Vacation Home Rentals By Owner In Siesta Key, FL

$1483.38

The Hummingbird | Located in Siesta Key Village w/ Private Pool, Walk to Beach!

Siesta Key, Florida, United States

The Hummingbird | 6BR/6BA | Sleeps 20 | Private Heated Pool | Heart of Siesta Key Villagebrbr Why You'll Love This HomebrThe Hummingbird is a rare, full-property rental comprised of four charming units—Lantana, Mimosa, Plumbago, and Vinca—creating the ultimate retreat for large families or groups. Featuring 6 private bedrooms, 6 full bathrooms, 4 full kitchens, and your very own private heated pool, this home is steps from both the beach and Siesta Key Village's best restaurants and shops.brbr☀️ Perfect ForbrMulti-family reunions, wedding groups, retreats, or any large gathering looking for the perfect balance of privacy and togetherness in an unbeatable walkable location.brbr Imagine ThisbrStart your day sitting on one of three private balconies or the screened front lanai. Then walk just 0.2 miles to sink your toes into the soft sands of Siesta Key Beach—ranked #1 in the U.S. After a beachside lunch, retreat to your tropically landscaped private pool and relax under swaying palms. With four kitchens and six bedrooms, your group can spread out or come together with ease, creating shared memories without sacrificing personal space.brbr Where Everyone Sleeps (Sleeps 20 Total)br Lantana - Lower Unit (2BR/2BA):br • Bedroom 1: King Bed – Sleeps 2, TVbr • Bedroom 2: King Bed – Sleeps 2, TVbr • Living Room: Queen Sleeper Sofa – Sleeps 2brMimosa - Lower Unit (1BR/1BA):br • Bedroom 1: King Bed – Sleeps 2, TVbr • Living Room: Queen Sleeper Sofa – Sleeps 2brPlumbago - Upper Unit (2BR/2BA):br • Bedroom 1: King Bed – Sleeps 2, TVbr • Bedroom 2: King Bed – Sleeps 2, TVbr • Living Room: Queen Sleeper Sofa – Sleeps 2brVinca - Upper Unit (1BR/1BA):br • Bedroom 1: King Bed – Sleeps 2, TVbr • Living Room: Queen Sleeper Sofa – Sleeps 2brbr Location Highlightsbr • 3-Minute Walk (0.2 mi) to Siesta Key Beachbr • 1-Minute Walk to Siesta Key Village (across from Gilligan's)br • Walkable to live music, cafés, boutiques & bike rentalsbr • 15-Minute Drive to Downtown Sarasotabrbr Home Featuresbr • 6 Bedrooms, 6 Full Bathroomsbr • 4 Full Kitchensbr • 3 Private Balconies + Screened-In Lanaibr • Private Heated Pool (Nov 15–Apr 15)br • 4 Living Rooms w/ Queen Sleeper Sofasbr • In-Unit Laundry in All Unitsbr • Pet-Friendly (Lower Floor Units Only – Confirm When Booking)br • 4 Dining Areas, Outdoor Lounge Furniturebr • Smart TVs, Free WiFibrbrNEED TO KNOW:br The Hummingbird is a combination of 4 individual units:br• Lantana (5251A)br• Mimosa (5251B)br• Plumbago (5251C)br• Vinca (5251D)brbrThese units do not share interior space and are accessed by separate exterior entrances unless the upper and lower access doors are opened between those units. All share access to the private heated pool, screened lanai, and outdoor lounging areas. Your stay is protected by our CottageClean Program, featuring a 6-hour deep clean, 35-point property inspection, and enhanced sanitization to give you full peace of mind. We aim for every guest to walk into a home that feels brand new. pool is heated from November 15 to April 15.

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$602.8

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Private Vacation Home

Plumbago | Prime Location in Siesta Key Village w/ Heated Pool, Walk to Beach!

Siesta Key, Florida, United States

Plumbago | 2 King Suites + Balcony | 0.2 Miles to Siesta Key Beachbrbr Why You'll Love This HomebrPerched above Siesta Key Village, Plumbago offers a peaceful second-floor retreat with two private king suites, a balcony for breezy mornings, and a shared heated pool just steps from white-sand beaches.brbr ‍ ‍ Perfect ForbrSmall families, couples, or close friends seeking comfort, privacy, and walkability in a beachside location.brbr ️ Imagine ThisbrStart your day on the private balcony with fresh coffee and ocean air, then stroll just 0.2 miles to Siesta Key Beach for swimming, shell hunting, or sunbathing on the powder-soft sand. After exploring the Village's local shops and eateries, cool off in the shared heated pool nestled among tropical landscaping. Back home, prep dinner in the full kitchen, stream a movie in the cozy living room, and retreat to two spacious king bedrooms for a restful night.brbr Where You'll Sleepbr- Bedroom 1: King Bed, Ensuite Bath, Second Floor, TVbr- Bedroom 2: King Bed, Shared Bath, Second Floor, TVbr- Living Room: Queen Sleeper Sofabrbr Explore the Areabr- 0.2 miles to Siesta Key Beachbr- 0.1 miles to Siesta Key Villagebr- Steps to dining, beach bars, and boutique shoppingbr- Easy access to bike rentals, live music, and sunset viewsbrbr Don't wait—this home books fast. Every stay is backed by our CottageClean™ Program, including a 6-hour deep clean and 35-point inspection before check-in—so you can arrive stress-free.brbr Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. This home is part of a duplex and may share walls, floor/ceiling, or outdoor spaces. Located on the second floor with front-facing stair access. Heated pool available November 15 – April 15. If any guest has difficulty with stairs, please contact us for alternative accommodations.

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$408.86

/ Nightly

Private Vacation Home

Canal Place Tropical Bungalow -Walk To Siesta Beach & Village - Bring your Pets!

