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58 properties available
Gulf Holiday Unit 7 by Tropical Sands Accommodations Minimum stay duration 3 days/nights Discover Gulf Holiday Unit 7, a one-bedroom, one-bathroom condo just a short 2-minute stroll from the award-winning Siesta Key Beach! This inviting retreat features a shared heated pool and a prime location near the shops, restaurants, and nightlife of Siesta
Villa Sand Dollar by Anna Maria VacationsWelcome to Villa Sand Dollar, a charming three-bedroom, two and a half bath Holmes Beach vacation rental just a 2-minute walk to the sugar white sands of Holmes Beach on Anna Maria Island This inviting coastal townhouse retreat offers a private pool, spacious outdoor living, and easy access to the Holmes Bea
Jamaica Royale 108 by Tropical Sands AccommodationsWelcome to Jamaica Royale 108, a beautifully remodeled two-bedroom, two-bath villa in the heart of Siesta Key. Just a five-minute walk from the world-famous Siesta Beach, this modern coastal retreat offers an open-concept layout, fresh tropical decor, and access to outstanding resort-style amenitie
The Midnight Turtle by Siesta Key Luxury Rental PropertiesWelcome to The Midnight Turtle, a beautifully refreshed four-bedroom, three-bath vacation rental tucked inside the exclusive Tortoise Estates community on South Siesta Key. This spacious coastal retreat offers private deeded beach access, a sparkling private pool, screened balconies, and ple
Gulf and Bay Club Unit C209 by Tropical Sands AccommodationsWelcome to Gulf and Bay Club Unit C209, a spacious two bedroom condo in the heart of Siesta Key, located within the beloved Gulf and Bay Club community. This updated coastal retreat offers a bright interior, comfortable furnishings, and convenient access to top resort-style amenities. With
Welcome to 81A by Exclusive Vacations, a design-forward luxury retreat inspired by the iconic architecture of Florida’s 30A and thoughtfully reimagined for Anna Maria Island. Located just two blocks from the beach and Pine Avenue, this five-bedroom, five-and-a-half-bath home offers a seamless blend of refined Mediterranean style, resort-level ameni
Palm Breeze by Anna Maria VacationsWelcome to Palm Breeze, a charming three-bedroom, two-bathroom Holmes Beach vacation rental perfectly located just moments from the beautiful Gulf beaches of Anna Maria Island. This inviting coastal retreat offers a relaxed island atmosphere with comfortable living spaces, a bright interior, and a fun game room co
The Coastal Nest by Tropical Sands AccommodationsWelcome to The Coastal Nest, an upscale three-bedroom, two-bath vacation home tucked away in a quiet residential neighborhood of Sarasota. Designed for comfort and longer stays, this inviting retreat offers a relaxed coastal atmosphere, thoughtful amenities, and a convenient island location ideal for
Midnight Cove II – Unit 133 1900 Cove II Place #133, Siesta Key FL 34242Welcome to Midnight Cove II – Unit 133, a freshly renovated, spacious 2 bedroom, 2 bathroom coastal condo perfectly situated in Siesta Key. Located within the sought-after Midnight Cove II bayside community, this beautifully updated retreat offers a relaxing escape with easy ac
Gulf Holiday Unit 8 by Tropical Sands Accommodations Welcome to Gulf Holiday Unit 8, a recently refreshed one bedroom, one bathroom condo perfectly located in the heart of Siesta Key Village and just a two-minute walk to Siesta Key Beach. Ideal for couples or small families, this cozy and budget friendly Siesta Key vacation rental offers updated in
Welcome to the ultimate Florida retreat at the newly renovated Midnight Cove II 311F! This 1st floor, 2 bed - 2 full bath condo with la washer and dryer is perfectly situated in the heart of Crescent Beach on Siesta Key, America’s #1 beach destination. Enjoy easy access with no stairs- just a short distance to a covered parking space and private he
Gulf and Bay Club Unit B408 by Tropical Sands AccommodationsWelcome to Gulf and Bay Club Unit B408, a comfortable two-bedroom, two-bath condominium located within the highly sought after Gulf and Bay Club community on Siesta Key. This well appointed retreat is ideal for extended stays, offering a relaxed coastal setting just a short walk from the b
