Vacation Home Rentals By Owner In Siesta Key, FL

$692.01

Blu Sky Cottage | Waterfront Pool Home, Resort-Style Backyard, Near Siesta Key Village

Siesta Key, Florida, United States

Blu Sky Cottage | Waterfront Pool Home, Resort-Style Backyard, Near Siesta Key Villagebrbr Why You'll Love This HomebrBlu Sky Cottage stands out for its rare combination of waterfront access and a resort-style backyard, offering a one of a kind setting on Siesta Key. The outdoor space is the true highlight, with a private saltwater pool and spa overlooking the canal, creating a seamless connection between relaxation and activity. The backyard is designed for both lounging and play, with space for outdoor dining, grilling, and games, all set against the water. With direct canal access, guests can utilize the complimentary kayaks and paddleboards, or bring a small boat and head out right from the property. Inside, the home features an open-concept layout with comfortable living and dining areas, along with a dedicated workspace complete with a printer for added convenience during longer stays.brbr ‍ ‍ Perfect ForbrFamilies or small groups looking for a waterfront stay with standout outdoor space, easy access to Siesta Key Village, and room to unwind between beach days.brbr ️ Imagine ThisbrSpend the morning out on the water, launching a paddleboard or kayak directly from the backyard. Return home to cool off in the pool or relax in the spa while overlooking the canal. Afternoons are easy here, grill lunch outside, gather around the shaded dining area, or play a casual game of cornhole in the yard. As the day winds down, head into Siesta Key Village for dinner or stay in and enjoy the quiet waterfront setting.brbr Where You'll Sleepbr• Bedroom 1: King Bedbr• Bedroom 2: King Bedbr• Bedroom 3: Queen Bed + Twin Bunk BedbrbrAccommodates up to 8 guests.brbr Explore the Areabr• 1.0 Mile to Siesta Key Beach – Powdery white sand and Gulf watersbr• 0.5 Miles to Siesta Key Village – Restaurants, shops, and nightlifebr• Canal Access – Paddleboarding, kayaking, and boating from the propertybrbr⌛ Don't WaitbrA rare Siesta Key find due to its waterfront setting and standout outdoor space, Blu Sky Cottage offers a resort-style backyard experience paired with a prime Siesta Key location. Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection.brbr Need to KnowbrPer Sarasota County regulations, this property allows one rental per 30-day period. Please contact us for more information. The pool is heated between November 15th and April 15th. Cooler temperatures may impact heating performance. Starter packs of kitchen and toiletry essentials are provided for your first couple of nights. Free high-speed WiFi is included. We happily welcome 1 small dog (up to 25 lbs) with a $250 fee per pet—breed guidelines apply to ensure a safe and comfortable stay for everyone.

3

Bed

2

Bath

8

Sleeps

$2486.0

/ Nightly

Private Vacation Home

New! Beach House with heated pool/spa water slide!

Siesta Key, Florida, United States

Discover your dream retreat in this stunning Siesta Key beach house! With 6 bedrooms & 6.5 baths, this home is perfect for families or groups. Dive into the heated pool featuring a thrilling water slide, or unwind in the serene spa. Centrally located in vibrant Siesta Key Village, you’re just a short stroll from pristine beaches, delightful restaurants, and charming shops. Enjoy coastal lifestyle with modern amenities and an inviting atmosphere, making it an ideal getaway for relaxation and fun!brbrEnjoy your beach days with ease. We supply beach towels, beach chairs, and a wagon to make your trips to the shore effortless.brbrPool Heating DisclaimerbrbrPlease note that pool heaters are weather-dependent. When outdoor air temperatures drop below 55°F, electric pool heaters will not operate, and pool water will remain cold. Even when temperatures rise slightly above 55°F but stay in the low 60s, the heater may produce minimal heat and may not significantly warm the pool.brbrThe only way to guarantee a consistently warm pool during colder months is with a gas pool heater, which can operate in very low temperatures but requires substantial gas usage to maintain warmth.brbrBy booking during cooler months, guests acknowledge that pool temperature and heater performance are directly affected by weather conditions, which are beyond the control of the property owner or management. We strongly recommend reviewing and acknowledging this information prior to booking to ensure clear expectations regarding pool heating during your stay.brbrImportant Note:brWhen you stay at our vacation rental homes, we want to ensure your experience is comfortable and convenient right from the start. Each home comes with a thoughtfully prepared starter pack to help you settle in seamlessly. This pack includes:brbr- *Laundry Detergent*: Enough for your initial laundry needs.br- *Dish Soap*: For easy clean-up after meals.br- *Dish Sponge*: Essential for washing dishes.br- *Dishwasher Pods*: A few pods to kickstart your dishwashing.br- *Toilet Paper*: Two rolls per bathroom to get you started.br- *Paper Towels*: One roll for quick clean-ups.br- *Extra Trash Bags*: To accommodate your waste disposal needs.brbrPlease note that we do not provide used kitchen items like oil, spices, or butter, ensuring a fresh start for your cooking adventures. Additionally, all homes are equipped with drip coffee makers, but remember to bring your own coffee filters to enjoy your morning brew.brbrWith these amenities, you can focus on enjoying your vacation without the worry of running out of essential supplies.brbrEarly Check In & Late Check Out:brFrom February through August, we regret to inform our guests that early check-ins and late check-outs will not be available. This decision is due to a high volume of reservations during these peak months, which unfortunately limits our ability to accommodate flexible check-in and check-out requests. We appreciate your understanding and encourage you to plan your arrival and departure times accordingly. Thank you for your cooperation!

Bed

Bath

Sleeps

$575.02

/ Nightly

Private Vacation Home

Gertrude's Siesta | Pool, Jacuzzi! 1-minute to Beach! 4-min Dining & Music!