Siesta Key, Florida, United States

SHORT WALK TO THE FAMOUS SIESTA WHITE SAND BEACH & QUAINT ISLAND VILLAGE. brbrEnjoy this ‘Old Florida Charm’ beach cottage. It has two bedrooms (one king and one queen) and two bathrooms (stall shower in one and tub/shower in the other.) The large living room has French doors leading onto a screened-in porch, which overlooks the brick walkway in the gardens. It has a large kitchen and bright dining room surrounded by windows, which have a view of the canal. The master suite has a beautiful bay window for gorgeous views of the gardens and a separate additional entrance for privacy that leads to the outdoor shower. Across the street is the canal and a dock for boating, kayaking, and fishing. It is only a short walk to the famous Siesta Key beach and village for all your shopping needs.brbrPets are welcome with a refundable pet deposit.brbrFor additional availability on Siesta Key please see our other listings:brBlue Lagoon VRBO#1043727 (2B/2B)brFern Haven VRBO#1044027 (Studio)brGarden Terrace VRBO#1043802 (Studio)brTropical Hideaway VRBO#1044034 (2B/1.5B)brLily Patch VRBO#10056 (2B/2B)

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$202.56

/ Nightly

Private Vacation Home

Coastal Canal Retreat- Peaceful Waterfront Stay On Siesta Key

Siesta Key, Florida, United States

Enjoy the best of Siesta Key from this beautifully renovated canal-front vacation home that blends modern comfort with relaxed Old Florida charm. Fully updated throughout, the home features a well-equipped kitchen, stainless steel appliances, quartzite countertops, terrazzo floors, ceiling fans in every room, central air conditioning, a washer and dryer, two televisions, high-speed internet, and updated furnishings throughout.brbrThe home offers two comfortable bedrooms, each with a queen bed. The primary suite overlooks the garden and includes a private ensuite bath with a spacious walk-in shower, along with direct access to a convenient outdoor shower. The second bedroom overlooks the canal, includes a television, and shares a guest bath that also features a walk-in shower. An additional built-in bunk nook provides sleeping space for two more guests.brbrOutdoor living is a highlight, with multiple inviting spaces including a screened front patio, a large screened lanai with grill and dining table overlooking the canal, and a backyard with artificial turf — ideal for relaxing, dining outdoors, or simply enjoying the peaceful waterfront setting.brbrBoating enthusiasts will appreciate the private dock with fishing access and an electric boat lift accommodating vessels up to approximately 25 feet or 13,000 lbs. Guests also have access to bikes, paddleboards, and surfboards for exploring the surrounding area.brbrLocated just minutes from world-famous Siesta Key Beach and vibrant Siesta Key Village, you’ll enjoy easy access to renowned restaurants, live music, shopping, and local events while still returning to a quiet residential setting.brbrSmall pets may be considered with owner approval.brbrImportant Note:brPer Sarasota County ordinance, this property allows one rental per 30-day period.

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$394.15

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Private Vacation Home

Tropical Hideaway Pet-Friendly Bungalow - Walk to Siesta Beach and Village

Siesta Key, Florida, United States

Tropical Hideaway – Your Private Oasis in Siesta KeybrbrEscape to the serene beauty of Siesta Key with a stay at the Tropical Hideaway, a secluded 2-bedroom, 1.5-bath bungalow nestled in the heart of the tranquil Palm Island neighborhood. Just a short stroll from the pristine Siesta Key Beach and the lively Village, this charming retreat offers the perfect blend of relaxation and convenience.brbrbrCharming and Comfortable LivingbrbrStep into a spacious open-concept living area adorned with tile flooring and ceiling fans, creating a cool and inviting atmosphere. The fully equipped kitchen boasts modern appliances, including a microwave, dishwasher, refrigerator, and oven with stovetop, making it ideal for preparing delicious meals.brbrRestful BedroomsbrbrThe master bedroom features a plush king-sized bed, a reclining chair, a TV, and a generous walk-in closet. The second bedroom offers a cozy queen-sized bed and ample closet space, ensuring a restful night's sleep for all guests.brFlorida RentalsbrbrOutdoor ParadisebrbrUnwind in the expansive two-story flagstone lanai, a hidden gem behind a zen gate, perfect for entertaining or simply relaxing. The covered porch houses an outdoor summer kitchen and dining area, seamlessly blending indoor comfort with outdoor living. An outdoor shower adds a touch of tropical luxury.brbrPet-Friendly RetreatbrbrBring along your furry friends! Tropical Hideaway welcomes pets, ensuring that every member of your family can enjoy the vacation.brbrModern AmenitiesbrbrHigh-speed WiFi InternetbrWasher and dryer for your conveniencebrNew HVAC system for optimal comfortbrCeiling fans throughoutbrbrPrime LocationbrbrLocated in a quiet, walkable, and pet-friendly neighborhood, you're never more than a mile away from the beach, restaurants, shopping, nightlife, or activities. Bicycles are provided so you can explore even more of the island.brbrFor additional availability on Siesta Key please see our other listings:brBlue Lagoon VRBO#1043727 (2B/2B)brCanal Place VRBO#1043736 (3B/2B)brFern Haven VRBO#1044027 (Studio)brGarden Terrace VRBO#1043802 (Studio)brLily Patch VRBO#10056 (2B/2B)

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$391.25

/ Nightly

Private Vacation Home

Pool Home w/ Spa, 3 King Beds, Lanais, Walk to Siesta Key Beach & Village Lux Mid-Century

Siesta Key, Florida, United States

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Majestic Coastal Escape – A Luxury Siesta Key Retreat! brbr brbrStep into a world where mid-century sophistication meets coastal serenity. Majestic Coastal Escape is more than just a home; it’s an architectural sanctuary. Featuring a rare triple-King layout, this 2,400 sq. ft. masterpiece boasts vaulted ceilings, exposed beams, and floor-to-ceiling glass that blurs the line between the designer interior and your private tropical oasis—complete with a modern pool and spa. brbr brbrLOCATION HIGHLIGHTS: brbr- Newly renovated mid-century modern home in desirable Siesta Key neighborhood brbr- Short 15-minute walk (0.7 miles) to Siesta Key Beach Access #8 brbr- 1.5 miles to Siesta Key Village for dining, shopping, nightlife, and entertainment brbr- Quiet residential area for privacy and relaxation brbr- Close to powdery white sands and crystal-clear Gulf waters brbr brbrPROPERTY FEATURES: brbr- 3 bedrooms/ 2 bathrooms home (2400+ sq ft) brbr- Private heated pool and spa surrounded by lush tropical greenery (note: pool heat is extra) brbr- Vaulted ceilings, exposed beams, curated artwork, and modern design brbr- Two enclosed lanais for outdoor living and shade brbr- Smart TV with streaming apps, Sonos sound system, high-speed WiFi brbr- Covered carport parking and outdoor BBQ grill brbr brbrLIVING ROOM: brbr- Open-concept living space with floor-to-ceiling glass sliders brbr- Striking decorative stone fireplace brbr- Views of pool and tropical landscaping brbr brbrKITCHEN AND DINING: brbr- Chef’s kitchen with soft-close cabinetry, large farmhouse sink, and high-end appliances brbr- Quartz countertops, ample prep space, and modern finishes brbr- Dining area for 10 guests brbr- Easy access to outdoor lanai for alfresco meals brbr brbrBEDROOMS AND BATHROOMS: brbr- Master bedroom: king bed, en-suite bath, and lanai access brbr- Master ensuite bathroom: spacious vanity, walk-in shower brbr- Second and third bedrooms with king-sized, low-profile beds brbr- Guest bathroom: tub/shower combo with spa styled vanity brbr brbrEXTRA PERKS: brbr- Poolside loungers, multiple seating areas, and outdoor dining for 10 brbr- Screened lanai for shade and privacy brbr- Complimentary beach items provided: a couple of beach chairs, a beach umbrella, and beach towels brbr- Exterior security cameras for added safety brbr brbrLOCAL FAVORITES: brbr-- Siesta Key Beach Access #8 for sunbathing, swimming, and shell-hunting brbr- Sunday night drum circle at the beach brbr- Siesta Key Village for boutique shopping, fine dining, and nightlife brbr- Short drive or free shuttle to the village from the home brbr brbrIMPORTANT INFO: brbr- No pets, no smoking, no parties brbr- Maximum occupancy 6 guests brbr- Pool Heat is optional. Extra fee applies. brbr brbrEXPERIENCE THE BEST OF SIESTA KEY IN THIS LUXURIOUS MID-CENTURY MODERN RETREAT, WHERE RELAXATION AND SOPHISTICATION MEET COASTAL CHARM.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

