Vacation Condo Rentals By Owner In Siesta Key, FL

The stunning vistas of The Jamaica Royale Penthouse welcome you to your dream condo located on the 8th floor, overlooking the magnificent Siesta Key Beach. This fully remodeled and elegantly furnished 2-bedroom, 2-bathroom condo is the perfect getaway for anyone looking to enjoy the beauty of the Gulf Coast.brbrAs soon as you step into the condo, you'll be struck by the stunning views of the beach, which can be enjoyed from every corner of the unit. The floor-to-ceiling windows flood the condo with natural light, creating a warm and inviting atmosphere, allowing you to soak in the breathtaking sunsets and the sparkling waters of the Gulf of Mexico. With a large wrap-around balcony, you can enjoy the breathtaking views from every angle, savoring the warm sun and gentle sea breeze.brbrThe living room boasts comfortable living room furniture and a large flat-screen TV, perfect for entertaining or relaxing with loved ones. The dining area is adjacent to the living room and seats six people comfortably. The kitchen is fully equipped with modern appliances, granite countertops, and all the cookware and utensils you'll need to whip up a delicious meal.brbrThe master bedroom is a true oasis of relaxation, boasting a comfortable king-size bed, luxurious linens, and an ensuite bathroom with a walk-in shower. The guest bedroom has two full-size beds and a flat-screen TV. Both bedrooms are tastefully decorated and have ample closet space. This condo also includes all the modern amenities you need for a comfortable stay, including air conditioning, high-speed internet, cable TV, and a washer and dryer.brbrThe Jamaica Royale complex features a range of amenities, including three heated pools, tennis courts, direct beach access, and beach amenities including chairs, umbrellas, and coolers.brbrLocated just minutes away from Siesta Key Village, you'll have easy access to restaurants, cafes, and shops. Whether you're looking to relax on the beach or explore the local area, this condo has everything you need for an unforgettable vacation. Book your stay today and experience the beauty of Siesta Key!brbr**Cancellation Policy**brBookings canceled at least 30 days before the start of the stay will receive a 100% refund minus Cancellation Fee's ($100 plus 6% Credit Card Processing Fee). Bookings canceled at least 14 days before the start of the stay will receive a 50% refund Minus Cancellation Fee's. Bookings canceled within the 14-day window are non-refundable. brbrReservations of 15 nights or more may be canceled at least 90 days before the start of the stay will receive a 100% refund minus Cancellation Fee's ($100 plus 6% Credit Card Processing Fee). Cancellations within 45 days of the check-in date and are refundable up to 50% minus Cancellation Fee's.brbrShould a refund be issued, a credit to the original credit card in the amount of the reservation minus the cost of the cancellation fees will be issued within 5 to 7 business days. brbrWhat's provided for your stay: Have fun at the beach with chairs, coolers, umbrellas, toys and more, pre-stocked into the villa prior to your arrival. Each residence has their own Property Liaison to ensure any problems or concerns will be resolved in an effective and timely manner.

2BR Penthouse - Stunning Beach Views on Siesta Key, Access to 3 pools

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$321.34

Discover the perfect retreat for your next vacation in this spacious two-bedroom, two-bathroom vacation rental. Professionally managed by Gulf Coast Vacation Rentals, this turnkey furnished condo offers everything you need for a comfortable and enjoyable stay, including a washer and dryer for added convenience, and a private garage for secure parking.brbrNestled in the heart of Siesta Key, guests staying here are just a leisurely stroll away from the #1 beach in America. Siesta Key is renowned for its world-famous, powdery white sandy beaches that stretch along the mesmerizing Gulf of Mexico. With this prime location, you can immerse yourself in the sheer beauty and tranquility of Siesta Key's coastal landscape.brbrThe condo's open and inviting layout creates a welcoming ambiance where you can relax and unwind. The well-appointed kitchen is fully equipped, allowing you to prepare delicious meals and snacks at your leisure. The living area provides a cozy space for lounging after a day of sun and surf, with ample seating and entertainment options for your enjoyment.brbrEach of the two bedrooms is designed with your comfort in mind, promising restful nights of sleep. Step out onto your private balcony to soak in the warm Siesta Key sun and take in the breathtaking views that stretch before you. Whether you're sipping your morning coffee or savoring a glass of wine at sunset, this outdoor space is a true oasis.brbrBeyond the comforts of your vacation home, Siesta Key offers a wealth of activities and attractions to explore. Delight in the island's vibrant dining scene, browse local boutiques, or engage in thrilling water sports adventures. The warm, sunny Siesta Key weather provides the perfect backdrop for outdoor fun and relaxation.brbrAs the day comes to a close, be sure to head to the beach for one of Siesta Key's spectacular sunsets, a sight that is nothing short of magical. The soft hues of orange and pink painting the sky as the sun dips below the horizon are truly unforgettable.brbrIn summary, our vacation rental on Siesta Key invites you to experience the ultimate beachfront getaway. With its spacious accommodations, unbeatable location, and modern amenities, it's the perfect home base for your Siesta Key adventure. So, why wait Come stay with us and enjoy the warm, sunny paradise that is Siesta Key, where memories are made and relaxation is a way of life. Book your stay today and start counting down the days until your beachfront escape!brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.

