Vacation Condo Rentals By Owner In Siesta Key, FL

15 SS Cottage by Tropical Sands Accommodations br brWelcome to 15 SS Cottage! Immerse yourself in beachfront living at this beautifully furnished island-style condo, located directly across the street from Siesta Key Beach. Only two blocks from the vibrant Siesta Key Village, this charming one bedroom, one bath home offers a cozy, relaxed vibe with everything you need for an unforgettable getaway, including outdoor dining and patio lounge chairs. Spend your days soaking up Gulf views and your evenings savoring meals at the area’s renowned restaurants, all while creating lasting memories with family and friends! brbrHighlights br• 2-minute walk from Siesta Key Beach br• 1 Bedroom / 1 Bath br• 1 King, 1 Sleeper sofa br• 2-block walk to Siesta Key Village  br• New gas grill  br• Private outdoor patio  br• Pet friendly with host approval br• Beach towels included br• Community laundry facility br• 2 Parking spaces br brEnjoy outdoor living in your private patio equipped with outdoor furniture including a table, chairs, and umbrella for dining, as well as a brand-new gas grill, perfect for evening barbecues or relaxing nights under the stars. Explore the beach and canal, both steps away, or head to the local Siesta Key Village shops, dining and more! br brThe interior cottage offers a warm and inviting space with island inspired decor. The upgraded kitchen includes a large refrigerator, stove, and Keurig coffee maker, great for quick breakfast or casual dinner prep. This space opens to the dining area for intimate meals and outdoor patio access for sunset dinners. The living room with a large LCD TV, sleeper sofa, and wireless internet creates a cozy environment for relaxing or viewing your favorite shows. br brThe primary bedroom features a luxurious king-sized bed and an LCD TV, providing a peaceful retreat. The bathroom is updated with modern fixtures and is easily accessible for relaxing after a day in the sun. The cottage’s design ensures comfort, relaxation, and a true island experience.brbrRoom Details br• Primary Bedroom: King bed br• Living Room: Sleeper sofa br brLocated just steps from Siesta Key Beach access and within two blocks of Siesta Key Village and all it has to offer, including Oyster Bar (SKOB), Daiquiri Deck, and of course, the Broken Egg. This condo offers an unbeatable location for your island retreat. Bring your furry friends and explore the pet friendly policies with a 45-pound weight limit, additional pet fee, and convenient outdoor dining on the private patio great for all to enjoy.br brBook your stay at this charming Siesta Key cottage today and enjoy effortless relaxation in paradise. With prime access to the Gulf’s powdery sands, top-rated dining, and easy walkability, this home promises a memorable vacation experience. Reserve now and leave your worries behind in this perfect island escape. br brbr- brThis home is managed by Tropical Sands Accommodations. brbrWith host approval before check-in, this property accepts pets. Weight restrictions apply. An additional pet fee will apply. See our Siesta Key Luxury Rental Properties Rental Policies for full details.  brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Tropical Sands Accommodations Rental Policies for full details. 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.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.

15 SS Cottage - Close to Beach and Village

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$270.07

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!

Gulf and Bay Club- B107 Awesome unit and walk right out to the pool

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$266.12

Gulf and Bay Club E104 by Tropical Sands Accommodations brCondo in Sarasota Florida br brYour perfect beach getaway awaits at Gulf and Bay Club E104! This two-bedroom, two-bath ground-floor condo is just a minute's walk from your private beach paradise! brbrHighlights br• Ground-floor beach condo br• Screened-in lanai with water views br• Washer and dryer in unit br• Less than a 1-minute walk to the beach br• Private Beach Access br• 3 Shared heated pools br• Shared Tennis, pickleball, Racquetball, basketball, and shuffleboard courts br• Shared Fitness Center br• Community electric vehicle chargers br• 1.8 miles to Siesta Key Village brbrEnjoy beachfront living at this fabulous condominium complex with private access to Siesta Key Beach's world-famous white sands. The complex features three heated pools, saunas, a hot tub, courts for tennis, pickleball, racquetball, shuffleboard, a fitness center, and tiki-themed BBQ areas.brbrInside, the condo offers an open living space with a nautical-themed seating area, TV, dining table, and a screened-in lanai with a bistro table. The fully equipped kitchen includes a suite of appliances and a Ninja air fryer. The primary bedroom features a comfortable King bed and an ensuite bathroom with a walk-in shower. The second bedroom, perfect for kids, has two twin beds and access to the hall bath with a shower and tub combination.