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$1122.48

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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.

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$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

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$883.81

/ Nightly

Private Vacation Home

Honeysuckle | Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

Siesta Key, Florida, United States

Honeysuckle | 3 King/Queen Bedrooms + Dual Kitchens | 0.2 Miles to Siesta Key Beachbrbr Why You'll Love This HomebrHoneysuckle brings together two ground-level units into one cozy, spacious retreat with dual kitchens, a screened front porch, and a 3-minute stroll to Siesta Key Beach. It's comfort, charm, and location—all in one.brbr ‍ ‍ Perfect ForbrMulti-gen families, couples traveling together, or small groups seeking flexible space and walkability in the heart of Siesta Key Village.brbr ️ Imagine ThisbrStart your day on the screened front porch as island life stirs around you. Head just 0.2 miles to the beach for a morning swim, or take a short walk into Siesta Key Village for local breakfast and boutique browsing. Spend your afternoon lounging by the heated pool surrounded by lush palms, then return home to prep dinner in one of two fully equipped kitchens. At night, everyone has their own quiet corner to unwind—whether it's watching a movie in one of two living rooms or resting in a private bedroom. Honeysuckle is all about flow, comfort, and connection.brbr Where You'll Sleepbr- Bedroom 1 (Lantana): King Bed, Ensuite Bath, TVbr- Bedroom 2 (Mimosa): King Bed, Shared Bath, TVbr- Bedroom 3 (Lantana): Queen Bed + Twin Bunk Bed, Shared Bath, TVbr- Living Room (Lantana): Queen Sleeper Sofabr- Living Room (Mimosa): Queen Sleeper Sofabrbr Explore the Areabr- 0.2 miles to Siesta Key Beachbr- 0.1 miles to Siesta Key Villagebr- Walk to beach bars, live music, and coastal cafésbr- Easy access to bike rentals, sunset cruises & paddle boardingbrbr Don't wait—this home books fast. Your reservation is backed by our CottageClean™ Program, featuring a 6-hour deep clean and 35-point inspection for total peace of mind.brbrNEED TO KNOW: This home is a part of a duplex unit, meaning that it could share a dividing wall, floor, ceiling, outdoor space, and/or amenities with another unit(s). This group of units is located on the first floor of the property, accessible by doors on both sides of the property. This pool is heated from November 15th to April 15th. Contact us directly for more information regarding any shared space for this vacation property.

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Bath

Sleeps

$728.14

/ Nightly

Private Vacation Home

PALM OASIS Location! Location! - 4 min walk to Beach, short stroll to Village

Siesta Key, Florida, United States

Newly remodeled pool home. Your home away from home is a perfect blend of luxury, comfort, and convenience- just steps from the soft, powdery sand of Siesta Key Beach - named #1 in the US and #4 in the world.brThis home is well suited for a multi generation family or 2 familiesbrThe large outdoor living space is a true oasis and includes a salt water pool with travertine pool deck, gas grill, bar with bar stools, outdoor shower, and plenty of seating both in the sun and shade. Covered lanai is equipped with ceiling fans.brQuiet, safe location, central to where you want to be. Beach access 11 (lifeguarded) is less than a 5 min walk.You can take advantage of having a lifeguard, yet this beach access is not very crowded because it is not near the beach parking lot.br Easy walk to Siesta Key Village for restaurants, shopping, live music, or take the free trolley that traverses the entire Key. Trolley stop is at beach access (4 min walk)brSpend your vacation without the hassle of traffic and looking for a parking space.brRelax at the beach during the day, then swim and lounge in the privacy of your own pool.brLiving area in the center of the home is open concept where everyone can gather - invites you to unwind and enjoy the company of your loved ones: If you are on kitchen duty:20 ft sliding doors bring in the outdoors so you won't miss a thing happening outside. brState of the art fully equipped kitchen with quartz counter tops and stainless steel appliances.brTwo bedrooms are located on each end of the living area so two families can each have their own space when desired.brFast Internet-br75 inch TV in living room with You Tube TV (64+ channels) . Each bedroom has a Roku TV for streaming.brbrBeach wagon, sand chairs, beach cooler and beach towels provided.brKeurig Duo coffeemaker, so make a whole pot or use K cupsbrbrNew listing for VRBO- to see reviews from previous platform, search the web for Palm Oasis Siesta Key, heading says Safe &Clean Palm Oasis