Siesta Key, Florida, United States

Kaia's Sara SeabrNewly remodeled with pool and jacuzzi, just 1-minute walk to Siesta Key beach! Poolside lounging and grilling, sunsets, sandbars, and on reef snorkeling and paddling. Just 4-min walk to shopping dining bars and live music. Book your getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta brbrWhat Guests Lovebr∙ Front Porch – southwesterly porch on the palms (shared)br∙ Beaches – 1-min walk to award winning beaches, white sand, calm waterbr∙ Relaxing – private balcony and patio with dining and loungingbr∙ Pool – beautiful heated pool with tropical plants just 1-minute walkbr∙ Reef Snorkeling – 70-yard walk to Point of Rocksbr∙ The Food –12 restaurants within 0.5 miles, 3 waterfront restaurants within 4 milesbr∙ Activities – Boat bike jet-ski & sport-fishing tours, marina and rentals 7-min awaybr∙ Sunsets –1-minute walk to best sunsets and whatever comes nextbr∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories – access Siesta Key's top attractions and beaches guaranteed fun for allbrbrThe BeachbrAccess to two private Siesta Key beaches. With no public parking nearby, this cove is one of Siesta's more exclusive beaches. The white quartz sand, tide pools, and calm, clear water are perfect for relaxing. A livelier scene with food, drinks, and the weekend drum circle is just a short beach walk north. Point of Rocks reef is only 60 yards south.brbrThe LocationbrNo car needed. Nestled on a quiet street with no traffic, businesses, or public parking. Walk 4-minutes two 12 bars and restaurants. Walk 7-minutes to Siesta's top eco-adventures boat, bike, jet-ski, and fishing tours. Prefer to relax Sunbathe at the beach, nap by the pool or enjoy Siesta s top-rated seafood, ice cream, and waterfront dining. Just a short stroll to favorites like Daiquiri Deck, Sniki-Tiki, Crescent Club, and Orange Octopus.brbrReef SnorkelingbrSiesta Key is already paradise now add one of the Gulf Coasts best snorkeling spots! Just 60 yards south, Point of Rocks offers safe, shallow waters filled with tide pools, colorful marine life, and shelling treasures. Most days you'll spot chameleons, sponges, mother-of-pearl shells, conch, and maybe even dolphins or turtles. Ideal for exploring by foot, snorkel, paddleboard, or kayak.brbrProperty TruthsbrTrying to find a storage solution, but cannot currently provide beach chairs or beach umbrellas at this location.brbrBedroom DetailsbrThis unit is two flights up with no one above it. There is a king bedroom, a bunkroom with full over full bunk, and a sofa. You can sleep up to 7 family style. Need more space We can get you an additional unit nearby.brbrBeach Items ProvidedbrWe provide beach towels. 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. 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.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.

Bed

Bath

Sleeps

$814.4

/ Nightly

Private Vacation Home

Siesta Vista, Spacious Waterfront Home. One Block to Beach & Village. Roof Deck!

Siesta Key, Florida, United States

Welcome to 455 Canal, a refined waterfront retreat in one of Siesta Key’s most coveted locations. Set along the tranquil Grand Canal and just a two-minute walk from the sugar-white sands of Siesta Key Beach, consistently ranked among the best in the U.S., this townhome offers the perfect blend of privacy, walkability, and coastal elegance.brbrThe sun-filled open-concept main level features a spacious living area, eat-in kitchen with breakfast bar, and dining space, all opening to front and rear balconies ideal for morning coffee or evening cocktails. A second living area on the ground floor opens directly to the pool, creating seamless indoor-outdoor living.brbrThe home sleeps 8 people across three bedrooms plus a loft. The primary suite offers a king bed, ensuite bath, and private balcony overlooking the pool and canal. Two additional bedrooms feature a queen bed and two full beds, each with ensuite baths. The loft on the fourth floor has twin beds and a low ceiling, making it perfect for children. brbrOutdoor living shines with a private heated pool, outdoor dining area, outdoor shower, private dock for fishing or spotting manatees, and a rooftop deck with sweeping Gulf views and stunning sunsets. With central air, elevator, garage parking, beach gear, and thoughtful amenities across four levels, comfort is effortless.brbrJust steps from Siesta Key Village’s shops, dining, and cafés, 455 Canal is more than a stay, it’s your private slice of island paradise.

Bed

Bath

Sleeps

$299.6

/ Nightly

Private Vacation Home

Our House at the Beach C-122 Salty Soul- Renovated!

Siesta Key, Florida, United States

Lake house offers a generous bi-level layout that includes separate dining and living rooms spaces. The eat-in kitchen is fully stocked with pots, pans, dishware, flatware, and has full-sized appliances, including a dishwasher, microwave and washer and dryer for your convenience. Off the large living room there is a balcony overlooking the grounds. The master bedroom suite also opens onto a balcony and has an en-suite bathroom with closets and dressing area. The second bedroom has an adjacent full second bathroom. Lake House offers central A/C, ample closets and storage space, high-speed Internet, telephone, cable TV in the living room and each bedroom, and garage parking for one car. The development includes a private pool, covered pavilion area with a BBQ, a picnic area and tennis courts. This Lake House unit is right across the street from Siesta KeyÃ‚Â¹s public beach, making a splash in the ocean or just a walk on the sugar sand beach a just a few steps away.

