Vacation Condo Rentals By Owner In Siesta Key, FL

$323.45

Gulf and Bay Club- B707

Siesta Key, Florida, United States

Come stay at this delightful 2-bedroom 2 bath condo with amazing views. Wake up to enjoy a spectacular view of Siesta Key Beach and Gulf and Bay Club's gorgeous courtyard. Have your morning coffee, take a stroll through the courtyard, and nestle your feet in the powder white sand of Siesta Key Beach. Yes, it's that easy! Gulf and Bay Club has 800 feet of its own private beach, so you never have to worry about any party crashers ruining your day. If hanging at the pool is more your style, enjoy one of three heated pools with Wi-Fi while soaking in the beach atmosphere. For those of you who want to stay active, there's a fitness center with a hot tub, six tennis courts, two pickleball courts, and shuffleboard. You can also melt your time away in any of the three saunas. There is plenty to keep you busy at Gulf and Bay Club! Whether a relaxing day on the beach or an action filled day on the tennis courts, head back to your fully equipped condo, kick back and unwind. There's plenty of room for family or friends with two queen beds in the master, two full beds in the guest room and full-size futon on the porch. If you want to entertain, we certainly have you covered on that! The kitchen is stocked with just about everything you can think of and plenty of wine glasses to go around. Great people and great memories are what Siesta Key is all about! We welcome you to make those memories right here in our little slice of paradise!

2

Bed

2

Bath

8

Sleeps

$323.45

/ Nightly

Condo

Gulf and Bay Club- C710

Siesta Key, Florida, United States

Imagine waking up to this magnificent Gulf view! Stunning top (7th) floor condo with a full view of the Gulf of Mexico, Island lagoons, and just a few steps to the Siesta Key beach, the #1 beach in the U.S. As you enter this totally renovated condo, you will be impressed with the open kitchen, a gourmet's dream. Features of the kitchen, with its tray ceiling and special lighting effects, include the solid wood cabinets, some with glass inserts, pull-out shelves in the lower cabinets and pantry, and quartz counter tops. The spacious island has an exquisite granite counter top. The neutral rectangular tiles in the kitchen truly compliment the granite. In the living area, the open concept allows for a full view of the Gulf and beach. This split bedroom plan allows for everyone's privacy. The entire condo was renovated within the past two years. In addition to the kitchen, the bathrooms were updated with new tile floors, vanities, designer sinks, faucets, and shower tile. Other updated features include plumbing and electrical updates, hot water heater, electric hurricane shutters, newer AC, and plantation shutters. The Gulf & Bay Club, located just south of Siesta Key Beach, is one of the most sought-after beach-front properties on Siesta Key. Its amenities include three pools, tennis courts, racquetball, pickle ball, large fitness facility, on-site management, Clubhouse with library and kitchen facilities, and 24-hour gated and manned security, as well as other amenities. This is a must see!

2

Bed

2

Bath

6

Sleeps

$313.12

/ Nightly

Condo

Gulf and Bay Club- A302 Coastal updates and amazing views!

Siesta Key, Florida, United States

Gorgeous updated unit with fabulous sunset views of the Gulf right from the lanai. Walk down the stairs and step right out onto beautiful Siesta Key beach. New furnishings and remodeled kitchen. Colorful, beachy decor that will please all. Hardwood floors in the living/dining area with carpeting in the bedrooms. You also have a beautiful view of the interior Courtyard which is lighted in the evenings and just beautiful. You will feel so at home!brbrThis property has an active Ring doorbell at the main entrance.

2

Bed

2

Bath

6

Sleeps

$313.12

/ Nightly

Condo

Gulf and Bay Club- E501 Unbelievable views!

Siesta Key, Florida, United States

A wonderful 2-bedroom/2-bath fully appointed condo nestled into a the only true resort on Siesta Key. Enjoy the state of the art fitness center, saunas/spas, 3 heated swimming pools, 8 tennis courts (2 converted for pickleball), shuffleboard, basketball/racquetball, tiki huts, grilling areas, 2 clubhouses, and if you like, Americas #1 beach is waiting just outside your door with some of the most spectacular sunsets on the planet. Welcome to Gulf and Bay Club!

2

Bed

2

Bath

4

Sleeps

$313.12

/ Nightly

Condo

Gulf and Bay Club- E505 Spectacular views!

