta Key Villagebrbr• Washer & dryerbrbr• Spacious outdoor seating & entertaining areasbrbrbrbr Bedrooms brbrbrbr• Primary Bedroom: King bed, ensuite bathroom with walk-in showerbrbr• Second Bedroom: Queen bed, hall bathroom access with walk-in showerbrbr• Third Bedroom: Full-over-Full bunk with twin trundle, hall bathroom accessbrbr• Fourth Bedroom: King bed, Jack-and-Jill bath with tub/shower combobrbr• Fifth Bedroom: Full-over-Full bunk, Jack-and-Jill bath with tub/shower combobrbrbrbrAdditional sleeper sofas provide extra accommodations.brbrbrbrGuest Access:brbrGuests have full access to the entire home, including a private heated pool and backyard—perfect for relaxing, entertaining, and enjoying your own secluded space.☀️brbrbrbrOther Things to Note:brbr ️ Beach-Ready Convenience brbrTo make your stay effortless, the home is fully stocked with beach chairs, a beach cart, and a beach umbrella, plus all bath towels, beach towels, and linens—just pack your bags and enjoy island time ☀️ brbrbrbr Parking InformationbrbrParking is available for up to 3 vehicles maximum. Please plan ahead and coordinate with your group accordingly.brbrbrbr Friendly Island ReminderbrbrThis home is located in a residential neighborhood. We kindly ask guests to be respectful of our neighbors by keeping noise at a considerate level day and night. Thank you for helping preserve the peaceful island atmosphere brbrbrbrInteraction with Guests:brbrIf you need anything during your stay, I’m always here to help! You can call or text me directly on my cell anytime. I’m available 24/7 to answer questions, share local tips ️, or assist with anything that comes up. Your comfort and peace of mind are my top priority! ✨

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$1168.08

/ Nightly

Private Vacation Home

Perfect for Families! Private Back Yard & Heated Pool - Bahama Mama

Siesta Key, Florida, United States

Bahama Mama by Siesta Key Luxury Rental Properties brHome in Siesta Key, Florida brbrSiesta Key Luxury Rental Properties - The Best Homes, Location, and Vacation Experience on Siesta Key! brbrWelcome to Bahama Mama, a stunning vacation home boasting five bedrooms and five bathrooms, located just a five-minute walk away from the picturesque Gulf of Mexico beaches! The backyard of this home is a true tropical paradise, featuring a sparkling pool with a spa, comfortable loungers, and a charming covered patio that includes an outdoor dining table, a television, and a BBQ grill. We can't wait to welcome you to this unforgettable retreat! brbrAt A Glance br• 5-minute walk to the beachbr• Near restaurants and boutiquesbr• Pool with in-ground spabr• BBQbr• Outdoor showerbrbrThe modern living space is adorned with coastal touches and a cozy seating area with a large TV. The fully equipped kitchen has stainless steel appliances, a spacious kitchen island that serves as an ideal spot for preparing large meals, seating for six guests to keep the cook company, and a unique banquette-style table that adds character to the dining area. brbrWhat makes this home's bedrooms so delightful and unique is that each one has an ensuite bathroom! You'll appreciate the thoughtful design that prioritizes both comfort and elegance, along with convenient amenities like televisions and plenty of storage space. The King and Queen rooms boast walk-in showers, while the bunk room features a shower and tub combo. brbrRoom Details br-Primary Bedroom: King bed and ensuite bathroom with walk-in shower br-Second Bedroom: King bed, pool access, and ensuite bathroom with walk-in shower br-Third Bedroom: King bed, pool access, and ensuite bathroom with walk-in shower br-Fourth Bedroom: Queen bed and ensuite bathroom with walk-in shower br-Fifth Bedroom: Full over full bunk bed and ensuite bathroom with shower and tub combo. br-Bonus: Queen sleeper sofabrbrThis lovely home is in the heart of Siesta Key Village, just one block from Ocean Boulevard's fabulous boutiques and restaurants and Siesta Key Beach, famous for its shimmering white sand and warm waters. brbr- brWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Siesta Key Luxury Rental Properties Rental Policies for full details. brbrThis property has an active Ring doorbell and additional video surveillance on the pool equipment only. brbrThis property participates in our Professional Linen Program. This ensures high-quality linens and towels are always included in your stay. These are professionally laundered at a commercial facility for every guest.brbr4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrPlease see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbrThis home is managed by Siesta Key Luxury Rental Properties. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

