Vacation Rentals By Owner In Siesta Key, FL

$311.33

Our House at the Beach C-102- Townhouse Near Beach and Pool!

Siesta Key, Florida, United States

Lake houses offer a generous bi-level layout that includes separate dining and living rooms spaces. The eat-in kitchen is fully stocked with pots, pans, dishware, flatware, and has full-sized appliances including a dishwasher, microwave and washer and dryer for your convenience. Off the large living room there is a balcony overlooking the Lake. The master bedroom suite also opens onto a balcony and has an en-suite bathroom with closets and dressing area. The second bedroom has an adjacent full second bathroom. Each Lake House offers central A/C, ample closet and storage space, cable TV in each bedroom and garage parking for one car. The development includes a private pool, covered pavilion area with a BBQ, a picnic area and tennis courts.

2

Bed

2

Bath

6

Sleeps

$301.29

/ Nightly

Condo

Midnight Cove II 211F - Bayfront Views and Modern Touches

Siesta Key, Florida, United States

This spectacular bayside condominium complex offers an unbeatable location on Siesta Key, complete with private beach access to the world-famous Crescent Beach, known for its sugar-fine, quartz-white sand. This charming 2-bedroom, 2-bathroom first-floor unit features calming beach decor and a screened-in lanai with beautiful views of the Intracoastal Waterway, ensuring a relaxing atmosphere just minutes from the heated swimming pool.brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrExplore the vibrant local community filled with shopping, dining, art, and culture. Take advantage of the FREE Siesta Key Breeze Trolley for easy access to the village without worrying about parking. Stroll to the beach via dedicated access and soak in the sun or enjoy the scenic surroundings on your way to nearby attractions.brbrMidnight Cove II is a spectacular bayside condominium complex with private beach access to Crescent Beach on Siesta Key and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details). brbrRoom DetailsbrLiving Room: Queen sleeper sofabrMaster Bedroom: Queen bedbrGuest Bedroom: Queen bedbrbrWith exciting seasonal events like live music and yoga classes, your stay will be filled with fun. Ready to pack your bags Book your stay at Midnight Cove II today, where relaxation and adventure await in this tropical oasis!

2

Bed

2

Bath

4

Sleeps

$278.78

/ Nightly

Condo

Midnight Cove II 955B: Tropical Getaway on Siesta Key with Pool and Beach Access

Siesta Key, Florida, United States

Welcome to Midnight Cove II 955B! This 2-bedroom, 2-bath Siesta Key condo captures the essence of Old Florida beach vibes while providing all the essentials for a delightful getaway. The spacious primary bedroom features a comfortable king bed with access to the lanai and tropical decor, along with a bathroom that includes a relaxing soaking tub. The second bedroom is equipped with two twin beds, making it perfect for families or friends.brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrThis corner unit on the 5th floor offers stunning views of the Intracoastal Waterway and is just a short walk to private beach access. Midnight Cove II is a spectacular bayside condominium complex with private beach access to Crescent Beach on Siesta Key and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details). brbrLocated only minutes from vibrant downtown Sarasota and attractions like the renowned Ringling Museum of Art, Midnight Cove II is ideally situated for exploring all that Anna Maria Island has to offer. Discover why Siesta Key beach, famous for its sugar-fine quartz-white sand, has been ranked the best beach in America.brbrReady to pack your bathing suit and flip flops Book your stay at Midnight Cove II 955B today and experience the perfect Siesta Key escape! Your idyllic beachfront getaway awaits!

2

Bed

2

Bath

4

Sleeps

$263.56

/ Nightly

Condo

Midnight Cove II 944C - Exceptional Water Views on Siesta Key

Siesta Key, Florida, United States

Welcome to Midnight Cove II 944C! This stylish 2-bedroom, 2-bath condo combines stunning modern comforts with elegant furnishings and delightful beach touches. Spanning 1,400 sq. ft., this inviting fourth-floor unit accommodates up to 4 guests and is easily accessible by elevator or stairs. brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrEnjoy the spacious kitchen and dining area, perfect for family meals, and relax on the 26-foot screened-in lanai, which offers striking views of the lagoon, canal, and docks—ideal for sipping your morning coffee or unwinding in the evening.brbrMidnight Cove II is a spectacular bayside condominium complex with private beach access to Crescent Beach on Siesta Key and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details). brbrMidnight Cove II is perfectly located to allow you to experience the charm of Sarasota, with Siesta Beach's sugar-fine sand and lively Siesta Village nearby, frequently rated among the best beaches in America.brbrReady to pack your bathing suit and flip flops Book your stay at Midnight Cove II 944C today and make lasting memories on beautiful Siesta Key!

2

Bed

2

Bath

4

Sleeps

$241.6

/ Nightly

Condo

Midnight Cove II 138F - Beautifully Appointed Vacation Rental!