Spacious 2BR Siesta Key condo with beach access - GBB 1241

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$322.31

Welcome to Gulf & Bay Club Bayside Unit 1344 on Siesta Key, proudly managed by Gulf Coast Vacation Rentals. This inviting two-bedroom condo is designed to make your stay memorable and relaxing. The spacious primary bedroom features a plush king bed, while the guest room is furnished with a comfortable queen bed—making it perfect for families or couples traveling together.brbrYou'll love the open-concept living area, which leads to a beautiful tiled lanai surrounded by sliding windows and doors. Whether you want to bask in the morning sunlight over breakfast or enjoy the evening breeze with a glass of wine, this space offers flexibility to enjoy the outdoors however you like.brbrThis fully furnished condo provides all the comforts of home, including a washer and dryer, a fully stocked kitchen, and even a private garage for your convenience. Step outside and you're just a short walk to the beach access, where the world-famous white sands of Siesta Key and the sparkling Gulf of Mexico await.brbrAs a guest at Gulf & Bay Club Bayside, you'll also have access to two heated pools—perfect for a relaxing swim any time of year—and pickleball courts for a bit of friendly competition. The resort-style amenities don't stop there: there's a fitness center, tennis courts, and a fishing dock for you to enjoy during your stay.brbrPlus, you're just a short distance from the vibrant Siesta Key Village, where you'll find a fantastic selection of shops, local restaurants, and cafes to explore. Whether you're in the mood for fresh seafood, unique boutiques, or a lively beachside atmosphere, it's all close by.brbrBook your stay at Gulf & Bay Club Bayside Unit 1344 and experience the perfect blend of comfort, convenience, and the coastal lifestyle that makes Siesta Key such a beloved destination. Let Gulf Coast Vacation Rentals make your getaway easy, relaxing, and unforgettable.brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.

Relaxing Siesta Key condo - pickleball - 2 heated pools - beach access - GBB 1344

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$226.38

Welcome to your spacious one-bedroom, one-bathroom vacation rental home at the Gulf and Bay Club Bayside, professionally managed by Gulf Coast Vacation Rentals, an idyllic retreat on the beautiful Siesta Key, just off the coast of Sarasota, Florida. Set amidst the natural splendor of this island paradise, our rental home promises an unforgettable beachfront experience like no other.brbrAs you step into our charming vacation rental, you'll immediately feel the coastal ambiance that permeates every corner of the space. The open and airy layout invites you to unwind and relax, creating a perfect home away from home. With a full kitchen, dining area, and a comfortable living space, you'll have all the conveniences needed to prepare meals, dine, and lounge in comfort.brbrThe bedroom offers a cozy haven for a restful night's sleep. These breathtaking vistas are a constant reminder that you're in a tropical paradise.brbrBut the true gem of this vacation rental is its location. Private access to Crescent Beach on the Gulf of Mexico is just a few steps away, allowing you to easily transition from the comfort of your vacation home to the powdery white sands and crystal-clear waters. Spend your days sunbathing, building sandcastles, or taking long walks along the shoreline. And don't forget to relish in the incredible sunsets that Siesta Key is renowned for – each one a masterpiece painted across the evening sky.brbrBack inside the rental, you'll find modern amenities to enhance your stay. Stay connected with a free high-speed internet connection, perfect for sharing your beachfront adventures with friends and family or catching up on work if needed. Additionally, the convenience of a garage adds to the ease of your stay, ensuring your vehicle remains secure and protected from the elements.brbrSiesta Key itself offers a myriad of attractions and activities to explore during your stay. Beyond the beach, you can discover the island's vibrant dining scene, indulge in watersports, explore local shops, or simply bask in the island's laid-back atmosphere. With its mix of natural beauty and cultural charm, Siesta Key has something for everyone.brbrSo, whether you seek relaxation, adventure, or a little bit of both, our vacation rental at Gulf and Bay Club Bayside is your gateway to an extraordinary coastal getaway. Book your stay today and start creating memories that will last a lifetime in this tropical paradise.brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.

