Home 5+ Bedroom Vacation Rentals In Siesta Key, FL

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Exceptional(3)

$1122.48

/ Nightly
Private Vacation Home

Coastal Luxury • Pool • Spa • Fire Pit • Sun Decks • Sunsets • Minutes to Beach

Siesta Key, Florida, United States

Luxury newly renovated custom home which includes all the amenities - Close to Siesta Key Village and all the beaches.br 6 Person Luxury Golf Cart available for rental. Golf cart rental available for extra charge. ( Inquire for quote )brbr Sweetwater RetreatbrA Rare Private Luxury Villa w/ Heated Saltwater Pool, Spa, Waterfall & Expansive Sun Decks | Fully RenovatedbrbrWake up to palm trees swaying and birdsong drifting through the air. Sweetwater Retreat is a newly renovated private luxury villa on Siesta Key, offering a level of space, privacy, and outdoor living that is increasingly rare — just minutes from the #1 beach in America.brDesigned for guests who value seclusion, Sweetwater delivers effortless island living in a setting that feels calm, refined, and entirely your own. Sip coffee at sunrise, enjoy the Florida sun across multiple private decks, float in the heated saltwater pool, unwind in the spa beneath the waterfall, and gather around the fire table as the sky turns gold at sunset. This is island living — elevated.brbr The SpacebrSleeps 12 | 5 Bedrooms | 4.5 Bathrooms 3 King Ensuite Primary Suites 1,000+ Sq Ft of Private Outdoor Living SpacebrbrCompletely reimagined from the inside out, this home blends modern comfort with relaxed coastal luxury — ideal for families, multi-generational trips, couples traveling together, and longer stays.brbr ️ Bedrooms & BathsbrEach bedroom is thoughtfully designed to offer privacy, comfort, and truly restorative sleep.br• Primary Master Suite: King bed, private ensuite bathroom, walk-in shower, soaking tub, dedicated workspacebr• Junior Master Suite: King bed, private ensuite bathroom, walk-in shower, dedicated workspacebr• Guest Suite: King bed with private ensuite bathroom, walk-in shower (brand-new spa-inspired addition)br• Loft Suite: Two full-size bunk beds, full bathroom, and access to a private sky deckbr• Bunk Room: Twin bunk beds — ideal for kids, with a convenient half bath just outside the roombrbrThroughout every bedroom: ✔ Hotel-quality linens, foam pillows & premium mattresses ✔ Blackout shades in bedrooms and attached bathrooms ✔ Smart TVs for personalized streaming br✔ Ceiling FansbrbrQuiet interiors, modern systems, and new windows create a peaceful environment designed for rest.brbr Open-Concept Kitchen & Living SpacesbrA beautifully designed, open-concept space made for connection and entertaining.br• Fully stocked chef’s kitchenbr• Stainless steel appliances with quartz countertops and backsplashbr• Oversized island seating up to 10 comfortablybr• Solid wood dining table seats 8 and extends to accommodate 10–12 guestsbr• Custom quartz bar, expands the kitchen, perfect for cocktails, coffee, or buffet-style gatheringsbr• Clean recessed lighting and soaring ceilingsbr• Extra-large windows filling the home with natural light and lush tropical viewsbr• Sonos sound system, providing seamless music brbr Outdoor Living | Over 1,000 Sq Ft of Private SpacebrThe outdoor experience is where Sweetwater truly shines.br• Heated saltwater pool & jet spa with soothing waterfall featurebr• Outdoor TV for poolside lounging, game days, and relaxed eveningsbr• Ultra-comfortable lounge chairs for all-day poolside relaxationbr• Expansive covered front deck with fire table and plush seating for 11 — ideal for sunset cocktailsbr• Upper sun deck with seating for 8, perfect for lounging, reading, or evening stargazingbr• Soft landscape and deck lighting creating a resort-like evening ambiancebr• Lush tropical landscaping and an 8-foot privacy fence for total seclusionbr• BBQ grill for memorable sunset dinnersbrHomes with this level of private outdoor living are rare on Siesta Key.brbr✨ Elevated Comfort Touches (Included)brThoughtful details throughout the home make your stay effortless and refined:br• Zoned climate control allowing guests to set comfortable temperatures by floor and living area and ceiling fans in every roombr• Dual water heaters providing consistent hot water for long showers and baths, even when multiple bathrooms are in usebr• Layered bedding with additional blankets throughout the homebr• Generous built-in and walk-in closets designed for longer, more comfortable staysbr• Thoughtfully designed lighting with adjustable brightness for relaxed eveningsbr• Plush bath and pool towelsbr• Hotel-style starter bath amenitiesbr• Reverse osmosis filtered drinking waterbr• Professional coffee setup (drip + pods)br• Curated coastal and Florida-inspired art that brings the outdoors inbr• Board games & poker set for slower evenings togetherbr• Luggage racks and bedroom benchesbr• Digital welcome guide with house details and local recommendationsbrbr LocationbrTucked away in a peaceful residential neighborhood, yet close to everything.br• Easy bike or golf-cart ride to Siesta Key Beach (#1 Beach in America)br• Minutes to Siesta Key Village dining, cafés, and boutiquesbr• Quick access to Sarasota’s art galleries, theaters, and fine diningbrbr⭐ Guest FavoritebrGuests consistently highlight the privacy, expansive outdoor spaces, and effortless indoor–outdoor flow. Favorite moments include slow mornings on the front deck, sun-filled afternoons by the pool, and sunset evenings on the upper deck watching the sky fade into night.brbr ️ Included Amenities ProgrambrYour stay includes a thoughtful collection of comforts and conveniences designed to make your time at Sweetwater effortless and enjoyable:br• Pool and spa heating for year-round comfortbr• Propane provided for the BBQ grill and fire tablebr• Weekly trash servicebr• Beach cruiser bikes, beach chairs, beach towels, and a beach wagonbr• Beach toys and gear for family-friendly funbr• Wine refrigerator for keeping your favorite bottles perfectly chilledbr• Complimentary high-speed Wi-Fi throughout the homebr• Private on-site parking for up to 4 vehiclesbrEvery detail at Sweetwater Retreat has been thoughtfully selected to make your stay feel effortless, comfortable, and truly elevated.brbr House Detailsbr• Check-in: After 4 PM | Check-out: 11 AMbr• Small pets considered with approval and feebr• Quiet residential neighborhoodbr• Ideal for longer stays and remote workbr• Mid-stay cleaning required for extended staysbrbr Guest AccessbrGuests enter via a secure keypad lock on the ground-level garage door. Detailed check-in instructions and your unique access code will be provided prior to arrival for a smooth, self-guided experience.brbr ️ Extended StaysbrFor stays longer than two weeks, a required mid-stay cleaning is scheduled every two weeks to maintain the home to the highest standards. Optional linen and towel replacement is available upon request.brbr PetsbrWell-behaved pets are welcome with prior approval and a pet fee of $25 per day per pet. Pets must remain off furniture, be crated if left unattended, and are not permitted in the pool or hot tub. Additional cleaning or damage related to pets may result in added fees.brbr Neighborhood & NoisebrLocated in a peaceful residential neighborhood. Guests are asked to keep noise at a respectful level at all times, especially during evening hours. Violations may result in fines or termination of the reservation without refund.brbr Minimum Age RequirementbrReservations are not accepted from guests under 25 years of age unless accompanied by an adult over 25.brbr⭐ Preferred Vendor ProgrambrOptional rentals and experiences at preferred rates, including:br• Golf carts, E-bikes, mopeds, and mini carsbr• Kayaks, paddleboards, umbrellas, and beach equipmentbr• Fishing charters, sunset cruises, eco-tours, and adventure experiencesbrAvailability is limited; advance reservations are recommended.brbr Safety & Peace of MindbrThe home is equipped with fire extinguishers, smoke and gas detectors, pool depth markers, and decibel-based noise monitoring (no recording). Exterior security cameras monitor the front door, garage doors and home equipment for added peace of mind. brbr Final ThoughtbrSweetwater Retreat is thoughtfully designed for guests seeking a calm, elevated escape — a place where privacy, comfort, and island beauty come together effortlessly.brWe look forward to welcoming you and helping you experience Siesta Key at its very best. brbrOther things to note:br1) Please respect sound ordinance rules. We ask guests to please be considerate of neighbors and mindful of noise levels. Noise violations may result in fines. br2) We allow up to 4 cars parked on the driveway. You are not allowed to park on the street or you will get a ticket. Absolutely no RV or trailer parking on Driveway.br3) Pool depth ranges from 3 feet to 4 feet. Children will need to be supervised. There is no lifeguard on duty. Swim at your own risk.br4) This house has stairs.br5) No refunds will be given due to acts of nature unless there is a mandatory evacuation or prolonged outage of essential utilities.br6) We have partnered with a Travel Insurance marketplace to offer you the opportunity for a little peace of mind through travel insurance that can potentially provide a full refund should life throw you some unexpected circumstances. Please inquire if you would like more information on travel insurance to insure your trip from unforeseeable events.brbrGuests enter the property via a keypad lock at the garage door. We will provide an access code and check-in instructions before arrival.brbrMonthly or longer stay`s require discounted house cleaning every 2 weeks paid by guest. Pets welcome. Pets need pre-approval. $25 per day per pet. Monthly discounts available. Pets are not allowed in the pool. Please keep pets off the furniture and crate your furry friends if you are planning on leaving them unattended.br• Must upload Government ID upon Booking if not already completed.br• No Smoking Anywhere in the home or near home openings. Smoking anywhere in home will result in a $500 remediation fee. Smoking is permitted outdoors. $50 cleaning fee if butts found on property.br• Quiet Hours between 10 pm and 8 am. Siesta Key has a noise ordinance program that is enforced by local law enforcement.
Bed 5

