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Properties Available 55 properties available
Tortuga Unit 406 by Tropical Sands Accommodations 30-night Minimum stay Welcome to Tortuga Unit 406, a bright and comfortable two-bedroom, two-bathroom condo located along the tranquil Midnight Pass Road on beautiful Siesta Key. Enjoy stunning beach views from your private balcony and effortless access to the island’s pristine private beach, situ
Tortuga Unit 406
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Delphina by Anna Maria Island AccommodationsWelcome to Delphina, a charming two-bedroom, two-bath waterfront villa nestled along a quiet canal in the heart of Holmes Beach. Designed for couples, small families, or friends traveling together, this inviting Anna Maria Island Accommodations home blends relaxed coastal comfort with unbeatable island co
Delphina
Cottage
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Mermaid’s Retreat by Anna Maria Island Accommodations Welcome to Mermaid’s Retreat, a bright and inviting two-bedroom, one-bath Holmes Beach vacation rental by Anna Maria Island Accommodations, perfectly positioned just steps from the sugar-white sands of the Gulf of Mexico. This charming upper-level condo offers the ultimate Anna Maria Island bea
Mermaid Retreat
Condo Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 baths
HalfBathrooms 1 Half baths
Guests 4 guests
Rating 4.8 (6)
MI Island Time by Anna Maria Island AccommodationsWelcome to MI Island Time, Michigan roots with island soul — a spacious four-bedroom vacation rental in the heart of Holmes Beach on Anna Maria Island, perfect for family reunions, friend getaways, and groups looking to embrace the island lifestyle. This coastal retreat offers a private pool, covere
MI Island Time
House
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Highlights • Private beach access • Shared pools • Tennis, pickleball, racquetball, basketball, and shuffleboard courts • Fitness Center • Community electric vehicle chargers Gulf and Bay Club B604 by Tropical Sands Accommodations Gulf and Bay Club B604 offers a serene escape with two bedrooms, two baths, and a stunning screened-in balcony. Marve
Gulf and Bay Club- B604
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Welcome to Midnight Breeze by Exclusive Vacations, a modern coastal luxury home located just one block from the Gulf in Holmes Beach. This four-bedroom, four and a half-bath retreat features a rooftop deck with outdoor kitchen and putting green, theater room, game room, resort style pool and spa, and elevator, all within a short walk or bike ride t
EXCLUSIVE COLLECTION EXCLUSIVE COLLECTION
Midnight Breeze
House Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 4 baths
HalfBathrooms 1 Half baths
Guests 8 guests
Rating 5 (1)
Gulf and Bay Club Unit E701 by Tropical Sands AccommodationsWelcome to Gulf and Bay Club Unit E701, a beautiful 2-bedroom, 2-bath condo located within the premier Gulf and Bay Club community on Siesta Key. Perfect for extended stays, this 28-night minimum rental combines the comforts of home with resort-style amenities, all just steps from the awar
Gulf and Bay Club- E701
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (1)
Jamaica Royale 106 by Tropical Sands AccommodationsWelcome to Jamaica Royale 106, a beautifully refreshed two-bedroom, two-bath garden view villa located in the highly sought after Jamaica Royale community on Siesta Key. Completely remodeled with an upscale coastal design, this spacious retreat offers modern finishes, comfortable living spaces, and
Jamaica Royale 106
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Sunset by Siesta Key Luxury Rental PropertiesWelcome to Sunset, a recently refreshed two-bedroom, one-bath vacation rental located on the west side of the Sunshine on Siesta property. This relaxed Siesta Key beach rental is ideal for couples, small families, and guests seeking a laid back coastal getaway near the island’s most popular attractions.
Sunset
Duplex Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Rating 5 (9)
Gulf and Bay Club Unit B110 by Tropical Sands AccommodationsWelcome to Gulf and Bay Club Unit B110, a spacious three-bedroom, two-bath condo perfectly situated within one of Siesta Key’s most sought-after beachfront communities. Located just a short five-minute stroll from world-famous Siesta Beach, this inviting retreat blends resort-style living
Gulf and Bay Club- B110
Condo
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
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
Gulf and Bay Club- C209
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Waves Edge by AMI LocalsWelcome to Waves Edge, a beautifully beachfront four bedroom Anna Maria Island vacation rental located in the heart of Anna Maria City, just moments from the Gulf beaches and the charming Pine Avenue shopping and dining district. This upscale coastal retreat blends classic island architecture with modern comforts, featuring
Waves Edge
House Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 3 baths
HalfBathrooms 1 Half baths
Guests 8 guests
Rating 4.5 (2)

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