Spacious condo on Siesta Key with beach access - GBB 1200

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$411.31

Embark on a remarkable vacation experience on Siesta Key within the luxurious confines of our generously proportioned three-bedroom, two-bathroom vacation rental, Professionally managed by Gulf Coast Vacation Rentals, nestled within the prestigious Gulf and Bay - Bayside community. This beautifully appointed condo promises an extraordinary retreat, boasting not only ample space but also a plethora of conveniences that will elevate your stay to the pinnacle of comfort and relaxation.brbrUpon entering this spacious haven, you'll be immediately struck by the welcoming ambiance that permeates every corner. The expansive living area invites you to unwind in style, with plush seating arrangements and a chic decor that exude both comfort and sophistication. Whether you're curling up with a good book, catching up on your favorite shows, or simply savoring the tranquil atmosphere, this living space is designed for maximum enjoyment.brbrThe adjacent dining area provides an elegant setting for memorable meals with your loved ones. The open layout seamlessly connects the dining space with the fully equipped kitchen, ensuring that preparing and sharing meals is a delightful experience. The kitchen is outfitted with modern appliances, ample counter space, and all the culinary essentials you might need during your stay.brbrRetreat to the serene bedrooms for a restful night's sleep. The master suite offers a luxurious king-sized bed and an en-suite bathroom, providing a private sanctuary for relaxation. The additional bedrooms are thoughtfully designed and tastefully decorated, ensuring that everyone in your group enjoys their own personal haven.brIn addition to the comfortable interiors, this condo also features a range of amenities for your convenience and enjoyment. You'll find a washer and dryer within the unit, allowing you to keep your beachwear fresh and ready for your next adventure. A private garage provides secure parking for your vehicle, ensuring peace of mind throughout your stay.brbrOne of the standout features of this vacation rental is its proximity to Siesta Key's world-renowned white sandy beach on the Gulf of Mexico. Guests have the privilege of being within walking distance of a beach access, where they can soak up the sun, swim in the crystal-clear waters, and witness breathtaking sunsets over the Gulf. Whether you're a beach enthusiast, a water sports aficionado, or simply someone who appreciates the beauty of nature, Siesta Key's beach offers an array of activities and sights to savor.brbrIn conclusion, our spacious three-bedroom, two-bathroom vacation rental in Gulf and Bay - Bayside on Siesta Key is the epitome of luxury and comfort. With its generously appointed living spaces, modern amenities, and proximity to the world-famous beach, it offers an idyllic retreat for those seeking warm and sunny Siesta Key experiences. We invite you to come stay with us and discover the perfect blend of relaxation and adventure in this tropical paradise. Book your unforgettable Siesta Key getaway today!brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.

Serene Siesta Key bayfront condo - 2 pools - pickleball - tennis - beach access - GBB1368

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$334.79

Immerse yourself in the peaceful charm of Siesta Key at this beautifully appointed vacation rental in Gulf & Bay Club Bayside, professionally manage by Gulf Coast Vacation Rentals. Situated directly along the intercoastal waterway, this spacious two-bedroom, two-bath residence offers a front-row seat to the natural beauty of Florida's Gulf Coast. From the comfort of your private lanai, you can relax as dolphins glide by and manatees surface in the calm waters—an unforgettable experience that captures the essence of island living.brbrInside, the home is newly furnished and thoughtfully designed for both comfort and style. Large windows fill the open-concept living and dining areas with natural light, while offering sweeping views of the harbor and surrounding tropical landscape. The fully equipped kitchen provides everything needed for your stay, and the in-unit washer and dryer add extra convenience.brbrBoth bedrooms are generously sized, providing ample space for families or couples traveling together. The primary suite features a comfortable king bed and an en-suite bath, while the second bedroom offers flexible sleeping arrangements and access to a full guest bathroom. A private garage is included for secure parking and easy storage of your beach gear.brbrLocated in the sought-after Gulf & Bay Club Bayside community, this property offers access to resort-style amenities including two heated pools, tennis and pickleball courts, a fitness center, and beach access just a short walk away. Enjoy a stroll through the gated, tropically landscaped grounds or head over to nearby Siesta Key Village for shopping, dining, and live entertainment.brbrWhether you're seeking a quiet retreat or an active beachside getaway, this vacation home provides the perfect blend of privacy, comfort, and convenience on one of Florida's most beautiful barrier islands.brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.

Relaxing 2BR Siesta Key condo with beach access - GBB 1365

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$287.2

Summary:brbrAmazing Gulf views from every room of this 3rd floor condo. Crescent Arms is a quiet, beach front, high rise condominium building that is ideally located for maximum fun and relaxation. Right on the beach with lounge chairs provided. We can comfortably accommodate 6 people. There are 2 double beds in one room and 1 King in the other. Our condo is on the side corner of the building with a view into the Gulf. From late fall to early spring, you can enjoy lavish sunsets right from the lanai.brbrbrbrThe Space:brbrAs close as you can get to the Gulf without being in the water!brbrbrbrEach bedroom has it's own flat-screen cable TV & ceiling fan.brbrbrbrThe unit also features a fully-equipped, modern kitchen and dining area.brbrbrbrHeated pool, covered parking. All the comforts of home. brbrbrbrPlenty of coin-operated laundry facilities are on-sitebrbrbrbrComputer is available in the clubhouse for guests to use during office hours. A printer is provided for airline boarding pass printing.brbrbrbrFree WiFibrbrbrbrGuest Access:brbrYou have full run of the entire condo.brbrbrbrThe Neighborhood:brbr-Nearby Sarasota has all the social and cultural attractions you could desire: Marie Selby Botanical Gardens, Mote Marine Aquarium, and The Ringling Brothers Museum of Art are all minutes away. brbrbrbr-A few miles north is St. Armand's Circle with its trendy shopping. brbrbrbr-Only one hour from Busch Gardens in Tampa. Two hours from Islands of Adventure, Epcot, Disney, and Universal Studios.brbrbrbrGetting Around:brbrIt’s easy to get around Siesta Key via the free trolley or multiple free ride services.brbrbrbrOther Things to Note:brbrWalking distance from shopping, restaurants, and stores.brbrbrbrPlenty of opportunities for shopping, golf, boating, fishing and much more.brbrbrbrInteraction with Guests:brbrWe are available 24/7 via text, email, or phone. And of course Airbnb messaging. We prefer to stay in contact and help you with any needs. We live just 10 minutes away so are able to stop by in case you need anything!