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Bath 4

Bath

Sleep 12

Sleeps

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Exceptional(3)

$2806.95

/ Nightly
Private Vacation Home

Gulf Views, Waterslide, Movie Room/Sports Ct

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 Over the Top, a striking beachfront vacation home that seamlessly blends thoughtful design, high-end amenities, and luxurious comfort across multiple levels of extraordinary living spaces. This vacation home embodies the elevated lifestyle that guests have come to expect from Vunique Vacations with nearly 5,000 square feet of interior living space, over 3,000 square feet of covered patios and balconies including the best rooftop space on Siesta Key, expansive Gulf views and elevator access on all levels, 8-bedrooms each with en suite baths, private beach access, a resort style pool with multiple water slides, a sport court, movie room, and so much more. Did we mention that this home showcases gulf views from every bedroom, common space, and balcony! brbrbrbrFloor Plan Description (by level):brbrbrbrGround Level:brbrThe ground level of this luxury home has been curated for entertainment and functionality, creating the ideal space to vacation better! Guests are greeted with a private entry foyer with staircase and elevator access to all levels above, including the rooftop deck. There are also 2 garages for covered parking (EV charger equipped) in addition to driveway parking provided. The home's beach gear is also stored here, including bikes, beach wagons and chairs, alongside a convenient fridge and freezer combination. From there, you'll step out to your private back yard oasis surrounded by lush native landscaping. The center piece of this level is the custom-designed, resort-style, heated saltwater pool and spa, featuring 2 waterslides: 1 for teens and adults and 1 for small children and toddlers as well as a poolside basketball hoop. Enjoy soaking in the sun, meals, and cocktails at multiple seating areas including 6 chaise loungers, soft seating and dining areas that accommodate 22. The outdoor kitchen includes a grill, sink, beverage fridge with ice maker, and ample countertop space. 4 TVs are placed throughout the covered pool patio and nestled into the -greenery wall' for seamless viewing and natural elements from all angles. A private sports court provides a space for activities like basketball, hockey, and soccer with provided equipment. There is also a putting green near the pool for additional entertainment as well as provided outdoor connect 4, bocce ball and jazzminton games. brbrbrbrThe First Level of Living (2nd Floor): brbrThis level sets the tone for relaxed entertainment and restful nights. At its center is the club room, a cozy retreat that includes theater seating for 6, and a media center (80”+ Smart TV w/ Surround Sound) for the perfect movie night and Nintendo Switch 2 gaming console. Off the club room you'll find a private balcony perfectly furnished with seating for 11. This outdoor living space is perfect for sunset cocktails or early morning coffee. Accommodations on this level include Master Bedroom 1, which features a king bed, Gulf views, a walk-in closet, and a spa-style en suite bath with a double vanity and a wet room with double shower and freestanding bathtub. Bedrooms 3, 4, and 5 offer balcony or Juliette balcony access, Gulf views, a king bed, storage and closet(s), and an en suite bathroom with vanity and walk-in shower. Bedroom 8 is the homes Bunk Room, offering Gulf views, two full-over-full bunks, TVs for each bottom bunk + wall mounted TV for the room, a workstation area and window bench, a closet, and an en suite bathroom with trough sink and dual faucets, and a shower bathtub combination. A half bath, and laundry room with 2 stackable washer/dryer units, are also located on this level.brbrbrbrThe Second Level of Living (3rd Floor): brbrThis level includes the heart of the home, the great room, with wide open and jaw dropping Gulf and Siesta Key Beach views! The kitchen is a chef's dream, fully outfitted with a 48-inch range, double wall ovens, a microwave drawer, 2 dishwashers, and a large island with bar seating for 7. With a coffee/beverage bar, and the adjacent pantry including a full-size refrigerator, sink and food storage, this kitchen is fully stocked! The dining space includes a large table accommodating 14 people and offers remarkable seated views. The living room offers the same amazing Gulf views, and a TV, an oversized custom modular sofa that comfortably seats 11, an electric fireplace for ultimate comfort. Adjacent to, and expanding the great room, is a large balcony, which is furnished with a dining table for 14 and soft seating for 5 - all overlooking the Gulf and Beach. Accommodations on this level include Bedrooms 6 and 7, both offering balcony or Juliette balcony access, Gulf views, a king bed, storage and closet(s), and an en suite bathroom with vanity and walk-in shower. The second master bedroom is also on this level, offering Gulf views, a king bed, a built-in bench and storage area, walk-in closet, and an en suite spa-style bathroom with a double vanity, a wet room with freestanding tub, and a stackable washer and dryer. A half bath is also located on this level.brbrbrbrThe Third Level of Living & Rooftop Deck (4th Floor): brbrAt the top of the estate awaits the crown jewel of the home: a rooftop deck that transforms entertaining into an experience by combining panoramic views, amenities, and thoughtful design into something unforgettable. This space includes a covered rooftop patio with seating for 11, an outdoor rated billiards table, and a large TV nestled into a lush faux greenery wall. It also offers an outdoor wet bar with beverage fridge and ice maker, sink, trash pull-outs, bar seating for 6, dining table seating for 8, and 2 more TVs. Outside of the covered rooftop space you'll find 6 loungers with side tables perfectly arranged for maximum sun exposure, as well as corn hole boards and a half bath.brbrbrbrGetting Around:brbrThe home is conveniently located to everything on Siesta Key. 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 to the mainland Sarasota area (5 minutes) and downtown Sarasota (20-25 min) for access to the Sarasota's Performing Arts scene, and numerous fantastic restaurants, shops, marinas, bars and entertainment, grocers, and more. And, day trips to Lido Key, Anna Maria Island, Venice Beach, Myakka State Park and so much more are all less than an hour away, as well as the amazing theme parks of Tampa and Orlando that are all just 1-2 hours away! So, whether you're relaxing poolside, entertaining on the rooftop deck, hosting friends and family, or planning a day trip or getting out on the town, this estate promises a vacation experience like no other.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
Bed 8

Bed

Bath 9

Bath

Sleep 22

Sleeps

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Exceptional(17)

$920.92

/ Nightly
Private Vacation Home

The Solaster | Pet Friendly Home on Siesta Key w/ 2 Heated Pools, Walk to Beach & South Village!

Siesta Key, Florida, United States

Solastar | A Luxury Island Escape, 2 Private Pools + 3-Min Walk to Crescent Beachbrbr Why You'll Love This HomebrThe Solaster is a rare Siesta Key gem—two private homes combined into one elegant retreat. With dual private pools, two living areas, and space for up to 20 guests, this home is ideal for multi-family escapes or large group getaways. Located just 0.2 miles to Crescent Beach, it's where privacy meets proximity.brbr ‍ ‍ Perfect ForbrPerfect for multi-family vacations, group getaways, or two families traveling together. Enjoy side-by-side privacy with the convenience of shared outdoor space and unbeatable walkability to the beach and village.brbr ️ Imagine ThisbrWake up in your own private villa just a 3-minute walk from Crescent Beach. Morning coffee on your screened-in porch, an easy stroll to grab breakfast in Crescent Village, and afternoons spent lounging in one of two fenced-in pool courtyards—your group can spread out or come together at will. Inside, you'll enjoy two full kitchens, two living rooms, and 6 bedrooms with comfort-driven design throughout. Come evening, grill out in the backyard, swap stories under the stars, and retreat to your own half of the duplex for a quiet night's rest.brbr Where You'll Sleepbr• Bedroom 1 (Morning Star): King Bed – Ensuite Bath, TVbr• Bedroom 2 (Morning Star): King Bed – Shared Ensuite Bath, TVbr• Bedroom 3 (Morning Star): Two Full Beds – Shared Hall Bath, TVbr• Queen Sleeper Sofa (Morning Star Living Room): Sleeps 2br• Bedroom 4 (Sun Star): King Bed – Ensuite Bath, TVbr• Bedroom 5 (Sun Star): King Bed – Shared Ensuite Bath, TVbr• Bedroom 6 (Sun Star): Two Full Beds – Shared Hall Bath,TVbr• Queen Sleeper Sofa (Sun Star Living Room): Sleeps 2brbr Explore the Areabr• 0.2 Miles to Crescent Beach Access #13br• 0.3 Miles to Point of Rocks Snorkeling Areabr• 0.2 Miles to Crescent Village (Restaurants, Shops, Bars)br• 1.2 Miles to Siesta Key Public Beachbr• 1.8 Miles to Siesta Key Villagebr• Walk to Local Ice Cream, Bike Rentals, Tiki Bars, and Boat Launchesbr• Peaceful, Walkable Southern Siesta Key Neighborhoodbrbr⌛ Don't WaitbrHomes with dual private pools, just 3 minutes from the beach don't stay open for long. With our CottageClean™ 35-point inspection and deep clean protocol, you can relax the moment you arrive. Reserve The Solaster now and give your group the space and setting to reconnect in paradise.brbr Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Free high-speed WiFi included. This is a single-level duplex home with two separate entrances, two living areas, and two private pools. Dog-friendly with a 25-pound limit and pet fee. The pool is heated between November 15 – April 15.
Bed 6

Bed

Bath 6

Bath

Sleep 20

Sleeps

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Exceptional(17)

$1248.7

/ Nightly
Private Vacation Home

Perfect for large groups, Steps to the Beach. Private Pool & Putting Green.