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$1478.33

/ Nightly

Private Vacation Home

Prime Location with Pool, Spa, and Fun Waterslide - Summer House

Siesta Key, Florida, United States

Summer House by Siesta Key Luxury Rental Properties brbrWelcome to Summer House, a six-bedroom, six-bathroom Siesta Key pool home ideally located just a three-minute walk to Siesta Key Beach and a two-minute walk to Siesta Key Village. This ground level vacation home is designed for family fun and relaxed island living, featuring a private pool with spa and waterslide, spacious outdoor living areas, and walkable access to the island’s most popular restaurants, shops, and attractions. With room for the whole group and parking for four vehicles, Summer House is the perfect setting for a classic Sarasota beach vacation. brbrHighlights br- 3-minute walk to Siesta Key Beach br- 2-minute walk to Siesta Key Village br- 6 bedrooms / 6 bathrooms br- 2 kings, 2 queens, 6 full beds (bunk beds) br- Private pool with spa and rock waterslide br- Outdoor living space and BBQ grill br- Outdoor shower br- Washer and dryer br- 4 parking spaces br- Dog friendly with host approval and fee brbrThe backyard at Summer House is built for memorable vacations. Guests can enjoy a private pool complete with a waterslide, and spa; perfect for both kids and adults. Multiple outdoor seating areas allow the group to spread out, including a covered porch with comfortable seating and a second entertaining area with an outdoor TV and bar top seating. Whether grilling, relaxing poolside, or unwinding after a beach day, this outdoor space elevates every stay. brbrInside, the home offers a bright and welcoming open layout with coastal decor throughout. The living area features comfortable seating and a large TV for movie nights or downtime between island adventures. The fully equipped kitchen includes stainless steel appliances, ample counter space, and everything needed to prepare meals for the group. Guests can enjoy casual seating at the kitchen island or gather around the breakfast nook style dining table and bar-top seating area. brbrEach of the six bedrooms is designed with comfort and privacy in mind and includes its own ensuite bathroom and television. The primary suite is the largest and features a king bed, beach design, generous space, and a spa like bathroom with a double vanity and walk-in shower. An additional king bedroom, as well as two queen bedrooms, provide relaxing retreats for adults, while two bunk rooms are perfect for kids or teens, offering fun sleeping arrangements without sacrificing comfort. brbrRoom Details br- Primary Bedroom: King bed and ensuite bathroom with double vanity and walk-in shower br- Second Bedroom: King bed and ensuite bathroom with walk-in shower br- Third Bedroom: Queen bed and ensuite bathroom with double vanity and walk-in shower br- Fourth Bedroom: King bed, porch access, and ensuite bathroom with walk-in shower br- Fifth Bedroom: Two full-over-full bunk beds and ensuite bathroom with walk-in shower br- Sixth Bedroom: Full-over-full bunk bed and ensuite bathroom with shower and tub combination brbrSummer House is centrally located near Siesta Key Village, placing guests within walking distance of dining, shopping, coffee shops, and ice cream stops. Siesta Key Beach is just minutes away, offering world-famous powdery white sand and stunning Gulf Coast sunsets. The home also includes a washer and dryer, professionally laundered linens, and exterior security monitoring for added peace of mind. brbrWith its unbeatable location near Siesta Key Beach, private pool with waterslide, and spacious layout designed for families and groups, Summer House by Siesta Key Luxury Rental Properties delivers the perfect balance of comfort, fun, and island convenience. Book your stay today and experience the best of Siesta Key living! brbr- brThis property participates in our Professional Linen Program. This ensures high quality linens and towels are Always included for your stay. These are professionally laundered at a commercial facility for every guest. brbrThis property has an active Ring doorbell and additional video surveillance on the pool equipment. brbrThis property allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated, see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbr4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrPlease see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbrThis home is managed by Siesta Key Luxury Rental Properties. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