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$556.09

/ Nightly

Private Vacation Home

Luxurious Sarasota Home with Pool

Siesta Key, Florida, United States

Summary:brbrEscape to luxury in our serene Sarasota home! - 3 spacious bedrooms with modern comforts - Private pool and hot tub for relaxation - Fully-equipped kitchen and elegant dining area - Comfortable lounge with large flat-screen HDTV - Spacious backyard with BBQ grill and free bikes - Prime location, just a 3-min drive to Siesta Beach - Experience a High-End Vacation Getaway in Sarasota! - Free parking and EV charger available.brbrbrbrThe Space:brbrEscape to luxury in our serene Sarasota home! Relax in your private oasis with a sparkling pool, hot tub, and expansive backyard. Enjoy the open-concept living area and three cozy bedrooms designed for ultimate comfort. brbrbrbrExperience a High-End Vacation Getaway in Sarasota! This stunning home offers a blend of luxury, comfort, and convenience, perfect for families and groups looking to enjoy the best of Sarasota. With a private pool, hot tub, and prime location, you’ll have everything you need for a memorable stay.brbrbrbrComfortable Accommodation:brbr- 3 Spacious Bedrooms:brbr - Primary Bedroom: King-sized bed, skylight, desk, reclining chair, and a large flat-screen HDTV with streaming services.brbr - Second Bedroom: Cozy queen-sized bed with backyard views.brbr - Nautical Room: Two comfortable full-sized beds and a wall-mounted TV.brbrbrbrInterior Feeling:brbr- 2 Modern Bathrooms:brbr - Both bathrooms feature walk-in showers, beautiful tilework, and are stocked with fresh towels and hair dryers.brbr- Fully-Equipped Kitchen:brbr - Stainless steel appliances, bar-style island, wrap-around countertops, and all the essentials for a home-cooked meal.brbr- Comfortable Lounge Area:brbr - Large flat-screen HDTV with streaming services, natural light from skylights, and a relaxing space for everyone to unwind.brbr- Dedicated Workspace:brbr - High-speed WiFi and a desk for remote work or planning your vacation activities.brbrbrbrOutdoor Bliss:brbr- Resort-Style Outdoor Space:brbr - Private Pool + Hot Tub: Perfect for relaxation and enjoyment.brbr - BBQ Grill + Outdoor Dining Area: Ideal for outdoor meals.brbr - Sunny Patio with Loungers: Perfect for sunbathing or reading a book.brbr - Spacious Fully-Fenced Backyard: Great for family fun and games.brbr - Free Bikes: Explore the local area and nearby beaches.brbrbrbrDelightful Dining:brbr- Spacious Indoor Dining Area:brbr - Elegant six-seater dining table for family meals and gatherings.brbrbrbrProfessional Cleaning:brbr- Free Parking + EV Charger:brbr - Convenient parking options and electric vehicle charging.brbrbrbrPrime Location:brbr- 3 Min Drive to Siesta Beachbrbr- 10 Min Drive to Crescent Beachbrbr- 13 Min Walk to a Local Beachbrbr- Easy access to Siesta Key Village and local restaurants.brbrbrbrWhy You’ll Love Staying Here:brbr- Private Pool and Hot Tub: Perfect for relaxation and family fun.brbr- Modern Comforts: Enjoy high-speed WiFi, a large flat-screen TV with streaming services, and a fully-equipped kitchen.brbr- Convenient Location: Quick access to Sarasota’s best beaches and local attractions.brbr- Family-Friendly: Spacious backyard, BBQ grill, and free bikes for exploring.brbrbrbrBook Your Stay at This Gorgeous Sarasota Home Today!brbrbrbrGuest Access:brbrThe entire property is exclusively yours during your stay, so relax and make yourself at home. You will have access to the entire house, backyard, pool, and all listed amenities. In addition to the spaces mentioned above, your stay includes:brbr • High-Speed Wi-Fibrbr • Free on-site parking & an EV Chargerbrbr • Complimentary Bicycles & a Kayakbrbr • Private Laundry Room with Washer & Dryerbrbr • Air Conditioning & Heatingbrbr • Children's Amenities (Crib, High Chair, Pack & Play, etc.)brbrbrbrThe Neighborhood:brbrExperience the Best of Siesta Key!brbrbrbrYour perfect Siesta Key vacation rental. Our property offers not just a fantastic home but also a prime location for exploring the stunning beaches and local attractions that make Siesta Key a top destination. Discover what makes our neighborhood so special!brbrbrbr ️ Just a 3-Min Drive to Siesta Key Beach!brbrEnjoy the famed Siesta Key Beach with its powdery white sand and crystal-clear waters in just a 3-minute drive from our property. Whether you're in the mood for a relaxing day on the beach, a swim in the Gulf, or a beachside picnic, Siesta Key Beach has it all.brbrbrbr ️ 10 Minutes to Crescent BeachbrbrExplore the serene beauty of Crescent Beach, just a 10-minute drive away. This beach offers gorgeous views, great swimming, and a more tranquil setting compared to the more popular beaches.brbrbrbr ‍♂️ 13-Min Walk to a Local BeachbrbrFor those who prefer to walk, you can reach a local beach in just 13 minutes on foot. Perfect for a leisurely stroll to enjoy the sun, sand, and sea whenever you like.brbrbrbr ️ Discover Local Dining & ShoppingbrbrSiesta Key Village is just a short drive away, offering an array of local restaurants, cafes, and boutiques. Savor fresh seafood, enjoy gourmet meals, or browse through unique shops and local crafts.brbrbrbr ‍♂️ Explore Scenic Paths & TrailsbrbrTake advantage of the bikes provided to explore the scenic paths and trails around Siesta Key. Enjoy a leisurely bike ride through the friendly neighborhood or venture out to discover new parts of the island.brbrbrbr Breathtaking SunsetsbrbrDon’t miss the chance to witness the stunning sunsets over the Gulf of Mexico. Find a cozy spot on the beach or a waterfront café and be mesmerized by the colorful skies as the sun dips below the horizon.brbrbrbr ‍♂️ Family-Friendly Fun & RelaxationbrbrOur neighborhood is perfect for families with activities like kayaking, paddleboarding, and shell hunting. Plus, our property features a private swimming pool and hot tub for relaxation after a day of fun.brbrbrbr Explore Nature & WildlifebrbrVisit the nearby Siesta Key Tropical Gardens and explore local wildlife and native plants. It’s a great way to connect with nature and enjoy the natural beauty of Siesta Key.brbrbrbr Convenient Access to SarasotabrbrWith easy access to major roads, you can also explore the wider Sarasota area and enjoy attractions such as museums, arts venues, and more.brbrbrbrWhy Stay with us brbr ️ 3-Min Drive to Siesta Key Beachbrbr ️ 10 Minutes to Crescent Beachbrbr ‍♂️ 13-Min Walk to a Local Beachbrbr ️ Vibrant Dining & Shopping in Siesta Key Villagebrbr ‍♂️ Scenic Biking & Walking Pathsbrbr Stunning Sunsets Over the Gulfbrbr ‍♂️ Private Pool & Hot Tubbrbr Explore Nature & Wildlifebrbr Easy Access to Sarasota AttractionsbrbrbrbrBook Your Siesta Key Escape Today!brbrbrbrGetting Around:brbrGetting Around Siesta Key!brbrbrbrOur prime location in Siesta Key offers you a variety of convenient and enjoyable ways to get around and explore the best of the area. Here’s everything you need to know about getting around during your stay:brbrbrbr Driving & ParkingbrbrFree Parking: Enjoy free parking at our property for your convenience.brbrEV Charger: We offer an EV charger for electric vehicles to keep your car charged and ready for your adventures.brbrbrbrLocal Attractions: Many of Siesta Key’s top attractions are just a short drive away, including Siesta Key Beach (3 minutes), Crescent Beach (10 minutes), and Siesta Key Village (5 minutes).brbrbrbr ‍♂️ Biking Around Siesta KeybrbrBikes Provided: We provide bikes for guests to use. Explore the scenic bike paths, nature trails, and charming streets of Siesta Key.brbrBike to the Beach: It’s an easy and enjoyable ride to Siesta Key Beach and local shops.brbrbrbr ‍♂️ Walking DistancebrbrLocal Beach: Take a 13-minute walk to a local beach for a relaxing day by the water.brbrSiesta Key Village: A short drive or a pleasant bike ride away, this vibrant area offers dining, shopping, and entertainment.brbrbrbr Public TransportationbrbrSiesta Key Breeze Trolley: The Siesta Key Breeze Trolley is a free service that offers stops around the island, including popular spots like Siesta Key Beach and Siesta Key Village. The nearest stop is just a short walk from the property.brbrSarasota Public Transit: For broader travel options, Sarasota County Area Transit (SCAT) offers bus routes connecting Siesta Key to the Sarasota mainland and surrounding areas.brbrbrbr Ride-Sharing ServicesbrbrConvenient Ride-Sharing: Services like Uber and Lyft are readily available for quick trips around Siesta Key and to Sarasota for dining, shopping, and entertainment.brbrbrbr Car RentalsbrbrCar Rental Options: If you need a rental car, there are several car rental agencies in the Sarasota area, including at the Sarasota-Bradenton International Airport (10 miles away).brbrbrbr Explore Beyond Siesta KeybrbrNearby Attractions: Use your rental car or ride-sharing to explore Sarasota and nearby destinations, including the Ringling Museum, St. Armands Circle, and Selby Gardens.brbrbrbr Local Tips & RecommendationsbrbrBeach Parking: Arrive early to find the best parking spots at Siesta Key Beach.brbrBike Safety: Wear a helmet and follow local biking regulations to stay safe while exploring.brbrPublic Transport: Check the Siesta Key Breeze Trolley schedule for current routes and times.