Siesta Key, Florida, United States

The whole group will enjoy the easy walking access to everything Siesta Key has to offer, from its iconic beach to its vibrant restaurants and shops. Or just relax at home with a game of ping pong, a swim in the private heated pool, and outdoor dining that’s perfect for everyone.brThe spacebrExclusive Amenities Include:br• Private Heated Poolbr• 5 Minute Walk to Siesta Key Villagebr• 2 Minute Walk to Siesta Key Beachbr• 6 Bedrooms, 4 Full Bathsbr• 2 King Bed, 6 Queen Beds, 2 Queen sleeper sofas (Sleeps 20)br• 2 Screened Balconies With Seating Areasbr• 2 Full Kitchensbr• Spacious Outdoor Lounge & Dining Spacebr• Putting Green with 3 holesbr• 2 Regular & Keurig Coffee Makers, 2 Dishwashers, 2 Washers & Dryers, and Kitchen Essentialsbr• Pet Friendly with a Feebr• Pack & Play, sheets, and booster seat availablebrbrStep into island serenity at Siesta Sea Life, a spacious duplex retreat just 2 minutes to Siesta Key Beach and 5 minutes to Siesta Key Village. With dual living spaces, a private heated pool, and room for up to 20 guests, this two-story tropical haven is perfect for families and groups who crave both comfort and coastal adventure.brbrIdeal for multi-family vacations, groups traveling together, or guests seeking privacy with shared outdoor spaces—especially when booking both sides together.brbrWake up to the sound of swaying palms from one of six second-floor bedrooms, then step onto your private screened balcony with a morning coffee in hand. After breakfast in your fully equipped kitchen, load up the beach caddy and head to the powdery sands just a minute away. Afternoons are made for lounging by your heated private pool, grilling in the tropical breeze, or rinsing off in the outdoor shower before heading into the Village for dinner. End your night streaming a movie on one of 8 HDTVs, or gather outside under the stars in the spacious lounge area.brbrWhere You’ll SleepbrAll bedrooms are located on the second floor. Each side of the duplex includes:brSea Esta (Left):br• Bedroom 1: King Bed, Shared Hall Bath, TVbr• Bedroom 2: Queen Bed, Shared Hall Bath, TVbr• Bedroom 3: Two Queen Beds, Ensuite Bath, TVbr•Living room: Queen Sleeper SofabrSea La Vie (Right):br• Bedroom 4: King Bed,Shared Hall Bath, TVbr• Bedroom 5: Queen Bed, Shared Hall Bath, TVbr• Bedroom 6: Two Queen Beds, Ensuite Bath, TVbr•Living room: Queen Sleeper Sofabrbr• 0.1 Miles to Siesta Key Beachbr• 0.3 Miles to Siesta Key Villagebr• Surrounded by Casual Eateries, Ice Cream Shops, Live Music, Boutiques, and Beach Gear Storesbr• Free Island Shuttle Access NearbybrbrThis duplex home offers the flexibility of booking both sides—with separate entrances and no shared interior space.brbrOther things to notebrNeed To Know: Pool is Heated November 15 – April 15. All rooms accessible via interior stairs only. Pet-friendly with fee. An exterior security camera monitors the front door.
Bed 6

Bed

Bath 4

Bath

Sleep 20

Sleeps

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Exceptional(26)

$911.39

/ Nightly
Private Vacation Home

Sandy Seahorse Cottage | Pet Friendly Home on Siesta Key w/ Private Pool, Short Walk to Beach

Siesta Key, Florida, United States

Sandy Seahorse Cottage | Sleeps 16 + Heated Pool + Walk to Crescent Beachbrbr Why You'll Love This HomebrPerfectly designed for large families or groups, Sandy Seahorse Cottage is a bright and breezy Siesta Key retreat just 2 minutes from the powder-soft sands of Crescent Beach. This fully renovated duplex includes two private cabanas, a heated pool, screened lanais, and stylish interiors that make it easy to relax, connect, and enjoy island life.brbr ‍ ‍ Perfect ForbrMulti-family vacations, reunions, or groups of friends looking to stay together—while enjoying the privacy of two separate cabanas and easy access to the beach and pool.brbr ️ Imagine ThisbrYour day starts with morning coffee on the screened lanai as palm fronds sway gently overhead. The kids are already grabbing beach towels, ready for the two-minute walk to Crescent Beach. After a sun-soaked afternoon on the shore, you return to your private oasis—where open living spaces invite you to cook, dine, and unwind together. Some gather around the pool, while others retreat to the cool, cozy living rooms. With space for up to 16 guests across two separate units, everyone gets their own slice of island comfort.brbr Where You'll SleepbrSandy Cabanabr • Bedroom 1: King Bed, Ensuite Bath, Single Level, TVbr • Bedroom 2: Queen Bed, Shared Bath, Single Level, TVbr • Bedroom 3: Two Twin Beds, Shared Bath, Single Levelbr • Bonus: Queen Air Bed – Stored in UnitbrSeahorse Cabanabr • Bedroom 4: King Bed, Ensuite Bath, Single Level, TVbr • Bedroom 5: Queen Bed, Shared Bath, Single Level, TVbr • Bedroom 6: Two Twin Beds, Shared Bath, Single Levelbr • Bonus: Queen Air Bed – Stored in Unitbrbr Explore the Areabr • 0.2 Miles (2-Min Walk) to Crescent Beach Accessbr • 0.4 Miles to South Village, 1.2 Miles to Siesta Key Village – Shops, Dining & Nightlifebr • Walkable to Local Cafés, Island Markets & Snorkeling at Point of Rocksbr • 2.4 Miles to Siesta Key Public Beach Pavilionbr • 15 Minutes to Downtown Sarasota – Museums, Theater & Bayfront Parksbrbr⌛ 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: This home is a combination of two units: Sandy Cabana (1104) and Seahorse Cabana (1106). Each cabana has its own private entrance and does not share indoor living space. Guests have access to the pool, which is heated seasonally from November 15–April 15. Contact us directly for more information about spaces or to reserve individual cabanas.
Bed 6

Bed

Bath 5

Bath

Sleep 16

Sleeps

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Exceptional(31)

