Vacation Rentals
Siesta Key Vacation Rentals
Tropical Sands Accommodations offers a premium selection of Siesta Key beach vacation rentals for weekly, monthly, or even shorter stays. Browse our full availability below!
413 properties available
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 wait
Midnight Cove II – Unit 832- Marina View1200 Cove II Place 832 Siesta Key FL 34242Welcome to Midnight Cove II 832! Nestled in laid-back Crescent Beach on Siesta Key, our community is brimming with enticing shopping, dining, art, and culture. Enjoy the convenience of the free Siesta Key Breeze Trolley, meaning no more parking hassles while you explo
Roll into the lap of luxury and enjoy a unit that is still sparkling new. Sleeping six, this condo is warm and sunny all day long with gulf views from almost every room. Best enjoyed from the large lanai, you can spend long mornings perched above the Gulf and gorgeous surrounding court yard. The master suite has a king size bed, flat screen TV, a r
Jamaica Royale Unit 067 by Tropical Sands AccommodationsWelcome to Jamaica Royale Unit 067, a beautifully updated two-bedroom, two-bath ground-floor condo with a fresh modern look and serene garden views. Ideally situated in the landscaped garden and pool area of the Jamaica Royale community, this spacious retreat offers comfort, convenience, and e
Completed renovated unit as of July 2025! ABSOLUTELY STUNNING UNIT 59! Completely remodeled in 2025! This sun-filled garden unit is steps to world renowned #1 Siesta Key Beach. One of the QUIETEST units at JR with all Hurricane safe windows and doors, including a separate key for the front and rear patio doors. Designer kitchen with stainless steel
Midnight Cove II – Unit 922 Let's Go to the Beach1100 Cove II Place 922 Siesta Key FL 34242Welcome to Midnight Cove II 922C! Crescent Beach on Siesta Key is a stunning island brimming with shopping, dining, art, and culture, making it the ideal vacation destination. Enjoy the convenience of the free Siesta Key Breeze Trolley, eliminating any parkin
Jamaica Royale 403 by Tropical Sands Accommodations Welcome to Jamaica Royale 403, an inviting beachfront condo in beautiful Siesta Key, Florida! This spacious 2-bedroom, 2-bathroom unit is perfect for families or friends looking for a relaxing beach getaway. Located just steps from the soft sands of Siesta Key Beach, this condo provides easy acces
Midnight Cove II – Unit 931 - I found paradise!1100 Cove II Place 931 Siesta Key FL 34242Welcome to Midnight Cove II 931C! Nestled in the picturesque Crescent Beach on Siesta Key, our vibrant community is alive with shopping, dining, art, and culture. Enjoy the convenience of the free Siesta Key Breeze Trolley, ensuring smooth exploration without t
Midnight Cove II – Unit 955 - Best View Ever!1100 Cove II Place 955 Siesta Key FL 34242Welcome 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
Jamaica Royale 803 by Tropical Sands Accommodations Welcome to Jamaica Royale 803, a beautiful beachfront condo in the gated Jamaica Royale community on Siesta Beach. This bright two-bedroom, two-bath retreat offers stunning Gulf views from the private balcony and all the comforts of home for a 7-night minimum stay. Stroll along the private beach p
Delightfully updated one bedroom one bath. This is a garden view unit located in the garden/pool area of our beautifully landscaped property. The bedroom has a king bed and a queen sleeper sofa in the living room. 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
Midnight Cove II – Unit 912 Midnight Oasis!1100 Cove II Place 912 Siesta Key FL 34242Welcome to Midnight Cove II 912C! Situated in the heart of Crescent Beach on Siesta Key, our community offers a delightful mix of shopping, dining, art, and culture that is sure to entertain you. Enjoy the complimentary Siesta Key Breeze Trolley, which takes the wo
Tell us what you're looking for and someone will contact you with available options.