Lanai and Beach Acess - Gulf and Bay Club E104

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$270.07

Freshly re-furnished and updated unit on the second floor with views of the gorgeous grounds of Gulf and Bay as well as a Gulf view! Gulf and Bay features 3 pools, tennis courts, fitness center, shuffle board, basketball/racquetball court, grilling areas, tropical landscaping, and beautiful ponds perfect for fishing. The ultimate resort on gorgeous Siesta Key! The large master suite has a King-sized bed, large flat screen tv, and plenty of drawer and closet space. The Master Bath features a 2 separate sinks with a shower and separate dressing area. The second bedroom is all new with a Queen-sized bed & full size bunk beds, big closets with organizers and flat screen tv. The second bath is right off the guest bedroom. The renovated kitchen has granite counters and all the amenities you could need! Bar area with 4 bar stools for extra seating. Separate desk area provides a perfect work space. Dining room features a table for 6. Living room has all brand-new couches (one of which features a pull-out bed) and large flat screen tv. The lanai has been incorporated into the unit and features a separate dining table for 6 with a gorgeous view! Perfect for eating your breakfast or watching the sunset. The laundry room features a washer/dryer in its own utility room. Cable tv and wireless internet are all part of this superb unit.

Gulf and Bay Club- B205

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$276.9

Jamaica Royale Unit 30 by Tropical Sands AccommodationsbrbrWelcome to Jamaica Royale Unit 30, a bright and newly renovated one-bedroom, one-bath vacation condo located in the heart of Siesta Key. Perfect for couples or small families, this coastal retreat offers a modern interior, beach access just steps away, and resort-style amenities within one of Siesta Key’s most popular beachfront communities. Enjoy sunny days on the white quartz sand of Siesta Beach and unwind in the comfort of your beautifully updated home away from home.brbrHighlightsbr• 1 Bedroom / 1 Bathroombr• 1 King Bed, 1 Queen Sleeper Sofabr• 7-night minimum (Saturday to Saturday)br• Newly renovated interior (June 2025)br• Less than a 5-minute walk to Siesta Beachbr• 3 community heated poolsbr• Shuffleboard and BBQ grilling stationsbr• Washer and dryer in unitbr• Beach chairs providedbr• Close to Siesta Key Village and local diningbr• 1 Parking spot assigned brbrLocated within the beloved Jamaica Royale community, guests can enjoy three heated swimming pools, shuffleboard courts, and BBQ grills, one located just steps from the beach. Relax beneath swaying palms, take a dip in the pool, or spend your afternoon walking along the shoreline collecting seashells. Siesta Key Public Beach is just half a mile away, offering tennis and volleyball courts, concession stands, and picnic areas for a fun day under the sun.brbrThis newly updated condo blends coastal comfort with modern upgrades. The open living area features new furnishings, a queen sleeper sofa, and a flat-screen TV for relaxing evenings. The fully equipped kitchen is beautifully renovated with granite countertops, white cabinetry, and stainless-steel appliances, making it easy to prepare home-cooked meals or quick beach snacks. Porcelain tile flooring runs throughout, creating a bright and airy atmosphere.brbrThe primary bedroom offers a king bed with luxury linens, ample storage, and a soothing color palette designed for relaxation. The full bathroom features a walk-in shower with grab bars for added convenience.brbrRoom Detailsbr• Primary Bedroom: King bedbr• Living Room: Queen sleeper sofabr• Bathroom: Walk-in shower with grab barsbrbrThis unit includes a washer and dryer, complimentary Wi-Fi, and beach chairs for guest use. Assigned parking is provided.brbrWhether you’re planning a weeklong beach retreat or an extended stay, Jamaica Royale Unit 30 by Tropical Sands Accommodations offers the perfect blend of comfort, convenience, and island charm. With updated interiors, resort-style amenities, and one of the best beachfront locations on Siesta Key, you’ll have everything you need for a memorable Gulf Coast escape.