$3133.33

/ Nightly
Private Vacation Home

Sunset Gazers Paradise - Resort Pool - Mini Golf

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:brbrEndless Horizon is the most accurate description for this luxury Siesta Key vacation rental that is located directly on the Gulf of Mexico and provides some of the most remarkable views of the Gulf, Big Pass, Lido Key, and greater Siesta Key and Sarasota areas! brbrbrbrThese views though! We cannot begin to tell you how impressive they are! It's always about the location and the view, and this home has both! With balconies on all levels, and gigantic fixed windows and sliding doors throughout, natural light abounds and there is not a bad view inside or outside of this home. Speaking of outside, you won't believe this backyard space. The charming heated, saltwater pool and spa is set next to the covered patio which connects the spaces for a perfect social setting, all of which stares directly out at the wide-open Gulf views. The covered patio is robust, with a full bar area with sink, smart TV, beverage fridge and bar top seating, as well as an outdoor grill and additional dining and seating options. Directly in front of these spaces you'll find the man-made beach area perfect for sunning, playing, or lounging in the seating or hammock that is hung between palms; and the turf area with more seating and play options, including putt-putt golf. Around the pool you'll find plenty of chairs and loungers, and a ping-pong table. These spaces are all within the fenced backyard (but open to the water) for privacy and security making it family friendly and perfect for the home's pet friendly policy (fees and restrictions apply).brbrbrbrThis nearly 5,500 square foot home has an elevator with service to all floors. This home provides 5 bedrooms (all with en suite baths), 4 of which have private balcony access and Gulf views, and 5 full baths and 2 half baths. There are 4 king beds and a custom king over king bunk bed. It comfortably sleeps 12 people in beds. The great room welcomes amazing views in this perfect gathering space that includes the kitchen, living, and dining areas of the home and a large balcony space with seating. 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 that is a wonderful secondary living space or -sunset room.'brbrbrbrFloor Plan Description (by level):brbr brbrGround Level:brbrFree parking for up to 4 vehicles depending on size (2 covered & 1-2 driveway spaces). You'll also find the fenced pool and backyard area (pet friendly - fees and restrictions apply), including the covered patio space and pool that was previously described. 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 ping pong table and beach equipment can be found here that 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 custom staircase that lead to the home's three (3) living levels above.brbrbrbrThe First Level of Living (2nd Floor):brbrThis level features a great room with a fully stocked kitchen that includes a top-of-the-line Wolf appliance package - gas cooktop with hood vent, double oven, full sized refrigerator (with ice maker) and freezer, and 2 dishwashers, as well as trash and recycling storage, microwave, toaster, coffee maker and more. There is also a beverage bar off the kitchen with a sink, Scotsman Brilliance nugget ice machine, beverage fridge with ice maker, and 2 wine fridges. These spaces are very well appointed with drinkware, 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 comfortably appointed with smart TV, and you guessed it, wide open views. The dining area here is comprised of an 8-person dining table, 8-person in-kitchen dining table, and 12 bar seats at the kitchen island and the beverage bar. Off the great room is a half bath, and the home's main balcony with additional dining and seating - and it's a guest favorite for sunset dining!brbrbrbrThe Second Level of Living (3rd Floor):brbrYou'll find 3 bedrooms on this level. Bedroom 3 has a private balcony, Gulf views, king bed, walk-in closet, and an en suite bath with walk-in shower and vanity. Bedroom 4 has peaking Gulf views, private balcony, king bed, and an en suite bath with walk-in shower and vanity. Bedroom 5 is the bunk room with a custom king over king bunk bed, custom bench and city closet for storage, and an en suite bath with walk-in shower and vanity. The laundry room has 2 stackable washer/dryer units and a utility sink.brbrbrbrThe Third Level of Living & Rooftop Deck (4th Floor):brbrThe club room welcomes picture perfect views of the Gulf of Mexico, Big Pass and Lido Key! It has been coined -the sunset room' and replaces an open-air rooftop space with a conditioned interior space with year around direct ocean and sunset views. It offers comfortable seating, smart TV, and Xbox gaming console. Master bedroom 1 is on this level with panoramic views you must see in person to believe. The room also offers a private balcony, king bed, walk-in closet, and an en suite bathroom with double vanity, walk-in shower, and free-standing bathtub. There is also a morning bar just outside this bedroom in the hallway with a beverage refrigerator and sink. Just down that same hallway is master bedroom 2. This bedroom has Gulf views, a private balcony with seating, king bed, and a large en suite bathroom with double vanity, walk-in shower, and private water closet.brbrbrbrGetting Around:brbrThis amazing home is a casual bike ride or walk to the world-famous Siesta Key Beach and Siesta Key Village for access to all the restaurants, entertainment, shopping, grocers, and more. It's just far enough from the Village that you are guaranteed private enjoyment, and just close enough that everything is still walkable or bike-able! 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
Bed 5

Bed

Bath 6

Bath

Sleep 12

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$1567.74

/ Nightly
Apartment

Gertrude's Siesta | 8-steps to Beach Path! 4-min Dining & Music! Hammocks, Snorkeling, Sunsets

Siesta Key, Florida, United States

The Coral Cabanas C, D, & PBbrJust 8-steps to path of Siesta Key Beach, world's best beach! 4-minute walk to bars, entertainment, shopping, dining, ice cream and live music of the South Village! Listing includes two side-by-side units including a 1BR and 2BR (total 3BR). Book your getaway now!brbrWhat Guests Lovebr∙ Separate Units – 2 units deliver space and privacy, perfect for large gatheringsbr∙ Beaches – 11-step walk to award winning Siesta Key beaches, calm shallow and clearbr∙ Relaxing –secluded spot with hammocks, alfresco-lounging, westerly facing deckbr∙ Reef Snorkeling – 60-yard walk to Point of Rocks, free snorkel gear providedbr∙ 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 –walk 30-seconds to Siesta Key's best sunsets and whatever comes nextbr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - 4-min walk to the South Village's 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 allbr∙ Price - this Siesta Key vacation rental listing is direct with the manager and is the guaranteed lowest costbrbrThe BeachbrSkip the crowds and commercial feel. Coral Cabanas offers Key West-style charm and beach access #13—quieter, more private, and just across the street. With no public parking nearby, this cove is one of Siesta's most 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 7 minutes to Siesta's top eco-adventures—boat, bike, jet-ski, and fishing tours. Prefer to relax Sunbathe on the balcony, nap in a hammock, 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 Coast's 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.brbrBedroom DetailsbrListing includes two side-by-side units including a 1BR and 2BR (total 3BR), one staircase above ground level. The 1BR unit has a large queen bedroom and a queen sleeper in the living room. You can sleep up to 11 family style. Need more space We can get you an additional unit nearby.brbrBeach Gear ProvidedbrWe provide beach towels, chairs, snorkel equipment, and umbrellas. There are also a few paddle boards available on a first come first serve basis and any other gear can be found for sale or rental 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 BringbrSiesta Key is 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 5

Bed

Bath 3

Bath

Sleep 18

Sleeps

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$477.27

/ Nightly
Private Vacation Home

Sundown Sanctuary! Modern home near the north end of Siesta Key!

Siesta Key, Florida, United States

Sundown Sanctuary by Siesta Key Luxury Rental Properties brbrWelcome to Sundown Sanctuary, a refined four bedroom, three and a half bath Siesta Key luxury rental that blends iconic mid-century modern design with effortless coastal living. Set along Midnight Pass Road in a tranquil North Siesta Key neighborhood, this architecturally significant estate offers a private 30-foot lap pool with waterfall, a serene Zen garden, and a detached two bedroom guesthouse. Tucked beside a protected nature preserve and just an 18-minute walk to the Beach, the home is also minutes from Siesta Village, making it ideal for families, couples, and design-forward guests seeking privacy, space, and island-inspired comfort. Four on-site parking spaces are available. brbrHighlights br• 18-minute walk to the Beach br• 4 Bedrooms / 3.5 Bathrooms br• 1 King, 4 Queens, 1 Queen Murphy bed br• Private 30-foot lap pool with waterfall br• Separate two-bedroom guesthouse with full kitchen br• Private Zen garden with pond and sculpture br• Adjacent to a Sarasota County nature preserve br• Screened porch and multiple outdoor lounge areas br• Beach chairs and beach cart provided br• Washer and dryer br• Pet-friendly with approval br• 4 Parking spaces brbrDesigned for luxury coastal living, Sundown Sanctuary’s outdoor spaces set the tone for a restorative stay. The private lap pool, accented by a cascading waterfall, anchors the gated courtyard and invites morning swims or sunset relaxation. Surrounding lounge seating, a shaded hammock area, and sculptural elements create a peaceful tropical retreat. The Zen garden offers a quiet escape among palms and stone pathways, while the screened porch and outdoor seating areas provide comfortable spaces to gather throughout the day. brbrInside, the home celebrates its mid century heritage with airy, open concept living spaces, floor to ceiling windows, and curated art pieces that feel both elevated and inviting. The main living area features modern furnishings and a sleek fireplace, creating a comfortable setting for relaxing evenings. The main floor bar kitchen includes a small fridge, counterspace, and stovetop for quick meals and snacks. A spacious dining area flows seamlessly into the living room, making the layout ideal for entertaining or unwinding after a day at the beach. The second level of the main house includes the full kitchen, outfitted with granite countertops, stainless steel appliances, and ample workspace for preparing everything from quick breakfasts to shared family dinners. brbrThe main house features two thoughtfully styled bedrooms on the second level, with calming tones and Scandinavian inspired details. The primary bedroom offers a king bed and shares a full bathroom with a shower and tub combination. The second bedroom includes a queen bed and shares the same bath. A bonus room with a queen Murphy bed provides additional flexibility for guests. On the ground floor of the main house, a full bathroom with walk-in shower adds convenience. br brThe detached guesthouse is perfect for extended families or guests seeking added privacy. It includes two queen bedrooms connected by a Jack-and-Jill bathroom with walk-in shower, along with a full kitchen, cozy living area with fireplace, and a screened porch overlooking the courtyard. brbrRoom Details brMain House br• Primary Bedroom (Second Floor): King bed, shared bath with shower and tub br• Second Bedroom (Second Floor): Queen bed, shared bath br• Bonus Room: Queen Murphy bed br• Ground Floor: Full bathroom with walk-in shower brbrGuesthouse br• Bedroom 1: Queen bed br• Bedroom 2: Queen bed, Jack-and-Jill bath with walk-in shower brbrGuests will enjoy thoughtful conveniences including an outdoor shower, BBQ grill, private parking, beach chairs, and a beach cart. The home’s location near a nature preserve enhances the sense of serenity while still offering easy access to the beach and island attractions, making it well-suited for Siesta Key weekly rentals or extended stays. brbrExperience a truly unique Siesta Key vacation home with pool at Sundown Sanctuary, where mid-century architecture meets tropical tranquility. From the Zen garden and private guesthouse to the sun-drenched courtyard and elegant interiors, every detail is designed for relaxed island living. Book your stay with Siesta Key Luxury Rental Properties today and discover one of Siesta Key’s most distinctive coastal retreats! brbr- brThis home is managed by Siesta Key Luxury Rental Properties. brbrThis home requires a minimum 30-night stay in accordance with local city regulations, and shorter stays are not permitted.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. 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. 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.
Bed 5

