Vacation Rentals By Owner In Siesta Key, FL

$182.2

Bay Oaks D11 on Siesta Key

Siesta Key, Florida, United States

Summary:brbrCome stay and relax on Siesta Key! Home of the #1 Beach in USA. Award-winning white sand beaches await. Beautiful first floor, 1 bedroom w/den in Bayside community of Bay Oaks. 3 TV's. Sleeps 4 (King in master bedroom, den has a twin bed and living room has a sleeper sofa. Complex offers swimming pool, tennis courts and pier for fishing on the intercoastal. No cable, Streaming only. High-speed internet. 1 week minimum.

1

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1

Bath

4

Sleeps

$182.2

/ Nightly

Apartment

Bay Oaks E74 Siesta Key

Siesta Key, Florida, United States

Summary:brbrCome stay and relax on Siesta Key! Home of the #1 Beach in USA. Award winning white sand beaches await. 4th floor unit is 1 bedroom, 1 bath on the corner with a washer/dryer. Complex offers community pool, tennis and community room. 1 assigned covered parking spot. Unit has 2 TVs, high-speed internet. 1-week minimum.

1

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1

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4

Sleeps

$329.37

/ Nightly

Condo

Welcome Sunrise to Sunset With Gulf to Bay views from Beautiful 2 Bedroom Condo

Siesta Key, Florida, United States

Nestled on the southernmost end of voted #1 Beach in America, The Pointe of Siesta Key is a true slice of paradise, surrounded by everything your heart desires.brbrStart your day with a refreshing workout at the gym, soak up the Florida sun by the pool, sizzle up a barbecue feast at the gazebo, or simply unwind with friends at the welcoming clubhouse.brbrFor those with a passion for angling, cast your line from the dock or explore the abundant fishing spots on the property. Here, every day feels like a waterfront adventure.brbrExperience Siesta Key living at its finest in this meticulously located condo, where the views stretch from sunrise to sunset, and the amenities are tailored for a life of leisure and enjoyment. This is more than just a rental; it's an invitation to embrace the coastal lifestyle and make lasting memories.

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$209.39

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Condo

Bay Oaks B-22

Siesta Key, Florida, United States

Summary:brbrSecond and third floor Bayfront townhome. Living area on second floor and interior stairs lead to bedrooms on third floor. Top of the line unit, offering travertine floors, new kitchen & baths, leather furnishings, 1/2 bath on the 2nd floor and 2 baths on the 3rd floor. Unit offers highspeed internet service. Screened & open balconies off the living room and master bedroom overlooking the bay and picnic area. Covered parking. King, Queen & sleeper, sleeps 6, 1 week minimum.

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$152.41

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Apartment

Modern Condo 2 minute walk to Beach- KING SIZE TEMPUR-PEDIC BED BEAUTIFUL POOL

Siesta Key, Florida, United States

Located in Siesta Key, enjoy what this 1-bedroom apartment has to offer. This beautiful space features a comfortable king bed and a cozy living room with a sofa bed, perfect for extra guests. Stay cool with air conditioning. The bathroom is clean and functional, making your stay hassle-free. Guests will find this marvelous apartment a relaxing retreat after a day of exploring. Feel free to reach out to us during your stay – we're happy to suggest local spots to check out.

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$294.63

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Condo

Expansive Gulf Views! Your Dream Rental | Private Beach | Pool | Steps to Siesta Key Village

Siesta Key, Florida, United States

Coastal Elegance with Unparalleled Ocean Views | Siesta Key brbr brbrExperience coastal luxury and breathtaking Gulf views from this serene 15th-floor retreat in an exclusive Siesta Key complex. This beautifully decorated condo offers private beach access and panoramic ocean views, creating the perfect setting for your Florida escape. brbr brbrHighlights brbr-15th-floor condo with sweeping Gulf of Mexico views brbr-Private balcony for sunrise and sunset viewing brbr-Private beach access to Siesta Key’s renowned quartz-crystal sands brbr-Elegant living area with floor-to-ceiling windows, comfortable seating, and flat-screen TV brbr-Fully equipped gourmet kitchen with modern appliances, granite countertops, and dining essentials brbr brbrBedrooms & Bathrooms brbrPrimary Suite brbr-King-size bed with premium linens brbr-En-suite bathroom brbrGuest Bedroom brbr-Queen-size bed brbr-Access to shared full bathroom brbr brbrAmenities brbr-Heated community pool brbr-Complimentary high-speed Wi-Fi throughout the condo brbr-On-site laundry facilities within the complex brbr-Secure parking for one vehicle brbr brbrImportant Information brbr-Non-smoking and pet-free property brbr-Application required prior to booking (please allow time for processing) brbr-Due to balcony design and high-floor location, not suitable for small children brbr brbrLocation brbr-Ideally situated just minutes from Siesta Key Village, where you can enjoy: brbr-Boutique shopping and local dining brbr-Beach bars and entertainment brbr-Kayaking, paddleboarding, and other water activities brbr brbrWhether you’re seeking a romantic getaway or a peaceful coastal retreat, this luxurious ocean-view condo provides the perfect backdrop for your Siesta Key vacation.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

1

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2

Bath

4

Sleeps

$450.7

/ Nightly

Condo

Gulf and Bay Club-B110- Just 5 minutes from Siesta Beaches!