Siesta Key, Florida, United States

A wonderful 2-bedroom/2-bath fully appointed condo nestled into a the only true resort on Siesta Key. Enjoy the state of the art fitness center, saunas/spas, 3 heated swimming pools, 8 tennis courts (2 converted for pickleball), shuffleboard, basketball/racquetball, tiki huts, grilling areas, 2 clubhouses, and if you like, Americas #1 beach is waiting just outside your door with some of the most spectacular sunsets on the planet. Welcome to Gulf and Bay Club!

2

Bed

2

Bath

4

Sleeps

$313.12

/ Nightly

Condo

Gulf and Bay Club- E308 Beautiful unit with awesome views!

Siesta Key, Florida, United States

Gulf and Bay Club- E308 br brWelcome to Gulf and Bay Club E308, a beautifully renovated two bedroom, two bath condo in the only true resort community on Siesta Key. Ideal for families or friends seeking Siesta Key vacation rentals that combine comfort, convenience, and island charm. This unique unit is just steps from Siesta Key Beach and offers sweeping views of the beach and the blue green waters of the Gulf. With modern upgrades throughout, raised ceilings, and an open, airy layout, this condo delivers a relaxed yet polished coastal experience in one of the most popular family friendly condos on Siesta Key. brbrHighlights br• Steps to Siesta Key Beach br• 2 Bedrooms / 2 Bathrooms br• 1 King bed, 2 Twin XL beds, 1 Queen sleeper sofa br• Lake and Gulf views br• Shared elevator br• Recently renovated interior br• Beach chairs, wagons, coolers, and extra towels br• 3 heated community pools br• Tennis courts and pickleball courts br• Fitness center, saunas, and spas br• BBQ grills and shaded seating areas br• Washer and dryer in unit br• 1 Covered parking br• Approximately 2 miles to Siesta Key Village brbrGulf and Bay Club is known for offering one of the most complete resort experiences on the island. Guests enjoy access to three heated swimming pools, including a large Gulf side pool, along with a modern fitness center, saunas, and relaxing spa areas. Tennis and pickleball courts, shuffleboard, and beautifully maintained grounds provide plenty of options for staying active or simply unwinding. With the beach just outside your door, it is easy to enjoy long walks on the sand, gentle Gulf breezes, and unforgettable sunsets during your stay. brbrThe electronic locked front entry opens into a stunning, fully renovated kitchen featuring white cabinetry, aqua glass tile backsplash, quartz countertops, and all new appliances. A large island with counter height seating creates a natural gathering spot, while a separate wine cave and beverage refrigerator add an extra touch of convenience. The dining area includes a 54-inch round off-white wooden table with cushioned chairs, perfect for shared meals or game nights. The living room has been extended into the lanai, creating an extra spacious area with comfortable seating, a queen sleeper sofa, a love seat, and a 52-inch LED Smart TV. A high-top table and chairs are perfectly positioned to maximize views of the beach. brbrThe primary bedroom is a peaceful retreat with a king bed featuring a Posturepedic mattress, sliding door access, Gulf views, a 32-inch LED TV, and a large walk-in closet with modern cabinetry and storage. The ensuite bathroom features a Cambria quartz double vanity and a spacious glass-walled shower with modern tiling, a corner seat, and a separate shower wand. The guest bedroom includes two extra long twin beds with Posturepedic mattresses, a 32-inch LED Smart TV, and a generous closet. The guest bathroom offers a quartz-topped vanity and a large tub and shower combination with glass sliders and beach inspired tile. brbrRoom Details br• Primary Bedroom: King bed, ensuite bathroom with walk-in shower br• Guest Bedroom: Two Twin XL beds, hallway bathroom with tub and shower br• Additional Sleeping: Queen sleeper sofa in the living area brbrThis condo includes a dedicated utility and laundry room with an upright side by side washer and dryer, ample cabinetry, a full size laundry board, and a drying rack. All ceilings have been raised to maximum height and feature dimmable downlights, while light oak wood grained ceramic flooring runs throughout the unit. The private covered parking space is conveniently located near the elevator and stairs. From this location, guests can easily access local dining, shopping, and the free Siesta Key trolley, making it a great choice for budget-friendly vacation rentals with premium amenities. brbrWith its recent renovation, breathtaking Gulf views, and resort style amenities, Gulf and Bay Club E308 is an exceptional choice for your next beach escape. Enjoy easy beach access, modern comforts, and the laid-back vibe that makes Siesta Key condos with pools so popular. Book your stay today and start enjoying everything Siesta Key has to offer!

2

Bed

2

Bath

4

Sleeps

$300.03

/ Nightly

Condo

Perfect Beachfront Couples Retreat at Jamaica Royale 002 in Siesta Key!