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$540.26

/ Nightly

Private Vacation Home

Casita Sun Star | Pet Friendly Home on Siesta Key, Heated Pool, Walk to Beach & South Village!

Siesta Key, Florida, United States

Casita Sun Star | A Siesta Key Gem with Private Pool + Walk to Beach & Villagebrbr Why You'll Love This HomebrCasita Sun Star is a vibrant and sunny retreat on Siesta Key, just 0.2 miles from Crescent Beach and steps from dining and shops in Crescent Village. With its own private heated pool, spacious layout, and bright, coastal vibes, this home offers an authentic island escape just minutes from it all.brbr ‍ ‍ Perfect ForbrPerfect for families, couples, or small groups looking for a single-level home with a private yard and pool, pet-friendly perks, and walkable access to Southern Siesta Key's best beaches and bites.brbr ️ Imagine ThisbrWake up to a soft breeze coming through your screened front porch and sip coffee before strolling just 0.2 miles to Crescent Beach. After a morning at the shore or snorkeling at Point of Rocks, return home to your fully fenced backyard and unwind in your private heated pool, surrounded by palms and privacy. Cook up something delicious in the fully equipped kitchen or grill under the stars. With 3 bedrooms and 3 full bathrooms, there's plenty of room for everyone to spread out and enjoy the sunshine.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Ensuite Bath, TVbr• Bedroom 2: King Bed, Shared Ensuite Bath, TVbr• Bedroom 3: Two Full Beds, Shared Hall Bath, TVbr• Queen Sleeper Sofa: Located in Living Room – Sleeps 2brbr Explore the Areabr• 0.2 Miles to Crescent Beach Access #13br• 0.3 Miles to Point of Rocks Snorkeling Spotbr• 0.2 Miles to Crescent Village (Restaurants, Shops, Bars)br• 1.2 Miles to Siesta Key Public Beach Accessbr• 1.8 Miles to Siesta Key Villagebr• Walk to Cafés, Bike Rentals, Boat Launches, and Live Musicbr• Located in a Peaceful, Walkable Southern Siesta Key Neighborhoodbrbr⌛ Don't WaitbrWith a private pool, fenced yard, pet-friendly policy, and accommodations for up to 10 guests, Casita Sun Star delivers the relaxing island experience you've been dreaming of. Your stay includes our CottageClean™ protocol—a 6-hour deep clean plus a 35-point inspection—so you can check in with complete confidence.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 unit with a shared wall but no shared amenities. Dog-friendly with a 25-pound limit and pet fee. When renting this unit, you will have access to a private fenced backyard and pool area along with access to the home from Crescent St. The pool is heated between November 15 – April 15.

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$591.11

/ Nightly

Private Vacation Home

Villa De Paradisio | Waterfront Home w/ Private Pool, Fishing Dock, Close to Beach & Village!