Siesta Key, Florida, United States

Gulf and Bay Club Unit B110 by Tropical Sands AccommodationsbrbrWelcome to Gulf and Bay Club Unit B110, a spacious three-bedroom, two-bath condo perfectly situated within one of Siesta Key’s most sought-after beachfront communities. Located just a short five-minute stroll from world-famous Siesta Beach, this inviting retreat blends resort-style living with all the comforts of home. Enjoy access to incredible community amenities, including heated swimming pools, a relaxing hot tub, tennis and pickleball courts, and a fitness center, all while being minutes from Siesta Key Village’s local restaurants, boutiques, and laid-back island nightlife.brbrHighlightsbr• 3 Bedrooms / 2 Bathroomsbr• 1 King, 2 Queens, 1 Twinbr• 28-night minimum staybr• Less than 5-minute walk to Siesta Beachbr• Access to shared heated pools and hot tubbr• Community tennis and pickleball courtsbr• Beach chairs providedbr• Washer and dryer in unitbr• Shared shuffleboard, cornhole, and fitness centerbr• Convenient location near Siesta Key VillagebrbrGuests of Gulf and Bay Club can unwind and enjoy Siesta Key’s relaxed coastal lifestyle with access to resort-style amenities. Spend your mornings soaking up the Florida sunshine by the heated community pools or taking a short walk to the beach’s soft white sands. Stay active with friendly matches on the tennis and pickleball courts or break a sweat in the fitness center before cooling off in the refreshing hot tub. The community also offers cornhole and shuffleboard courts, adding extra fun to your stay.brbrStep inside to a bright and inviting open layout designed for comfort and connection. The living area features plush seating and a large smart TV, perfect for cozy movie nights or catching up after a day on the beach. The fully equipped kitchen includes a refrigerator, oven, microwave, dishwasher, toaster, and drip coffeemaker, making meal prep simple and convenient. Gather around the dining table for family meals or plan tomorrow’s adventures with ease.brbrThe primary suite provides a restful retreat with a king bed, smart TV, spacious closet, and a private ensuite bathroom featuring dual vanities and a walk-in shower. The second bedroom offers two queen beds, ideal for families or friends, while the third bedroom is furnished with a comfortable twin bed. A shared hallway bathroom includes a shower and tub combination for added convenience.brbrRoom Detailsbr• Primary Bedroom: King bed, ensuite bathroom with walk-in showerbr• Second Bedroom: Two queen beds, shared hallway bath accessbr• Third Bedroom: Twin bed, shared hallway bath accessbrbrThis condo also includes a washer and dryer, complimentary Wi-Fi, and provided beach chairs for your convenience. One designated parking space is available for guest use.brbrWhether you’re planning an extended stay or a month-long escape to paradise, Gulf and Bay Club Unit B110 by Tropical Sands Accommodations offers everything you need for a relaxing Siesta Key getaway. Enjoy the community’s endless amenities, stroll to the beach, and explore Siesta Key Village just minutes away. Book your next coastal retreat today and experience the laid-back beauty of Florida’s Gulf Coast!