Bed

Bath

Sleeps

$2479.18

/ Nightly

Private Vacation Home

Steps to Beach/Siesta Village-Resort Pool w/Slide

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:brbrFor the home, let’s start with the outdoor covered patios, balconies, pool area, and entertainment spaces. The saltwater pool is a true resort style pool, with a waterslide, beach entry, sun shelf with loungers, and heated spa. The pool patio is mostly a covered space, with a sunken outdoor living room with (80’ + TV), bar area with 2 (65’ TV’s), pool and ping pong tables, outdoor connect 4 and outdoor grill (natural gas). These spaces are all within the fenced in back yard for privacy and security making it family friendly and perfect for the home’s pet friendly policy (fees and restrictions apply). The fun with these exterior spaces doesn’t end on the ground level though. As you go up, you’ll find multiple balconies with seating and amazing views on all levels, ending at the roof top deck that features wide open Gulf of Mexico, Siesta Key Beach, and City views. brbr brbrOnce inside this approximately 4,000 square foot home, you will immediately notice the elevator with service to all floors, as well as the vaulted ceilings, beautiful carpentry and interior design, the quality craftsmanship and spacious feel throughout. This home has 7 bedrooms (all with en suite baths), 7 full baths and 1 half bath. There are a total of 6 king beds, and 2 sets of full over full bunk beds that comfortably sleep 18 people in beds. The great room is set up as the perfect gathering space as it includes the kitchen, living, and dining areas of the home. The kitchen is a fully stocked kitchen, and we mean that because we know how important it is to you, our valued guests! Not only is it stocked, but it’s stocked with the products and manufacturers you trust. There are 2 balconies off this great room space. Additionally, this home features a media center or secondary living space. The media center features a wet bar, living area and media centre (80”+ Smart TV w/ Surround Sound), and access to a balcony and the rooftop deck. brbr brbrFloor Plan Description (by level): brbr brbrGround Level: brbrThis home provides free parking on the ground level via covered parking for 2 vehicles, with the driveway accommodating another 2 vehicles depending on size. 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. The pool, as previously described, is incredible! The covered patio nearby includes a sunken living area with TV and ample seating, bar area with seating for 12, beverage refrigerator, ice maker, TV, and outdoor grill (natural gas). There are ceiling fans throughout this space, and a ping pong and a pool table for added fun. The home’s beach equipment is stored in the pool patio too, which includes 2 beach wagons, 2 coolers, 6 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 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 above from this covered patio space. brbr brbrThe First Level of Living (2nd Floor): brbrThis level has a great room with the fully stocked kitchen with full sized pantry, range with cooktop and oven, full sized refrigerator (with ice maker) and freezer, 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 features a smart TV with streaming services and ample seating. The dining area here seats 15 persons comfortably, with 10 persons at the dining table and 5 additional seats available at the kitchen island bar top. There are also 2 balconies on this level. The front balcony has tables and chairs, and peaking Gulf views down Columbus Drive. The rear balcony overlooks the pool, and it features outdoor seating and lounging space. There are 3 bedrooms on this floor including the master bedroom. The master features a king bed with 'his and her' walk-in closets, and an oversized en-suite bathroom with double vanities, a large 'wet room' with oversized shower and soaker tub, and a private water closet. Bedrooms 2 and 3 are also on this level, each featuring king beds, smart TVs, and en Suite bathrooms with walk-in showers. The laundry room with 2 stackable washer/dryer units is also located on this level. brbr brbrThe Second Level of Living (3rd Floor): brbrThis level’s main space is the media center. It features a wet bar with beverage fridge and bar top seating for 8 people, and a living area with large smart TV, Nintendo Switch 2 gaming console, and balcony access with views of the city, Siesta Key Beach, and the Gulf of Mexico. This balcony provides stair access to the rooftop deck. There are also 4 bedrooms on this floor; bedrooms 4, 5 and 6 feature king beds, smart TVs with en suite baths, and walk-in showers. The final bedroom, bedroom 7, is the bunk room with 2 full over full bunk beds and an en suite bath with a shower/tub combo that is shared with the media center. brbrbrbrThe Rooftop Deck:brbrFeatures views, views, and more views. This tasteful space provides comfortable seating, perfect for enjoying sunrise over the Siesta Key Village, 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 perch overlooking all of Siesta Key.brbrbrbrGetting Around:brbrIf 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 (excluding rooftop deck), 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

Bed

Bath

Sleeps

$617.02

/ Nightly

Private Vacation Home

Elegantly decorated home located on a quiet cul-de-sac w/200 feet of waterfront.

Siesta Key, Florida, United States

The Waterside home is elegantly decorated and located on a quiet cul-de-sac boasting 200 feet of waterfront. It has a large landscaped fenced yard, pool & lanai, canal views, and large lighted boat dock for your use. The spacious master suite is located on the opposite side of the house, with an amazing closet and water views. You will enjoy water views and wood floors throughout the home. A stylish chef’s kitchen with bar seating is the center of the home. The dining room will be home to all the great meals, laughs, and memories you will make.brbrClose to the world-famous No. 1-rated Siesta Key Beach, Siesta Key Village, Morton’s Market, Beach Road, easy access on and off the key because of proximity to the North bridge, multiple beach accesses, short boat ride to Sarasota bay, fabulous dining on and off the key, and it is just a short drive to downtown Sarasota for more dining, theatre, the arts, St. Armands Circle, and so much more. Just bring your flip flops & sunscreen and get ready for a vacation of a lifetime!