Siesta Key, Florida, United States

Villa De Paradisio | Heated Pool, Canal Access, 0.6 Miles to Siesta Key Beachbrbr Why You'll Love This HomebrExperience waterfront bliss with a heated pool, lush tropical landscaping, and seamless canal access. Stylish coastal interiors blend modern comfort with relaxed island vibes just minutes from Siesta Key Beach and Village.brbr ‍ ‍ Perfect ForbrFamilies and groups up to 12 seeking upscale relaxation, outdoor adventures, and easy beach access.brbr ️ Imagine ThisbrYou wake to golden sunlight filtering through palms, the gentle splash of water from your private canal dock nearby. Spend your days kayaking through peaceful waterways, cooling off in your heated pool, or sharing laughter-filled dinners under the covered porch's shaded retreat. Evenings invite cozy movie nights in plush seating or stargazing from the tropical backyard oasis.brbr Where You'll Sleepbr• Bedroom 1: King Bed, First Floor, Ensuite Bath, TVbr• Bedroom 2: Two Twin Beds, Second Floor, Shared Bath, TVbr• Bedroom 3: King Bed, Second Floor, Ensuite Bath, TVbr• Bedroom 4: Four Twin Beds, Second Floor, Shared Bathbr• Living Room: Queen Sleeper Sofabrbr Explore the AreabrWalk 12 minutes to Siesta Key Beach's pristine white sand and turquoise Gulf waters. Stroll 5 minutes to Siesta Key Village for boutique shopping, dining, and nightlife. Your vacation hub combines island charm with vibrant local flavor.brbr⌛ 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 for your safety and comfort.brbr PLEASE NOTE: There is a 1 rental per 30 day period, per Sarasota, FL ordinance, contact us for more information. Reservation must follow under the accordance of the Sarasota County code regulations. This pool is heated from November 15th to April 15th.

Bed

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Sleeps

$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.

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$1040.81

/ Nightly

Private Vacation Home

Monarch Villa | Ocean Views, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!

Siesta Key, Florida, United States

Welcome to Monarch Villa – Your Ideal Siesta Key GetawaybrbrDiscover the perfect vacation retreat at Monarch Villa, an exquisite property offering the flexibility to tailor your stay to your exact needs. Part of the Casa De Mariposa duplex, Monarch Villa can be rented separately for a more intimate experience or as part of the entire property for larger groups. Whatever your plans, this remarkable villa has everything you need to enjoy the best of Siesta Key.brbrSpacious, Stylish AccommodationsbrThis beautifully appointed vacation home features three spacious bedrooms and three full bathrooms, ensuring comfort and privacy for all guests. With two king beds, two twin beds, and a sleeper sofa, Monarch Villa accommodates up to 8 guests. Every room is designed with high-quality linens and coastal touches to ensure a restful and relaxing stay.brbrBreathtaking Gulf Views & Outdoor LivingbrStep out onto one of the villa's four private balconies and experience stunning Gulf views and the refreshing coastal breeze. The second and third-floor balconies offer sweeping beach-facing views, perfect for savoring the natural beauty of Siesta Key and enjoying a morning coffee or evening sunset. These outdoor spaces create a seamless connection between your indoor retreat and the natural beauty that surrounds you.brbrFully Equipped Kitchen & DiningbrThe full kitchen at Monarch Villa is ideal for preparing delicious meals during your stay. Whether you're whipping up a quick breakfast or enjoying a home-cooked dinner with friends and family, you'll find all the essentials you need to make your time in the kitchen a breeze. The open layout makes it easy to share moments with your loved ones while cooking and dining together.brbrPrivate Cabana Room & Shared Heated PoolbrDownstairs, enjoy the luxury of your own private cabana room that leads directly to the shared heated pool and outdoor lounging area. This relaxing oasis is perfect for taking a refreshing dip, lounging by the poolside, or making unforgettable memories in the sunshine. The pool area is meticulously maintained and offers a welcoming space for relaxation.brbrFor added fun, Monarch Villa provides a ping pong table in the 2-car garage, ensuring plenty of entertainment for guests of all ages.brbrPrime Location – Steps from Siesta Key Beach & VillagebrThe location of Monarch Villa simply cannot be beat. Just steps from Siesta Key Beach, you'll have easy access to the powder-soft sand and crystal-clear waters of one of Florida's most famous beaches. Whether you're swimming, sunbathing, or simply walking along the shore, the beach is your backyard.brbrAdditionally, Monarch Villa is less than half a mile from Siesta Key Village, a vibrant hub of dining, shopping, and entertainment. From delicious restaurants to quirky boutiques, the village offers everything you need for a memorable vacation.brbrIdeal for Families & GroupsbrWhether you choose to rent Monarch Villa separately or as part of Casa De Mariposa, this beautiful property is perfect for family getaways, reunions, or group vacations. With spacious accommodations, unbeatable amenities, and a prime location, Monarch Villa offers a welcoming and luxurious base for exploring all that Siesta Key has to offer.brbrBook Your Siesta Key Stay at Monarch VillabrReady to experience the best of Siesta Key Monarch Villa offers the perfect balance of luxury, comfort, and location. With stunning Gulf views, private pool access, and proximity to both the beach and the village, your dream vacation awaits. Book your stay today and create lasting memories at Monarch Villa.brbrExclusive Amenities Include:br• Semi Private Heated Pool (when renting both units, pool is private)br• Breathtaking Gulf Views on the 2nd & 3rd floor balconiesbr• Less than .5 miles to Siesta Key Villagebr• Less than 20 ft to Siesta Key Beachbr• Duplex Unit, Access to Left Side of Buildingbr• 3 Bedrooms (All Master Bedrooms), 3 Full Bathsbr• 2 King Beds, 2 Twin Beds, 1 Sleeper Sofa (Sleeps 8) with linens providedbr• 4 Spacious Balconiesbr• Ping Pong Tablebr• Private 2 Car Garagebr• Free WiFi & 5 HDTV'sbr• Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, and Kitchen Essentials Providedbr• Starter Pack of Toiletry Essentials Included - Shampoo, Conditioner, Hand / Face Soap, Body Lotion, & Makeup Wipesbr• Starter Pack of Home Essentials Included - Dish Soap, Dish Sponge, Dishwasher Tablets, Laundry Tablets, & Cleaning Wipesbr• Beach Towels, Chairs, Cooler, & Caddy Providedbr• Private Cabana Roombr• Gas Grillbr• 4 Bikesbr• Enhanced cleaning protocols provided by our CottageClean Teambr• Island Shuttle Transportation AvailablebrbrMonarch Villa can accommodate up to 8 guests with a bedding configuration as follows:brbr• Bedroom # 1: King Bed (1) - Sleeps: 2br• Bedroom # 2: King Bed (1) - Sleeps: 2br• Bedroom # 3: Twin Bed (2) - Sleeps: 2br• Living Room: Sleeper Sofa (1) - Sleeps: 2brbrWe go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol within our CottageClean Program. After our six hour in-depth cleaning of your home, we complete a 35 point property inspection to ensure that you feel tremendously safe and happy with this amazing home. This allows you to vacation worry free regarding the cleanliness of your home and truly relax as soon as you arrive. Our goal is to have you feel like you are walking into a brand new vacation home that no one has ever stayed at before!brbrNEED TO KNOW: This home is a part of a duplex unit, meaning that it could share a dividing wall, floor, ceiling, outdoor space, and/or amenities with another unit(s). When renting this unit, you will have access to the pool area along with the left side of the building (facing from Calle Del Invierno) which includes the first, second, and third floors. This pool is heated from November 15th to April 15th. Contact us directly for more information regarding any shared space for this vacation home.brbrThis home has stairs. If any member of your party has difficulty with stairs, please contact us to discuss alternative accommodations.