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Sleeps

$405.6

/ Nightly

Condo

Siesta Key Beach Condo • 2BR, 3 bed, 2 1/2 bathroom, Duplex Condo • Heated Pool

Siesta Key, Florida, United States

Siesta Beach is TripAdvisor's No. 1 U.S. beach for 2026!brbrSiesta Key Beach Retreat • 2BR (3 bed, 2 1/2 bathroom) Duplex Condo • Heated PoolbrbrWelcome to your perfect Siesta Key island escape—a bright and comfortable 2-bedroom, 3-bed duplex condo located inside the beautiful Bay Oaks community, one of the most peaceful and scenic spots on the island. Surrounded by mature oak trees, tropical landscaping, and waterfront views, this relaxing retreat offers the perfect balance of resort amenities, quiet island living and beach proximity (the public beach access points are a short walk down the street). brbrWhether you're planning a family beach vacation, couples getaway, or relaxing winter retreat, this condo gives you everything you need to experience the laid-back charm that makes Siesta Key one of the most loved beach destinations in the United States.brbrComfortable Coastal LivingbrInside the condo you’ll find a bright and welcoming coastal space designed for comfort after long days in the sun.brThe open living area features comfortable seating, a 55 smart TV for streaming your favorite shows, and plenty of natural light and pool view lanai. The space flows into a fully equipped kitchen and dining area, making it easy to gather for meals, games, or planning your next beach adventure.brThe condo comfortably sleeps up to six guests with a practical layout perfect for families or small groups.brSleeping arrangements include:br• Primary bedroom with a comfortable King Size bedbr• Second bedroom with 2 full-sized bedsbr• Spacious living area for relaxing after beach daysbrBoth bedrooms have bathrooms/showers inside of the room.brWith three total beds, everyone has space to unwind and recharge for the next day’s island adventures.brThis is a 2nd floor unit (with both bedrooms on the 3rd floor) so you'll need to walk up a flight of 15 steps to reach the front door of the unit.brbrResort-Style AmenitiesbrGuests enjoy access to the Bay Oaks community amenities, which offer a true resort-style experience in a quiet tropical setting.brAmenities include:br• Heated resort-style swimming poolbr• Private bayfront fishing pier perfect for sunrise views and dolphin sightingsbr• Tennis and pickleball courtsbr• BBQ and picnic areasbr• Clubhouse with billiards and lounge spacebr• Beautiful walking paths shaded by large oak treesbrThe bayfront pier is one of the hidden gems of the property—many guests start their mornings here watching dolphins, manatees, and boats glide along the Intracoastal Waterway.brbrMinutes to the BeachbrOne of the best parts of this location is how easy it is to enjoy the beach.brYou’re just a short, 5 minute walk or bike ride to Crescent Beach, famous for its calm turquoise water and soft white quartz sand. Siesta Key Beach—often ranked among the best beaches in the world—is also only minutes away.brEven better, the free Siesta Key trolley stops right outside the community, giving you easy access to:br• Siesta Key Beachbr• Siesta Key Village restaurants and nightlifebr• Local shops and boutiquesbr• Waterfront dining spotsbrYou can explore the entire island without needing to drive.brbrThe Perfect Island LocationbrBay Oaks is loved by visitors because it offers peaceful tropical surroundings while still being close to everything.brWithin minutes you’ll find:br• Beachfront restaurants and tiki barsbr• Fresh seafood diningbr• Kayak and paddleboard rentalsbr• Sunset cruises and dolphin toursbr• Snorkeling at Point of Rocksbr• Shopping and nightlife in Siesta Key VillagebrAfter a full day of island adventures, return to your quiet retreat to relax by the pool or enjoy a peaceful evening under the palms.brbrWhy Guests Love Staying HerebrGuests consistently love this condo for its:br• Relaxing tropical atmospherebr• Spacious 2-bedroom layout with 3 bedsbr• Heated resort poolbr• Beautiful bayfront fishing pierbr• Walkable beach accessbr• Free island trolley conveniencebrWhether you're here to soak up the sun, explore the island, or simply relax in a tropical setting, this Siesta Key duplex condo offers the perfect home base for an unforgettable vacation.brbrBefore booking, PLEASE ask me ANYTHING! I'm happy to address any questions and provide you a full list of my favorite things to do in and around Siesta Key so you can start planning your vacation immediately.

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$339.25

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Private Vacation Home

Siesta Key Village Townhome with Heated Pool and Walking Distance to Beaches

Siesta Key, Florida, United States

Service Highlights:br- Professionally laundered linens & towels with each reservation.br- Exceptional clean rating.br- No keys to pickup or check-in process, simply arrive and enjoy your stay.br- Inspection prior to arrival to ensure all mechanics of the home are fully functional.brbrUpscale town home with private heated pool in superb location. Find yourself just around the corner from Siesta Key village and a short walk or bike ride to Siesta Key beach. Situated on a quiet street with lush landscaping, this town home can sleep up to 6 guests. brbrOn the first floor you will find a family room with electric fireplace, comfortable sofas, and TV with surround sound. The perfect area to enjoy family movie night. The kitchen is fully equipped to handle just about any cooking need and is open to the living room / dining room area of the first floor. Through the back you can step out onto the patio and private pool area great for soaking in the Florida sun. brbrMoving up to the second floor you will find additional sitting area overlooking the family room and second bedroom with queen size bed. Just another half a floor up, you find the master suite furnished with queen-size bed and ensuite bathroom. Both bedrooms, living room, and family room have TV's and wireless internet is accessible throughout the property. brbrMINIMUM STAY REQUIREMENTS: 1 week minimum reservation required usually Saturday to Saturday. No pets (no exceptions).brbrProperty Notes:brbrNo PetsbrbrNo SmokingbrbrPool Heating: Can be heated for $105/weekbrbrMinimum Age: 23brbrOptional:brProperty has an awning over the rear patio. This can be utilized however with a $500 security deposit only.