Siesta Key, Florida, United States

Jamaica Royale 002 by Tropical Sands Accommodations brbrWelcome to Jamaica Royale 002 – Your Perfect Couples Getaway in Siesta Key! Experience the ultimate romantic escape at Jamaica Royale 002, an inviting ground-floor beach condo featuring one bedroom and one bathroom. Ideal for couples seeking a tranquil vacation, this charming retreat is just seconds away from private access to one of the best beaches in the world, Siesta Key Beach. Enjoy the vibrant local scene with restaurants, boutiques, coffee shops, and ice cream parlors within easy reach, making it perfect for leisurely strolls and delightful dining experiences. brbrHighlights br• Private Beach Access br• Ground level br• In-unit Washer and Dryer br• Patio with Seating br• 3 Shared Heated Pools br• Community Shuffleboard Court br• Two Shared BBQ Areas br• 1 Assigned Parking Spot brbrJamaica Royale is a gated beachfront complex offering private access to the stunning white sands of Siesta Key Beach. Enjoy three heated community pools, shuffleboard courts, two laundry rooms, shared gas grills, and outdoor showers for the perfect vacation in Sarasota, Florida. brbrInside Jamaica Royale 002, you'll find a stylish living room with full leather furniture and a smart TV for cozy movie nights. The elegant kitchen features stainless steel appliances, a large island with seating, and a seamless connection to the patio area, perfect for Al Fresco dining. Whether you're preparing a romantic dinner or enjoying breakfast in bed, this condo is ideal for culinary delights. brbrThe spacious primary bedroom includes two cozy queen beds, providing ample space for couples to relax and store luggage. The modern bathroom boasts high-end fixtures, ensuring a luxurious and relaxing experience. br brDon't miss out on this stunning vacation opportunity! Book your stay at Jamaica Royale 002 today and soak up the sun, sand, and sea in beautiful Siesta Key. Bring your beach essentials and get ready to create unforgettable memories with your special someone in this idyllic getaway!brbrThis unit has a 7-night minimum rental policy during peak season and a 5-night minimum during off-season. Shorter 4-night stays may be considered to fill calendar gaps. A Saturday to Saturday arrival and departure pattern may be required select times of the year.

1

Bed

1

Bath

4

Sleeps

$313.73

/ Nightly

Condo

Gulf and Bay Club- A310 Great updates and view!

Siesta Key, Florida, United States

Beautifully updated and furnished property with everything you would expect from a resort on Siesta Key. Enjoy the finest beach in America, visit one on the 3 swimming pools on site, get in a workout at state of the art fitness facility, play a game of tennis or pickleball or just relax in this beautifully appointed condo. This unit is situated on the 3rd floor as well as being an end unit. You will enjoy the extra light coming in through the living room and kitchen windows and your view out into the courtyard is magnificent.

2

Bed

2

Bath

4

Sleeps

$300.03

/ Nightly

Condo

Jamaica Royale 004 Updated and close to the beach!