Jamaica Royale 030 Nicely Updated!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$270.07

Gulf and Bay Club – C105 by Tropical Sands Accommodations brCondo in Siesta Key, Florida brbrDiscover Gulf and Bay Club—C105, a delightful two-bedroom, two-bathroom condo located on the ground floor. Perfect for families, couples, and friends, this inviting retreat offers the perfect escape, just a short stroll from the pristine Siesta Key Beach and the vibrant shops and restaurants of Siesta Village, which is only a quick Siesta Key Breeze Trolley ride away. brbrHighlights br• Private Beach with Secured Access br• 3 Shared Heated Pools br• Shared Tennis, Pickleball, Racquetball, Basketball, and Shuffleboard courts br• Shared Fitness Center br• Community Electric Vehicle Chargers br• 1 Assigned Covered Parking Spot br• Shared BBQ areas brbrGulf and Bay is a fabulous beachfront condominium complex with private beach access to Siesta Key Beach and its world-famous white sands and warm waters. This complex features three heated pools, saunas, a hot tub, activity courts for tennis, pickleball, racquetball, and shuffleboard, a fitness center, and numerous tiki-themed BBQ areas surrounding the facility lakes. brbrThis fully appointed condo captures beach vibes with bright furnishings and ample lounge space, perfect for relaxation after a sunny day. The chic, fully equipped kitchen opens to a cozy dining area for shared meals. Retreat to the primary bedroom featuring a comfortable king bed and an ensuite bathroom with a walk-in shower, while the second bedroom, equipped with two twin beds, is ideal for kids or guests, complemented by an additional hall bathroom with a shower-tub combo for convenience.brbrDon’t miss your chance to experience the ultimate beach getaway at Gulf and Bay Club – C105. Book your stay today and immerse yourself in the coastal charm of Siesta Key, where unforgettable memories await!

Gulf and Bay Club C105: Siesta Key Condo with Direct Pool and Beach Access!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$270.07

This unit has had a full remodel and is just wonderful. The view out through the courtyard and to the Gulf is breathtaking. And by having an end unit, you also get to enjoy extra natural light and views out of your kitchen and living room windows to the side. The lanai is comfortably set up with table/chairs for dining and a gliding loveseat for enjoying the view. Come and enjoy this unit and you may not want to leave. There is alot of comfort and additional amenities.

Gulf and Bay Club- C201 Beautiful updates!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$270.07

This unit has had a full remodel and is just wonderful. Check out the amazing kitchen! The view out through the courtyard and to the Gulf is breathtaking. The lanai is comfortably set up with table/chairs for dining and a gliding loveseat for enjoying the view. Come and enjoy this unit and you may not want to leave. There is a lot of comfort and additional amenities. Enjoy this amazing property with all its amazing amenities including: over 800' of private beach, 3 pools, 8 tennis courts, pickle ball, fitness center and more!

Gulf and Bay Club- C202 Amazing kitchen!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$269.34