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$566.32

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Private Vacation Home

Siesta Sandals at Siesta Key

Siesta Key, Florida, United States

If a Quaint & comfortable little beach house is what you are looking for than this is it! 3 Bedroom 2 baths, 1950s beach house done just right, nothing left out. Hardwood floors throughout, tile floors in Kitchen. Screened in private heated pool just off a private deck. (spa is maintained at pool temperature but can be remotely heated) Located on the canal, perfect for pulling a small boat up to the dock, no lift available. This Beach House is about 3 blocks to Siesta Village and an additional 2 blocks to the beach. Great to walk to restaurants, bars and enjoy the local entertainment. High speed internet available. Park your car and forget about driving it for the rest of your trip. Sleeps 6. King, Queen, and Queen hide away.

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Sleeps

$237.42

/ Nightly

Apartment

Midnight Cove 1-831

Siesta Key, Florida, United States

Summary:brbrDiscover your dream vacation in this beautiful 3rd floor walk-up Siesta Key condo! This 2-bedroom, 1.5-bath condo is located near the beach and offers a range of amenities, including pools, tennis courts, and a workout facility. Enjoy the convenience of a fully equipped kitchen and a comfortable living space with a balcony. Perfect for families or groups of friends, this apartment sleeps 6 and is ideally located for exploring the best of Siesta Key. Experience the ultimate beach vacation! 1 week minimum stay.brbrbrbrOther Things to Note:brbrMust be 25 years old or older to book.

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$508.5

/ Nightly

Condo

2 BR/2 BA Beachfront Condo on Siesta Key

Siesta Key, Florida, United States

This two bedroom/two bath condo is clean and waiting for your arrival! Centrally located on Midnight Pass in the gated community of the Sarasota Surf and Racquet Club, this unit has everything at your fingertips for the perfect vacation. Resort accommodations include two heated pools (one bordering the white Siesta Key sand), fitness center, private beach, business center, 24-hr security and office staff onsite to help with check-in and answer any questions you may have during your stay. You can walk the beach while watching the sunrise, or head one mile into the the famously known Siesta Key Village. The Resort provides lounge chairs at the pool and at the beach. Umbrellas are available to rent for a small fee. Beach front grills are available to reserve on a first come first serve basis.brbrThis fifth floor unit that has an amazing view of Siesta Key Beach. There is an elevator in the building. For your convenience laundry facilities are available on the 5th floor.br

2

Bed

2

Bath

6

Sleeps

$598.91

/ Nightly

Condo

2 units next to each other on the #1 Beach in USA. Perfect vacation in Paradise

Siesta Key, Florida, United States

Siesta Key gulf side rental on one of the widest and most beautiful stretches of beach in the world. See why siesta key's beach has been rated #1 in the USA! There is a one month minimum rental for this property. You could be one of the first to stay here after a gut renovation down to the studs. This 1800 square foot, 2 bedroom 3.5 bath condo has a beachside pool that is unique on siesta key! And right next to this 1800 square foot unit separated by a carport is a 550 Square foot newly renovated condo that makes a perfect mother-in-law, nanny, or additional family suite. Enjoy each other's company during the day, but be able to relax and wind down in your own separate space at night. brEverything is brand new with ocean views from the second level of this two level condo. Very open floor plan with two bedrooms and a pull out sofa. Please call or e-mail with questions. Must see to appreciate these one-of-a-kind properties on Siesta Key. Two 60 HD tvs as well as a 30 in the bedroom. All new furniture, chefs kitchen, 4.5 baths, W/D in unit. Sleeps up to 10 between the two units. No pets no smoking. This is truly a one of a kind property with nothing like it on Siesta Key! Inquire today!!brbrPAYMENT SCHEDULEbrbrRefundable security deposit of $500.00 due within 14 days from the date you receive the contract plus $300 for each rental month.brbrBalance of total rent is due 90 days prior to arrival.brbrRates are discounted 5% for the third or more consecutive monthsbrbrStay must be continued occupancy in the same villa.brbrCANCELLATIONbrbrIf cancellation is 90 days or more prior to the rental start date, all monies will be refunded less $50.00 clerical fee.brbrIf cancellation is less than 90 days of rental start date, no refund of monies collected shall be made.brbrNo refunds for early departures.brbrSecurity deposit ($500.00) will be refunded in full for all cancellations. Any changes to the initial contract will be a charge of $50 per changebrbrOccupancy Rates quoted are for:brbrfour (4) people for a two (2) bedroom villabrbrMaximum Occupancybrbr2 bedroom villa - 6 peoplebrbrMust be 26 years of age to rent a villabrbrRecycling Guidelines and Rules & Regulations will be available in each villa. Cleaning fee included in rent.brbrNO PETSbrbrNO SMOKING IN VILLAbrbrTop 10 Beaches in the World 2017 Traveller's Choice Awards! Siesta Key #1 and only beach in the United States recognized!brbr1. Baia do Sancho, Fernando de Noronha, Brazilbrbr2. Grace Bay, Providenciales, Turks and Caicosbrbr3. Eagle Beach, Palm - Eagle Beach, Aruba, Caribbeanbrbr4. Playa Paraiso, Cayo Largo, Cubabrbr5. Siesta Beach, Siesta Key, Florida, United Statesbrbr6. La Concha Beach, San Sebastian - Donostia, Spainbrbr7. Playa Norte, Isla Mujeres, Mexicobrbr8. Radhanagar Beach, Havelock Island, Indiabrbr9. Elafonissi Beach, Elafonissi, Greecebrbr10. Galapagos Beach at Tortuga Bay, Puerto Ayora, Galápagos Islands