Siesta Key, Florida, United States

Jamaica Royale 004 by Tropical Sands AccommodationsbrbrWelcome to Jamaica Royale 004, a beautifully remodeled one-bedroom, one-bath garden villa located at the beachfront Jamaica Royale resort on Siesta Key. Recently updated with modern finishes, marble and granite accents, and stylish coastal décor, this inviting vacation rental offers a comfortable island retreat just steps from the world famous white sands of Siesta Key Beach. Nestled within the lushly landscaped garden area of the property, guests can enjoy a peaceful setting while still being close to the beach, pools, and resort amenities.brbrHighlightsbr• Garden villa at the beachfront Jamaica Royale resortbr• Short walk to Siesta Key Beachbr• 1 Bedroom / 1 Bathroombr• 2 Queen Bedsbr• Recently remodeled interiorbr• Private patio with partial Gulf viewsbr• Three heated community poolsbr• Shuffleboard courtsbr• Community grilling and picnic areasbr• Washer and dryer in unitbrbrJamaica Royale is a popular Gulf-front resort community known for its beautifully maintained tropical landscaping and direct access to the powdery white sands of Siesta Key Beach. Guests staying in Villa 004 can easily spend their days enjoying the beach or relaxing at one of the three heated freshwater pools located throughout the property. Challenge friends to a game of shuffleboard or enjoy a casual outdoor meal at the community grilling area. With the beach just steps away, guests can take advantage of swimming in the Gulf, shell collecting, or watching the famous Siesta Key sunsets.brbrInside, the condo features a thoughtfully updated interior with modern appliances and stylish finishes. The fully equipped kitchen includes updated appliances, granite countertops, and everything needed to prepare meals during your stay. Whether preparing breakfast before heading to the beach or enjoying a relaxing dinner at home, the kitchen makes dining easy and convenient. The comfortable living area offers cozy seating and a television, creating the perfect place to relax after a day exploring Siesta Key. Built-in speakers throughout the condo allow guests to enjoy music while unwinding in the space. Sliding glass doors lead to the private patio where guests can enjoy the peaceful garden surroundings and a glimpse of the Gulf.brbrThe bedroom is designed for comfort and relaxation and features two queen beds, making this villa a great option for couples, friends, or small families traveling together. The room includes comfortable furnishings, ample storage, and a welcoming atmosphere for a restful night’s sleep. The bathroom is conveniently located off the hallway and includes a walk-in shower and single vanity.brbrRoom Detailsbr-Bedroom: Two Queen bedsbr-Hallway Bathroom: Full bathroom with walk-in shower and single vanitybrbrAdditional conveniences include an in-unit washer and dryer, built-in speaker system with docking station, high speed internet, and a private outdoor patio complete with lounge seating and a table for enjoying morning coffee or evening drinks. The villa’s garden location places guests close to the beach and the resort’s amenities while still offering a quiet and relaxing setting.brbrWhether you are planning a romantic getaway, a small family vacation, or a relaxing beach escape, Jamaica Royale 004 by Tropical Sands Accommodations offers the perfect combination of comfort, location, and resort style amenities. With its updated interior, private patio, and easy access to Siesta Key Beach and the community pools, this charming villa is an ideal place to experience the beauty of Siesta Key. Book your stay today and start planning your unforgettable island vacation.brbrThis unit has a 7-night minimum rental policy during peak season and a 5-night minimum during off-season. Shorter 4-night stays may be considered to fill calendar gaps. A Saturday to Saturday arrival and departure pattern may be required select times of the year.

1

Bed

1

Bath

4

Sleeps

$300.03

/ Nightly

Condo

Jamaica Royale 020 Beautiful!

Siesta Key, Florida, United States

Jamaica Royale Unit 020 by Tropical Sands AccommodationsbrbrWelcome to Jamaica Royale Unit 020, a beautifully updated one-bedroom, one and a half-bath coastal retreat with a freshly renovated interior. Set within the lush, landscaped grounds of Jamaica Royale and just a short walk to the private Siesta Key Beach access, this ground-floor condo offers comfort, style, and the ideal location for couples and small families. Enjoy easy access to the three heated pools, shuffleboard courts, and Siesta Key’s famous powder-soft sand while staying close to the island’s dining, shopping, and attractions along Midnight Pass and Siesta Key Village.brbrHighlightsbr• 1 Bedroom / 1.5 Bathroomsbr• King bed + Queen memory foam sleeper sofabr• Ground-floor condo with private paver patiobr• Updated coastal decor with new furnishingsbr• Short walk to Siesta Key Beachbr• Access to three heated poolsbr• Washer and dryer in unitbr• 65 TV with Blu-ray + streaming abilities in the living roombr• 55 TV with Blu-ray + streaming abilities in the bedroombr• Accommodates up to 4 guestsbr• Saturday-to-Saturday stay requiredbrbrJamaica Royale Unit 020 offers all the comforts of home in a tropical resort-style setting. Enjoy access to three heated pools, beautifully maintained garden walkways, and a private beach area exclusively for Jamaica Royale guests, consistently ranked among the top beaches in the world. The furnished paver patio provides an inviting outdoor space to unwind with a morning coffee or enjoy sunset breezes after a day in the sun.brbrDesigned with modern coastal flair, this condo features driftwood-inspired decor, porcelain plank tile flooring, and granite countertops throughout. The open living area includes a queen memory foam sleeper sofa, a 55” TV with Blu-ray player, and Netflix streaming for cozy evenings indoors. The updated kitchen includes all essential appliances, cookware, and ample counter space, making it easy to prepare meals or enjoy takeout from Siesta Key’s popular eateries.brbrThe primary bedroom offers a King bed, flat-screen TV, and a security safe for added convenience. A shared hallway bathroom features a walk-in shower and a single vanity. An additional half bath in the hallway provides extra space and comfort for guests.brbrRoom Detailsbr• Primary Bedroom: King bedbr• Living Room: Queen memory foam sleeper sofabr• Bathroom: Hallway bathroom with walk-in showerbr• Additional: Half bath located in hallwaybrbrUnit 020 includes a washer and dryer, complimentary Wi-Fi, Netflix access, a security safe, and beach toys. A pack-and-play is available upon advance request. The central Siesta Key location provides quick access to Siesta Key Village, Crescent Beach shops, Siesta Beach Pavilion, bike rentals, kayaking tours, and local restaurants.brbrWith its updated coastal design, private patio, access to world-famous Siesta Key Beach, and top-tier community amenities, Jamaica Royale Unit 020 is the perfect home base for a relaxing and memorable island vacation. Book your stay with Tropical Sands Accommodations and enjoy the best of Siesta Key living.