Bed

Bath 4

Bath

Sleep 10

Sleeps

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Exceptional(75)

$1556.03

/ Nightly
Private Vacation Home

Ultimate Family Reunion: Pool, Game Room, 3 mins to Beach - Surf View

Siesta Key, Florida, United States

Surf View by Siesta Key Luxury Rental PropertiesbrbrSurf View is a spacious eight bedroom, eight and a half bath Siesta Key luxury rental designed for large families and group gatherings seeking relaxed coastal living. Ideally located just a three-minute walk to Siesta Key Beach and steps from Siesta Key Village, this inviting retreat places guests near some of the island’s most popular restaurants, boutiques, bars, and ice cream shops. With multiple living areas, a private pool and spa, and generous outdoor entertaining space, Surf View offers the perfect setting for memorable family vacations and reunions on Florida’s Gulf Coast. brbrHighlights br• 3-minute walk to Siesta Key Beach br• 3-minute walk to Siesta Key Village dining and shopping br• 8 Bedrooms / 8.5 Bathrooms br• 7 King beds, 1 Twin-over-Full bunk bed with Twin trundle br• Private pool with in-ground spa br• Outdoor dining and lounge area with two grills br• Balcony spaces br• Indoor wet bar br• Ping Pong, and pool table br• Beach chairs, wagon, and cooler provided br• 2 Sets of washer and dryer br• Dog-friendly with host approval br• Parking for up to 6 vehicles brbrThe backyard at Surf View is a tropical retreat surrounded by lush Florida foliage, offering space to relax and reconnect. Guests can enjoy refreshing swims in the private pool, unwind in the in-ground spa, or lounge poolside while the kids play. The outdoor dining area and BBQ grills make family meals easy and enjoyable, creating a natural gathering spot after beach days or evenings spent exploring Siesta Key Village. brbrInside, Surf View offers multiple levels of thoughtfully designed living space, allowing everyone room to spread out. The third floor serves as the main living level and features a fully equipped kitchen with ample counter space, bar seating, and everything needed to prepare meals for a crowd. Next, It's a cozy seating area with a TV and a formal dining table for shared meals and celebrations. The second floor features a large family room with generous seating, a TV, and an indoor wet bar, which includes a coffee maker, in addition to the coffee maker located in the main kitchen. On the ground level, an additional living area with a ping pong and pool table provides extra entertainment for guests of all ages. brbrEach bedroom at Surf View is designed with comfort in mind, offering a dresser, TV, and ensuite bathroom. King suites provide a restful retreat with walk-in showers or shower and tub combinations, while select bedrooms include private balconies for peaceful moments outdoors. The bunk bedroom is perfect for younger guests, featuring a twin-over-full bunk bed with a twin trundle and convenient bathroom access. With a layout that balances privacy and togetherness, every guest can enjoy a comfortable night’s sleep. brbrRoom Details br• First Bedroom (2nd Floor): King bed, balcony, ensuite bathroom with shower and tub combo br• Second Bedroom (2nd Floor): King bed, ensuite bathroom with walk-in shower br• Third Bedroom (2nd Floor): King bed, ensuite bathroom with shower and tub combo br• Fourth Bedroom (2nd Floor): King bed, ensuite bathroom with shower and tub combo br• Fifth Bedroom (2nd Floor): King bed, balcony, ensuite bathroom with shower and tub combo br• Sixth Bedroom (3rd Floor): King bed, ensuite bathroom with shower and tub combo br• Seventh Bedroom (3rd Floor): King bed, ensuite bathroom with shower and tub combo br• Eighth Bedroom (3rd Floor): Twin-over-Full bunk bed with Twin trundle, balcony, hall bathroom with walk-in shower brbrSurf View places guests just steps from the heart of Siesta Key Village and a short walk to Siesta Key Beach. This Siesta Key vacation home includes an in-home washers and dryers, multiple living spaces for large groups, and parking for up to six vehicles, making group travel and extended stays easy. With host approval prior to arrival, dogs are welcome, allowing guests to enjoy a pet-friendly Siesta Key getaway. Whether spending the day at the beach, dining nearby, or relaxing poolside, Surf View offers convenience and comfort in one of the island’s most walkable locations. brbrDesigned for unforgettable family gatherings, Surf View by Siesta Key Luxury Rental Properties combines spacious accommodations, resort-style amenities, and an unbeatable location near the beach and village. From poolside afternoons to evenings spent exploring Siesta Key’s vibrant dining scene, this home delivers the perfect balance of relaxation and island adventure. Book Surf View today and experience the best of Siesta Key!brbr- brThis property has an active Ring doorbell and additional video surveillance on the pool equipment only. 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. brbr6 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.
Bed 8

Bed

Bath 8

Bath

Sleep 20

Sleeps

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Exceptional(44)

$1630.5

/ Nightly
Private Vacation Home

Home with Gulf Views, Private Heated Pool, Spa, Game Room! - Sunset View

Siesta Key, Florida, United States

Sunset View by Siesta Key Luxury Rental Properties brbrWelcome to Sunset View, an eight bedroom, five and a half bath Siesta Key luxury rental just four houses from Siesta Key Beach. This four story coastal retreat blends spacious living, modern coastal design, multiple balconies, and a private heated pool and spa. Designed for large families and group getaways, the home offers two full living areas, a game room, and quick access to Siesta Key Village, making it an ideal destination for memorable beach vacations. brbrHighlights br• 2-minute walk to Siesta Key Beach br• 8 Bedrooms, 5.5 Bathrooms br• 6 Kings, 1 Twin over Full Bunk with Twin Trundle, 1 Twin over Twin Bunk with Twin Trundle, 1 Queen Futon br• Private Heated Pool with In-Ground Spa br• Ping Pong Table br• Indoor Bar and Wet Bar br• Multiple Balconies with Beach Views br• Near Siesta Key Village br• 6 Parking Spaces brbrYour private tropical backyard oasis is the perfect place to unwind after a day on the soft white sands of Siesta Key Beach. The sparkling heated pool and in-ground spa invite guests of all ages to relax, while the surrounding lounge chairs offer plenty of comfort. The covered patio steals the show with its outdoor dining table, cozy seating, and a stylish poolside bar complete with a sink, fridge, television, and plenty of bar stools for laid-back afternoons or sunset gatherings. Inside, entertainment is effortless thanks to an indoor game room with ping pong and multiple balconies offering refreshing Gulf breezes. brbrSunlight fills the home’s primary living space on the second floor, where a charming nautical inspired seating area creates an inviting atmosphere. This level features a beautifully designed kitchen equipped with appliances, ample cookware, generous island seating, and a dining table ideal for shared meals. The third floor living area offers a second gathering space with a large sectional, a new PlayStation, stylish dining table, and a wet bar with wine fridge, perfect for evening cocktails or game nights with family. brbrThe home’s most luxurious accommodations can be found on the second and fourth floors, where two serene primary suites offer king beds, private balconies, walk-in closets, and spa-inspired ensuite bathrooms with double vanities, walk-in showers, and relaxing soaking tubs. Four additional king bedrooms provide elevated comfort, including two ensuite bathrooms featuring modern vanities and walk-in showers. Two bunk rooms create the perfect layout for younger guests or larger families, including a twin over full bunk with trundle and a twin over twin bunk with trundle. A hall bathroom with walk-in shower, a half bath, and laundry rooms on two levels add to the convenience. brbrRoom Details br-Primary Bedroom (4th Floor), King bed, balcony, ensuite bathroom with walk-in shower and soaking tub, rollaway twin bed br-Second Bedroom (2nd Floor), King bed, balcony, ensuite bathroom with walk-in shower and soaking tub br-Third Bedroom (4th Floor), King bed, ensuite bathroom with walk-in shower and soaking tub br-Fourth Bedroom (3rd Floor), King bed, ensuite bathroom with double vanity and walk-in shower br-Fifth Bedroom (3rd Floor), King bed br-Sixth Bedroom (3rd Floor), King bed, queen futon br-Seventh Bedroom (3rd Floor), Twin over Full Bunk with Twin Trundle br-Eighth Bedroom (4th Floor), Twin over Twin Bunk Bed with Twin Trundle brbrSunset View includes an indoor game room, multiple balconies, indoor and outdoor bar areas, and a prime location just steps from Siesta Key Beach. Guests are only minutes from Siesta Key Village, where boutique shops, restaurants, ice cream spots, and nightlife create the perfect island experience. brbrWith its private pool and spa, elegant living spaces, game room, and unbeatable proximity to the beach, Sunset View by Siesta Key Luxury Rental Properties offers everything you need for an unforgettable coastal getaway. Enjoy relaxed island living steps from the Gulf and minutes from the best of Siesta Key. brbrBook your stay at Sunset View today and start planning your dream vacation! brbr- brThis 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 for your stay. These are professionally laundered at a commercial facility for every guest. brbrThis property does not allow pets. brbr6 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 a refund.
Bed 8