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$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

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$409.31

/ Nightly

Condo

Gertrude's Siesta | Palm View Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!

Siesta Key, Florida, United States

The Bayside UnitbrSecond floor bayside Siesta Key vacation rental with 40-foot balcony, tennis/pickleball courts, elevator, private beach and complimentary beach chaises, two heated pools, bay-front lounging area, hot tub, causeway on inter-coastal, boat moors, fitness center, fishing pier, and beautifully manicured grounds stretching from Beach to Bay. Enjoy resort amenities in the heart of Siesta Key. Book a getaway now!brbrWhat Guests Lovebr∙ Resort Amenities – heated pools, jacuzzi, gym, pickle, tennis, and boat moorsbr∙ The Balcony – royal palm views from balcony connecting bedrooms and living areabr∙ The Grounds – fishing causeway, private bay and Siesta Key beach access, lined by royal palmsbr∙ Private Beach – 4-min walk to private beach and Siesta Key's widest whitest sandsbr∙ Restaurants – 2-min walk to free trolley to all Siesta's shopping dining and entertainmentbr∙ Sunsets –walk 4-min to best sunsets in America or just enjoy from your balconybr∙ Activities – scooter, golf cart, bike and kayak rentals nearby br∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories – perfect fit for all with resort amenities and trolley to all top attractionsbr∙ Price - this Siesta Key vacation rental listing is direct with the manager and is the guaranteed lowest costbr brbrThe BeachbrOur beach is a private Siesta Key beach with the widest whitest sands, free chaise lounges, and umbrella rentals. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing.brbrThe LocationbrWith so many amenities, and all of it free of charge, a 3-night stay here will feel like a two-week getaway. If you get the most from a vacation when you don't have search or worry about anything, this unit is not a plus for you it's a must! Although you could easily take a free trolley 1-mile any direction to dozens of shops and restaurants, you can also satisfy every vacation desire without ever putting on your shoes or leaving this resort. You can swim in pools or in the Gulf, fish the inter-coastal, exercise in the gym, sleep in the sun, explore Siesta Key's best beach, make Sandcastles, and even sightsee all in a safe environment and right on your property. The beach here has the whitest sand on the island, but some of the best moments are watching boats and dolphins pass from the private balcony or nearby bay-front pool.brbrBedroom DetailsbrThis is a 2nd-floor unit with an elevator. This two-bedroom unit has a king bedroom, a queen bedroom with additional full sized trundle, and a sleep sofa in the living room. You can sleep up to 6. If you need more space, I can get an additional unit nearby. brbrBeach Gear ProvidedbrWe provide beach towels, and the resort provides free chaise loungers and umbrella rentals. If you have any issues just reach out and we will do whatever we can. Correction for Air-b-n-b listings this location doesn't provide snorkeling gear but this and anything you need can be rented or purchased nearby.brbrImportant Resort Limitsbr1) Expect a special experience where each visitor's peaceful enjoyment is respected. The minimum age for visitors not accompanied by a parent or guardian is 25 years. Stay up as late as you want, but the “quiet neighbor times” begin 10 PM. After 10 PM relocate the party to nearby Siesta Village or the Crescent Beach area. 2) Just one parking space per unit. However, cars are not necessary and an additional emergency parking space is available 1 mile away. If any of these limits are not a fit for you, please let me know, I have other properties available.brbrHousehold Items ProvidedbrThis vacation rental comes with 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. 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 cannotpurchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.brbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.