Siesta Key, Florida, United States

Experience the best of coastal living at Midnight Cove II 138F, a spectacular bayside condominium complex offering private beach access to Siesta Key Beach and its world-renowned pure white sands and breathtaking sunsets. This beautifully renovated 2-bedroom, 2-bathroom vacation rental is ideal for families or couples seeking a luxurious escape. Located on the Intracoastal Waterway, this 3rd-floor unit boasts stunning views and is just steps away from sandy shores.brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrInside, you'll find a bright and inviting living area complemented by tropical decor, a fully equipped kitchen with modern appliances, and a cozy dining area perfect for family meals. The primary bedroom includes a king bed and a private ensuite bathroom, while the second bedroom features a queen bed, ensuring ample comfort for everyone. brbrMidnight Cove II is a spectacular bayside condominium complex with private beach access to Crescent Beach on Siesta Key and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details).

2

Bed

2

Bath

6

Sleeps

$264.83

/ Nightly

Condo

Midnight Cove II 943C: Family Friendly Condo with Shared Pool and Tennis

Siesta Key, Florida, United States

Welcome to Midnight Cove II 943C!This delightful 2-bedroom, 2-bathroom condo is perfectly situated in the heart of Siesta Key, surrounded by a vibrant community filled with shopping, dining, art, and culture. The primary bedroom features a luxurious king bed and an ensuite bathroom with a walk-in shower and double vanity, while the second bedroom is equipped with two twin beds, making it ideal for families or friends.brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrTake advantage of the complimentary Siesta Key Breeze Trolley, allowing you to explore the area without the worry of parking. Enjoy a leisurely stroll to the beach via our dedicated access point and embrace the joy of sand between your toes.brbrMidnight Cove II is a spectacular bayside condominium complex with private beach access to Crescent Beach on Siesta Key and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details). brbrLocated only minutes from downtown Sarasota and attractions like the renowned Ringling Museum of Art, Midnight Cove II is your ideal base for discovering the beauty of Florida’s Gulf Coast. Siesta Beach, frequently rated as the best beach in America, is just a stone’s throw away.brbrReady to pack your bathing suit and flip flops Book your stay at Midnight Cove II 943C today and experience why Siesta Key deserves a spot on your bucket list! Your perfect getaway awaits!

Bed

Bath

Sleeps

$233.62

/ Nightly

Condo

Midnight Cove II 134F - Bayside Views!

Siesta Key, Florida, United States

Discover Midnight Cove II 134F, a stunning 2-bedroom, 1.5-bath Firethorn unit located in a spectacular bayside condominium complex that offers private beach access to Siesta Key Beach, renowned for its world-famous white sands and breathtaking sunsets. This inviting rental is perfect for families or couples looking to enjoy the beauty and tranquility of a Siesta Key getaway.brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrThis recently updated 3rd-floor unit features tropical decor throughout, creating a relaxed island atmosphere. The spacious living area offers a cozy retreat, perfect for unwinding after a day in the sun. Enjoy meals at the dining table or prepare delicious dishes in the fully equipped kitchen, complete with modern appliances for your convenience. Step out onto your screened-in lanai, where a dining table offers scenic views of the Intracoastal Waterway—perfect for enjoying morning coffee or evening dinners while keeping an eye out for dolphins and manatees.brbrThe primary bedroom features a comfortable king bed and stylish decor, while the second bedroom includes a cozy queen bed. The well-appointed bathroom offers a convenient walk-in shower, making it simple for guests to refresh after their beach adventures. brbrTake advantage of resort-style amenities, including a heated pool, tennis courts, a BBQ area, and more! Book your stay at Midnight Cove II today and immerse yourself in the vibrant charm of Siesta Key! Don’t miss your chance to create lasting memories in this tropical paradise!brbrMidnight Cove II is a spectacular bayside condominium complex with private beach access to Crescent Beach on Siesta Key and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details).

2

Bed

1

Bath

4

Sleeps

$233.85

/ Nightly

Condo

Escape to Midnight Cove II 117F: Siesta Key Condo with Stunning Water Views!

Siesta Key, Florida, United States

Discover the perfect escape at Midnight Cove II, a stunning bayside condominium complex offering private beach access to the world-renowned pure white sands and breathtaking sunsets of Siesta Key Beach. Ideal for those seeking a vibrant setting, this 2-bedroom, 1.5-bathroom first-floor unit provides spectacular views of the Intracoastal Waterway and the Stickney Point Bridge. Enjoy the convenience of being steps from the thriving culture and entertainment of Siesta Village.brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrMidnight Cove II is fully equipped with luxurious amenities, including a heated pool, two tennis courts (one with pickleball), a basketball court, a fitness room, and a BBQ area with grills and tables. Additional features include bike racks, a beautiful observation deck, and private docks available for rent (contact for details).brbrInside, this beautifully updated unit features tiled floors, an extended living area, and a fully equipped kitchen complete with a wine fridge for storing your favorite beverages. The dining area is perfect for entertaining family and friends. The primary bedroom offers serene comfort with an ensuite, while the well-appointed second bedroom is ideal for guests.brbrReady to experience the ultimate Siesta Key getaway Book your stay for a minimum of 7 nights, or explore purchasing your own piece of paradise with our on-site agent. Whether you visit for a week or decide to stay forever, Midnight Cove II is your perfect retreat!