Bed

Bath

Sleeps

$2445.5

/ Nightly

Private Vacation Home

Siesta Key Luxe w/ Pool, Rooftop & Steps to Beach

Siesta Key, Florida, United States

Wake up to sun-soaked island days and effortless coastal luxury at Siesta Palooza, a stunning eight-bedroom retreat designed for unforgettable Siesta Key getaways. Just a short stroll from the beach, this upscale home blends resort-style amenities with relaxed island living, giving your group space to connect, unwind, and celebrate every moment together.brbrThe backyard sets the tone for vacation mode. Spend your days floating in the sparkling private pool, easing into the in-ground spa, or gathering under the covered patio with plush seating, a dining table, and grill for long, laughter-filled evenings. A dedicated game room with a TV and ping pong table adds playful energy, while the rooftop deck invites you to soak up the sun, savor the breeze, and enjoy elevated views of your surroundings.brbrInside, the home feels bright, welcoming, and thoughtfully designed for both comfort and togetherness. The main living area offers coastal-inspired seating and a large TV, perfect for movie nights or relaxed afternoons. The fully equipped kitchen is a dream for home chefs, featuring high-end appliances, generous counter space, and a large island with seating that naturally brings everyone together. Adjacent modern dining areas flow seamlessly to the deck, making shared meals and celebrations feel effortless.brbrWith eight beautifully styled bedrooms, everyone has their own retreat at the end of the day. Five king suites, including a spacious primary suite, offer comfort and privacy, while a queen room and two bunk rooms make this home ideal for families and groups of all ages. Each bedroom includes a TV, dresser space, and either an ensuite bathroom or convenient access to one. Multiple sleeper sofas add flexibility, and a washer and dryer ensure your stay stays easy and carefree.brbrUpstairs, a fourth-floor hangout space with video games and a large convertible sofa creates the perfect spot for teens, kids, or late-night lounging. Whether your group wants to spread out or come together, Siesta Palooza adapts effortlessly to your pace.brbrThe location ties it all together. Walk to nearby grocery stores, restaurants, shops, and lively nightlife, or head to the world-famous Siesta Key Beach just minutes away by foot or bike. From sunrise beach walks to sunset swims and evenings under the stars, every part of your stay feels close, convenient, and completely indulgent.brbrSiesta Palooza is more than a place to stay; it’s where beach days turn into poolside nights and memories are made without effort. Book your stay and experience Siesta Key the way it was meant to be enjoyed.brbrEnjoy your beach days with ease. We supply beach towels, beach chairs, and a wagon to make your trips to the shore effortless.brbrPool Heating DisclaimerbrbrPlease note that pool heaters are weather-dependent. When outdoor air temperatures drop below 55°F, electric pool heaters will not operate, and pool water will remain cold. Even when temperatures rise slightly above 55°F but stay in the low 60s, the heater may produce minimal heat and may not significantly warm the pool.brbrThe only way to guarantee a consistently warm pool during colder months is with a gas pool heater, which can operate in very low temperatures but requires substantial gas usage to maintain warmth.brbrBy booking during cooler months, guests acknowledge that pool temperature and heater performance are directly affected by weather conditions, which are beyond the control of the property owner or management. We strongly recommend reviewing and acknowledging this information prior to booking to ensure clear expectations regarding pool heating during your stay.brbrImportant Note:brWhen you stay at our vacation rental homes, we want to ensure your experience is comfortable and convenient right from the start. Each home comes with a thoughtfully prepared starter pack to help you settle in seamlessly. This pack includes:brbr- *Laundry Detergent*: Enough for your initial laundry needs.br- *Dish Soap*: For easy clean-up after meals.br- *Dish Sponge*: Essential for washing dishes.br- *Dishwasher Pods*: A few pods to kickstart your dishwashing.br- *Toilet Paper*: Two rolls per bathroom to get you started.br- *Paper Towels*: One roll for quick clean-ups.br- *Extra Trash Bags*: To accommodate your waste disposal needs.brbrPlease note that we do not provide used kitchen items like oil, spices, or butter, ensuring a fresh start for your cooking adventures. Additionally, all homes are equipped with drip coffee makers, but remember to bring your own coffee filters to enjoy your morning brew.brbrWith these amenities, you can focus on enjoying your vacation without the worry of running out of essential supplies.brbrEarly Check In & Late Check Out:brFrom February through August, we regret to inform our guests that early check-ins and late check-outs will not be available. This decision is due to a high volume of reservations during these peak months, which unfortunately limits our ability to accommodate flexible check-in and check-out requests. We appreciate your understanding and encourage you to plan your arrival and departure times accordingly. Thank you for your cooperation!

8

Bed

8

Bath

25

Sleeps

$2558.46

/ Nightly

Private Vacation Home

Luxury House w/ Heated Pool & Spa, Walk to Beach

Siesta Key, Florida, United States

Step into effortless island living at Point Break, a refined eight-bedroom coastal retreat where location, comfort, and resort-style design come together just moments from Siesta Key Beach and the heart of Siesta Key Village. Designed for memorable group getaways, this home places you steps from sugar-white sand, vibrant dining, and laid-back nightlife, while offering a private oasis to return to at the end of each perfect day.brbrThe backyard is your personal resort. Start mornings lounging on the sun shelf of the sparkling pool, spend afternoons floating beneath blue skies, and wind down in the in-ground spa as the evening air cools. A spacious covered patio creates an inviting setting for shared meals, casual conversation, and relaxed poolside lounging, while the adjacent game room adds energy with ping pong and foosball for friendly competition between swims.brbrInside, the main living floor is bright, social, and beautifully appointed. A vibrant, chef-inspired kitchen anchors the space with high-end appliances, abundant cookware, and a sweeping island that naturally draws everyone together. A wet bar nearby makes entertaining easy, whether you are mixing drinks for dinner or toasting the sunset. The indoor dining area offers stylish seating for group meals, while the outdoor balcony dining table extends the experience into the open air. After beach days, settle into the comfortable living room, then head upstairs to the rooftop deck to take in glowing sunsets and the gentle sounds of the island.brbrEach bedroom is thoughtfully designed to feel like a private retreat. The primary suite offers coastal charm, balcony access, and a spa-like ensuite bathroom, creating a peaceful escape. Five king guest rooms feature tropical touches, premium mattresses, and a mix of private balconies and well-appointed bathrooms, giving every adult guest space to relax in comfort. Two bunk rooms are perfect for kids or teens, offering a fun, shared layout with balcony access and a connecting bathroom. A fourth-floor bonus room with a sleeper sofa and gaming setup provides an ideal hangout space between beach adventures.brbrThe home’s layout balances togetherness with privacy, making it easy for large groups to gather while still enjoying personal downtime. An elevator adds convenience, and thoughtful details throughout ensure your stay feels seamless from arrival to departure.brbrLocation is one of Point Break’s greatest luxuries. Walk to coffee shops, grocery stores, boutiques, restaurants, and live music venues, or take a short stroll to the world-famous shoreline of Siesta Key Beach. Whether your days are filled with sun, sand, and surf or leisurely exploring the village, everything you want is right outside your door.brbrPoint Break offers the freedom to experience Siesta Key at its best, blending vibrant island energy with the comfort of a private luxury home. Reserve your stay and let your next unforgettable beach escape begin here.brbrEnjoy your beach days with ease. We supply beach towels, beach chairs, and a wagon to make your trips to the shore effortless.brbrPool Heating DisclaimerbrbrPlease note that pool heaters are weather-dependent. When outdoor air temperatures drop below 55°F, electric pool heaters will not operate, and pool water will remain cold. Even when temperatures rise slightly above 55°F but stay in the low 60s, the heater may produce minimal heat and may not significantly warm the pool.brbrThe only way to guarantee a consistently warm pool during colder months is with a gas pool heater, which can operate in very low temperatures but requires substantial gas usage to maintain warmth.brbrBy booking during cooler months, guests acknowledge that pool temperature and heater performance are directly affected by weather conditions, which are beyond the control of the property owner or management. We strongly recommend reviewing and acknowledging this information prior to booking to ensure clear expectations regarding pool heating during your stay.brbrImportant Note:brWhen you stay at our vacation rental homes, we want to ensure your experience is comfortable and convenient right from the start. Each home comes with a thoughtfully prepared starter pack to help you settle in seamlessly. This pack includes:brbr- *Laundry Detergent*: Enough for your initial laundry needs.br- *Dish Soap*: For easy clean-up after meals.br- *Dish Sponge*: Essential for washing dishes.br- *Dishwasher Pods*: A few pods to kickstart your dishwashing.br- *Toilet Paper*: Two rolls per bathroom to get you started.br- *Paper Towels*: One roll for quick clean-ups.br- *Extra Trash Bags*: To accommodate your waste disposal needs.brbrPlease note that we do not provide used kitchen items like oil, spices, or butter, ensuring a fresh start for your cooking adventures. Additionally, all homes are equipped with drip coffee makers, but remember to bring your own coffee filters to enjoy your morning brew.brbrWith these amenities, you can focus on enjoying your vacation without the worry of running out of essential supplies.brbrEarly Check In & Late Check Out:brFrom February through August, we regret to inform our guests that early check-ins and late check-outs will not be available. This decision is due to a high volume of reservations during these peak months, which unfortunately limits our ability to accommodate flexible check-in and check-out requests. We appreciate your understanding and encourage you to plan your arrival and departure times accordingly. Thank you for your cooperation!