Bed

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$702.74

/ Nightly

Condo

Beautifully Updated Gulf View, 2 Bed, 2 Bath with Loft, Sleeping 6

Siesta Key, Florida, United States

Beautifully updated from head to toe! Do not miss out on this top tiered 3 bedroom unit! Tile throughout with brand new furniture in all rooms. Top of the line appliances make this a chef's dream. You will have a washer and dryer in the guest bedroom closet. With 3 bedrooms and king beds in each room, this is perfect for a family or a couples retreat. Eat your breakfast with a view of America's #1 beach!

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$392.22

/ Nightly

Villa

Island House Beach Resort V31

Siesta Key, Florida, United States

NEW PHOTOS COMING SOON!!!brbrIsland House Beach Resort – Siesta Key, Florida (Crescent Beach)brbrThis beautifully appointed 2-bedroom, 2-bathroom villa offers comfort, style, and privacy just steps from the beach. The primary ensuite features a king-size bed, while the guest bedroom includes 2 twin beds, making it ideal for families or friends traveling together.brbrEnjoy the spacious living and dining areas, a fully equipped kitchen with updated countertops, modern appliances, and a private screened lanai perfect for relaxing after a day in the sun.brbrFor your convenience, the villa includes three large flat-screen TVs, central heating and air conditioning, and all the amenities you need for a comfortable stay.brbrExperience the privacy and ease of your own standalone villa, while being part of the beautiful Island House Beach Resort community. Just a short walk through the resort brings you to the powdery white sands and turquoise waters of the Gulf of Mexico—perfect for relaxing in the sun, sand, and surf.brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

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Bath

Sleeps

$268.15

/ Nightly

Condo

Resort Style Condo | Pretty Pond Views | Walk to Siesta Key Beach | Pool | Tennis!

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 Siesta Bayside Fountain View! brbr brbrThis is the perfect condo for your next beach getaway. Located across the street from Siesta Key beach through a private access point, this is a two bedroom condo with a screened in lanai overlooking a pond and banyan tree. With porcelain tile floors and bright & cheerful furnishings, you are sure to have an amazing time on Siesta Key. brbr brbrLOCATION HIGHLIGHTS: brbr- Just a 5-minute drive to Siesta Key Village with dining, shopping, and nightlife brbr- Nearby intracoastal bay access for fishing and boating brbr- Free shuttle service available to explore the area without driving brbr- Private beach access across the road brbr- Two heated community pools, Tennis courts brbr- Down the street from public beach brbr brbrPROPERTY FEATURES: brbr- 2 Bedroom/ 1 bathroom ground floor condo (959 sq ft) brbr- Screened lanai pond view brbr- Keyless entry and self check in brbr- Dedicated WIFI and cable brbr- Central A/C brbr- Parking in the driveway brbr- Private washer and dryer brbr brbrLIVING ROOM: brbr- Comfy couch with access to the screened lanai brbr- Big TV with cable brbr- Open concept brbr brbrKTICHEN AND DINING: brbr- Fully equipped kitchen with pots, pans, dishes, and small appliances brbr- Dining table seats 4 brbr brbrBEDROOMS AND BATHROOMS: brbr- Master bedroom: king bed and TV with Xfinity cable brbr- Guest bedroom: full bed with sliders brbr- Bathroom: large separate vanity room, tub/shower combo brbr brbrEXTRA PERKS: brbr- Complimentary beach items: a couple of beach chairs, a beach umbrella, and beach towels brbr brbrLOCAL FAVORITES: brbr- South end: - Clayton’s Grill, Miguel’s, Captain Curt’s, Anna’s Deli, Orange Octopus, Crescent Beach Grocery brbr- Village: Daquiri Deck, Siesta Key Oyster Bar, Another Broken Egg, Old Salty Dog, Siesta Market, Beach Club, Big Tiki Lounge brbr brbrIMPORTANT INFO: brbr- Other than the beach access, no gulf side amenities (including their pool) are not available brbr- Garage is accessed weekly by staff to remove garbage brbr- Parking restrictions: no boats, motorcycle, trailers, jet skis, oversized or commercial vehicles allowed. brbr- Golf carts are allowed but must be stored in the garage or driveway brbr- Parking passes and onsite check in required brbr- AC maintenance is scheduled for Dec 2 between 8am -12 pm brbr brbrCOME MAKE LASTING MEMORIES IN THIS LITTLE SLICE OF PARADISE!brbrWe help make the most of your vacation by providing Xplorie's Free Admission to some of the area’s top attractions each and every day including a choice of a free bike rental, kayak rental, a dolphin cruise tour, or admission to the Ringling Museum ! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA with advance reservation. The fare is free but please tip the driver. Limited to one activity for just one person each day (other members of the group can partake but will need to pay). Create exciting memories, have more fun, and truly experience the Beaches of Sarasota! Book now for an amazing vacation experience! Activities are subject to change and based on availability; non-cumulative and non-transferrable.brbrbrbrimg src=https://admin.itrip.net/upload/360/marketingimageitripsarasota.1718820503.jpg alt=marketing /brbrbrbrFeel free to book for a month or longer but Xplorie is not available for booking 25 days or longer.brbrThis property does not allow Emotional Support Animals in addition to their no pet policy.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.brbrParking passes: 1 parking pass is provided. There is a fee for extra parking passes.