Beach & Pool Open! Beachfront View Every Room

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$314.9

This lovely, 1-bedroom, 1-bathroom features a queen bed, offering sleeping space for 2. This vacation home is located at a waterfront community on Siesta Key. It features a stunning space with a full kitchen, and living room. Enjoy Wi-Fi, a flat screen TV in the bedroom and living room and coin operated laundry facilities on the premises. The condo is located on the 2st floor, and allows easy access to and from the water at your leisure. Located between the bay and the beach, this unit offers easy access to a fishing pier with cleaning station, boat access, a heated pool and outdoor grill facilities on-site. Just walk across Midnight Pass to your dedicated beach access to our world-famous Siesta Key Beach, ranked #1 in US, and just one mile from Siesta Village, for enjoying the many restaurants, shops, and live entrainment the island has to offer!br*Located on the second floor. Stairs only. Guests must be able to use stairs.brbrBedroom 1- QueenbrbrAdded Amenities Included in Your Stay:brComplimentary Bicycles Rentals,brOne Complimentary Parking Space,brWifi,brBeach Chairs,brBeach Towels,brBeach Wagon,brBeach Cooler,brPartner Property Pool/Hot tub Access,brAccess to Siesta Beach Pickleball Courts,brSiesta Key Trolley - Free-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!brbr*Minimum Age to Book: 21br*To book a Beachside Managed Property Between February 1st and April 15th, the booker must be 27 years old or older. br*Security Authorization Hold taken upon check-in. Amount: $500

Renovated Condo with Siesta Key-Beach Access!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$308.82

This property sits on beautiful Crescent Beach and the Gulf of America. The grounds offer tremendous landscaping and green space. Amenities include a salt water heated pool, hot tub, tennis/pickleball court and oversized deck with gazebo and gas grills. Stay here for private beachfront access and walk right out to the beautiful white quartz sands of Crescent Beach & Siesta Key Public Beach. Voted #1 Beach in the United States numerous times by Travel Channel's Top 10 US Beaches! Sunsets are magnificent! Maximum 4 guests. Property has elevator nearby to make moving in and out easy. Building 1, Top Floor, Unit 405. ******Condo recently renovated. Remodeled Kitchen and Baths - New cabinets and countertops, appliances, sinks, faucets, window treatments, mirrors and lighting.brbr

Siesta Key-Siesta Dunes-Beautiful Condo with a View of the Gulf of America

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$118.38

Harbor Towers Yacht and Racquet Club is located on the inter-coastal waterway on Siesta Key in Sarasota, Florida. From the marina you can fish or relax and read a good book while you watch the boat traffic go by from your comfortable seat in the gazebo or bench at water's edge. The beautiful gulf beaches are conveniently located right across the street.brbrHarbor Towers features beautiful tropical landscaped grounds, a deep-water harbor that can accommodate boats up to 50 feet in length, and two gorgeous swimming pools (adult and children). Tennis is played on our three Har-Tru courts right next to the Inter-coastal Waterway. If you like a brisk workout you will enjoy our exercise room with state-of-the-art exercise equipment.brbrMy unit is one of the best views in the building. It is located on the 4th floor overlooking the ocean.brbrHarbor Towers is a secure building requiring entry at all doors with special fob's given out only to owners and guests. Night time security is provided and automatic entry gates secure the grounds at all times.brbrAfter one visit to Harbor Towers Yacht and Racquet Club you will want to come back every year!brbr2 weeks (14 day) minimal- rules of the condo association.