Bed

Bath

Sleeps

$245.44

/ Nightly

Private Vacation Home

Suite w/ Shared Pool, Free WiFi, Central AC - Steps to the White Sand Beach

Siesta Key, Florida, United States

Parrot Beach Cottages Suite #4brbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrParrot Beach Cottages on Siesta Key is mere steps - approximately 150 feet - from the beach and the emerald water, situated just behind the waterfront properties and within walking distance of Siesta Key Village. Occupying roughly 275-300 square feet, Suite #4 is small but fully furnished, offering one queen bedroom, a queen-size sleeper sofa, a bathroom, and a compact kitchen that can accommodate up to two adults and two small children.brbrThis suite is located on the second floor at Parrot Beach Cottages, up a flight of approximately 12 steps. It's a small space, so if you're using the sleeper sofa (which has a thin mattress and is really only suitable for small kids), you'll likely want to stow it during the day to maximize the living room. The bathroom, which has pocket doors on either side that make it accessible from both the living room and the bedroom, has a single sink, a toilet, and a shower/tub combination. On the grounds of the property, you'll also have access to a small deck that's shared with another suite, an outdoor pool downstairs, and one reserved, off-street parking space to make your stay all the more convenient.brbrParrot Beach Cottages is a two-story building that sits 150 feet from Siesta Key Public Beach Access 2, providing you with unbeatable access to one of the top white sand beaches in the world. This area of the beach is a favorite for sunbathing, swimming, romantic sunset walks, small beach weddings, skim boarding, paddleboarding, kayaking, shore fishing, and much more. Fishermen catch everything from snapper and mackerel to snook and jacks. You'll be within walking distance of a number of businesses that rent all sorts of gear, from kayaks and paddleboards to bikes and video game systems. Due to how close the complex is to the beach, several rental outfitters will bring kayaks, paddleboards, and bikes right to the property and pick them up when you're done!brbrThe suite is also within easy walking distance of Siesta Key Village, where you'll find shops, restaurants, live music, and more. Or, head into town for other local adventures, including the world-renowned Ringling Museum, the Marie Selby Botanical Gardens, Mote Marine, Jungle Gardens, and outdoor shopping and dining on St. Armands Circle.brbrThings to know:brThere are three other suites available to rent at the Parrot Beach Cottages fourplex - Suite #1, Suite #2, and Suite #3brFree high-speed WiFibrSmoke-free propertybrSmall kitchen (without a dishwasher)brBedroom is small with only a few feet on each side of the bed; no TV in the bedroombrThe suite has limited storage (one small closet)brThe shower features grab barsbrSnowbird-friendlybrPlease note that the shared pool is small, about 15 feet by 10 feet and about four to six feet deepbrThe overall property is very small, so there is no extra vehicle or visitor parking. There's also no nearby on-street parking. Guests love the location (truly walking distance to the beach and the village) and the more private feel of the beach, since this is a dead-end road and there is no nearby public parkingbrThere is a new home being built on the lot next door. Construction work is permitted by Sarasota County daily from 7:00am to 7:00pm.brbrParking notes: There is free parking available for 1 vehicle.brThis rental is located on floor 2.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Bed

Bath

Sleeps

$726.43

/ Nightly

Private Vacation Home

Paradise Retreat

Siesta Key, Florida, United States

This stunning property offers a waterfront oasis, a short stroll away from the village. With 3 bedrooms and 3 full bathrooms, including 2 master suites and a private deck, this home is designed for ultimate comfort and relaxation. The split plan layout provides guests with their own separate areas to unwind. You'll love the impressive patio area, which leads to an oversized saltwater pool surrounded by Travertine pavers - perfect for soaking up the sun and enjoying a peaceful afternoon.

Bed

Bath

Sleeps

$1341.28

/ Nightly

Private Vacation Home

Toes In The Sand | Cottage with Private Pool, Walk to SK Beach and Village ️

Siesta Key, Florida, United States

Toes In The Sand | Charming Siesta Key Cottage, Heated Pool, 1-Min Walk to Beach & Village Vibesbrbr Why You'll Love This HomebrThis vintage-inspired Siesta Key cottage puts you just 1 minute from the famous white sands of Siesta Beach. With a private heated pool, charming interiors, and walkable access to both the beach and Siesta Village, Toes In The Sand offers the best of Florida's coast wrapped in old-Florida charm.brbr ‍ ‍ Perfect ForbrCouples, small families, and laid-back beach lovers seeking a private retreat just steps from the shore and Siesta Key's vibrant village life.brbr ️ Imagine ThisbrYou wake up to the sound of swaying palms and distant waves. Slip on your flip flops, grab the beach caddy, and in under 60 seconds you're sinking your feet into Siesta Key's award-winning powder-white sand. After sun-filled adventures, return home to cool off in your private pool, pour a chilled drink, and settle into the Florida room as golden hour lights up the palms. At sunset, stroll to the Village for live music, fresh seafood, and tropical cocktails—all without needing a car. This is beach life, simplified and elevated.brbr Where You'll Sleepbr• Bedroom 1: Queen Bed, Ensuite Bath, TVbr• Bedroom 2: Queen Bed, Hall Bath, TVbr• Florida Room: Full Futonbrbr Explore the Areabr• 0.1 Miles (1-Minute Walk) to Siesta Key Beach Main Entrancebr• 0.3 Miles to Siesta Key Village: Restaurants, Bars, Shops & Ice Creambr• Walk to Siesta Key Village for Live Music, Waterfront Dining & Nightlifebr• Surrounded by a Bike-friendly, Pedestrian-friendly Coastal Communitybrbr⌛ Don't wait—homes this close to the beach book quickly. Your stay includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point post-stay inspection. Reserve your beach escape today and arrive at a home that feels brand new.brbr Need to Know: This pool is heated from November 15th to April 15th.