Bed

Bath

Sleeps

$245.17

/ Nightly

Condo

Experience Paradise at Midnight Cove II: Modern Siesta Key Condo

Siesta Key, Florida, United States

Discover the perfect getaway at Midnight Cove II, a stunning bayside condominium complex offering private beach access to the world-renowned pure white sands and breathtaking sunsets of Siesta Key Beach. This tropical oasis is ideal for those seeking a vibrant destination filled with shopping, dining, art, and culture. Ride the FREE Siesta Key Breeze Trolley and enjoy all that Siesta Village has to offer without the hassle of parking.brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrMidnight Cove II is a spectacular bayside condominium complex with private beach access to Crescent Beach on Siesta Key and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details). brbrInside our tastefully updated 1st floor, 2-bedroom, 2-bathroom Firethorn unit, you'll find modern furnishings and tile throughout. The unit boasts a spacious living room with a large flat-screen HD TV, a fully equipped kitchen, and dining area. The primary bedroom offers serene comfort, while the additional bedroom provides ample space for guests. Enjoy stunning views from the screened lanai and the convenience of an in-unit washer/dryer.brbrReady to book your Siesta Key condo and experience paradise Book today and make it a reality!

Bed

Bath

Sleeps

$190.62

/ Nightly

Condo

Condo with Bay Views, Beach Access! - Midnight Cove II 137

Siesta Key, Florida, United States

Midnight Cove II – 137 by Tropical Sands Accommodations brbrWelcome to Midnight Cove II – 137 by Tropical Sands Accommodations, a comfortable two bedroom, one and a half bathroom third floor condo overlooking the Intracoastal Waterway. Perfect for families seeking an easy and relaxing Siesta Key vacation, this home offers private beach access, peaceful water views, and access to a variety of community amenities. Located just a four-minute walk to Crescent Beach, and a quick two-minute walk to the trolley stop, guests can easily explore Siesta Key Village for dining, shops, and entertainment. Boat lovers will appreciate the availability of private docks within the community. brbrHighlights br• 4-minute beach access to Crescent Beach br• 2 bedrooms / 1.5 bathrooms br• 1 king bed, 1 full bed with trundle br• Private balcony with water views br• Community pool br• Tennis, pickleball, basketball, and racquetball courts br• Fitness center br• Private docks (availability varies) br• 2-minute walk to trolley stop brbrMidnight Cove II provides a blend of recreation and relaxation, making it an excellent choice for Siesta Key vacation rentals. Guests can enjoy a heated community pool, private beach access to Crescent Beach, and an impressive range of community amenities including tennis courts, pickleball, basketball, bike racks, a fitness room, grilling areas with picnic tables, and a scenic observation deck overlooking the bay. Private docks are available to rent for guests bringing a boat. brbrInside the condo, the living room provides a welcoming space with comfortable seating, a TV, and plenty of natural light from the sliding doors that open to the private balcony. The balcony’s water views and outdoor seating make it a relaxing place to enjoy your morning coffee or unwind in the evenings. The dining area includes a table perfect for family meals and conversation. The kitchen is well equipped with appliances, granite countertops, cookware, and utensils, offering everything needed for simple meal preparation during your stay. brbrThe primary bedroom features a king-sized bed, soft bedding, a television, and ample storage. The guest bedroom includes a full bed with a trundle, making it perfect for children or additional family members, and also includes its own TV. The main bathroom features a walk-in shower, while a convenient half bathroom is located in the hall for added flexibility and comfort. brbrRoom Details br• Primary Bedroom: King bed, TV br• Guest Bedroom: Full bed with trundle, TV br• Primary Bathroom: Walk-in shower br• Half Bathroom: Hall access brbrGuests will enjoy private beach access, beautifully maintained landscaping, and convenient proximity to Crescent Beach, Siesta Key Village, and nearby Sarasota attractions. The community’s central location makes it easy to enjoy water sports, dining, shopping, and family friendly fun. brbrWith water views, private beach access, and a variety of community amenities, Midnight Cove II – 137 by Tropical Sands Accommodations offers a wonderful setting for a family-friendly Siesta Key getaway. brbrBook your stay today and start planning your perfect island vacation!

Bed

Bath

Sleeps

$440.1

/ Nightly

Condo

Jamaica Royale T64 Great location!