1

Bed

1

Bath

2

Sleeps

$300.03

/ Nightly

Condo

Jamaica Royale 3 Updated and close to the beach!

Siesta Key, Florida, United States

Jamaica Royale Unit 003 by Tropical Sands AccommodationsbrbrWelcome to Jamaica Royale Unit 003, a charming ground-floor one-bedroom, one-bath condo with a freshly updated interior. Located just steps from the beautifully landscaped garden and pool area of Jamaica Royale and within walking distance of world-famous Siesta Key Beach, this bright and inviting retreat is perfect for couples and small families seeking a relaxed, walkable beach escape. Enjoy direct access to three heated pools, a private stretch of beach, and the unbeatable convenience of staying in the heart of Siesta Key’s Midnight Pass, close to Siesta Key Public Beach and Siesta Key Village.brbrHighlightsbr• 1 Bedroom / 1 Bathroombr• Bedroom with two Queen bedsbr• Ground-floor garden-view condobr• 3 heated pools in the communitybr• Short walk to Siesta Key Beachbr• Walk-in shower with seat and grab barsbr• Washer and dryer in unitbr• Accommodates up to 4 guestsbr• Saturday-to-Saturday stay requiredbr• Convenient mid-island location near dining, shopping, and Siesta Key attractionsbrbrRelax into the island lifestyle with access to three sparkling heated pools, beautifully maintained outdoor lounging areas, and a private beach exclusively for Jamaica Royale guests. The ground-floor location offers easy access to the garden pathways, making your morning stroll to the beach or pool effortless. Whether you prefer sunbathing by the pool, collecting shells along the shoreline, or enjoying a peaceful scenic walk, this community provides a serene and welcoming resort atmosphere.brbrInside, Unit 003 features a newly refreshed and updated interior designed for comfort and ease. The open living area includes cozy seating, a TV for relaxing after beach days, and sliding doors that bring in natural light from the garden setting. The fully equipped kitchen includes essential appliances, cookware, and dining space so you can prepare meals at home or enjoy takeout from Siesta Key’s popular local restaurants.brbrThe spacious bedroom offers two Queen beds, a TV, and plenty of storage, providing a restful place to unwind after exploring Siesta Key. The bathroom features a walk-in shower with grab bars and a built-in shower seat, offering added accessibility and convenience.brbrRoom Detailsbr• Primary Bedroom: Two Queen bedsbr• Bathroom: Walk-in shower with grab bars and shower seatbrbrThis condo includes a washer and dryer, complimentary Wi-Fi, assigned parking, and easy access to the community walkway system that leads directly to the pool and beach. Its central location along Midnight Pass makes it simple to reach Siesta Key Village, Crescent Beach shops, Siesta Beach Pavilion, bike rentals, and waterfront dining.brbrWith its unbeatable location, updated interior, and access to Jamaica Royale’s outstanding amenities, Jamaica Royale Unit 003 is the perfect place to enjoy a relaxing Siesta Key getaway. Book your stay with Tropical Sands Accommodations and experience the comfort, convenience, and beauty of this beloved beachfront community.brbrThis unit has a 7-night minimum rental policy however shorter 4-night stays may be considered to fill calendar gaps. A Saturday to Saturday arrival and departure pattern may be required select times of the year.

1

Bed

1

Bath

4

Sleeps

$301.36

/ Nightly

Condo

Gulf and Bay Club- A609 Amazing views!

Siesta Key, Florida, United States

A wonderful 2-bedroom/2-bath fully appointed condo nestled into a the only true resort on Siesta Key. Enjoy the state of the art fitness center, saunas/spas, 3 heated swimming pools, 8 tennis courts (2 converted for pickleball), shuffleboard, basketball/racquetball, tiki huts, grilling areas, 2 clubhouses, and if you like, Americas #1 beach is waiting just outside your door with some of the most spectacular sunsets on the planet. Welcome to Gulf and Bay Club!

2

Bed

2

Bath

6

Sleeps

$307.98

/ Nightly

Condo

Jamaica Royale 007 Awesome updates & close to the beach!