Harbor Towers 417 by Tropical Sands Accommodations br brWelcome to the perfect Gulf Coast retreat at Harbor Towers 417, a beautifully updated Bayfront condominium nestled directly on the Gulf Coast Intracoastal Waterway. This charming fourth-floor residence offers stunning bay views, near Siesta Key’s powdery sands and warm Gulf waters. With two bedrooms and two bathrooms, it provides a serene escape for families or friends seeking relaxation, outdoor activities, and island adventures. Located within the Harbor Towers Yacht and Racquet Club, guests enjoy access to two heated pools, tennis courts, a fitness center, and scenic water views! brbrHighlights br• Bay Views br• 10-minute walk to Siesta Key Beach br• 2 Bedroom / 2 Bathroom br•13-night minimum stay communitybr• 1 King, 1 Queen, 1 Sleeper sofa br• Private screened-in lanai br• Two heated pools br• Three Community tennis courts and fitness center br• Beach chairs br• Short walk or trolley ride to Siesta Key Village br• Two-week minimum stay br brRelax and unwind with two resort style heated pools and scenic water views from the screened-in lanai. Play tennis on the three courts, stay active in the fitness center, or explore Siesta Key’s beaches and village via the free Siesta Key Breeze Trolley right outside your complex. The outdoor grilling patio and water views create a tranquil setting for memorable outdoor meals and relaxing afternoons. br brThe spacious interior boasts a fully equipped kitchen with modern appliances, perfect for preparing meals and snacks. The chic living room with plush seating and a large TV creates a cozy atmosphere for relaxing after a day of beach adventures. The screened-in lanai extends your living space with beautiful views of the bay and a full dining set for outdoor meals. br brThe primary bedroom features a king-sized bed, lovely beach decor, and a modern ensuite bathroom with a walk-in shower. The second bedroom offers a queen-sized bed with an ensuite bathroom featuring a shower and tub combination, accessed via the bedroom and the living area. A sleeper sofa in the living room provides additional sleeping space, supported by a washer and dryer for added convenience. brbrRoom Details br• Primary Bedroom: King bed, ensuite bathroom with walk-in shower  br• Second Bedroom: Queen bed br• Living Room: Sleeper sofa br brGuests enjoy access to a washer and dryer, outdoor seating, and the complex’s outdoor pools and tennis courts. Explore the on site Marina available for use with an additional fee, registration, and documentation. Situated across from Siesta Key Beach and near the village shops, Harbor Towers 417 provides the perfect base for exploring the island and relaxing in style.br brBook your stay today at Harbor Towers 417 and indulge in a waterfront escape, amenities, and a prime location. Enjoy stunning bay views, beach days, and island adventures in this upscale condo. Reserve your dates now for an unforgettable Gulf Coast vacation! br brbr- brThis home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. brbrThis property does not allow pets of any kind. brbr1 car maximum is able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Tropical Sands Accommodations 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.

Beautifully Updated Unit with Bay Views! - Harbor Towers- 417

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$277.14

Jamaica Royale 028 by Tropical Sands AccommodationsbrbrWelcome to Jamaica Royale 028, a completely renovated one-bedroom, two-bath villa offering a unique blend of luxury, advanced technology, and unbeatable beachfront location on Siesta Key. Located within the highly sought after Jamaica Royale community, this modern retreat is just steps from the powdery white sands of Siesta Key Beach and a short distance to Siesta Key Village. Designed for guests seeking both comfort and innovation, this villa delivers an elevated island experience.brbrHighlightsbr• Newly renovated luxury villa with modern designbr• Direct beach access to Siesta Key Beachbr• 1 Bedroom / 2 Bathroomsbr• Queen bed, Queen sleeper sofa plus Full Sleeper Sofabr• Private courtyard patio with lounge seating and diningbr• 3 heated community poolsbr• Shuffleboard courtsbr• Community BBQ grilling areasbr• In unit washer and dryerbr• Gigabit WiFi and smart home featuresbr• 1 Assigned Parking Spot brbrJamaica Royale offers a true resort style experience with direct access to Siesta Key Beach and beautifully landscaped tropical grounds. Guests can spend their days relaxing on the world famous quartz sand, enjoying one of three heated pools, or gathering at the community grilling areas. The peaceful setting combined with prime beach access creates the perfect balance of relaxation and convenience.brbrInside, the villa features a bright and open layout with sleek, modern finishes and cutting edge technology throughout. The living room is designed for entertainment and relaxation, featuring an 85-inch Samsung Neo QLED 4K TV, surround sound system, and comfortable seating including both a Queen sleeper sofa and a Full sleeper sofa for additional guest accommodations. High speed internet and integrated smart features make this an ideal space for both leisure and remote work.brbrThe fully upgraded kitchen is a standout feature, equipped with top of the line appliances including a French door refrigerator, advanced cooking range with air fryer functionality, additional convection and microwave oven, and premium small appliances such as an espresso machine, Vitamix blender, and indoor grill. Whether preparing a quick breakfast or a full meal, the kitchen is designed for convenience and performance.brbrThe primary bedroom offers a relaxing retreat with a high end bed, large 77-inch smart TV, and ample storage. The villa includes two bathrooms, including a spa style bathroom featuring a multi head walk-in shower designed for a luxurious experience.brbrRoom DetailsbrPrimary Bedroom: Queen bed with smart TVbrLiving Room: Queen Sleeper sofa and Full sleeper sofabrBathrooms: Two full bathrooms including spa style walk-in showerbrbrStep outside to your private courtyard patio, complete with chaise lounges and a dining set, offering both sun and shade throughout the day. This outdoor space is perfect for morning coffee, afternoon relaxation, or evening meals in a peaceful garden setting.brbrAdditional amenities include an in unit washer and dryer, climate controlled air conditioning and heating, and enhanced connectivity with USB charging stations throughout the villa. Located near Siesta Key Village, guests can easily explore local dining, shopping, and entertainment via the free trolley or a short walk.brbrWhether you’re seeking a high tech getaway or a luxurious beach retreat, Jamaica Royale 028 by Tropical Sands Accommodations offers a one of a kind experience in one of Siesta Key’s most desirable beachfront communities. Book your stay today and enjoy modern coastal living at its finest.brbr-brThis 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.