Siesta Key, Florida, United States

Welcome to Jamaica Royale – Unit T64, a bright and airy two-bedroom, two-bathroom beachfront penthouse located on world-renowned Siesta Key Beach. This stunning condo offers panoramic Gulf views, updated interiors, and an open layout perfect for families and couples seeking a relaxing island escape. With a 7-night minimum stay, guests can fully unwind and enjoy the island lifestyle. Spending days by the three shared heated pools, strolling the private beach just steps away, and exploring Siesta Key’s vibrant dining and shopping scene only minutes from the property.brbrHighlightsbr• Beachfront penthouse condo with Gulf viewsbr• 2 Bedrooms / 2 Bathroomsbr• 2 King beds + Queen sleeper sofabr• 7-night minimum stay br• Private balcony overlooking Siesta Key Beachbr• Fully equipped kitchen with modern updatesbr• Washer and dryer in-unitbr• Three shared heated poolsbr• Private beach access just steps awaybr• Outdoor BBQ area and picnic tablesbr• Shuffleboardbr• Reserved parking near elevatorbrbrWake up to breathtaking beach views from your private balcony or sip morning coffee while watching the gentle waves roll across the white quartz sand of Crescent Beach. Spend the day relaxing by one of the resort style heated pools, strolling along the Gulf shoreline, or enjoying a cookout at the community BBQ area. Pickleball courts are also located within walking distance, offering another fun way to enjoy the sunshine. With its prime location and comfortable modern features, this beachfront condo has everything you need for the perfect Siesta Key vacation.brbrThe spacious open concept living area offers plush seating, a flat-screen TV, and sliding glass doors that lead directly to the large balcony with seating for six. The fully equipped kitchen features updated cabinetry, a dishwasher, and a breakfast bar for casual dining, while offering a stunning view of the Gulf from the window. The adjacent dining area comfortably seats six guests, creating the perfect space for shared meals or evening card games.brbrThe primary bedroom features a king bed, flat-screen TV, balcony access, and an ensuite bathroom with a walk-in shower. The second bedroom also includes a king bed and flat-screen TV, with convenient access to a hallway bathroom featuring a shower/tub combination. A queen sleeper sofa in the living room offers additional sleeping space for guests, bringing the total capacity to six.brbrFrom its stunning Gulf views and modern interior to its unbeatable beachfront location, Jamaica Royale – Unit T64 is the ultimate Siesta Key retreat. Relax, recharge, and create unforgettable memories on Florida’s most beautiful beach! Book your stay today with Tropical Sands Accommodations!

Bed

Bath

Sleeps

$382.7

/ Nightly

Condo

Experience Jamaica Royale T63: Top Floor Condo with Gorgeous Beach Views!

Siesta Key, Florida, United States

Jamaica Royale T63 by Tropical Sands Accommodations brCondo in Siesta Key, Florida brbrWelcome to Jamaica Royale T63, a beautiful top-floor condo with 2 bedrooms and 2 bathrooms, ideal for families or small groups. Located in the heart of Siesta Key, this unit offers stunning views of the famous Siesta Key Beach, just steps from your door. Explore nearby attractions, including Siesta Village’s charming shops and restaurants, all within a short ride on the Siesta Key Breeze Trolley.brbrHighlights br• Private Beach Access br• Balcony with Beach Views br• In-unit Washer and Dryer br• FIOS Wi-Fi 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. brbrThe inviting living area features comfortable furnishings, perfect for relaxation after a day at the beach. The full kitchen includes essential appliances and a washer and dryer for convenience. The dining area flows from the kitchen, ideal for family meals. Step onto your private balcony to enjoy stunning views and fresh Gulf breezes.brbrJamaica Royale T63 boasts a coastal primary bedroom with a king bed and an ensuite bathroom with grab bars for safety. The guest bedroom has a queen bed and a twin bed, accommodating up to five guests. With two televisions and secure FIOS Wi-Fi, this condo ensures all your entertainment needs are met.brbrBook your stay today and make unforgettable memories on the beautiful shores of Siesta Key!

Bed

Bath

Sleeps

$445.1

/ Nightly

Condo

Jamaica Royale T62: Stunning Beach Views and Comfort for Couples!

Siesta Key, Florida, United States

Jamaica Royale T62 by Tropical Sands Accommodations brCondo in Siesta Key, FloridabrbrEscape to Jamaica Royale T62, a top-floor beachfront retreat with 2 bedrooms and 2 bathrooms, perfect for couples. Enjoy stunning views of Siesta Beach from every room, just steps from the sand. Located in the heart of Siesta Key, you’re minutes away from delightful restaurants and shops in Siesta Village.brbrHighlights br• Private Beach Access br• Balcony with Beach Views br• In-unit Washer and Dryer 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. brbrThe spacious living room features colorful furnishings, a flat-screen TV, and beach views through a wall of windows leading to your private balcony, perfect for enjoying Gulf breezes. The well-equipped kitchen flows into a dining table for four, ideal for intimate dinners with a view.brbrJamaica Royale T62 offers a luxurious primary bedroom with balcony access, a plush king-size bed, and a full private bath. The guest room also has a king-size bed and walk-in closet for added comfort and privacy.brbrDon’t miss your chance for the perfect romantic getaway at Jamaica Royale T62! Book your stay today and create unforgettable memories in beautiful Siesta Key!