Bed

Bath 5

Bath

Sleep 21

Sleeps

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Exceptional(75)

$1782.5

/ Nightly
Private Vacation Home

Siesta Home with Pool & Waterslide - Sunset Splash

Siesta Key, Florida, United States

Sunset Splash by Siesta Key Luxury Rental Properties brbrWelcome to Sunset Splash, a legendary eight bedroom, seven and a half bathroom ground-level vacation home. Just a 2-minute walk to Siesta Key Beach and steps from Siesta Key Village, this private pool home is designed for unforgettable group getaways. The true WOW factor is the resort style backyard with a pool, waterslide, in-ground spa, and sun loungers, paired with walkable access to the island’s most iconic dining and shopping. With three parking spaces and a spacious layout, Sunset Splash is ideal for large families and groups looking to stay close to the action while enjoying premium amenities. brbrHighlights br• 3-minute walk to Siesta Key Beach br• Steps to Siesta Key Village shops and dining br• 8 Bedrooms / 7.5 Bathrooms br• 6 kings, 1 twin-over-full bunk with trundle, 1 full over full bunk with trundle, 1 queen sleeper sofa br• Private pool with waterslide and in-ground spa br• Outdoor dining area, sun loungers br• BBQ grill br• Dog friendly with approval br• 3 parking spaces brbrEnjoy a private backyard retreat at Sunset Splash featuring a private pool with a waterslide and an in-ground spa, perfect for cooling off after beach days or relaxing in the evenings. The outdoor space includes sun loungers, a dedicated outdoor dining area, and a BBQ grill, creating an ideal setup for group meals, poolside lounging, and laid back island living just steps from the beach. brbrInside, the home offers a bright and welcoming layout with beach decor throughout. The spacious living room features multiple sofas and chairs to comfortably gather your entire group. Barn doors open to a beautiful dining room with direct access to the outdoor deck and grill. The fully equipped kitchen includes stainless steel appliances, ample counter space, and cookware essentials, making it easy to prepare meals for large groups. brbrSunset Splash features two primary bedrooms, each designed as a private retreat. One primary suite includes a standalone soaking tub, while the other offers a walk-in shower. Four additional king bedrooms each include their own ensuite bathrooms, providing privacy and comfort. Two bunk rooms are ideal for kids or teens and share a convenient hallway bathroom with a walk-in shower. Every bedroom includes a TV and professionally laundered linens for a restful night’s sleep. brbrRoom Details br- Primary Bedroom: King bed, ensuite bathroom with double vanity and walk-in shower br- Second Bedroom: King bed, patio access, ensuite bathroom with double vanity, walk-in shower, and tub br- Third Bedroom: King bed, ensuite bathroom with walk-in shower br- Fourth Bedroom: King bed, ensuite bathroom with walk-in shower br- Fifth Bedroom: King bed, ensuite bathroom with walk-in shower br- Sixth Bedroom: King bed, ensuite bathroom with walk-in shower br- Seventh Bedroom: Twin-over-full bunk bed with trundle br- Eighth Bedroom: Full-over-full bunk bed with trundle br- Living Room: Queen sleeper sofa brbrSunset Splash is located just a short walk from Siesta Key Beach and Siesta Key Village, making it easy to split your days between the Gulf shoreline and shops, coffee spots, ice cream stops, and local dining. The home is dog friendly with host approval prior to arrival. For parking, a maximum of 3 vehicles may park at the home. This property also has an active Ring doorbell and additional video surveillance on the pool equipment only. brbrWith its unbeatable location near Siesta Key Beach and Siesta Key Village, an incredible private pool setup, and spacious accommodations for large groups, Sunset Splash by Siesta Key Luxury Rental Properties delivers the ultimate island escape. Book your stay today and make memories that last a lifetime! brbr- brThis property has an active Ring doorbell and additional video surveillance on the pool equipment only. 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. brbr3 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.
Bed 8

Bed

Bath 7

Bath

Sleep 23

Sleeps

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$1989.51

/ Nightly
Private Vacation Home

Sea Spray – Ultimate Beach & Boater’s Paradise

Siesta Key, Florida, United States

Summary:brbrSea Spray is an 8BR/6.5BA luxury retreat just steps from Siesta Key Beach with a private dock and resort-style pool . Enjoy a waterslide, grotto, swim-up bar, spa, rooftop deck, game room, and beach views. Walk to Siesta Key Village or head out by boat for the ultimate beach and boating getaway ️⚓✨.brbrbrbrThe Space:brbr Sea Spray – Ultimate Beach & Boater’s Paradise brbr 538 Canal Rd, Siesta KeybrbrbrbrWelcome to Sea Spray, an unforgettable 8-bedroom, 6.5-bathroom luxury retreat just one block from Siesta Key Beach and directly across the street from your private dock ️⚓. Built for entertaining and relaxation, this coastal showstopper features a backyard resort-style waterpark, beach views, a rooftop deck, and endless amenities for the entire group.brbrbrbrStep outside to your private oasis featuring a heated lagoon-style pool with rock waterslide, waterfall, grotto, swim-up bar, sun shelf, and spa. Whether you’re lounging poolside, grilling dinner, or challenging friends to ping pong and foosball, every moment feels like a vacation highlight.brbrbrbrInside, elevator access brings you to an expansive main living level with plush seating, a gourmet kitchen with dual islands, and seamless indoor-outdoor flow to balconies and the rooftop deck—perfect for sunsets, cocktails, and coastal breezes . Walk to the beach, stroll to Siesta Key Village, or head out by boat, kayak, or paddleboard from your dock—this home truly has it all.brbrbrbr✨ Highlights ✨brbrbrbr• ️ Less than 5-minute walk to Siesta Key Beachbrbr• ⚓ Private dock across the streetbrbr• Resort-style heated pool with waterslide, grotto & swim-up barbrbr• In-ground spa & sun shelfbrbr• Rooftop deck with beach viewsbrbr• Perfect for boaters & water loversbrbr• Game room with ping pong & foosballbrbr• BBQ grill, outdoor TV & diningbrbr• ️ Walk to Siesta Key Village dining & shoppingbrbr• Dog friendly (approval & fee)brbr• Elevator accessbrbr• Laundry roombrbrbrbr Bedrooms & Sleeping Arrangements brbrbrbr• Primary (3rd Floor): King bed, private balcony, walk-in closet, ensuite bath with walk-in shower & soaking tubbrbr• 2nd Bedroom (3rd Floor): King bed, shared ensuite bathbrbr• 3rd Bedroom (3rd Floor): Twin-over-Full bunk with twin trundle, shared ensuite bathbrbr• 4th Bedroom (3rd Floor): King bed, balcony access, ensuite bath with walk-in showerbrbr• 5th Bedroom (2nd Floor): King bed, balcony access, ensuite bath with walk-in showerbrbr• 6th Bedroom (2nd Floor): King bed, Jack-and-Jill bath with walk-in showerbrbr• 7th Bedroom (2nd Floor): King bed, Jack-and-Jill bath with walk-in showerbrbr• 8th Bedroom (2nd Floor): Two twin bunk beds, ensuite bath with walk-in showerbrbrbrbrAdditional Sleeping:brbr• Living Room: Sleeper sofabrbrbrbrGuest Access:brbrGuests have full access to the entire home, including a private heated pool/spa and a fully fenced 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 4 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! ✨
Bed 8

Bed

Bath 6

Bath

Sleep 22

Sleeps

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$1617.99

/ Nightly
Private Vacation Home

Bahama Mama | Tropical Retreat on Siesta Key

Siesta Key, Florida, United States

Summary:brbrBahama Mama is a five-bedroom, five-bath island retreat just a five-minute walk to Siesta Key Beach . Enjoy a private tropical backyard with a pool, spa, covered patio, BBQ, and outdoor dining. Inside features coastal décor, a fully equipped kitchen, and ensuite baths for every bedroom. Steps from Siesta Key Village shops and restaurants, this home is perfect for families or groups seeking the ultimate beach getaway! ️✨brbrbrbrThe Space:brbr Bahama Mama | Tropical Pool Retreat Near Siesta Key Beach ️brbr 5227 Calle Menorca, Siesta KeybrbrbrbrWelcome to Bahama Mama, your island escape just a five-minute walk from the sugar-white sands of Siesta Key Beach! ☀️ This five-bedroom, five-bathroom home is designed for laid-back luxury, featuring a private tropical backyard with a sparkling pool, in-ground spa, and a shaded patio perfect for outdoor living. Located steps from Siesta Key Village, you’ll be close to dining, shopping, and endless island fun.brbrbrbrInside, coastal charm meets modern comfort with an open living space, plush seating, and a large TV for movie nights . The fully equipped kitchen shines with stainless steel appliances, a spacious island with seating for six, and a cozy banquette dining area—perfect for meals and memories. Each bedroom offers a private ensuite bath, creating a relaxing retreat for every guest.brbrbrbr✨ Highlightsbrbrbrbr 5-minute walk to Siesta Key Beachbrbr Private pool with in-ground spabrbr Covered patio with TV, BBQ & outdoor diningbrbr Outdoor showerbrbr ️ Near Siesta Key Village dining & boutiquesbrbr All bedrooms feature ensuite bathroomsbrbrbrbr ️ Bedroom DetailsbrbrPrimary Bedroom: King bed, ensuite bath with walk-in showerbrbrSecond Bedroom: King bed, pool access, ensuite bath with walk-in showerbrbrThird Bedroom: King bed, pool access, ensuite bath with walk-in showerbrbrFourth Bedroom: Queen bed, ensuite bath with walk-in showerbrbrFifth Bedroom: Full-over-full bunk bed, ensuite bath with tub/shower combobrbrBonus: Queen sleeper sofabrbrbrbrGuest Access:brbrGuests have full access to the entire home, including a private heated pool/spa and a fully fenced 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 4 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! ✨
Bed 5