Bed

Bath

Sleeps

$783.42

/ Nightly

Private Vacation Home

Last Minute Luxury Beachside Home 100 ft Walk to Siesta Key Beach Pool

Siesta Key, Florida, United States

Spacious Mediterranean-style vacation home, approx. 100 ft walk to the beach, located just across the street.brFrom the driveway, it’s an approx. 100-foot walk with a single street crossing to reach the world-famous white sands of Siesta Key Beach.brQuick and easy beach access with no parking hassles and no long walks.brEasy, Car-Free VacationbrThis area is highly walkable:brBeach access: about 100 ft walk + one street crossingbrCoffee shops and cold drinks within walking distancebrRestaurants, bars, and shops nearbybrFree island trolley / local shuttle service (free to ride, tipping customary)brA car is not required, but a private garage and additional parking are available.brHome Featuresbr• 3 bedrooms / 3 bathroomsbr• Sleeps up to 8 guestsbr• 2,056 sq ft of spacious living areabr• Poolbr• Private garagebr• Balconybr• Central air conditioning & high-speed Wi-Fibr• Smart TVs with streaming servicesbr• Fully equipped kitchenbr• Washer & dryerbrSleeping Arrangementsbr• Primary bedroom: King bed, en-suite bathroom, balconybr• Guest bedroom 1: King bed, en-suite bathroombr• Guest bedroom 2: King bedbr• Common area: Two twin bedsbrA spacious, well-located beachside vacation home offering a short walk to the beach across the street and a relaxed Siesta Key lifestyle.brImportant Note This is a private unit within a multi-unit property. Each unit has its own private entrance and is designed to ensure comfort and privacy for all guests.br--brThank you.brBalazs Szabobrcell:941-350-8281brbr

Bed

Bath

Sleeps

$860.69

/ Nightly

Private Vacation Home

Last Minute Availability Siesta Key Dream 100 ft to Beach Walk Everywhere

Siesta Key, Florida, United States

brJust steps from Siesta Key Beach, enjoy a spacious Mediterranean-style getaway with easy beach access right across the street.brWalk about 100 feet from your driveway, cross one small street, and you’re on the world-famous white sands. Quick and easy beach access with no parking hassles and no long walks.brEasy, Car-Free VacationbrThis area is highly walkable:brBeach access: about a 100 ft walk + one street crossingbrCoffee shops and cold drinks within walking distancebrRestaurants, bars, and shops nearbybrFree island trolley / local shuttle service (free to ride, tipping customary)brA car is not required, but a private garage and additional parking are available.brHome Featuresbr• 3 bedrooms / 3 bathroomsbr• Sleeps up to 8 guestsbr• 2,056 sq ft of spacious living areabr• Poolbr• Private garagebr• Balconybr• Central air conditioning & high-speed Wi-Fibr• Smart TVs with streaming servicesbr• Fully equipped kitchenbr• Washer & dryerbrSleeping Arrangementsbr• Primary bedroom: King bed, en-suite bathroom, balconybr• Guest bedroom 1: King bed, en-suite bathroombr• Guest bedroom 2: King bedbr• Common area: Two twin bedsbrA spacious, well-located beachside vacation home offering a short walk to the beach and a relaxed Siesta Key lifestyle.brImportant NotebrThis is a private unit with its own separate entrance. The property includes another unit, but each space is fully independent to ensure comfort and privacy for all guests.brbrcell:941-350-8281brbr

Bed

Bath

Sleeps

$1192.01

/ Nightly

Private Vacation Home

Latitude Adjustment | Waterfront Home w/ Private Heated Pool! Walk to Siesta Village & Beach!

Siesta Key, Florida, United States

Latitude Adjustment | Private Heated Pool + Walk to Siesta Key Beachbrbr Why You'll Love This Homebr Step into Latitude Adjustment, a luxurious waterfront villa on Siesta Key's serene canals. With sun-drenched balconies, a private heated pool, and direct canal access, this home balances elegant design with effortless coastal living for families and friends alike.brbr ‍ ‍ Perfect Forbr Ideal for large families, groups of friends, or multi-generational gatherings seeking space, comfort, and a prime waterfront location.brbr ️ Imagine Thisbr Wake to the gentle lapping of canal waters and enjoy your morning coffee on one of two balconies overlooking the serene waterfront. Spend your days kayaking from your private dock, sunbathing by the heated pool, or strolling just 2 minutes to Siesta Key Beach. Evenings are for alfresco dining, sunset cocktails, or stargazing in your secluded backyard oasis. Every moment invites relaxation, connection, and fun.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Shared Bath, Ground Floor, TVbr• Bedroom 2: Queen Bed, Shared Bath, Main Floor, TVbr• Bedroom 3: King Bed, Ensuite Bath, Upper Floor, TV br• Bedroom 4: Two Full Beds, Ensuite Bath, Upper Floor, TVbrbr Explore the Areabr• Private canal access for kayaking and fishingbr• 0.1 miles to Siesta Key Beach – pristine white sands and turquoise waters (2-minute walk)br• 8-minute drive to Siesta Key Village – vibrant shops, restaurants, and entertainmentbr• Nearby local parks, boutiques, and waterfront dining within a short strollbr• Coastal energy and serene island vibe make every outing memorablebrbr⌛ Reserve With Confidence - Your stay includes our CottageClean™ program: 6-hour deep clean plus a 35-point inspection, ensuring a pristine, worry-free vacation.brbr Need to Know: This home is part of a duplex and may share a wall, floor, ceiling, or outdoor space with another unit. Your rental includes access to the private backyard and right side of the building. Pool heated from November 15 – April 15. This home has stairs. If any guest has difficulty, contact us for alternative accommodations.