Bed

Bath

Sleeps

$444.9

/ Nightly

Condo

Make Memories at Jamaica Royale T54 – Your Ideal Siesta Key Beach Condo!

Siesta Key, Florida, United States

Jamaica Royale T54 by Tropical Sands Accommodations brCondo in Siesta Key, Florida brbrWelcome to Jamaica Royale T54, a beautifully decorated beach condo with 2 bedrooms and 2 bathrooms, perfect for families. Located on stunning Siesta Key Beach, this spacious unit offers breathtaking views of the #1 beach, just steps away. Enjoy nearby attractions like Siesta Key Village, packed with restaurants, shops, ice cream parlors, and coffee shops—all easily accessible via the Siesta Key Breeze Trolley. brbrHighlights br• Private Beach Access br• Balcony with Beach Views br• In-unit Washer and Dryer 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. brbrThe open-concept living area invites relaxation with its coastal-inspired seating, featuring comfortable sofas and a flat-screen TV. The kitchen boasts granite countertops, high-end stainless steel appliances, and a peninsula that seats four, seamlessly flowing into the dining area for family meals and fun games. Step outside to the spacious balcony, where stunning beach views provide the perfect backdrop for morning coffee or sunset cocktails, letting you fully embrace the tropical atmosphere of Siesta Key. brbrThe condo features a luxurious primary bedroom with a king bed and an ensuite bathroom, complete with a walk-in shower for your convenience. The second bedroom is designed for comfort, equipped with two queen beds and direct access to a hall bathroom featuring a shower-tub combo.brbrDon’t miss out on the opportunity to experience the best of Siesta Key. Book your stay at Jamacia Royale T54 today and create unforgettable memories by the beach!

Bed

Bath

Sleeps

$440.1

/ Nightly

Condo

Jamaica Royale T53 Great updates and views!

Siesta Key, Florida, United States

Jamaica Royale T53 by Tropical Sands AccommodationsbrbrWelcome to Jamaica Royale T53, a beautifully renovated two-bedroom, two-bath Gulf view condo located in the highly sought after Jamaica Royale community on Siesta Key. Positioned in Tower I on the 5th floor with convenient elevator access, this bright and spacious vacation rental offers stunning beach views, a private balcony, and direct access to the world famous Siesta Key Beach. Just a short ride from Siesta Key Village, guests can enjoy the perfect blend of beachfront relaxation and nearby dining, shopping, and entertainment.brbrHighlightsbr• Gulf view condo in Jamaica Royale Tower Ibr• Direct beach access to Siesta Key Beachbr• 2 Bedrooms / 2 Bathroomsbr• 1 King bed, 2 Queen bedsbr• Private balcony with beach viewsbr• 3 heated community poolsbr• Shuffleboard courtsbr• Community BBQ grilling areasbr• In unit washer and dryerbr• Elevator accessbr• 1 assigned parking spacebrbrJamaica Royale is known for its prime beachfront location and resort style amenities. Guests of T53 can spend their days lounging on the powdery white sands of Siesta Key Beach or relaxing by one of the three heated community pools. The spacious private beach area offers plenty of space to unwind, while the community grilling areas provide the perfect setting for outdoor dining with family and friends.brbrInside, the condo features a spacious open concept living area designed for comfort and connection. The living room offers plush seating, a large television, and a wall of windows that fill the space with natural light while showcasing beautiful Gulf views. Sliding glass doors lead to the private balcony, creating seamless indoor and outdoor living. The fully equipped kitchen includes full size appliances, ample counter space, and a center island, making it easy to prepare meals and gather together. The adjacent dining area and outdoor balcony seating offer multiple options for enjoying meals with a view.brbrThe primary bedroom is a relaxing retreat featuring a king bed, direct balcony access, and an ensuite bathroom with a walk-in shower and single vanity. The guest bedroom is ideal for families or groups, offering two queen beds and comfortable furnishings. A second full hallway bathroom includes a shower and tub combination, providing convenience and flexibility for all guests.brbrRoom Details:brPrimary Bedroom: King bed with ensuite bathroom featuring walk-in showerbrGuest Bedroom: Two Queen bedsbrHallway Bathroom: Shower and tub combinationbrbrAdditional amenities include an in unit washer and dryer, secure wireless internet, and elevator access for easy arrival and departure. Located just south of Siesta Key Village, guests can easily hop on the free trolley or take a short walk to explore local restaurants, shops, and nightlife. The location also provides quick access to Crescent Beach, Sarasota, and St. Armands Circle for even more Gulf Coast experiences.brbrWhether you're planning a relaxing beach getaway or a fun filled Siesta Key vacation, Jamaica Royale T53 by Tropical Sands Accommodations offers the perfect combination of comfort, location, and stunning Gulf views. Book your stay today and experience the best of Siesta Key living.