Bed

Bath 5

Bath

Sleep 12

Sleeps

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$2019.94

/ Nightly
Private Vacation Home

Summer House | Walk to Beach & Siesta Key Village

Siesta Key, Florida, United States

Summary:brbrSummer House is a spacious 6-bedroom, 6-bath ground-level vacation home just a 2-minute walk to Siesta Key Beach and Village. Enjoy a resort-style pool with spa and waterslide, plus outdoor seating, swings, BBQ, and TV. Inside offers an open living area, full kitchen, and private ensuite bathrooms for every bedroom—perfect for families and group getaways on Siesta Key. ☀️ ️brbrbrbrThe Space:brbr☀️ Summer House | Walk to Beach & Village Paradise ️brbr 99 Avenida Messina, Siesta KeybrbrbrbrWelcome to Summer House, a vibrant ground-level retreat designed for unforgettable island getaways This spacious six-bedroom, six-bath home is just a 2-minute walk to the world-famous white sands of Siesta Key Beach and the lively shops and restaurants of Siesta Key Village. With resort-style outdoor living and room for the whole crew, this home is made for gathering, relaxing, and making memories.brbrbrbrStep outside to your private backyard oasis featuring a show-stopping pool with a grotto, rock waterslide , and soothing spa . Lounge under the covered porch, sway on outdoor swings, or enjoy drinks at the bar-top while watching the outdoor TV . Fire up the BBQ and let the good times roll!brbrbrbrInside, you’ll find a bright, welcoming living space with cozy seating, a large TV, and an open kitchen fully equipped with stainless steel appliances. The island seating and indoor dining area make shared meals and game nights easy and fun. Each of the six bedrooms offers a private ensuite bathroom, TV, and plenty of storage—perfect for families and groups traveling together.brbrbrbr✨ Highlightsbrbr• ️ 2-minute walk to Siesta Key Beachbrbr• ️ 2-minute walk to Siesta Key Villagebrbr• Pool with spa & waterslidebrbr• Spacious outdoor living & entertainment areasbrbr• BBQ grillbrbr• ️ 6 bedrooms / 6 ensuite bathroomsbrbr• TVs in every bedroombrbrbrbr Bedroomsbrbr• Primary Bedroom: King bed, ensuite bath with walk-in shower & double vanitybrbr• Bedroom 2: King bed, ensuite bath with walk-in showerbrbr• Bedroom 3: King bed, ensuite bath with walk-in shower & double vanitybrbr• Bedroom 4: King bed, porch access, ensuite bath with walk-in showerbrbr• Bedroom 5: Two Full-over-Full bunk beds, ensuite bath with walk-in showerbrbr• Bedroom 6: Full-over-Full bunk bed, ensuite bath with tub/shower combobrbrbrbrGuest Access:brbrGuests have full access to the entire home, including a private heated pool/spa and a fully fenced 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 4 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! ✨
Bed 6

Bed

Bath 6

Bath

Sleep 20

Sleeps

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$1416.86

/ Nightly
Private Vacation Home

On The Rocks – Walk to Beach & Siesta Key Village!

Siesta Key, Florida, United States

Summary:brbrOn The Rocks is a 5BR/5BA Siesta Key retreat just steps from the beach and Siesta Key Village . Enjoy a private pool with waterslide, sun shelf, spa, putting green, and covered patio with TV and BBQ ⛳ . With king suites, a bunk room, and walkable dining, shopping, and nightlife, this vibrant getaway is perfect for unforgettable island fun ☀️.brbrbrbrThe Space:brbr On The Rocks – Walk to Beach & Village Fun! brbr 309 Calle Miramar | Siesta KeybrbrbrbrLet the fun begin at On The Rocks, a vibrant 5-bedroom, 5-bathroom island escape located less than a 5-minute walk to Siesta Key Beach and just one short block from Siesta Key Village ️. With a private pool and waterslide, putting green, spa, and stylish indoor-outdoor living, this home is designed for unforgettable vacations with family and friends.brbrbrbrStep inside to a bright, coastal-inspired living space filled with beachy blues and relaxed island décor . The fully equipped kitchen features stainless steel appliances, custom cabinetry, and a stunning dining table perfect for gathering everyone together. The living room opens to a private balcony overlooking the pool—an ideal spot for morning coffee or evening cocktails .brbrbrbrOut back, your private resort-style oasis awaits! Lounge on the sun shelf, zoom down the waterslide, soak in the in-ground spa, or practice your swing on the putting green ⛳. A covered patio with comfy seating, TV, BBQ grill, and outdoor dining makes entertaining effortless. A grassy side yard offers space for kids and pups to play .brbrbrbr✨ Highlights ✨brbrbrbr• ️ Less than a 5-minute walk to Siesta Key Beachbrbr• Private pool with sun shelf, waterslide & in-ground spabrbr• ⛳ Putting green & grassy play areabrbr• Covered patio with TV, BBQ & outdoor diningbrbr• Steps to Siesta Key Village restaurants & shopsbrbr• Dog friendly with approval & feebrbr• Washer & dryerbrbrbrbr Bedrooms brbrbrbr• Primary Bedroom (2nd Floor): King bed, private balcony, ensuite bathroom with walk-in showerbrbr• Second Bedroom (2nd Floor): King bed, ensuite bathroom with walk-in showerbrbr• Third Bedroom (2nd Floor): King bed, ensuite bathroom with walk-in showerbrbr• Fourth Bedroom (2nd Floor): King bed, ensuite bathroom with walk-in showerbrbr• Fifth Bedroom (2nd Floor): Full-over-Full bunk bed with Twin trundlebrbr• Living Room Bonus: Queen sleeper sofabrbrbrbrGuest Access:brbrGuests have full access to the entire home, including a private heated pool/spa and a fully fenced 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 5 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! ✨
Bed 5

Bed

Bath 5

Bath

Sleep 15

Sleeps

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$1668.87

/ Nightly
Condo

Dry Dock | Canal-Front Retreat on Siesta Key

Siesta Key, Florida, United States

Summary:brbrDry Dock is a spacious canal-front townhome just a 2-minute walk to Siesta Key Beach . This 6-bedroom, 6.5-bath retreat sleeps 16 and features a private pool & hot tub, shared dock, rooftop deck with Gulf views, elevator, ping pong table, and included kayak & paddle board . Walk to Siesta Key Village for dining and shopping, then relax in modern coastal comfort—perfect for unforgettable group getaways!brbrbrbrThe Space:brbr Dry Dock | Canal-Front Retreat on Siesta Keybrbr 515 Canal Rd Unit B, Siesta Key, FLbrbrbrbrWelcome to Dry Dock, a stunning canal-front townhome just one short block from the powdery white sands of world-famous Siesta Key Beach ️. Designed for memorable group getaways, this spacious retreat pairs modern coastal style with unbeatable amenities—including a shared dock, rooftop deck with sweeping views, and a private pool and hot tub. With an elevator for easy access and Siesta Key Village only steps away, island living doesn’t get easier than this!brbrbrbr✨ Highlightsbrbrbrbr• Canal-front home with dock accessbrbr• ‍♂️ 2-minute walk to Siesta Key Beachbrbr• ‍♀️ Private pool & hot tubbrbr• Rooftop deck with Gulf viewsbrbr• Dog friendly (w/ approval & fee)brbr• Elevatorbrbr• Ping pong tablebrbr• ️ Professional linen programbrbr• Kayak & paddle board includedbrbrbrbr Inside the HomebrbrbrbrSpread over two residential levels above the garage, Dry Dock comfortably sleeps up to 16 guests with six bedrooms and six and a half bathrooms. The open-concept living room features an oversized sectional—perfect for movie nights or reconnecting after a beach day . Step onto the balcony to sip coffee while watching boats glide by on the canal.brbrbrbrThe fully equipped kitchen shines with stainless steel appliances, generous counter space, and a large island with seating for six. A banquet-style dining table seats 12, allowing the entire group to gather, dine, and celebrate together ️.brbrbrbrOutdoors, paradise awaits —an expansive covered patio with an outdoor bar, TV lounge, and ping pong table, plus a sparkling pool and hot tub surrounded by loungers. Launch a kayak or paddle board right from the dock, or head upstairs to the rooftop deck for sunset cocktails and endless Gulf views .brbrbrbr ️ Bedrooms & Sleeping Arrangements (Sleeps 18)brbrbrbr• Primary Bedroom (2nd Level): King bed, ensuite bath with tub/shower combobrbr• Bedroom 2 (3rd Level): King bed, ensuite with walk-in shower & private balconybrbr• Bedroom 3 (3rd Level): King bed, ensuite with walk-in shower, shared canal-view balconybrbr• Bedroom 4 (3rd Level): King bed, ensuite with walk-in shower, shared balconybrbr• Bedroom 5 (3rd Level): Two twin bunk beds, ensuite bath with tub/shower combobrbr• Bedroom 6 (2nd Level): Full-over-full bunk bed, ensuite bath with tub/shower combobrbrbrbrTraveling with a big group ✨ Rent the neighboring townhome, Salty Dog, just next door! With a mirrored layout and shared location, both homes together can comfortably host larger families or groups while still offering everyone space, privacy, and easy island living.brbrbrbrGuest Access:brbrGuests have full access to the entire home, including a private heated pool/spa and a fully fenced 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 4 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! ✨
Bed 6