4

Bed

3

Bath

10

Sleeps

$1098.49

/ Nightly

Private Vacation Home

King beds-NO Bunks, Roku TV in bedrooms, Private Beach Access & Pool

Siesta Key, Florida, United States

Just a 5-minute walk to #1 beach in America!br-Heated pool*, Floats, Sun loungersbr-Equipped kitchen, drip & Keurig coffee makers, BBQ grillbr-King & queen size beds, NO BUNKS!!br-Garage parking, Close to trolley stopbr-Avoid crowded public beach with private access, beach wagon, chairs, umbrellas, & towels for guest usebrbrPLEASE READ LISTING THOROUGHLY TO ENSURE YOU HAVE ALL THE IMPORTATNT DETAILS!brbrDINING:br- Indoor dining table seating for 8br- Granite kitchen island seating for 3br- Upstairs on balcony outdoor table seating for 6br- Downstairs in pool area outdoor table seating for 6brbrLIVING ROOM:br- 75 Smart TV with Roku (for guests' protection)br- Access to huge balconybr- Board gamesbrbrBEDROOM 1br-King size bedbr- Ensuite Bath: walk in shower, dual vanities, soaking tubbr- Smart Roku TVbrbrBEDROOM 2br- King size bedbr- Ensuite Bath: walk in shower, single vanitybr- Blackout curtainsbr- Smart Roku TVbrbrBEDROOM 3br- King size bedbr- Ensuite Bath: walk in shower, single vanitybr- Blackout curtainsbr- Smart Roku TVbrbrBEDROOM 4br- Queen size bedbr- DeskbrbrBEDROOM 5 (downstairs suite)br- Queen size bedbr- Queen size sofa sleeper (made upon request)br- Ensuite bath: walk in shower, single vanitybr- Walk in closetbr- TV with Rokubr- Kitchenette: refrigerator, microwave, & sinkbr- Sliding glass doors to access pool areabrbrAVAILABLE UPON REQUEST:br- Twin rollaway bedbr- Pack N Playbr- HighchairbrbrStep into a world of luxury living at our 3,000+ square feet home. Everyone will have ample space to unwind; plus enjoy all the amenities you'll need to have a relaxing & memorable stay. brbrThis spacious 5-bedroom, 4.5-bath home offers accommodations for up to 10 guests comfortably. It is a two-level retreat that features an elevator for easy access between your two levels, making it the perfect choice for travelers of all ages & abilities.brbrOnly minutes away from incredible downtown Sarasota & St. Armand's Square!! brAnd is centrally located on Siesta Key Island with the Publix grocery store, Siesta Key Village, & 7-Eleven less than 2 miles from the property.brbrIMPORTANT HOUSE INFO & RULESbrbr** NO PARTIES OR LARGE GATHERINGS: Any parties, events, or gatherings that EXCEED the number of guests on the reservation are STRICTLY PROHIBITED! Violations will result in an immediate $1,000 fee & possible removal from the property without refund. brbr** NO THIRD-PARTY RESERVATIONS: Person making the reservation MUST be present during the stay. We do not allow making a reservation on behalf of a friend, family member or co-worker. Please have the person who is staying book themselves. brbr**OCCUPANCY: Only the number of guests listed in your reservation are allowed on the property at any time. Unauthorized guests may result in additional charges & cancellation of your reservation. brbr** NO SMOKING: There is NO SMOKING (this includes cigarettes, cigars, vaping & any controlled substances (including marijuana) INSIDE & OUTSIDE on the property. Any evidence of smoking on the property, a minimum $500 fee will be charged.brbr** PET POLICY: This home is NOT pet friendly. We make no exception to the rule no matter the size, type or behavior of animal.brbr** PARKING (FOUR CAR MAX): Two midsize vehicles or smaller can park in the (empty) garage, with two additional parking spots on side of house to accommodate 2 midsize vehiclesbrNOTE: Vehicles that are larger than midsize, please contact to discuss parking options.brbr** QUIET HOURS: Please respect our neighbors by observing quiet hours from 10:00 PM to 8:00 AM. All of our communities have noise ordinances requiring guests to keep noise to a minimum, specifically after 10 PM and before 8 AM. Law enforcement officials may be summoned to the property if you are deemed to be in violation of these ordinances. You may also be subject to a fine.brbr** EARLY LUGGAGE DROP OFF: Our team needs this time to prepare the home uninterrupted. Upon booking, we can offer recommendations to where to leave your luggage while you wait, should you have an early flight.brbr** POOL HEATING: The pool is heated from October through February ONLY.brbr**We STRONGLY RECOMMEND purchasing travel insurance AHEAD of your stay.**brbrbrThis property is the entire 2nd floor & half of the ground floor. brbrThere are 3 exterior security cameras that record when someone enters the property from the driveaway & side of the home that runs along the street. Used to primarily protect the property, & to monitor weather situations.brbrView a video tour of the property here for more details: https://youtu.be/pibCeOe3lSA

5

Bed

4

Bath

10

Sleeps

$377.75

/ Nightly

Private Vacation Home

Modern home near the beach with heated pool.

Siesta Key, Florida, United States

Relax with the whole family at this peaceful place to stay. The 3 bedroom and 2 bath home located only 5 min drive or 15 min walk to Sista Key Beach. Siesta Key village just 3 minutes by car where you can shop and dine through a variety of restaurants and stores.br The master bedroom has king sized bed, double closets and an en-suite bathroom with a walk in shower. The second guest bedroom has a queen sized bed and the third guest bedroom has two twin beds. The guest bathroom has a stall shower. The cleaning fees $350

Bed

Bath

Sleeps

$3035.66

/ Nightly

Private Vacation Home

Luxury Villa*Pool*Hot Tub*Dolphins*Close to Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$1456.39

/ Nightly

Private Vacation Home

Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!