Bed

Bath

Sleeps

$493.42

/ Nightly

Condo

Jamaica Royale T52 Beautifully updated and great view!

Siesta Key, Florida, United States

Jamaica Royale T52 by Tropical Sands AccommodationsbrbrWelcome to Jamaica Royale T52, a beautifully upgraded two-bedroom, two-bath Gulf-view condo located in Tower I at the beachfront Jamaica Royale resort on Siesta Key. This spacious vacation rental features a gourmet chef’s kitchen, comfortable coastal living spaces, and a large private balcony where guests can enjoy breathtaking sunsets and warm Gulf breezes. Perfectly positioned on the Gulf side of Midnight Pass Road, Jamaica Royale provides direct access to the world famous white sands of Siesta Key Beach along with resort style amenities, making this condo an ideal retreat for families, couples, or friends seeking the ultimate beach vacation.brbrHighlightsbr• Gulf view tower condo at the Jamaica Royale beachfront resortbr• Private balcony with sunset viewsbr• Located directly on Siesta Key Beachbr• 2 Bedrooms / 2 Bathroomsbr• 1 King, 2 Full Bedsbr• Gourmet stainless chef’s kitchen with granite countertopsbr• Three heated community poolsbr• Shuffleboard courtsbr• Community grilling and picnic areasbr• Washer and dryer in unitbrbrJamaica Royale is a beloved Gulf front resort community known for its beautifully landscaped grounds and direct access to Siesta Key Beach. Guests staying in Tower Unit T52 can enjoy resort style amenities while still experiencing the comfort and privacy of a fully equipped vacation condo. Spend the day relaxing beside one of the three heated freshwater pools located throughout the property, including the beachfront pool just steps from the sand. Enjoy a friendly game of shuffleboard or gather with family and friends at the community grilling area for a casual outdoor meal while enjoying the island breeze. With direct beach access from the property, guests can easily enjoy swimming, shelling, or sunset walks along the shoreline of Siesta Key Beach.brbrInside, the condo features an open and welcoming layout designed for comfort and relaxation. The living room includes a large sectional sofa and comfortable seating, making it the perfect place to unwind after a day at the beach. Guests can enjoy movie nights on the large smart television with streaming capabilities while relaxing in the cozy living space. The gourmet kitchen is a standout feature of the condo, offering stainless steel appliances, granite countertops, and modern cabinetry. Fully equipped with cookware, tableware, and small appliances, the kitchen provides everything needed to prepare meals during your stay. The nearby dining area offers ample seating for enjoying family meals or gathering together after a day of island adventures. Sliding glass doors lead to the large private balcony where guests can sip morning coffee, take in Gulf views, and enjoy the famous Siesta Key sunsets.brbrThe primary bedroom provides a relaxing retreat featuring a king bed with a premium mattress designed for a restful night’s sleep. Guests can unwind while watching the flat screen television or simply enjoy views of the Gulf from the comfort of the room. The ensuite bathroom includes a walk-in shower and single vanity. The guest bedroom is perfect for families or groups and features two full beds, a television, and ample storage space. A hallway bathroom with a walk-in shower provides convenient access for guests staying in this room. Both bedrooms offer comfortable furnishings and a peaceful atmosphere designed to help guests recharge after a day exploring Siesta Key.brbrRoom Detailsbr-Primary Bedroom: King bed with ensuite bathroom featuring walk-in shower and single vanitybr-Second Bedroom: Two Full bedsbr-Hallway Bathroom: Full bathroom with walk-in shower and single vanitybrbrAdditional conveniences include an in-unit Bosch washer and dryer, high speed internet, smart televisions, hair dryers, a secure safe for valuables, and thoughtful guest amenities designed to make your stay comfortable and convenient. The private balcony features outdoor seating where guests can relax while enjoying Gulf breezes and sunset views.brbrWhether you are planning a relaxing beach getaway or a memorable Siesta Key vacation, Jamaica Royale T52 by Tropical Sands Accommodations offers the perfect combination of comfort, upgraded amenities, and beachfront location. With stunning Gulf views, a gourmet kitchen, and direct access to Siesta Key Beach and the resort’s three heated pools, this condo provides everything needed for an unforgettable island escape. Book your stay today and start planning your perfect Siesta Key vacation.

2

Bed

2

Bath

6

Sleeps

$584.82

/ Nightly

Condo

Beachfront Bliss: Jamaica Royale T51 - Private Balcony with Beach Views!