Siesta Key, Florida, United States

Jamaica Royale 007 by Tropical Sands AccommodationsbrbrWelcome to Jamaica Royale 007, a completely renovated one-bedroom, one-bath garden view villa offering a fresh take on relaxed Key West inspired living on Siesta Key. Ideally located just steps from Pool #2 and a short stroll to the powdery white sands of Siesta Key Beach, this thoughtfully upgraded retreat blends modern design, comfort, and convenience in one of the island’s most desirable beachfront communities.brbrHighlightsbr• Newly renovated villa with coastal modern designbr• Steps to Garden Pool #2br• Short walk to Siesta Key Beachbr• 1 Bedroom / 1 Bathroombr• King Tempur Pedic bed, Queen sleeper sofabr• 75” Smart TV in living room, 65” Smart TV in bedroombr• 3 Shared heated Poolsbr• Community Shuffleboard Courtbr• Two shared BBQ areas br• Beach chairs and beach gear providedbr• In unit washer and dryerbr• 1 Assigned Parking Spot brbrJamaica Royale offers a true resort style experience with direct access to Siesta Key Beach, three heated pools, shuffleboard courts, and community grilling areas. Guests can enjoy the ease of stepping out to the pool just feet from the patio or taking a short walk to the Gulf to experience one of Florida’s most famous beaches.brbrInside, the villa showcases a refreshing mid century coastal design with an open, comfortable layout. The living room features a 75-inch glare free smart TV with DIRECTV streaming and app access, along with a queen sleeper sofa fitted with a Tempur Pedic mattress for added comfort. Sliding glass doors open to the patio, creating seamless indoor and outdoor living.brbrThe fully updated kitchen is equipped with Cambria solid surface countertops and GE Monogram appliances, offering both style and functionality. A spacious dining area with a round glass top table and seating for six provides the perfect space for meals, games, or gathering after a day at the beach.brbrThe bedroom is designed as a relaxing retreat with a king Tempur Pedic mattress, a 65-inch smart TV, and an oversized closet for storage. The spacious bathroom offers a spa like feel with a curb less entry walk-in shower, nonslip tile flooring, grab bars, and a large vanity with additional storage.brbrRoom DetailsbrPrimary Bedroom: King Tempur Pedic bedbrLiving Room: Queen sleeper sofa with Tempur Pedic mattressbrBathroom: Walk-in shower with grab bars and curb less entrybrbrAdditional amenities include a utility room with a washer and dryer, Dyson vacuum, 4 Tommy Bahama folding beach chairs, and a variety of beach gear including beach toys (skim board, boogie board, pool noodles, and inflatable floats). Guests can enjoy both east and west facing patio spaces, offering sunny morning coffee spots and shaded relaxation throughout the day. Located just minutes from Siesta Key Village and accessible by the free trolley, guests can easily explore local dining, shopping, and entertainment.brbrWhether you're planning a relaxing beach escape or an extended stay, Jamaica Royale 007 by Tropical Sands Accommodations offers a beautifully upgraded and thoughtfully designed retreat in the heart of Siesta Key. Book your stay today and experience elevated island living.br-brThis unit has a 7-night minimum Saturday to Saturday rental policy or can be booked for fewer nights of 4 or more if there are gaps around other guest reservations. We will do our best to accommodate any request.

1

Bed

1

Bath

4

Sleeps

$302.72

/ Nightly

Condo

Gulf and Bay Club B307 – Beachfront Resort Condo with Gulf Views!