Jamaica Royale 028 Washer and Dryer Plus Half Bath

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$270.07

Come and enjoy a newly renovated and furnished 2 bedroom condo at the resort style Gulf and Bay Club. Enjoy this nicely appointed modern 1350 square foot condo for beautiful sunsets and tropical views Ã‚ All of the furnishings are brand new and will sleep a minimum of six people with 2 full baths The unit has large sliding windows Ã‚ that give you an outdoor feel with lots of seating to watch sunsets and lush tropical nights at gulf and bay. The renovations offer a custom built kitchen cabinetry and built ins in both bedrooms. This condo also sports recessed dimmable lighting throughout the unit. The master bed room offers a king size bed, a double sink bathroom with a multihead shower, custom cabinets and a walk in closet. Ã‚ The guest bedroom has a queen size bed and a twin size day bed with trundle that sleeps 4.Ã‚ br br br br Gulf and Bay is set on beautiful siesta key beach with white sands and sensational sunsets. Condo overlooks one of 3 heated pools. There is a main larger lap pool, 8 beautiful tennis courts and a great fitness center. You will make lots of memories at Gulf and Bay.

Gulf and Bay Club- C207

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$270.07

Coastal Living at it's best! Beautifully decorated condo was fully renovated in 2021 and features 2 bedrooms, 2 baths with 1445 square feet of living space. This 2nd floor unit has beautiful views of the gulf, as well as the lakes and beautiful manicured grounds. Crown moldings, recessed lighting, plantation shutters and custom cabinetry throughout. The master suite has a king bed, large screen TV, walk-in closet and master bath with double sinks, body shower and direct access to the lanai where you will enjoy your morning coffee. He split plan has the guest bedroom with 2 full beds, TV, large closet, full bath with tub in the hallway. Unit has a laundry room with a washer and dryer.br br Kitchen has new granite countertops, a breakfast bar, updated appliances including a microwave, Keurig, and everything you will need to cook and entertain. The dining room seats 6 and the living room has 2 couches (one with a queen sleeper) for plenty of seating. Large screen TV, blue-ray, and a beautiful view! Lanai has comfortable seating for relaxing in the Coastal Lifestyle. There is a desk area in kitchen for catching up on emails using the high-speed wireless internet.br br The Gulf and Bay Club, located just south of Siesta Key Beach, is one of the most sought-after properties on Siesta Key. Its amenities include 3 heated pools, tennis courts, racquetball, pickle ball, large fitness facility, grilling areas, on-site management, 24- hour gated and manned security, and the best sunsets on the key! The ultimate place to stay on Siesta Key!