Siesta Key, Florida, United States

Jamaica Royale T51 by Tropical Sands Accommodations brCondo in Siesta Key, Florida brbrYour ideal beachfront escape awaits! This beautifully designed 2-bedroom, 2-bathroom condo is the perfect retreat for families, friends, or couples seeking relaxation in a luxurious tropical setting. Located just steps away from Siesta Key's famous quartz white sandy beach, you'll enjoy private beach access and immerse yourself in the tranquil beauty of this picturesque paradise. brbrHighlights br• Private Beach Access br• Private Balcony br• Beach Views br• In-unit Washer and Dryer br• 3 Shared Heated Pools br• Community Shuffleboard Court br• Two Shared BBQ Areas br• 1 Assigned Parking Spot brbrConveniently situated just a short stroll from the Siesta Key Breeze Trolley, you'll be minutes away from the vibrant Siesta Key Village. Explore a delightful selection of dining options, charming shops, inviting coffee shops, and lively bars—all within easy reach! brbr Jamaica Royale is a gated beachfront complex that offers exclusive access to the stunning white sands of Siesta Key Beach. The property features three heated community pools, shuffleboard courts, two laundry rooms, shared gas grills, and outdoor showers, allowing you to enjoy the perfect vacation experience in Sarasota, Florida. brbrStep inside to discover a spacious living room equipped with flat-screen TVs and comfortable seating, ideal for unwinding after a fun-filled day in the sun. The kitchen boasts a full array of appliances and cookware, along with the convenience of an in-unit washer and dryer. Gather in the inviting dining area that accommodates everyone, perfect for creating cherished memories together. brbrThe primary bedroom is a serene sanctuary, complete with a king-sized bed, ensuite bathroom, and direct access to the outdoor patio. The additional bedroom is thoughtfully furnished with two queen beds, ensuring comfort for every guest. Both bedrooms are equipped with fresh linens, a TV, and ample storage space, providing a restful retreat after days of beach fun. brbrDon’t miss out on the ultimate beach retreat! Reserve your stay at Jamaica Royale T51 now and experience the perfect blend of relaxation and adventure in one of Florida’s premier vacation destinations!

2

Bed

2

Bath

6

Sleeps

$440.1

/ Nightly

Condo

Jamaica Royale T43 Nice updates and Great views!

Siesta Key, Florida, United States

Escape to the shores of Siesta Key and enjoy a beachfront getaway at Jamaica Royale – Unit T43. This beautifully maintained two-bedroom, two-bath condo features updated kitchen cabinets, bright coastal decor, and relaxing views of the Gulf of Mexico from your private balcony. With a 7-night minimum stay, guests can settle in and fully embrace island life. Spending days lounging by one of three heated pools, strolling the soft white sands of Siesta Beach, or exploring the charming boutiques and restaurants of Siesta Key Village nearby.brbrHighlightsbr• Updated kitchen cabinets and modern appliancesbr• Private balcony with Gulf and pool viewsbr• 7-night minimum stay br• 2 Bedrooms / 2 Bathroomsbr• 2 King beds + queen sleeper sofa in living roombr• Three shared heated pools and direct beach accessbr• Outdoor grilling area and picnic spotsbr• Shuffleboardbr• Washer and dryer in unitbr• Reserved parking steps from the elevatorbrbrLocated within the sought-after Jamaica Royale community on Crescent Beach, this condo places you close to the island’s best attractions. Enjoy easy access to nearby pickleball courts within walking distance of the complex or walk or drive to Siesta Key Village for shopping, dining, and live entertainment. Spend the day relaxing by one of the resort-style heated pools, strolling along the Gulf shoreline, or enjoying a cookout at the community BBQ area. For more coastal adventures, explore nearby Turtle Beach or spend an afternoon at the boutiques and cafes of St. Armands Circle.brbrStep inside and discover a bright, open concept living area designed for both comfort and connection. The living room features plush seating, a flat-screen TV, and sliding glass doors that lead to the private balcony, perfect for morning coffee or evening sunsets. The fully equipped kitchen showcases updated cabinetry, modern appliances, and a breakfast bar for casual meals, while the adjacent dining area comfortably seats six for shared dinners or game nights.brbrThe primary bedroom offers direct access to the balcony and includes a king bed, television, and ensuite bathroom with a walk-in shower. The second bedroom is equally inviting with a king bed, TV, and convenient access to the hallway bathroom, which features a shower and tub combination. In the living room, a queen sleeper sofa provides extra space for guests who prefer their own sleeping arrangement.brbrWith its updated interior, beachfront access, and convenient amenities, Jamaica Royale – Unit T43 offers the perfect Siesta Key retreat for families, couples, and snowbirds alike. Reserve your stay today and experience why this beachside community remains one of Florida’s most beloved destinations.

2

Bed

2

Bath

6

Sleeps

$556.12

/ Nightly

Condo

Jamaica Royale T41: Family-Friendly Beachfront Condo with Panoramic Views!