Siesta Key, Florida, United States

Gulf and Bay Club- B307 br brWelcome to Gulf and Bay Club B307, a comfortable and inviting two-bedroom, two-bath condo located within the only true resort community on Siesta Key. Perfect for families or friends looking for Siesta Key vacation rentals that balance comfort, convenience, and island charm, this condo places you just steps from Siesta Key Beach, consistently ranked among the top beaches in the country. brbrHighlights br• Steps to Siesta Key Beach br• 2 Bedrooms / 2 Bathrooms br• 1 King bed, 2 Queen beds br• Lake and Gulf views br• Screened lanai with seating br• 3 heated community pools br• Tennis courts and pickleball courts br• Fitness center, saunas, and spas br• BBQ grills and shaded seating areas br• Washer and dryer in unit br• 2 miles to Siesta Key Village br• 1 Covered parking brbrGulf and Bay Club is known for offering one of the most complete resort experiences on Siesta Key. Guests enjoy access to three heated swimming pools, a fitness center, saunas and spas, and beautifully maintained grounds. Tennis lovers will appreciate the eight tennis courts, with select courts converted for pickleball, along with shuffleboard and basketball and racquetball courts. Tiki huts, grilling areas, and shaded seating spaces create plenty of opportunities to relax outdoors, while the beach is literally just outside your door. brbrInside, this condo offers a bright and welcoming layout designed for easy island living. The living area features comfortable seating and a TV, making it a great place to unwind after a day at the beach. Sliding doors lead to the screened lanai, where you can enjoy peaceful views and ocean breezes with your morning coffee or evening drink. The fully equipped kitchen includes granite countertops, stainless steel appliances, and all the essentials needed to prepare meals at home. A cozy dining area makes it easy to enjoy casual breakfasts or relaxed dinners together. brbrThe primary bedroom features a king bed, a calm coastal feel, and a private ensuite bathroom with a walk-in shower. This space is designed for rest and relaxation after long days in the sun. The second bedroom offers two queen beds and its own ensuite bathroom with a walk-in shower, making it ideal for kids, couples, or friends traveling together. Both bedrooms provide comfortable sleeping arrangements and plenty of privacy. brbrRoom Details br• Primary Bedroom: King bed, ensuite bathroom with walk-in shower br• Second Bedroom: Two queen beds, ensuite bathroom with walk-in shower brbrThis condo includes a washer and dryer for added convenience, as well as covered parking. Located along Midnight Pass Road, you are close to local dining and shopping, with easy access to the free Siesta Key trolley for exploring the island. From here, it is simple to enjoy the laid back vibe that makes Siesta Key condos with pools such a popular choice for families and couples alike. brbrWith unbeatable beach access, resort-style amenities, and a comfortable island setting, Gulf and Bay Club B307 is a fantastic option for your next Florida getaway. Enjoy relaxed days on Siesta Key Beach, evenings watching the sunset, and all the comforts of home in one of the most sought after budget friendly vacation rentals on the island. Book your stay today and start making unforgettable Siesta Key memories!

2

Bed

2

Bath

4

Sleeps

$523.83

/ Nightly

Condo

Jamaica Royale 006 close to the beach!

Siesta Key, Florida, United States

Delightfully updated one bedroom one bath. This is a garden view unit located in the garden/pool area of our beautifully landscaped property. Enjoy any of the three heated pools, shuffleboard and BBQ after a day of relaxing on our famous sandy white beach RATED #1 in the WORLD by Dr. Beach in 2011 and 2017. Delight in sunset evenings or relax on your back patio. you will love this unit! This unit has a 7 night minimum Saturday to Saturday rental policy, but can be booked for less to fill gaps. We will do our best to accommodate any request.

1

Bed

1

Bath

4

Sleeps

$427.85

/ Nightly

Condo

Gulf and Bay Club- F406 Amazing views!

Siesta Key, Florida, United States

A wonderful 3 bedroom, 2 bath corner unit with a direct view overlooking the Gulf of Mexico and America's #1 rated Siesta Beach. If youâ„¢re looking for a beach retreat where you can watch the beautiful sunsets over the Gulf from your lanai and fall asleep to the sound of waves hitting the white sandy beach, youâ„¢ll find it here! If youâ„¢re looking for resort living, Gulf and Bay Club is the best Siesta Key has to offer, with its 3 heated swimming pools, 8 tennis courts (including clay and hard-courts, and 2 converted for pickleball), an extensive fitness center, saunas, hot tub, shuffleboard, basketball, and racquetball, not to mention clubhouses with social and athletic activities, multiple scenic grilling and outdoor eating areas, and 24 hour gated access. Reserve your time now for that sensational Florida vacation youâ„¢ve been dreaming about!

3

Bed

2

Bath

6

Sleeps

$393.84

/ Nightly

Condo

Jamaica Royale 012 Updated and beachy!

Siesta Key, Florida, United States

Lovely 2 Bedroom/1 Bath Condo. Updated to make your stay pleasant and relaxing with all the comforts of home. Completely renovated in 2025. The living room features plenty of seating, including a Recliner, comfortable Sleep Sofa, and 42-inch TV (cable provided and USB port in the back if you need it.) Washer/Dryer in the unit. Both a Keurig AND regular coffee maker are available. Ceiling fans in both bedrooms. Walk-in Shower. Free Wi-Fi. We have furnished and stocked the unit with the thought of what would we like to find when we rent a condo. We want you to enjoy your stay.br br Patio is only steps away from (1) of the (3) Heated Pools on the grounds. Only a short walk further and you find yourself on the soft white sand of world-famous Siesta Key Beach. Comfortable Lounge Chairs provided at the pools AND the beach. Have fun playing shuffleboard and enjoy easy access to a BBQ area. On-site management makes it easy to get questions answered and any unexpected issues addressed. br br br Leave your car parked while here and take advantage of the many easy FREE transportation services on the island including the Trolley and Shuttle services. Bike rentals are also available in multiple locations.br br This unit has a 7-night minimum Saturday to Saturday rental policy but can be booked for less to fill gaps. We will do our best to accommodate any request.