Gulf and Bay Club- D209

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$270.07

Newly renovated 101D, is a ground floor walk out unit. It’s conveniently located just a few steps from the heated salt-water pool and a short stroll through the beautiful grounds to the world famous Siesta Key Beach. An end unit makes for a bright interior with side windows in the kitchen and living room. Brand new kitchen upgrades include granite counters, tile backsplash and a large soaking sink . Both the master and the 2nd baths are updated with new vanities, lighting, and walk-in tile showers with grab bars. Fresh decor updates throughout entire unit. This is a wonderful place to kick back and enjoy your stay!

Gulf and Bay Club- D101 Ground floor walk out!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$373.73

Fisherman’s Cove – A207 by Tropical Sands Accommodations brbrWelcome to Fisherman’s Cove – A207, a beautifully remodeled one-bedroom, one-bathroom beachfront condo located directly on Turtle Beach in Siesta Key. Situated on the second floor, this inviting retreat offers full Gulf views, allowing you to relax to the sound of the waves and enjoy unforgettable sunset views from your screened-in lanai. With direct beach access, a shared heated pool, and classic island charm, this condo is ideal for couples looking for affordable beachfront stays and laid-back Siesta Key vacation rentals. brbrHighlights br• Beachfront condo on Turtle Beach br• 1 bedroom / 1 bathroom br• 1 king bed, 1 sleeper sofa br• Full Gulf views br• Screened-in lanai br• Shared heated pool br• Shared shuffleboard courts br• Shared BBQ area br• Boat docks available br• 1 parking space br• Community laundry facilities brbrGuests at Fisherman’s Cove – A207 enjoy a variety of shared amenities designed to enhance the beachfront experience. Spend your days lounging by the shared heated pool, grilling in the shared BBQ area, or enjoying friendly games on the shuffleboard courts. The screened-in lanai offers a peaceful place to take in Gulf views and ocean breezes, while nearby boat docks are available by application for guests looking to explore the water. brbrInside, the condo features a bright and comfortable living space with coastal decor and thoughtful updates throughout. The living area includes comfortable seating and opens directly to the screened lanai, creating a seamless indoor-outdoor feel. The kitchen is well-equipped for preparing meals, snacks, or beach-day refreshments, making your stay both convenient and comfortable. brbrThe primary bedroom includes a king bed and an ensuite full bathroom, providing a private and relaxing retreat. The living area includes a sleeping sofa, providing additional flexibility for guests. The condo includes one full bathroom, conveniently located near both the bedroom and main living area. brbrRoom Details br• Primary Bedroom: King bed br• Living Area: Sleeper sofa br brThis condo places you close to local favorites, including waterfront dining at Ophelia’s on the Bay and Turtles Restaurant, both just a short walk away. The Turtle Beach location offers a quieter alternative to busier areas of Siesta Key while still delivering easy access to beaches, dining, and outdoor activities that make Sarasota vacation rentals for couples so appealing. brbrIf you are looking for a beachfront Siesta Key condo with stunning Gulf views, direct beach access, and a relaxed island atmosphere, Fisherman’s Cove – A207 by Tropical Sands Accommodations is an excellent choice. Book your stay today and enjoy the beauty of Turtle Beach from your own Gulf-front retreat! br-br1 WEEK MINIMUM RENTAL REQUIREDbrbrThis home is managed by Tropical Sands Accommodations.    brbrThis property does not allow pets of any kind.    brbr1 car maximum is able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.   brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Tropical Sands Accommodations 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.

Fisherman's Cove -A207-Full Gulf front!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$356.97