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$887.12

/ Nightly

Private Vacation Home

La Contento Casa | Pet Friendly, Waterfront Home on Siesta Key w/ Private Heated Pool & Kayaks!

Siesta Key, Florida, United States

La Contento Casa | Private Heated Pool, Walk to Siesta Key Village and Beachbrbr Why You'll Love This HomebrAwaken to sun-drenched mornings and tranquil canal views in this inviting waterfront retreat. La Contento Casa offers a seamless blend of indoor comfort and outdoor serenity, promising an escape where every moment feels like a breath of fresh air.brbr ‍ ‍ Perfect ForbrFamilies seeking a memorable beach vacation, couples desiring a peaceful waterfront escape, or small groups looking for a comfortable and convenient base to explore Siesta Key.brbr ️ Imagine ThisbrYour day begins with a gentle breeze drifting in as you relax on your covered back porch, watching the palms sway. After a leisurely breakfast prepared in the gourmet-grade kitchen with its convenient window pass-through to the patio, you gather your beach essentials—provided for your convenience—and take the short, invigorating 10-minute walk to Siesta Key Beach, feeling the world-famous white sands beneath your toes.brbrBack at La Contento Casa, the private heated pool is waiting, followed by an afternoon lounging by the water, perhaps with a drink crafted at your outdoor bar with sink. As evening approaches, the scent of a home-cooked meal fills the air, enjoyed alfresco with the canal views as your backdrop. Later, unwind in the spacious living area, sharing stories and laughter, before drifting off to sleep in one of the comfortable king beds, dreaming of another perfect day in paradise.brbr Where You'll Sleepbr- Bedroom 1: King Bed, shared bath, main floor, TV br- Bedroom 2: King Bed, shared bath, main floor, TV br- Bedroom 3: Two Twin Beds, shared bath, main floor, TV br- Bonus Room: Two Rollaway Beds, located in common areabrbr Explore the AreabrDiscover the best of Siesta Key with ease. 0.4 miles to Siesta Key Beach, renowned for its crystal-white quartz sand. Enjoy a delightful stroll or quick drive to Siesta Key Village (1.4 miles), offering an array of charming boutiques, diverse dining options, and vibrant coastal energy.brbr Your Siesta Key Escape AwaitsbrDon'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.brbrNeed to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Free High-Speed WiFi. This pool is heated between November 15 - April 15. Please note: There is 1 rental per 30 day period, per Sarasota, FL ordinance. Contact us for more information. Reservation must follow under the accordance of the Sarasota County code regulations.

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Sleeps

$1480.04

/ Nightly

Private Vacation Home

Casa Mahalo | Pet Friendly, Ping Pong Table, Private Heated Pool, Steps to Beach!

Siesta Key, Florida, United States

Casa Mahalo | Top-Floor Luxe Retreat Steps from Siesta Key Beachbrbr Why You'll Love This HomebrPerched high above the palms, Casa Mahalo delivers an elevated island experience just a 2-minute walk from Siesta Key Beach. This third-floor sanctuary blends tropical elegance with breezy, sunlit spaces—and features a private heated pool and cabana for unforgettable outdoor living.brbr ‍ ‍ Perfect ForbrFamilies, couples, or friends seeking an upscale beach escape with walkable access to Siesta Key Village.brbr ️ Imagine ThisbrStart your day on the oversized balcony with ocean-kissed breezes and a fresh cup of coffee. After a leisurely walk to the powdery white sands of Siesta Key Beach, return for a dip in your private heated pool or relax in the cabana lounge with a chilled drink. Inside, the open-concept kitchen and living area provide a stylish backdrop for group dinners or game nights. When the sun sets, toast to another perfect day under the starry island sky before retreating to your plush king suite for a restful night.brbr Where You'll Sleepbr• Bedroom 1: King Bed + Twin Chair Sleeper, Ensuite Bath, TVbr• Bedroom 2: King Bed, Shared Bath, TVbr• Bedroom 3: King Bed, Shared Bath,TVbr• Bedroom 4: Queen Bed + Twin Rollaway, Shared Bath, TVbr• Extra Sleeping: Queen Sleeper Sofa in Living RoombrTotal: 4 Bedrooms | 3 Bathrooms | Sleeps up to 12brbr Explore the Areabr• 0.1 miles (2-minute walk) to Siesta Key Beachbr• Steps from Siesta Key Village dining, music, and nightlifebr• 4.5 miles to Downtown Sarasota for art, culture, and diningbr• 6.5 miles to St. Armands Circle for boutique shopping and coastal charmbrNo car required—everything you need is within walking distance.brbr⌛ Don't WaitbrCasa Mahalo books quickly! Your stay includes CottageClean™, our 6-hour deep clean and 35-point inspection for a spotless, like-new experience.brbrNeed to Know: This home occupies the entire 3rd floor of a luxury duplex. Two garage spaces on the 1st floor (left side only). Shared structure, but private pool and backyard for your unit. The pool is heated November 15 – April 15. This property requires stair access. Contact us for alternatives if mobility is a concern.

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$674.11

/ Nightly

Private Vacation Home

Serenity Cottage | Multilevel Home on Siesta Key w/ Private Pool & Spa, Short Walk to Beach!