Harbor Towers & Yacht Club racket and

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$335.44

Casa Mar is located on the Oceanside of Midnight Pass rd. Our condo is about 100 yards to the beach. If you love to walk or run along the beach in the morning, suntan on soft, white sand in the afternoon, and watch spectacular sunsets over the beach horizon in the evenings - this is the perfect vacation spot for you and your family. Casa Mar is located in the middle (widest section) of Crescent Beach providing plenty of uncrowded and private space. This 1 story, 1 bedroom/1 bath condominium (unit # 61) has been remodeled/updated and has new appliances and furniture. It is beautifully decorated with art purchased from local artists. There is a designated parking spot in front of the condo. The master bedroom has a king size sleigh bed (electric adjustable), dresser and separate TV. The living room has (2) leather recliners, a queen sofa couch (with a new foam mattress) and a smart TV. The eat in kitchen boosts a banquette and is well equipped for those that like to cook. Plus, there are 3 outdoor gas grills in the courtyard. The glassed/screened courtyard room has a love seat and chair. It is the perfect place for enjoying your morning coffee while looking out at the palm lined courtyard. We recently built a patio which provides a great place to enjoy a cocktail while watching the sunset paint the evening sky orange and pink. We like to vacation in comfort and have worked hard to keep this condo in excellent condition with high end furniture and decor. brbrThe resort offers (2) heated pools, shuffle board courts, and gas grill/picnic areas in the courtyard between the condo's. The resort also has a tennis court with PickleBall Court Lines, a community room for large gatherings and two laundry rooms. Casa Mar is a safe family-friendly resort with private walkway access through the courtyard to the beach and private parking spots for each condo. The Beach has (2) covered Lanai's, and lounge chairs for the guests use - all at no charge. brWe hope you will decide to rent unit # 61 and have such a wonderful time you'll want to come back year after year.brbrKeywords: Condominium, Beachside, Oceanside, Gulf of Mexico Side

Amazing 1 Br/1 Ba Condo at Casa Mar

Siesta Key, Florida, United States

Bed

Bath

4

Sleeps

$259.42

Three Sandy Sisters by Siesta Key Luxury Rental Properties is a charming two bedroom, two bath villa offering the perfect balance of relaxed coastal living and resort style amenities. Located along scenic Midnight Pass Road, this Siesta Key vacation rental provides easy access to Siesta Key Beach entry through the Aloha Kai community, along with bayfront amenities just steps away. Ideal for couples, small families, or friends traveling together, this tranquil retreat combines Old Florida character with modern comfort in one of the island’s most desirable areas. brbrHighlights br• 6-minute walk to private beach access through Aloha Kai Community br• 2 Bedrooms / 2 Bathrooms br• 1 King bed, 2 Double beds br• Private patio and side courtyard with seating br• Private dining area and BBQ grill br• Heated community pool br• Community fishing pier br• Bayfront dock for drop off and loading only br• Easy access to Siesta Key Breeze Trolley stop br• 2 parking spaces brbrThree Sandy Sisters offers a peaceful private outdoor setting that enhances the relaxed island experience. Guests can enjoy a secluded back patio shaded by mature oak trees, complete with comfortable seating for morning coffee or evening conversations. A private outdoor dining area with BBQ grill makes it easy to enjoy meals outside after a day at the beach. In addition, a charming side courtyard provides another quiet space for unwinding in a serene, residential setting. brbrInside, the villa features a bright and welcoming living room with plush seating and a TV, creating a comfortable space for movie nights or relaxing after a day on Siesta Key Beach. The Florida room is filled with natural light and offers an inviting spot to read, lounge, or enjoy views of the outdoor patio. The updated kitchen provides modern appliances, generous counter space, and everything needed for easy meal preparation. The dining area offers a cozy setting for shared meals and casual gatherings. brbrThe primary bedroom offers a peaceful retreat with a king bed, private patio access, and an updated ensuite bathroom featuring a walk-in shower. The second bedroom is well suited for additional guests, offering two double beds and convenient access to the second full bathroom. Both bedrooms are designed for comfort and relaxation, providing restful spaces after full days spent at the beach or exploring the island. brbrRoom Details br• Primary Bedroom: King bed, ensuite bathroom with walk-in shower, private patio access br• Second Bedroom: Two Double beds brbrThree Sandy Sisters offers a quiet residential setting with excellent walkability. Guests are just a short walk from private beach access through the Aloha Kai community, the heated community pool, fishing pier, and a bayfront dock for kayak or canoe drop off. Easy access to the Siesta Key Breeze Trolley allows for effortless trips to Siesta Key Village, nearby beaches, and local dining. This Siesta Key vacation rental includes two designated parking spaces and provides the perfect balance of privacy, comfort, and island convenience. brbrBlending Old Florida charm with modern convenience, Three Sandy Sisters by Siesta Key Luxury Rental Properties offers a serene escape just moments from the best of Siesta Key. From private beach access and bayfront amenities to comfortable interiors and tranquil outdoor spaces, this villa is ideal for guests seeking a laid-back island getaway. Book your stay at Three Sandy Sisters today and experience the relaxed rhythm of Siesta Key living! brbr- brThis home is managed by Siesta Key Luxury Rentals Properties a Siesta Key property management company. brbrThis property does not allow pets of any kind. brbr2 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbrPlease remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions, including fines and/or termination of your rental agreement without refund.

Three Sandy Sisters: Old Florida Charm!