Jamaica Royale 010 by Tropical Sands AccommodationsbrbrWelcome to Jamaica Royale 010, a beautifully renovated two-bedroom, two-bath poolfront villa offering true beachside bliss on Siesta Key. This ground floor retreat combines modern coastal design with unbeatable proximity to both the pool and the powdery white sands of Siesta Key Beach. Thoughtfully updated and fully furnished, this villa is perfect for families, couples, or small groups seeking comfort, convenience, and a prime island location near Siesta Key Village.brbrHighlightsbr• Fully renovated poolfront villa with modern coastal designbr• Closest 2 bedroom/2 bathroom villa to the beach on the North side with morning sun and afternoon shadebr• 2 Queen beds, plus Sleeper sofa and reclinerbr• Ground floor unit with direct pool accessbr• In unit washer and dryerbr• 3 heated community pools. Unit located near Pool #2.br• Shuffleboard courtsbr• Community BBQ grilling areasbr• 1 Assigned parking Spot brbrJamaica Royale offers a true resort style experience with direct beach access and beautifully maintained grounds. Guests can relax by one of the three heated pools, enjoy a casual cookout at the community grilling areas, or take just a few steps to the Gulf to experience Siesta Key’s world famous white sand beach. The poolfront location of this villa makes it easy to transition from your patio to a refreshing swim or a relaxing day in the sun.brbrInside, the villa features a bright and stylish interior with sleek finishes and coastal inspired decor. The open living space is designed for comfort and ease, offering a sleeper sofa and a reclining chair, perfect for unwinding after a day at the beach. The updated kitchen is fully equipped for everyday living, providing everything needed to prepare meals and gather with family and friends.brbrEach bedroom is thoughtfully designed to offer privacy and comfort, both featuring queen beds and private ensuite bathrooms. Televisions in each bedroom provide added convenience for relaxing evenings. The layout is ideal for couples traveling together or families wanting separate, comfortable spaces.brbrRoom DetailsbrPrimary Bedroom: Queen bed with ensuite bathroombrSecond Bedroom: Queen bed with ensuite bathroombrLiving Room: Sleeper sofabrBathrooms: Two ensuite bathrooms with walk-in showersbrbrAdditional amenities include an in unit washer and dryer, convenient parking right outside your door, and a private patio space perfect for enjoying your morning coffee or relaxing in the shade after a day at the beach. 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 enjoying the pool just steps away, relaxing on the patio, or taking a quick stroll to the beach, Jamaica Royale 010 by Tropical Sands Accommodations delivers the perfect blend of location, comfort, and coastal charm. Book your stay today and experience the best of Siesta Key living.

Jamaica Royale 10 UPDATED POOL VILLA STEPS TO BEACH

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$356.58

Jamaica Royale Unit 033 Tropical Sands AccommodationsbrbrWelcome to Jamaica Royale Unit 033, a newly refreshed two bedroom, one bathroom coastal villa located in the lush garden and pool area of the beloved Jamaica Royale community on Siesta Key. Just steps from a sparkling heated pool and a short walk to the world renowned Siesta Beach, this ground level villa offers a king bedroom, a twin bedroom with two twin beds, and comfortable open living spaces perfect for families, couples, or small groups looking to unwind in a prime beachside setting.brbrHighlightsbr• 2 Bedrooms / 1 Bathroombr• 1 King bed, 2 Twin bedsbr• Ground level villa with pool just outside the patiobr• 3 heated community poolsbr• 5 minute walk to Siesta Beach (private beach access)br• Shuffleboard court and BBQ areasbr• Community tennis courts nearbybr• Assigned parking spacebr• Updated interior (June 2025)brbrJamaica Royale offers guests exceptional amenities designed for sunny Siesta Key living. Enjoy three heated pools, including one conveniently located right outside the villa’s patio. Relax on the community’s private section of Siesta Beach, complete with lounge chairs, or take advantage of the BBQ grills at the beachside Tiki Hut or at the community patio. Shuffleboard courts and nearby county tennis courts provide fun options for active guests throughout their stay.brbrInside, the open living area provides a cozy space to relax with a large flat screen TV, comfortable seating, and a bright, welcoming atmosphere. The fully equipped kitchen includes essential appliances, cookware, and plenty of counter space, making it easy to prepare meals from morning breakfast to evening dinners. A dining area offers room for everyone to gather and enjoy a shared meal after a day of sun and sand.brbrThe primary bedroom features a comfortable king bed, closet storage, and a peaceful ambiance for restful nights. The guest bedroom includes two twin beds, perfect for families or friends sharing the space. The shared hallway bathroom offers convenience with a walk in shower and a single vanity sink, providing everything guests need to refresh after beach days.brbrRoom Detailsbr• Primary Bedroom: King bedbr• Second Bedroom: Two twin bedsbr• Bathroom: Shared hallway bath, walk in shower only, one vanity sinkbrbrThis villa includes WiFi, cable TV, assigned parking, and access to all Jamaica Royale amenities. Guests are just minutes from Siesta Key Village, local restaurants, shopping, live music, and the Siesta Key Breeze Trolley for carefree island exploring.brbrWith updated interiors, a pool just steps from your patio, and unbeatable access to Siesta Beach, Jamaica Royale Unit 033 delivers the ideal Siesta Key vacation experience. Book your stay with Tropical Sands Accommodations today and enjoy the relaxed coastal lifestyle that keeps guests returning year after year.