2

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1

Bath

4

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$652.68

/ Nightly

Condo

Anchorage 211 in Siesta Key

Siesta Key, Florida, United States

Anchorage #211 Spacious & Modern Fresh Interior Design! King Bed Master! Enjoy our gorgeous Mid-Century Modern FL condo with high-end finishes, artwork and spectacular lighting. On the inter-coastal and across the street from America's #1 beach! The entire length of the condo is floor to ceiling windows/sliders with walk-out lanai. The scene out the windows of green treetops and blue sky is so peaceful. Rare, spacious 3-bedroom condo with TVs in every room, 4 comfy Q/K beds, 2.br 5 baths, full kitchen and 3 seating areas. This is not your average FL-decorated condo. Come be pampered in our condo with white leather sofas, Danish furnishings, signed artwork, 75 flat screen TV in living room and nice flat screens in all bedrooms. Not only is the condo huge with 2,400 sq ft of indoor living space and over 700 sq ft of outdoor lanai space, but the layout of the bedrooms is ideal. The condo is arranged with the primary suite on one end of the condo and the other 2 bedrooms on the other end. This allows for maximum privacy. Primary bedroom has king bed with on-suite custom bathroom and walk-in closet. Other 2 bedrooms have queen beds and share a bathroom. Condo even has 2 separate heating & cooling systems for maximum comfort. All beds are comfy with nice spreads and comfy pillows. Kitchen is cute with all you need to cook, plus bar/seating area adjacent to kitchen. Elegant to everyday dining! Modern glass-top Mid-Century Modern dining table for 6, outdoor table for 2, high-top table that can seat 4 - total of 12 seats. There are 2 comfortable seating areas in living space with 2 sofas, 5 extra-comfy chairs and 3 ottomans. High-end beautiful rugs throughout to make it feel like home. Plus, plenty of outdoor seating on the open-air lanai. Lots of books in condo, plus beach chairs, umbrella, beach cart, cooler, noodles, beach toys, beach towels. Start-up supplies like, toilet paper, soap, dishwasher pod, dishwashing liquid, paper towels. There will also be salt, pepper and various other spices, tea etc. If you are lucky, some coffee, but don't count on it! Feel free to leave your non-perishables for our next guests. Enjoy all the amenities of The Anchorage Yacht & Tennis Club - full access elevator, newly resurfaced lighted tennis courts, pickle ball, large heated Olympic-size pool with nice pool loungers, tables and chairs, clubhouse, basketball goal, shuffleboard, corn hole, new gas grills, free boat docking on the Inter-coastal waterway (great for fishermen/women), kayak rack, and in-house office/rental manager! You can check-out convenient items like, tennis/pickleball racquets, shuffleboard/corn hole equipment, movies etc. Convenient private beach access across the street - just for Anchorage owners and guests. You will also have use of our personal covered parking space close to the front entry. Plenty of uncovered parking available as well. Our unit is located on the 2nd floor. Convenient stairs on either end of building for quick and easy access to condo. Or if you don't do stairs, you may get from car to kitchen with NO stairs. The nice bank of 2 indoor elevators can be accessed by a ramp and lets out very near our front door. (Our unit is also all on one level with no interior stairs.) Note - there is a convenient washer and dryer on each end of the floor - a load currently costs $1.50 in quarters. (might be a good idea to bring quarters)We have been visiting Siesta Key for over 35 years. We love our condo location because it is right next to the south bridge (only 2 bridges on and off the Key). This convenient location was a key selling point for us. Quick access to condo and very little traffic to mess with! Plus, the beach is absolutely beautiful at our access point. Important Note - our condo is on the opposite side of the building from the bridge - so you do not hear traffic!Over the years the south part of the Key has become a really fun place to walk around. Places around us include - Orange Octopus' excellent ice cream, Crescent Market - convenient small grocery store + smoothie bar, Captain Curt's good food and fun with nightly entertainment, Daiquiri Deck, bike/scooter/golf cart/etc. rentals, major boating facility, pizza, fresh fish, 7-Eleven, Annie's Deli, NEW Mini-Donut shop (with coffee too), Coconuts clothing/t-shirts, Tommy Bahama clothing coming soon, and lots more. You really don't have to drive once you get here, unless you just want to venture out. Siesta Key Village is where most of the bars and restaurants are located on the Key (half way between the south and north bridge). It's a lot of fun, but can be hard to find a parking spot. The Key has added a fun open-air trolley system that will take you to/from The Village for free. We have a pick-up/drop-off point right in front of our condo. Fun activity for the kids too. Yah!Just a note on our calendar and booking rules - check-in/out on Saturdays, 2-week minimum stay during peak winter months. Our on-site rental manager will send you an email with all check-in information and will be on-site during your stay to help with any questions. You must be at least 25 years old to rent our condo. The Anchorage is not a noisy, party environment, although you will have lots of fun here! Do not book our unit for a big Spring Break Party. We have full-time owners who live in the building. Gated entry onto the property. You will be given a code for use during your stay. Our covered patio parking spot will be available for your use during your stay. There is also plenty of shared parking on the front and back of the property. There is a FREE trolley you can catch right outside our condo entry that will take you down to the popular Siesta Village. You could vacation here without a car. Of course a car gives you more options.br Amenities Include:br - TUB/SHOWER: Ybr - Balcony: YESbr - BBQ Grill: 2 GASbr - Beach Access: PRIVATEbr - Bed Size 1st/Master: Kingbr - Bed Size 2nd Rm: Queen bedbr - Bed Size 3rd Rm: 2 Queen bedsbr - Beds Pull-out: Sleeper Sofa in LVRMbr - Elevator: Ybr - Floor No.: 2nd Floorbr - Internet Access: 8016 - 5177187628br - Walk in shower: Ybr - Parking: 25br - Parking Space Type: MARKED SPOTbr - PICKLEBALL: YESbr - Island View: ISLANDbr - Tennis Courts: Ybr - Pool: Y