Siesta Key, Florida, United States

Bed

Bath

6

Sleeps

$399.15

High Tide – Bright Siesta Key Village Duplex with Lanai & Shared Poolbrbr Why You'll Love This HomebrPerched just two blocks from the powdery sands of Siesta Beach, High Tide is a sunny second-floor duplex offering charm, comfort, and easy access to everything Siesta Key has to offer. With a screened lanai, shared heated pool, and walkable proximity to shops and restaurants in Siesta Key Village, this coastal escape is ideal for laid-back travelers who love convenience wrapped in classic beachy vibes.brbr ‍ ‍ Perfect ForbrSmall families, couples, or island explorers who want a private retreat just steps from the beach, with shared outdoor space and pet-friendly perks.brbr ️ Imagine This...brRise with the sound of swaying palms and start your day on the lanai with a fresh cup of coffee and tropical breezes. When you're ready, grab your flip-flops and stroll just minutes to Siesta Beach for a swim or sunrise walk. After soaking up the sun, head into Siesta Village for shopping and lunch at a local favorite. In the afternoon, cool off in the shared pool or relax in the shady backyard while grilling dinner. Later, unwind on the lanai as the stars come out and the village hums with music just a block away.brbr Where You'll Sleepbr• Bedroom 1: King Bed (1), Ensuite Bathroom with Walk-In Shower, TVbr• Bedroom 2: Queen Bed (1), Access to Shared Hall Bathroom with Shower/Tub Combo, TVbr• Living Room: Full Sleeper Sofa (1)brbr Explore the AreabrHigh Tide places you just 0.2 miles from Siesta Beach and 0.1 miles from Siesta Key Village, putting dining, shopping, live music, and water rentals all within walking distance. Venture beyond the Key to visit downtown Sarasota (approx. 7 miles), where The Ringling Museum, or St. Armands Circle are waiting for an upscale day trip.brbr Book Your Stay at High Tide Today!brWith its unbeatable location and thoughtful comforts, High Tide makes it easy to settle into the Siesta Key lifestyle. Everything you need is right at your doorstep—whether that's beach towels and pool time or a stroll through the Village. Your perfect island escape starts here.brbrPlease Note: This unit is part of a two (2) Unit Separate Duplex with no access to each other. This is the upper unit. This home being a part of a duplex unit, means that it could share a dividing wall, floor, ceiling, outdoor space, and/or amenities with the other unit. When renting this unit, you will have access to the shared backyard along with the side of the building, shared pool and yard area with barbecue. This pool is heated from November 15th to April 15th. Your furry friend is welcome! This property is dog-friendly for dogs under 25 lbs with an additional $250 pet fee. Breed restrictions apply. Please notify us in advance if you'll be bringing a pet. Contact us directly for more information regarding any shared space for this vacation home. Starter packs of kitchen and toiletry essentials are provided. Washer/dryer in-unit.

High Tide – Pool, Grill, Pet Friendly, Located in the Heart of SK!

Siesta Key, Florida, United States

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Bath

Sleeps

$353.3

Low Tide – Cozy Siesta Key Village Duplex with Pool & Lanaibrbr Why You'll Love This HomebrWelcome to Low Tide, a bright and charming first-floor duplex tucked just two blocks from world-famous Siesta Beach. With a screened lanai, shared heated pool, and walkable access to the Village's restaurants, cafés, and shops, this home is your launchpad for laid-back island adventures. Casual, comfortable, and refreshingly coastal—Low Tide is your peaceful slice of Siesta Key.brbr ‍ ‍ Perfect ForbrCouples, small families, or snowbirds seeking easy beach access, walkable dining, and a quiet retreat with shared outdoor amenities.brbr ️ Imagine This...brWake up to sunshine filtering through palm leaves and head out for a barefoot stroll to the beach—just a five-minute walk away. After a swim in the warm Gulf waters, wander into Siesta Key Village for brunch, boutique shopping, or a daiquiri on the patio. Spend lazy afternoons back at Low Tide: curl up on the screened lanai with a good book, fire up the grill in the shared backyard, or take a dip in the pool. As evening falls, you'll love walking into the Village for seafood and ice cream before returning home to your cozy retreat under the stars.brbr Where You'll Sleepbr • Bedroom 1: King Bed (1), Ensuite Bathroom with Walk-In Shower, TVbr • Bedroom 2: Twin Beds (2), Access to Shared Hall Bathroom with Shower/Tub Combo, TV br • Living Room: Full Sleeper Sofa (1)brbr Explore the AreabrLow Tide is located just 0.2 miles from Siesta Beach and 0.1 miles from Siesta Key Village, placing you within effortless reach of the area's best dining, live music, beach bars, and coastal activities. Rent bikes, kayaks, or paddle boards nearby—or take a short drive to explore downtown Sarasota (about 7 miles), where The Ringling Museum or Selby Gardens await.brbr Book Your Stay at Low Tide Today!brLow Tide delivers that local Siesta Key vibe with the comforts of home. From beach days to breezy evenings on the lanai, every detail has been considered to make your getaway easy and enjoyable. When you arrive, you'll find fresh linens, clean spaces, and everything ready for your relaxing stay.brbrPlease Note: This unit is part of a two (2) Unit Separate Duplex with no access to each other. This is the lower unit. This home being a part of a duplex unit, means that it could share a dividing wall, floor, ceiling, outdoor space, and/or amenities with the other unit. When renting this unit, you will have access to the shared backyard along with the side of the building, shared pool and yard area with barbecue. This pool is heated from November 15th to April 15th. Your furry friend is welcome! This property is dog-friendly for dogs under 25lbs with an additional $250 pet fee. Breed restrictions apply. Please notify us in advance if you'll be bringing a pet. Contact us directly for more information regarding any shared space for this vacation home. Starter packs of kitchen and toiletry essentials are provided. Washer/dryer in-unit.