Jamaica Royale 033 Close to pool!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$353.31

Jamaica Royale Unit 021 Tropical Sands AccommodationsbrbrWelcome to Jamaica Royale Unit 021, a beautifully refreshed one bedroom, one bathroom coastal retreat located in the heart of Siesta Key. Just steps from the world famous powder soft sands of Siesta Beach, this updated garden level condo offers two queen beds, modern conveniences, and easy access to the community’s three heated pools. Perfect for couples or small families seeking a relaxed beach getaway near Siesta Key Beach and Siesta Key Village.brbrHighlightsbr• 1 Bedroom / 1 Bathroombr• 2 Queen bedsbr• Washer and dryer in unitbr• 3 heated community poolsbr• 4 minute walk to Siesta Beach (via private beach access)br• Shuffleboard and BBQ areabr• Updated interiorbr• One assigned parking spacebr• Close to dining and shopping in Siesta Key VillagebrbrGuests of Jamaica Royale enjoy access to three sparkling heated swimming pools, beautifully landscaped grounds, and private beach access leading directly to the iconic white quartz sand of Siesta Beach, ranked among the best beaches in the United States. Shuffleboard courts and community BBQ areas add fun and convenience for laid back vacation days. Unit 021 is located in the quiet garden area, offering a peaceful setting after time in the sun.brbrStep inside to an inviting living room with comfortable seating, a flat screen TV, and coastal inspired decor. The fully equipped kitchen includes essential appliances, cookware, and ample counter space for preparing meals or beach snacks. A cozy dining table offers a welcoming place to gather after a day by the water.brbrThe bedroom is designed for comfort, featuring two queen beds, new cottage style furnishings, and a flat screen TV. The updated hallway bathroom includes grab bars for added convenience, along with a walk in shower and a spacious vanity.brbrRoom Detailsbr• Bedroom 1: Two queen beds, TVbr• Bathroom 1: Shared hallway bath, walk in shower only, one vanity sinkbrbrThis condo includes a washer and dryer, cable TV, Wi Fi, community beach amenities, and convenient assigned parking. Guests will also enjoy close proximity to Siesta Key Beach, local restaurants, boutiques, and the free Siesta Key Breeze Trolley.brbrWith updated interiors, great community amenities, and a truly unbeatable location near the shimmering shores of Siesta Beach, Jamaica Royale Unit 021 is the ideal Siesta Key escape. Reserve your stay with Tropical Sands Accommodations and start planning your beach vacation today.

Jamaica Royale 021 Nice unit, close to the pool!

Siesta Key, Florida, United States

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Bath

Sleeps

$323.45

A beautifully updated 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!

Gulf and Bay Club- B608 Beautiful and great view!

Siesta Key, Florida, United States

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Bath

Sleeps

$323.45

B708 has one of the best views at Gulf & Bay Club as it looks over the grounds to the Gulf/Beach during the day as well as the lighted interior courtyard in the evening. With its newly renovated marble bathrooms as well as new carpeting/updated furniture and bedding this unit gives you the best there is to offer in a home away from home unit. Although not called The Penthouse, it is located on the top floor of the complex making it one of only a few units in the rental program that offer this outstanding view. With the larger floor plan in the B building, this unit is equipped with 2 Queen beds in the Master and 2 Double beds in the guest room. All new Flat Panel high definition TV's.

Gulf and Bay Club- B708 Great views!

Siesta Key, Florida, United States

Bed