Siesta Key, Florida, United States

Las VentanasbrResort-like setting with semi-private pool, rooftop deck, in-house elevator, and 5 terraces in heart of Siesta Village! Just 1-minute walk to Siesta's best Beach and the shopping dining and entertainment of the village! Spacious, bright, airy, and surrounded by palms. Experience Siesta Key's top attractions without sacrificing space and comfort. Book a getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiestabrbrWhat Guests Lovebr∙ Terraces and Rooftop –beautiful views from five balconies and rooftop terracebr∙ Semi-private Pool – heated pool and sun shelves shared with just one other unitbr∙ The Beaches – 1-minute to Siesta Key's top beaches with white sand and calm clear waterbr∙ Restaurants – 1-minute walk to the shopping dining and entertainment of the Siesta Villagebr∙ Gulf Breezes –Ventanas means “Windows” and 3000 ft.² of windows catch sea breezes day and nightbr∙ Relaxing – 5 baths and a balcony off every bedroombr∙ Sunsets –walk 1-minute to best sunsets or just enjoy from your rooftop deckbr∙ Activities – a few free bikes and paddleboards provided, but scooter and golf cart rentals nearby br∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories – walk to all Siesta Key's 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 LocationbrYou aren't planning one vacation, you're planning vacations for every individual in your party. Whether it's solitude or activities, this property will deliver what they need. It's just steps to the top attractions on the island including 4 beach accesses, and 20 bars and restaurants. Walk right 450ft to the best beaches in America or left 450ft to the world-famous shopping dining and entertainment of the Siesta Key Village. This area has - ice-cream, tide pools, daiquiris, dolphins, fresh oysters, white-quartz-sand, big breakfast, sunsets, amazing seafood, white lagoons, craft beer, sand dollars, live music, shopping, and gourmet donuts. Back at the house, you'll enjoy a semi private pool (shared with just one other unit), as well as private features including - four private gathering areas for your bonding enjoyment including a poolside swim-out room with wet bar, and a rooftop sundeck with ocean views and wet bar. When you'd prefer to relax, you'll find lots of bright and airy out the way rooms and terraces for quiet decompressing.brbrBedroom DetailsbrThis is a huge 4BR, you can sleep up to 13 family style. The master suite (large) has two queen beds with bath en-suite, a twin bed in the alcove and a large terrace. Bedroom #2 has a king bed and terrace. Bedroom #3 has a queen bed with bath en-suite and a terrace. Bedroom #4 is a swimout apt with a queen bed, living room, TV, full bath en suite, and private lanai poolside.brbrBeach Gear ProvidedbrWe provide beach towels, chairs, carts, umbrellas, bikes and paddle boards. 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.

Bed

Bath

Sleeps

$387.15

/ Nightly

Private Vacation Home

Gulf Villa | Beachfront Vibes & Dock | Pool | BBQ

Siesta Key, Florida, United States

Welcome to Gulf Villa — your renovated 2‑bedroom waterfront escape on Siesta Key. Enjoy peaceful Grand Canal views from your private porch, then walk just 3 minutes to world‑famous Siesta Key Beach or the Village for dining, shopping, and nightlife. Bright, stylish interiors and unbeatable location make this vacation rental ideal for couples, families, or friends seeking comfort and relaxation.brbr☀ Beach Accessbr☀ Private Dockbr☀ Poolbr☀ BBQ Grillbr☀ Patiobr☀ Pet Friendlybrbr :br : Private outdoor seating overlooking the scenic Grand Canal for morning coffee or evening sunsets.br : A leisurely 3‑minute walk to Siesta Key Beach and steps from Siesta Village shops and restaurants.br : Bright, open‑concept living and dining with modern finishes and comfortable furnishings.br : Two queen beds plus flexible living space—ideal for families or friends.br : Guest‑only heated in‑ground pool, pool deck with loungers, and a gas grill for outdoor meals.br : Private guest‑only boat/fishing dock on the Grand Canal for memorable waterfront moments.br : Beach wagon, chairs, and towels provided so you can head to the sand without the hassle.br : Smart TVs in living room and bedrooms, on‑site laundry, complimentary Wi‑Fi, and off‑street parking.brbrOpen, airy living areas flow into a fully equipped kitchen—perfect for family breakfasts or casual dinners. Two comfortable bedrooms offer restful nights, while the living room and porch expand your space for relaxing and entertaining. Thoughtful touches throughout make Gulf Villa a welcoming base for your Siesta Key getaway.brbr Guests have full access to the villa, the guest‑only heated pool and lounge areas, the private canal dock, and on‑site laundry. We supply beach essentials and parking to keep your stay easy and stress‑free.brbr brSet in the heart of Siesta Key, Gulf Villa places you minutes from powder‑white sand, waterfront dining, and local shops. Walk to the Village for fresh seafood, live music, and island vibes—no long drives required.brbr brbr☀ Waterfront tranquility with direct canal access.br☀ Renovated, comfortable interiors and resort‑style amenities.br☀ Walk everywhere: beach, Village, and local hotspots.br☀ Family‑friendly layout with practical beach gear and parking.brbr to enjoy a perfect blend of comfort, style, and convenience at Gulf Villa.brbr★ :br ☀ Sarasota Beach: 4 min walkbr ☀ Siesta Key Craft Festival: 7 min walkbr ☀ Sunset Beach: 10 min walkbr ☀ Point Of Rocks: 9 min drivebrbr★ :br ☀ Gilligan`s Island Bar & Grill: 5 min walkbr ☀Summer House Resturant: 5 min walkbr ☀ Lobster Pot Restaurant: 6 min walkbrbr★ :br ☀ CVS Pharmacy: 12 min drivebr ☀ Sarasota Memorial Hospital: 14 min drivebrbr★ :br ☀ Beach Rd @ Calle De La Siesta: 3 min walkbr ☀ Ocean Blvd @ Calle Miramar NB: 4 min walkbr ☀ Ocean Blvd @ Canal Rd SB: 6 min walkbrbr★ :br ☀ Sarasota Bradenton International Airport: 26 min drivebrbrb ★☆ Upcoming Events in Siesta Key Beach:/bbr☀ Thunder By The Bay Music & Motors Festival: Feb 13–15, 2026br☀ `Say I Do Again` Vow Renewal Ceremony: Saturday, Feb 14, 2026br☀ Elton John Tribute Concert: Feb 27, 2026br☀ Guns N` Roses Tribute Concert: Feb 28, 2026br☀ Sarasota Jazz Festival: Mar 9–14br☀ Sarasota County Fair: Mar 13–22br☀ Spring Break Season: All Monthbr☀ Siesta Key Drum Circle: March, 2026 Every Sunday in br☀ Siesta Key Farmers Market: March 2026, Every Sunday (9:00 AM – 1:00 PM) br☀ Embracing Our Differences (Outdoor Art Exhibit)—till April 13, 2026

2

Bed

2

Bath

5

Sleeps

Vacation Home Rentals By Owner In Siesta Key, FL

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$860.69

$1192.01

$1098.49

$377.75

$3035.66

$1456.39

$387.15

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