Siesta Key, Florida, United States

Jamaica Royale T41 by Tropical Sands Accommodations brbrWelcome to Jamaica Royale T41, a bright and spacious two-bedroom, two-bath beachfront condo offering spectacular panoramic views of the Gulf of Mexico. Located in the Tower 1 building of the Jamaica Royale complex on Siesta Key Beach, this stylish retreat is just steps from the sugar-white sands and turquoise waters that make Siesta Key world famous. Perfect for families or couples, you’ll love being close to the Siesta Key Breeze Trolley, which provides easy access to Siesta Key Village’s restaurants, shops, and beachside entertainment.brbrHighlightsbr• Beachfront condo with panoramic Gulf viewsbr• 2 Bedrooms / 2 Bathrooms (Sleeps 6)br• Private beach accessbr• Private balcony with seatingbr• 3 Heated community pools + shuffleboardbr• Walking distance to pickleball courtsbr• Fully equipped kitchen with dining areabr• TVs in every bedroombr• 1 Assigned parking spacebr• 7-night minimum stay (Saturday to Saturday)brbrGuests will enjoy the private access to Siesta Key Beach, three heated freshwater pools, and the relaxing atmosphere of this beautifully landscaped community. Spend your afternoons lounging poolside, playing pickleball or shuffleboard, or enjoying a cookout at one of the community BBQ stations. The gated Jamaica Royale complex provides a true resort-style setting, perfect for making lasting vacation memories.brbrStep inside and experience a bright, open living area filled with natural light and modern coastal decor. Large windows and sliding doors showcase incredible Gulf views, creating a relaxing backdrop for your stay. The living room offers comfortable seating and a Smart TV, while the fully equipped kitchen includes all the essentials for home-style cooking, plus a dining area for shared meals. Enjoy dining inside or step out onto the private balcony to savor your morning coffee or a sunset cocktail while watching the waves.brbrThe primary bedroom features a king bed, TV, private balcony access, and an ensuite bathroom with a walk-in shower. The guest bedroom includes two full beds, a TV, and easy access to the second bathroom, which offers a shower/tub combo. Both bedrooms are designed with guest comfort in mind, featuring plush linens, ample storage, and coastal-inspired touches.brbrRoom Detailsbr• Primary Bedroom: King bed, balcony access, ensuite bath with walk-in showerbr• Guest Bedroom: Two Full beds, hall bath with shower/tub combobrbrDiscover beachfront bliss at Jamaica Royale T41 by Tropical Sands Accommodations, where stunning Gulf views, private beach access, and resort-style amenities create the perfect Siesta Key getaway.brbrBook your stay today and enjoy the beauty and relaxation of Florida’s Gulf Coast!

Bed

Bath

Sleeps

$584.82

/ Nightly

Condo

Unwind at Jamaica Royale T31: Beachfront Condo with Gulf Views & Modern Comforts

Siesta Key, Florida, United States

Jamaica Royale T31 by Tropical Sands Accommodations brbrExperience breathtaking sunset views and warm Gulf breezes from the private balcony of Jamaica Royale T31, a two-bedroom, two-bath beachfront condo in Tower 1. This ideal retreat is perfect for families or friends seeking a relaxing getaway along the beautiful shores of Siesta Key. brbrHighlights br• Private Beach Access br• Private Balcony with Beach Views br• 3 Shared Heated Pools br• Community Shuffleboard Court br• Two Shared BBQ Areas br• 1 Assigned Parking Spot brbrConveniently located just a short stroll from the Siesta Key Breeze Trolley, you’ll be minutes away from the vibrant Siesta Key Village. Explore an array of dining options, charming shops, delightful ice cream parlors, inviting coffee shops, and lively bars—all within easy reach! 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. brbrSteph inside to a comfortable living space with a large seating area, modern kitchen, and dining room table. Both bedrooms are designed for your comfort, offering cozy furnishings, TVs, and ample storage to ensure a restful stay. The primary bedroom includes an ensuite bathroom for added convenience, while the guest bedroom is easily accessible to the second bathroom. brbrBStepook your stay at Jamaica Royale T31 today and create unforgettable memories with family and friends on the stunning Siesta Key Beach!

2

Bed

2

Bath

4

Sleeps

Vacation Rentals By Owner In Siesta Key, FL

$311.33

$301.29

$278.78

$263.56

$241.6

$264.83

$233.62

$233.85

$245.17

$190.62

$440.1

$382.7

$445.1

$444.9

$440.1

$493.42

$584.82

$440.1

$556.12

$584.82

Rent a place that suits your needs

Most popular vacation rentals in Siesta Key

$2522.03

$2135.02

$2157.13

$2193.20

$2342.88

$2445.50

$2479.18

$3229.57

$3133.33

$3110.58

Most Popular Cities in Florida