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Select Dates for Price

Canal-Front Home with Pool, Dock, and Rooftop Near Siesta Key Beach - Salty Dog

Siesta Key, Florida, United States

Salty Dog by Siesta Key Luxury Rental Properties brbrWelcome to Salty Dog, a stunning six-bedroom, four-bathroom canal-front home just a two-minute stroll from the renowned Siesta Key Beach and a short walk or bike ride to vibrant Siesta Key Village. This luxurious retreat perfectly blends adventure, relaxation, and family fun. brbrHighlights br• Canal Front Home br• Shared Dock br• Rooftop Deck with Beach Views br• 2-minute walk from the beach br• Private Heated Pool with In-Ground Spa br• Dog Friendly with approval and additional fee br• Ping Pong Table br• Kayak and Paddleboard with Life Vests br• Professional Linen Program brbrEnjoy easy access to kayaking and fishing right from your shared dock. Unwind by the heated pool, relax on the rooftop deck while taking in spectacular beach views, and enjoy meals on the outdoor patio. brbrStep inside to a welcoming ground level featuring a large 2+ car garage, and foyer. The main level boasts an elegant great room with a gourmet kitchen equipped with stainless steel appliances and an expansive dining table for fourteen. Adjacent is a beach-themed seating area with a large HDTV and a balcony offering lovely views of the pool and canal. brbrSalty Dog is designed for family gatherings, with spacious bedrooms, each featuring a TV and cozy bedding. The primary bedroom is a serene retreat with balcony access and a luxurious ensuite bathroom, complete with a double vanity, soaking tub, and walk-in shower. The home also includes three additional king suites and two cheerful kids' rooms that share a shower and tub bathroom. brbrRoom Details br- Primary Bedroom, 2nd floor: King bed with outdoor balcony access and an ensuite bathroom featuring a walk-in shower and standalone tub br- Second Bedroom, 3rd floor: King bed with an ensuite bathroom with a walk-in shower br- Third Bedroom, 3rd floor: King bed with an ensuite bathroom with a walk-in shower br- Fourth Bedroom, 3rd floor: King bed with an ensuite bathroom with a walk-in shower br- Fifth Bedroom, 3rd floor: King bed br- Sixth Bedroom, 3rd floor: Full over Full bunk brbrDon’t miss out on Salty Dog, your ideal Siesta Key vacation destination. Book now for an unforgettable experience in paradise! brbr-brThis property participates in our Professional Linen Program. This ensures high quality linens and towels are Always included for your stay. These are professionally laundered at a commercial facility for every guest.brbrThis property has an active Ring doorbell, active video surveillance on the exterior public approach areas, and the pool equipment. brbrThis property allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbr4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrThis home is managed by Siesta Key Luxury Rental Properties. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