Bed

Bath

Sleeps

$326.73

/ Nightly

Condo

Anchorage PH-6

Siesta Key, Florida, United States

brbrPenthouse Unit with Sweeping Views of the Gulf of Mexico and the Inter-Coastal WaterwaybrbrWe invite you to stay in our spacious 1,250 square foot 2 bedroom 2 bathroom condominium at The Anchorage Yacht and Tennis Club which is ideally situated across the street from the #1 rated Siesta Key Crescent Beach. The Anchorage Yacht and Tennis Club offers all the amenities of a resort and all the comforts of a private residential condominium/community in one convenient location.brbrAs you enter the condo, your eye is immediately drawn to the bright and cheery living space and wall of sliding glass doors that open up to the balcony. Southern exposurebathes the condo in sunshine through large sliding glass doors in each room. The sliding gass doors open to create an indoor/outdoor living space where you can relax with picturesque views of the Intercoastal Waterway and the Gulf of Mexico. Prepare your favorite meals in the fully stocked kitchen connected to the living space. The large master suite boasts an ensuite bathroom with separate dressing area, walk-in closet and balcony access. The spacious guest bedroom also has a walk-in closet and balcony access. Complementary Wi-Fi is provided in the condo and through out The Anchorage complex.brbrThe Anchorage is known for its amenities which include private gated beach access (across the street), heated Olympic-sized pool, lighted tennis and shuffleboard courts, BBQ grills, exercise room and free boat docking. The Anchorage complex backs up to the Intercoastal Waterway with a serene park-like setting where you can grill, picnic, fish or just relax and watch the boats go by.brbrEvery imaginable beach vacation option can be found within walking distance of The Anchorage including restaurants (many with live entertainment), shops, a market, charter boats, rental of fishing equipment, jet ski, kayak/paddleboard, para-sailing and bike rentals. You can also hitch a free trolley ride to Siesta Key Village to explore other shopping, dining and entertainment options.brbrBook your stay today and experience the magic of the Anchorage Yacht and Tennis Club and Siesta Key!brbrAmenities Include:brbr- Coin operated washer dryer: Ybrbr- TUB/SHOWER: Nbrbr- Balcony: YESbrbr- BBQ Grill: 2 GASbrbr- Beach Access: PRIVATEbrbr- Bed Size 1st/Master: KINGbrbr- Bed Size 2nd Rm: 2 DOUBLESbrbr- Elevator: 2brbr- Exercise Facility: Yesbrbr- Floor No.: 10th Floorbrbr- Internet Access: WIFIbrbr- Walk in shower: Ybrbr- Parking: YESbrbr- Parking Space Type: 90brbr- Electric Stove: Ybrbr- View: CANALbrbr- PICKLEBALL: Ybrbr- Gulf View: Ybrbr- Island View: Ybrbr- Tennis Courts: Ybrbr- Pool: Ybrbr

2

Bed

2

Bath

6

Sleeps

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