Low Tide – Pool, Pet Friendly, In SK Village - Walk Everywhere!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$344.67

Our House at the Beach E-301brCondo in Sarasota, Florida brbrHighlightsbr• Across the street from Siesta Key Beachbr• Shared Poolbr• Private Balconybr• Two Tennis Courtsbr• Shared BBQ areabrbrOur House at the Beach is located directly across the street from Siesta Key Beach, home to mesmerizing white sands and unforgettable Florida sunsets. This complex is set around a scenic lake and features a private community pool, a covered pavilion area with a BBQ, a picnic area, and two tennis courts for guests to enjoy. This beautifully updated third-level condo includes a fully equipped kitchen, a separate dining room, and a balcony off the cozy living room with views of the Gulf of Mexico! The primary bedroom has a King bed, a walk-in closet, a TV, and an ensuite bathroom with double sinks and a walk-in shower. The second bedroom boasts water views, a TV, and two twin beds. A washer and dryer are available for guest use.

Our House at the Beach E-301

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$220.04

Gorgeous condo across from the Siesta Key Beach (#1 beach in U.S.)! During your stay you'll have access to the tennis courts and the pool located on the property. Only 5 mins from Siesta Key Village! Walking distance from many restaurants including, Captain Kurt's, Daquiri Deck, Crescent Club, etc.

Beautiful Condo with Private Access to Siesta Key Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$314.02

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Lulu's Key House Kemp Ridley! brbr brbrThis oasis on Siesta Key is just paradise. The condo is only a couple of blocks away from the beach and rests in Siesta Key Village where you will find lots of great dining, amazing shops, coffee houses and night life are steps away. The beach and the crystal clear waters of the Gulf of Mexico is also about a 5 minute walk. You don't need a car. Your vacation destination is here! brbr brbrLOCATION HIGHLIGHTS: brbr- Ground-level unit in Siesta Key Village – Steps to dining, shops, coffee houses, and nightlife brbr- Just a 5-minute walk to Siesta Key Beach and the Gulf of Mexico brbr- No car needed to enjoy restaurants, beach, and village attractions brbr- Quiet back location within 4-unit complex brbr brbrPROPERTY FEATURES: brbr- 1 bedroom/ 1 bathroom ground floor condo (640 sq ft) brbr- Heated communal pool, 5 ft at deepest with outdoor shower brbr- Crown molding, quartz counters, stainless kitchen appliances, porcelain plank tile, plantation shutters brbr- Shared stackable washers/dryers on-site at no charge brbr brbrLIVING ROOM: brbr- Large Smart TV with cable and Frontier TV service brbr- Free WiFi and USB charging port brbr- Queen sofa sleeper for extra guests brbr brbrKITCHEN AND DINING: brbr- Fully stocked modern kitchen with stainless steel appliances, dishes, utensils, and cookware brbr- Quartz countertops and tiled floors brbr- Dining area for 4 brbr brbrBEDROOMS AND BATHROOMS: brbr- King bed with comfortable mattress brbr- Wall-mounted TV with cable in bedroom brbr- Bathroom with walk-in shower and glass doors brbr brbrEXTRA PERKS: brbr- Complimentary beach items provided: beach chairs, umbrella, cart, and beach towels brbr brbrLOCAL FAVORITES: brbr- Steps to Siesta Key Village for shopping, restaurants, bars, and coffee shops brbr- Short walk to Siesta Key Beach and Gulf waters brbr brbrIMPORTANT INFO: brbr- 1 assigned parking space labeled “Kemp Ridley” brbr- No smoking or pets allowed brbr- Option to rent multiple units or the entire 4-plex for a private group stay brbr- Confirm approval for special vehicles including boats, motorcycles, trailers, jet skis, kayaks, golf carts, or oversized/commercial vehicles brbr- Flexible dates of stay brbr brbrYOUR VACATION STARTS THE MOMENT YOU BOOK AT LULU'S KEY HOUSE!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.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$189.15