Bed

Bath 6

Bath

Sleep 16

Sleeps

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$1361.41

/ Nightly
Condo

Salty Dog | Siesta Key Canal-Front Escape!

Siesta Key, Florida, United States

Summary:brbrSalty Dog is a canal-front Siesta Key retreat just 2 minutes from the beach ️ This 6BR luxury townhome features a private heated pool and spa, rooftop deck with beach views, shared dock with kayaks, and ping pong. Walk to Siesta Key Village, relax in spacious king suites, and enjoy elevator access, dog-friendly stays, and resort-style comfort for the whole family ✨ brbrbrbrThe Space:brbr Salty Dog | Canal-Front Escape Near Siesta Key Beach ️brbr 515 Canal Rd Unit A, Siesta Key, FLbrbrbrbrWelcome to Salty Dog, a luxurious canal-front townhome designed for unforgettable Siesta Key vacations! Just a 2-minute walk to Siesta Key Beach and minutes from Siesta Key Village, this six-bedroom retreat blends beach life, boating fun, and resort-style comfort. Paddle from the dock, relax on the rooftop deck with beach views, or unwind by your private heated pool and spa—this home truly has it all.brbrbrbrInside, enjoy bright coastal style and plenty of space to gather. The main living level features an open great room with plush seating, a large HDTV, and a gourmet kitchen with stainless steel appliances and a spacious dining table for 14—perfect for family meals and celebrations. Sliding doors open to a balcony overlooking the pool and canal, bringing the outdoors in ✨.brbrbrbrThe canal-side backyard invites adventure and relaxation alike, with kayak and paddle board access, a shared dock for fishing, a ping pong table, and sun-soaked outdoor spaces. After a beach-filled day, retreat to thoughtfully designed bedrooms offering comfort, privacy, and room for everyone.brbrbrbr⭐ Highlightsbrbr• Canal-front townhome with shared dockbrbr• ️ 2-minute walk to Siesta Key Beachbrbr• Rooftop deck with beach viewsbrbr• Private heated pool & in-ground spabrbr• Kayak & paddle board with life vestsbrbr• Dog friendly (approval & fee required)brbr• Elevator access to all floorsbrbr• Ping pong tablebrbr• Professional Linen Programbrbrbrbr ️ Bedrooms & Sleeping Arrangementsbrbr• Primary Bedroom (2nd Floor): King bed, private balcony, ensuite with walk-in shower & soaking tubbrbr• Second Bedroom (3rd Floor): King bed, ensuite with walk-in showerbrbr• Third Bedroom (3rd Floor): King bed, ensuite with walk-in showerbrbr• Fourth Bedroom (3rd Floor): King bed, ensuite with walk-in showerbrbr• Fifth Bedroom (3rd Floor): King bedbrbr• Sixth Bedroom (3rd Floor): Full-over-Full bunk bedbrbrbrbrTraveling with a big group ✨ Rent the neighboring townhome, Dry Dock, just next door! With a mirrored layout and shared location, both homes together can comfortably host larger families or groups while still offering everyone space, privacy, and easy island living.brbrbrbrGuest Access:brbrGuests have full access to the entire home, including a private heated pool/spa —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 4 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! ✨
Bed 6

Bed

Bath 5

Bath

Sleep 14

Sleeps

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Exceptional(68)

$1,787

/ Nightly
Private Vacation Home

Sunset Gulf – Luxury Siesta Key Retreat with Pool! Beach Access!

Siesta Key, Florida, United States

Sunset Gulf by Siesta Key Luxury Rental Properties brbrWelcome to Sunset Gulf, an eight bedroom, five and a half bath Siesta Key luxury rental just three houses from the nearest Siesta Key Beach access. This four story coastal retreat features a private heated pool and spa, sweeping Gulf views, multiple balconies, and an elevator connecting every floor. Perfect for large families and multi family vacations, this home offers a refined blend of relaxed coastal living and exceptional proximity to Siesta Key Beach and Siesta Key Village, placing you minutes from island dining, shopping, and the iconic Gulf shoreline. brbrHighlights br• 1-minute walk to Siesta Key Beach br• 8 Bedrooms, 5.5 Bathrooms br• 6 Kings, 1 Twin over Full Bunk with Twin Trundle, 2 Twin over Twin Bunks br• Private Heated Pool with In-Ground Spa br• Private Elevator br• Multiple Private Balconies with Gulf Views br• Indoor Game Room with Ping Pong br• Poolside Bar and TV br• 6 Parking Spaces brbrStep into your private tropical outdoor oasis, designed for both relaxation and fun. The heated pool and in-ground spa are surrounded by ample lounge seating for soaking up the Florida sunshine. A covered patio creates the perfect place for outdoor meals, complete with a dining table, gas grill, spacious seating area, and a poolside bar with fridge, sink, and television. Inside, guests will love the indoor game room, private elevator, and multiple balconies offering peaceful Gulf breezes and sunset views. brbrThe home’s main living level on the second floor features an inviting open concept layout, perfect for gathering with family and friends. A large sectional and loveseat frame the bright living area, complete with a large TV for movie nights. The modern kitchen includes stainless steel appliances, spacious countertops, ample cookware, and bar seating alongside a dining table for shared meals. On the third floor, a stylish lounge offers additional seating and a full bar plus a new PlayStation for entertainment. Sliding doors open to a balcony with wide Gulf views, creating a breezy spot to enjoy morning coffee or sunset cocktails. brbrTwo luxurious primary bedrooms serve as serene retreats, each offering a king bed, private balcony, walk-in closet, and spa like ensuite bathroom featuring a soaking tub, double vanities, and walk-in shower. Four additional king bedrooms provide elevated comfort, including ensuite options with walk-in showers and modern coastal finishes. The two bunk rooms, one with a twin over full bunk and trundle, the other with two twin over twin bunks; are perfect for children and teens. A hall bathroom with walk-in shower, a convenient half bath, and laundry rooms on two levels enhance the overall convenience of the home. brbrRoom Details br-Primary Bedroom (4th Floor): King bed, balcony, ensuite bathroom with walk-in shower and soaking tub, full-size futon br-Second Bedroom (2nd Floor): King bed, balcony, ensuite bathroom with walk-in shower and soaking tub br-Third Bedroom (4th Floor): King bed, ensuite bathroom with walk-in shower and soaking tub br-Fourth Bedroom (3rd Floor): King bed, ensuite bathroom with single vanity and walk-in shower br-Fifth Bedroom (3rd Floor): King bed, shares a hall bathroom with walk-in shower br-Sixth Bedroom (3rd Floor): King bed, shares a hall bathroom with walk-in shower br-Seventh Bedroom (3rd Floor): Twin over Full Bunk with Twin Trundle, shares a hall bathroom with walk-in shower br-Eighth Bedroom (4th Floor): Two Twin over Twin Bunk Beds, shares a hall bathroom with walk-in showerbrbrSunset Gulf includes a private elevator, indoor game room, multiple balconies, a full bar area, and convenient beach access just steps away from the home. Guests will also enjoy being minutes from Siesta Key Village, known for its vibrant dining, ice cream shops, boutiques, and live music. brbrWith its private pool and spa, Gulf view balconies, game room, and unbeatable beach proximity, Sunset Gulf by Siesta Key Luxury Rental Properties delivers the perfect blend of upscale comfort and effortless coastal living. Create unforgettable memories on one of America’s top beaches and enjoy the very best of Siesta Key. brbrBook your stay at Sunset Gulf today and start planning your dream beach getaway! brbr- brThis 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 for your stay. These are professionally laundered at a commercial facility for every guest. brbrThis property does not allow pets. brbr6 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.
Bed 8

Bed

Bath 5

Bath

Sleep 23

Sleeps

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