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Sleeps

$1280.58

/ Nightly

Private Vacation Home

Waterfront Home w/ Dock, Heated Pool/Spa, Rooftop w/ Gulf Views

Siesta Key, Florida, United States

Dry Dock by Siesta Key Luxury Rental Properties brbrWelcome to Dry Dock, a refined canal-front Siesta Key luxury rental offering the perfect blend of waterfront adventure and relaxed island living. This six bedroom, six and a half bath house is located just a three-minute walk to Siesta Key Beach and within easy walking distance of Siesta Key Village. With a private pool and hot tub, shared dock access, elevator, and rooftop deck with Gulf views, Dry Dock is ideal for large families, multifamily groups, and extended stays seeking effortless coastal comfort near the best of Sarasota’s beach attractions. brbrHighlights br- 3-minute walk to Siesta Key Beach br- Canal-front home with shared dock access br- 6 bedrooms / 6.5 bathrooms br- 4 king beds, 6 twin beds (bunk beds) br- Private pool and hot tub br- Rooftop deck with Gulf views br- Elevator access to all living levels br- Ping pong table br- Two kayaks and beach wagon br- Outdoor dining area with BBQ grill br- Washer and dryer in unit br- Dog friendly with approval br- Four parking spaces br- Professional Linen Program brbrThis canal front retreat offers resort style outdoor living designed for both relaxation and play. The backyard features a private pool and hot tub surrounded by lounge seating, perfect for cooling off after a day at the beach. Guests can enjoy direct access to the shared dock for kayaking, paddleboarding, boating, or fishing, with two kayaks included for easy water exploration. The rooftop deck provides an elevated island experience, offering sweeping views toward the Gulf. The covered patio adds another layer of outdoor comfort with a bar, seating for five, outdoor television, and ping pong table. brbrDry Dock offers two levels of spacious living above the garage, easily accessed by an elevator. The open concept living area is designed for gathering, featuring an oversized sectional sofa where guests can relax after beach days or enjoy movie nights together. Sliding doors lead to a second level balcony overlooking the canal. The fully equipped kitchen features stainless steel appliances, generous counter space, and an island with seating for six, making it ideal for preparing group meals. The dining area comfortably seats twelve, allowing all eighteen guests to dine together in one shared space, perfect for family meals, takeout nights, or board games. brbrThe primary bedroom offers a serene retreat with calming coastal tones, generous closet space, and an ensuite bathroom with a shower and tub combination. Additional bedrooms feature king beds with ensuite bathrooms, many offering walk-in showers and private or shared balcony access overlooking the canal. Younger guests will love the thoughtfully designed bunk rooms, each offering a bright, beachy atmosphere and plenty of space to relax. These rooms are ideal for kids or teens traveling together and maintaining the same level of comfort and quality found throughout the home. Each bunk room includes its own ensuite bathroom, providing privacy and convenience for larger groups. brbrRoom Details br- Primary Bedroom (Second Level): King bed, ensuite bathroom with shower and tub combination br- Second Bedroom (Third Level): King bed, ensuite bathroom with walk-in shower, private balcony br- Third Bedroom (Third Level): King bed, ensuite bathroom with walk-in shower, shared balcony br- Fourth Bedroom (Third Level): King bed, ensuite bathroom with walk-in shower, shared balcony br- Fifth Bedroom (Third Level): Twin over twin bunk bed, ensuite bathroom with shower and tub combination br- Sixth Bedroom (Second Level: Two twin bunk beds, ensuite bathroom with shower and tub combination brbrDry Dock is dog friendly with prior approval and an additional non-refundable pet fee. This home is located near popular island favorites including Daiquiri Deck and Gilligan’s Island Bar. Guests will also appreciate the option to rent the neighboring unit, Salty Dog, which shares a mirrored layout, ideal for doubling accommodations for larger groups. brbrWith canal front access, a private pool and hot tub, rooftop Gulf views, and a walk to beach location, Dry Dock by Siesta Key Luxury Rental Properties offers an elevated beach getaway designed for unforgettable group vacations. Book your stay today and experience the best of Siesta Key waterfront rentals and luxury coastal living! brbr- brSiesta Key Luxury Rental Properties Pet Policy: Dogs are allowed under certain conditions and ALL animals, including service animals, must be disclosed and approved before arrival. We cannot accept cats. Please note that an additional non-refundable pet fee will be charged upon approval by Siesta Key Luxury Rental Properties. Weight limit of 50 lbs max total for 1 or 2 dogs combined. No dangerous breeds are allowed. Please see our Siesta Key Luxury Rental Properties Rental Policies for complete details. brbrThis property has an active Ring doorbell, active video surveillance on the exterior public approach areas, and the pool equipment. brbrThis property participates in our Professional Linen Program. This ensures high quality linens and towels are always included in your stay. These are professionally laundered at a commercial facility for every guest. brbrIf you have any questions concerning our home, rates, amenities, policies, or anything else, please send us an inquiry. One of our professional reservationists and property managers would be happy to help answer your questions. You are a couple of clicks away from paradise, and we look forward to seeing you soon.

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Sleeps

$926.68

/ Nightly

Private Vacation Home

Spacious Siesta Key Paradise-Canal front, private pool, walk to SK Beach/Village

Siesta Key, Florida, United States

Beaches, Boating and Bistros! Live the island lifestyle in this spacious 5 bedroom, 4 bathroom house located on desirable Palm Island on Siesta Key. Lounge in the heated pool and spa or enjoy your favorite libation at your private Waterfront Tiki Bar. brbrThe best location on Siesta Key. 7 minute walk to Siesta Key Beach, 9 minute walk to Siesta Key Village. Large private heated pool with hot tub.brbrHouse is located on the Grand Canal with access to the Intercostal Waterway, with private dock. Large private deck right on the canal for relaxing or entertaining. Also has Tiki Bar adjacent to pool and dock, with large fire pit area. Large heated pool has ample chase lounges, chairs and dinning area that seats 10. Pool area also has large spa whirlpool.brbrThe 5 bedrooms will accommodate 10 people. Master suite and 3 other bedrooms on main(second) floor, along with 3 full bathrooms. Master suite is equipped with Spa/Hydro Massage Tub. The lower floor has a bonus area with large bar room and large rec room with high quality ping pong table. Ground floor also has one bedroom and full bathroom. brbrHuge open living space, with massive kitchen and dinning area that seats 10 or more. Dinning area leads right into family area with two full couches and 70' TV. This area is connected to a bar top table area for drinks/eats over looking the pool and canal area. On the other side is a large sitting area for reading or just relaxing and admiring the views of pool and canal area. Both family area and sitting area lead to very large deck by way of large sliding glass doors that open completely up.brbrThe large second floor deck overlooks the pool, the canal and the Tiki area. Deck has large six seat table, with patio couch and coffee table, in addition to a sitting area with Adirondacks chairs.brbrLocation is a quick walk to Siesta Key Beach. Beach cart, beach chairs and umbrella provided. Also, just a few minute walk to the Siesta Key Village, filled with tons of fun restaurants, bars, and shopping.brbr

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