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Harbor Towers 3rd Fl Views of the Bay! brbr brbrThis lovely 2 bedroom/2-bathroom condo, which comfortably sleeps 5 guests, resides in Harbor Towers on Siesta Key. Harbor Towers is a premier complex with loads of amenities that sits directly on the bay where you can watch incredible morning sunrises. Close to famous Siesta Key beach (2 min. drive/15 min. walk) with its fabulous powdery white sands is just a short bike ride or Trolley ride away. Harbor Towers offers resort style amenities including 2 heated swimming pools, 3 clay tennis courts, and clubhouse with grilling station. brbr brbrLOCATION HIGHLIGHTS: brbr- Bayfront condo in Harbor Towers on the Intracoastal, gated community brbr- 2-minute drive or 15-minute walk to Siesta Key Beach brbr- Easy bike or trolley ride to beach access brbr- Close to Siesta Key Village dining, shops, and live music brbr- Resort-style community with sunrise bay views brbr- 2 heated pools and 3 Har-Tru clay tennis courts brbr- Clubhouse with grilling station and lounge area brbr brbrPROPERTY FEATURES: brbr- 2 bedroom / 2 bathroom 3rd floor condo (1257 sq ft) brbr- Has bay and pool views brbr- Located in a gated community with secure entry brbr- Private WiFi and cable brbr- New washer/dryer inside the unit brbr- One assigned parking spot brbr- Central AC with ceiling fans brbr brbrLIVING ROOM: brbr- Sleeper sofa, loveseat, and chair brbr- TV for entertainment brbr- Access to enclosed balcony brbr brbrKITCHEN AND DINING: brbr- Updated kitchen with stainless steel appliances brbr- Stone countertops and white cabinetry brbr- Dining table seats 4 brbr brbrBEDROOMS AND BATHROOMS: brbr- Master bedroom: King bed, bay and pool views, TV brbr- Master ensuite bathroom: spacious vanity with walk-in shower brbr- Guest bedroom: Queen bed + Twin bed, TV brbr- Guest ensuite bathroom: separate vanity area, walk-in shower brbr brbrEXTRA PERKS: brbr- Complimentary beach chairs, umbrella, and towels brbr brbrLOCAL FAVORITES: brbr- Siesta Key Beach with powdery white sand brbr- Crescent Beach access nearby brbr- Local dining, bars, and boutiques just a trolley ride away brbr brbrIMPORTANT INFO: brbr- 2-week minimum stay required brbr- Quiet hours enforced by the community brbr- No parties or smoking allowed. No pets brbr- Only 1 parking spot. Parking restrictions: no trailers, oversized vehicles, boats, or commercial vehicles. No Motorized Carts or Scooters Allowed brbr brbrSTEP INTO COMFORT, CONVENIENCE, AND RELAXATION - RESERVE YOUR STAY NOW!brbrPlease note, each unit is only allowed 1 parking spot. brbr brbrStarting June 1st, the complex has scheduled a roof repair. They are expecting to be done in 4-5 weeks (weather permitting). brbrCrane will be up front. Carport repairs will take place starting June 8, 2026. Please use caution around work areas. Thanks for your understanding.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Resort Style, Heated Pools plus Kiddie Pool, Walk to the Beach, On Bay, Tennis Courts

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$440.73

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Lulu's Key House Leatherback! brbr brbrThe condo is only a couple of blocks away from the beach and rests in Siesta Key Village where you will find lots of great dining, amazing shops, coffee houses and more, all a short walk away. brbrNew furnishing! brbr brbrLOCATION HIGHLIGHTS: brbr- Just a couple of blocks to Siesta Key Beach and Gulf waters brbr- Steps to restaurants, shops, coffee houses, and nightlife brbr- No car needed to enjoy the village and beach brbr brbrPROPERTY FEATURES: brbr- 2 bedroom/ 2 bathroom ground floor unit (851 sq ft) brbr- Crown molding, solid stone counters, stainless kitchen appliances, porcelain wide plank tiles, plantation shutters brbr- Shared stackable washers/dryers in building brbr- Heated communal pool on-site with loungers and umbrella, outdoor shower brbr- Front porch with swing brbr brbrLIVING ROOM: brbr- Large Smart TV with cable and Frontier service brbr- Free WiFi and USB charging port brbr- Spacious seating area for family and guests brbr brbrKITCHEN AND DINING: brbr- Modern kitchen with quartz countertops and tiled floors brbr- New stainless steel appliances including dishwasher and microwave brbr- Fully stocked with dishes, utensils, and small appliances brbr- Dining table seats 6 brbr brbrBEDROOMS AND BATHROOMS: brbr- Master bedroom: king bed with memory foam mattresses, flat screen and closet space brbr- Master ensuite bathroom: vanity and walk-in shower brbr- Guest bedroom: king bed with TV and cable brbr- Guest bathroom: vanity, tub/shower combo brbr brbrEXTRA PERKS: brbr- Complimentary beach items provided: beach chairs, beach cart, umbrella, and beach towels brbr brbrLOCAL FAVORITES: brbr- Steps to Siesta Key Village for shopping, dining, bars, and coffee shops brbr- Short walk to Siesta Key Beach and Gulf waters brbr- Perfect location for a car-free vacation brbr brbrIMPORTANT INFO: brbr- Two assigned parking spots marked “Leatherback” brbr- Option to rent multiple units or the entire 4-plex for private group stay brbr- Confirm approval for special vehicles including boats, motorcycles, trailers, jet skis, kayaks, golf carts, or oversized/commercial vehicles brbr- Flexible dates of stay brbr brbrDON'T WAIT - MAKE THIS TRIP YOURS!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.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

$185 Free Activities Daily, LuLu's Leatherback Near Beach/Village, Heated Pool, Beach Gear Included

Siesta Key, Florida, United States

Bed