Onsite Grills and BBQ Areas
354 properties available
Harbor Towers Unit 321 by Tropical Sands AccommodationsWelcome to Harbor Towers Unit 321, a spacious one-bedroom, one-bath condo in one of Siesta Key’s most desirable gated waterfront communities. Perfect for couples, seasonal guests, or extended stays with a 13-night minimum requirement, this inviting retreat offers scenic views, a bright enclosed
Harbor Towers 321
Condo
2
bedrooms
2
baths
4
guests
4.3
(3)
A wonderful 2-bedroom/2-bath fully appointed condo nestled into a the only true resort on Siesta Key. This condo has a king in the master and 2 full size beds in the guest bedroom. 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
Gulf and Bay Club- E705
Condo
2
bedrooms
2
baths
6
guests
Jamaica Royale 072 by Tropical Sands AccommodationsWelcome to Jamaica Royale 072! A newly renovated two-bedroom, two-bath garden-view condo in the desirable pool #2 area of the Jamaica Royale complex. This beautiful retreat features modern updates, coastal decor, and a relaxing patio surrounded by lush landscaping. Guests will love the easy access
Jamaica Royale 072
Condo
2
bedrooms
2
baths
5
guests
5
(3)
Jamaica Royale 083 by Tropical Sands AccommodationsWelcome to Jamaica Royale 083, a beautifully refreshed two-bedroom, two-bath garden view villa located directly on the Gulf at the highly sought after Jamaica Royale resort on Siesta Key. Recently updated with new paint, flooring, and furnishings in June 2025, this inviting vacation rental offers a
Jamaica Royale 083
Condo
2
bedrooms
2
baths
6
guests
5
(2)
Jamaica Royale 801 by Tropical Sands AccommodationsWelcome to Jamaica Royale 801, a top-floor beachfront condo offering breathtaking panoramic views of the Gulf of Mexico. Perfect for couples or small groups, this two-bedroom, two-bath vacation home combines coastal comfort, modern finishes, and the convenience of being just steps from the soft whi
Jamaica Royale 801
Condo
2
bedrooms
2
baths
4
guests
5
(1)
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 bea
Gulf and Bay Club- B608
Condo
2
bedrooms
2
baths
6
guests
Just across the street from the acclaimed #1 Beach in the US. This beautiful 2 bedroom/2 bath condo has all the comforts of home! This condo offers a fully equipped kitchen, spacious living room, dining area, washer and dryer and balconies off of both the living room and dining room. Linens and towels are also provided. The facilities include a hea
Our House at the Beach E-603
Condo
2
bedrooms
2
baths
6
guests
5
(6)
Harbor Towers Unit 319 by Tropical Sands AccommodationsHarbor Towers Unit 319 is a spacious three-bedroom, two-bath condo located within the gated waterfront Harbor Towers community on Midnight Pass Road in Siesta Key. Designed for families or small groups, this inviting retreat offers a comfortable layout, bright coastal interiors, and a screened
Harbor Towers 319
Condo
3
bedrooms
2
baths
6
guests
Gorgeous updated unit with fabulous sunset views of the Gulf right from the lanai. Walk down the stairs and step right out onto beautiful Siesta Key beach. New furnishings and remodeled kitchen. Colorful, beachy decor that will please all. Hardwood floors in the living/dining area with carpeting in the bedrooms. You also have a beautiful view of th
Gulf and Bay Club- A302
Condo
2
bedrooms
2
baths
6
guests
Enjoy beautiful views of Siesta Key Beach from this 2-bedroom/2-bath fully appointed condo located within the premier resort on Siesta Key. Enjoy your morning coffee or evening refreshments from the glass enclosed lanai overlooking the gulf and the tropical courtyard. The master bedroom has a king-size bed, television, full ensuite bath, and walk-
Gulf and Bay Club- A510
Condo
2
bedrooms
2
baths
6
guests
First floor townhouse, few steps inside and outside, no elevator. Garage has a max height of 70"Our House at the Beach is located directly across the street from Siesta Key Beach, home to mesmerizing white sands and unforgettable Florida sunsets. This complex is set around a scenic lake and features a private community pool, a covered pavilion area
Our House at the Beach C-121
Condo
2
bedrooms
2
baths
4
guests
5
(7)
This 3 bedroom- 2 1/2 bath corner unit is a slice of "vacation heaven ". The views of the beautiful Siesta Key beach as well as the Gulf of Mexico from nearly every room in this condo is nothing less than SPECTACULAR!!! The open floor plan is very spacious and comfortable. Gorgeous unit with tasteful and pristine decor.A totally renovated unit in 2
Gulf and Bay Club- B601
Condo
3
bedrooms
2
baths
1
Half baths
6
guests
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