Siesta Key, Florida, United States

Serenity Cottage | Heated Pool & Spa + 2‑min Walk to Crescent Beachbrbr Why You'll Love This HomebrSunlight fills every corner of this stylish duplex retreat as you step in, with a private heated pool & spa, screened outdoor dining, and balconies that offer calm ocean breezes.brbr ‍ ‍ Perfect ForbrFamilies, small groups, and multi‑generational guests seeking peaceful coastal access, modern design, and a touch of luxury in a serene setting.brbr ️ Imagine ThisbrStart your morning with coffee on the balcony overlooking lush greenery. After brunch, stroll just 0.1 miles to Crescent Beach or take a short drive to Siesta Key Village. Return to slip into your heated pool, then fire up the gas grill in the screened patio. Evenings come alive with movies on one of four HDTVs or spa time under a starlit sky.brbr Where You'll SleepbrBedroom 1: King Bed, Ensuite Bath, TVbrBedroom 2: Queen Bed, Shared Bath, TVbrBedroom 3: Twin‑Over‑Full Bunk Bed, Shared Bath, TVbrbr Explore the Areabr• 0.1 miles to Crescent Beach – Quiet shoreline and seashell walksbr• Short drive to Siesta Key Beach – Powdery white sands & turquoise watersbr• Near Siesta Key Village – Dining, boutiques, live music & coastal energybr• Residential area with easy walkability and coastal charmbrbr Don't Wait - This coastal sanctuary books quickly. Your reservation includes our CottageClean™ program: a 6‑hour deep clean and 35‑point inspection, so you can arrive with peace of mind.brbrNeed to Know: Shared Space Note: This home is part of a duplex. You'll have access to your private backyard and pool area, while potentially sharing walls or outdoor walkways with the adjacent left-side unit. The pool and spa are heated between November 15 and April 15. Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights.

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$762.79

/ Nightly

Private Vacation Home

Sol y Mar | Pet Friendly, Siesta Key Duplex Home w/ Pool Access, Private Beach Access Included!

Siesta Key, Florida, United States

Sol Y Mar | Private Duplex Near Siesta Key Beach - Two Casitas, One Island Escape, Walk to Siesta Key's Crescent Beach, HOA Poolbrbr Why You'll Love This HomebrSol Y Mar offers a rare island setup with two private casitas side by side, ideal for groups who want togetherness without sacrificing space. Walk to Siesta Key's Crescent Beach, relax by the HOA pool, and enjoy breezy outdoor living in South Siesta Key.brbr ‍ ‍ Perfect ForbrMulti-family groups, friends traveling together, snowbirds, and pet lovers looking for walkable beach access and flexible living space.brbr ️ Imagine ThisbrYou cross the Siesta Key bridge and feel the pace slow. Mornings begin with coffee on the patio. Barefoot walks lead to powdery white sand and calm Gulf water. Afternoons drift between the beach and pool. Evenings end grilling outdoors as the sun sets and island breezes roll in.brbr Where You'll SleepbrCasita Marbr• Bedroom 1: Queen Bedbr• Bedroom 2: Two Twin BedsbrCasita Solbr• Bedroom 3: Queen Bedbr• Bedroom 4: Two Twin Bedsbrbr Explore the Areabr• 0.1 miles to Crescent Beach – Quieter section of Siesta Key with powder-white sandbr• 0.1 miles to Crescent Village (South Village) – Dining, bars, and island essentialsbr• 0.3 miles to Point of Rocks – Top snorkeling spot with clear water and marine lifebr• 2.3 miles to Siesta Key Beach – Public beach with amenities and wide shorelinebr• 2.5 miles to Siesta Key Village – Shopping, restaurants, nightlife, and eventsbr• Free Siesta Key Trolley – Easy island-wide transportation from South Village stopsbrbr About Siesta Key's Crescent Beach (Local Favorite)brCrescent Beach is one of Siesta Key's three main beaches, along with Siesta Beach and Turtle Beach, sharing the island's famous powdery white sand. Part of Siesta Key Beach, it's known for a more relaxed, less crowded vibe, with excellent shelling, swimming, and snorkeling at Point of Rocks. This Siesta Key beach feels quieter and more private—perfect for guests who prefer a serene beach experience.brbr⌛ 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: Sol Y Mar is a duplex property made up of two side-by-side units. When reserving the full property, you'll enjoy exclusive use of both interiors. Outdoor areas, the HOA pool, and some exterior spaces may be shared per community guidelines. Beach chairs and umbrella available through Calini Beach Club. Contact us directly for more information regarding any shared space for this vacation home. Dog-Friendly With a Fee (1 dog up to 25lbs).

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$386.07

/ Nightly

Private Vacation Home

Casita Sol | Pet Friendly, Siesta Key Duplex Home w/ Pool & Private Beach Access Included!

Siesta Key, Florida, United States

Casita Sol | Walk to Siesta Key's Crescent Beach, HOA Pool, Easy Island Livingbrbr Why You'll Love This HomebrCasita Sol delivers relaxed island comfort with a location that makes beach days effortless and dining walkable. Everything you love about Siesta Key is right outside your door.brbr ‍ ‍ Perfect ForbrCouples, small families, snowbirds, and pet travelers seeking a quiet beach setting with easy access to island hotspots.brbr ️ Imagine ThisbrMorning sunshine fills the space as you plan the day. A short walk takes you to Crescent Beach's soft white sand. After a swim, you return for lunch, a pool dip, or a shaded break on the patio before heading out for dinner nearby.brbr Where You'll Sleepbr• Bedroom 1: Queen Bedbr• Bedroom 2: Two Twin Bedsbrbr Explore the Areabr• 0.1 miles to Crescent Beach – Calm water and expansive shorelinebr• 0.1 miles to Crescent Village (South Village) – Restaurants, bars, and essentialsbr• 0.3 miles to Point of Rocks – Excellent snorkeling and marine lifebr• 2.3 miles to Siesta Key Beach – Public beach with amenitiesbr• 2.5 miles to Siesta Key Village – Shopping, dining, nightlifebr• Free Siesta Key Trolley – Ride the island without drivingbrbr About Siesta Key's Crescent Beach (Local Favorite)brCrescent Beach is one of Siesta Key's three main beaches, along with Siesta Beach and Turtle Beach, sharing the island's famous powdery white sand. Part of Siesta Key Beach, it's known for a more relaxed, less crowded vibe, with excellent shelling, swimming, and snorkeling at Point of Rocks. This Siesta Key beach feels quieter and more private—perfect for guests who prefer a serene beach experience.brbr⌛ 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: Casita Sol is one side of a duplex and may share walls, outdoor areas, and the HOA pool with the neighboring unit. Interior spaces are fully private. Beach chairs and umbrella available through Calini Beach Club. Contact us directly for more information regarding any shared space for this vacation home. Dog-Friendly With a Fee (1 dog up to 25lbs).

2

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4

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Vacation Home Rentals By Owner In Siesta Key, FL

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$540.26

$591.11

$920.92

$1040.81

$887.12

$1480.04

$674.11

$762.79

$386.07

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