2

Bed

1

Bath

6

Sleeps

$412.04

/ Nightly

Condo

Gulf and Bay Club- A403-Excellent Views.Steps from Siesta Beach

Siesta Key, Florida, United States

A wonderful 2-bedroom/2-bath condo with great views! located in the only true resort on Siesta Key. The amenities on the property compare to no other on Siesta Key. Enjoy the state of the art fitness center, saunas/spas, 3 heated swimming pool, 8 tennis courts , shuffleboard, basketball/racquetball, tiki huts, grilling areas, 2 clubhouses.....Not to mention BEAUTIFUL SIESTA KEY BEACH as your back yard.

2

Bed

2

Bath

6

Sleeps

$280.49

/ Nightly

Condo

Jamaica Royale 037 Updated with a pool view!

Siesta Key, Florida, United States

Enjoy the morning sun on the patio of this lovely updated 1 bedroom 1 bath garden view unit located in the garden/pool area of a beautifully landscaped property. This unit offers 2 queen-size beds and a sofa sleeper in the living room. This unit is very fresh and updated. Simply walk right out your patio door to one of our three pools. A very short walk to the community patio BBQ and shuffleboard, unless you want to BBQ at sunset on the beach. There is also a Tiki hut where you could either hide from the sun or enjoy your beachside BBQ. This unit has a 7 night minimum Saturday to Saturday rental policy, but can be booked for less to fill gaps. We will do our best to accommodate any request..

1

Bed

1

Bath

4

Sleeps

$280.49

/ Nightly

Condo

Jamaica Royale 038 Close to the pool!

Siesta Key, Florida, United States

Jamaica Royale 038 by Tropical Sands AccommodationsbrbrWelcome to Jamaica Royale 038, a newly renovated one-bedroom, one-bath garden-view condo ideally located within the Jamaica Royale beachfront complex on Siesta Key. This inviting retreat offers a fresh, coastal-inspired interior with an updated bathroom, modern comforts, and direct access to the pool just steps from the patio. Perfect for couples or solo travelers, guests will love being close to the private white sands of Siesta Key Beach, local dining, and the island’s vibrant outdoor activities.brbrHighlightsbr• Newly renovated interiorbr• Garden-view condo steps from the poolbr• 1 Bedroom / 1 Bathroom (Sleeps 4)br• Beachfront gated complex with private beach accessbr• 3 Heated community pools + shuffleboardbr• Walking distance to pickleball, tennis, and volleyball courtsbr• Fully equipped kitchenbr• Private patio with outdoor seatingbr• Walk-in shower with shower seatbr• 7-night minimum stay (Saturday to Saturday)brbrSpend your days swimming in any of the three heated freshwater pools, grilling at the community BBQ areas, or playing a round of shuffleboard beneath the palms. Guests also enjoy private beach access to Siesta Key’s soft quartz sand, as well as nearby tennis and volleyball courts for outdoor fun. Whether you’re here for a relaxing beach escape or local water events, Jamaica Royale offers the ideal setting for your coastal getaway.brbrStep inside to a bright, open living area featuring comfortable seating, a queen sleeper sofa, and a Smart TV for relaxing evenings. The fully equipped kitchen includes full-size appliances, cookware, and everything needed to prepare meals at your convenience. Sliding glass doors open to the private patio, offering direct access to the pool area and lush tropical surroundings, perfect for morning coffee or evening relaxation.brbrThe primary bedroom features a king bed, fresh coastal decor, and plenty of storage space for your belongings. The remodeled bathroom includes a walk-in shower with grab bars and a built-in seat for added comfort and accessibility.brbrRoom Detailsbr• Primary Bedroom: King bedbr• Living Room: Queen sleeper sofabr• Bathroom: Walk-in shower with seat and grab barsbrbrDiscover relaxed island living at Jamaica Royale 038 by Tropical Sands Accommodations, where a newly renovated interior, poolside convenience, and resort-style amenities make every stay unforgettable.brbrBook your Siesta Key escape today and enjoy your perfect Gulf Coast retreat!

1

Bed

1

Bath

4

Sleeps

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