Siesta Key Homes with Association Recreation - Owned Community Features

Welcome to Siesta Key, Florida, a stunning barrier island known for its pristine beaches, vibrant culture, and laid-back lifestyle. Nestled in Sarasota County, Siesta Key boasts some of the finest sandy shores in the world, with Siesta Beach consistently ranked among the top beaches in the United States. The island’s warm, turquoise waters and breathtaking sunsets create an idyllic setting for both relaxation and adventure.

Siesta Key is not just about its natural beauty; it also offers a welcoming community atmosphere. Here, you’ll find charming boutiques, delightful restaurants, and lively entertainment options, making it a perfect destination for both residents and visitors. The island’s unique blend of tranquility and excitement ensures there’s always something to do, whether it’s indulging in fresh seafood at a local eatery or enjoying a day of paddleboarding in the Gulf.

For those seeking a home in this paradise, Siesta Key offers a variety of properties within Association Recreation - Owned Communities. These homes provide an exceptional lifestyle with access to exclusive amenities, including clubhouses, swimming pools, and recreational facilities. Living in one of these communities means you can enjoy a strong sense of camaraderie with your neighbors while taking advantage of the well-maintained surroundings.

Whether you’re looking for a vacation getaway or a permanent residence, Siesta Key’s homes with Association Recreation - Owned Community features present a unique opportunity to embrace the coastal lifestyle. Experience the charm and beauty of Siesta Key, where every day feels like a vacation!

Newest Siesta Key Homes with Association Recreation - Owned Community Features

9393 Midnight Pass Road Unit 205, Sarasota image

9393 Midnight Pass Road Unit 205, Sarasota — North $650,000

This beautifully renovated 2-bedroom, 2-bath condominium overlooking the bay was freshly painted on 9/8/2026 and is truly move-in ready. Turnkey furnished with an open ki...

2 Beds
2 Baths
Pointe On Midnight Pass SubDv.
34242 Zip Code

6140 Midnight Pass Road Unit 101, Sarasota image

6140 Midnight Pass Road Unit 101, Sarasota — N/A $875,000

Experience the ultimate Siesta Key beach get-away in your TURNKEY FURNISHED, west-facing condo at Horizons West and just steps from your private beach with plenty of beac...

1 Beds
1 Baths
Horizons West SubDv.
34242 Zip Code

6480 Midnight Pass Road Unit 612, Sarasota image

6480 Midnight Pass Road Unit 612, Sarasota — South Tower $1,325,000

Welcome to the ultimate Siesta Key getaway at Unit 612 in Siesta Breakers! This beautifully updated penthouse is completely move-in ready and offered TURNKEY FURNISHED—ju...

2 Beds
2 Baths
Siesta Breakers SubDv.
34242 Zip Code

6265 Midnight Pass Road Unit 102, Sarasota image

6265 Midnight Pass Road Unit 102, Sarasota — Excelsior Beach To Bay 8 $700,000

Virtually Staged. Experience the world renowned beaches of Siesta Key in this rarely available first floor luxury condominium steps away from your private deeded beach ac...

2 Beds
2 Baths
Excelsior Beach To Bay SubDv.
34242 Zip Code

5880 Midnight Pass Road Unit 307, Sarasota image

5880 Midnight Pass Road Unit 307, Sarasota — Casarina $1,400,000

A TRUE 3-bedroom condo residence in desirable Casarina, a premier building positioned directly on the quartz white sands of #1 Siesta Key beach and the Gulf of Mexico. S...

3 Beds
2 Baths
Casarina SubDv.
34242 Zip Code

1900 Cove Ii Place Unit 127, Sarasota image

1900 Cove Ii Place Unit 127, Sarasota — Bldg 1 $575,000

Welcome to this gorgeous WATER FRONT condo in desirable Midnight Cove II on beautiful Siesta Key! This coastal designed, TURNKEY furnished 2 bedroom beauty is move-in rea...

2 Beds
2 Baths
Midnight Cove Ii SubDv.
34242 Zip Code

6300 Midnight Pass Road Unit 809, Sarasota image

6300 Midnight Pass Road Unit 809, Sarasota — Crystal Sands $1,795,000

From its elevated eighth-floor setting at Crystal Sands, this turnkey-furnished residence captures an extraordinary panorama of the Gulf of Mexico and Siesta Key’s renown...

2 Beds
2 Baths
Crystal Sands SubDv.
34242 Zip Code

5855 Midnight Pass Road Unit 222, Sarasota image

5855 Midnight Pass Road Unit 222, Sarasota — 5855 $625,000

Turnkey and ready for its next chapter, this spacious residence in the curve of Harbor Towers Yacht & Racquet Club is one of the largest floor plans in the building, feat...

2 Beds
2 Baths
Harbor Towers Y & R SubDv.
34242 Zip Code

19 Whispering Sands Drive Unit 201, Sarasota image

19 Whispering Sands Drive Unit 201, Sarasota — 19 Nt $874,900

ENDLESS POSSIBILITIES ON SIESTA KEY. Welcome to 19 Whispering Sands Drive, Unit 201, an exceptional opportunity to create your own Gulf Coast retreat in one of Siesta Key...

2 Beds
2 Baths
Whispering Sands SubDv.
34242 Zip Code

6006 Midnight Pass Road Unit 60, Sarasota image

6006 Midnight Pass Road Unit 60, Sarasota — G $479,000

Beautifully Updated One-Bedroom Condo on Siesta Key Enjoy the best of island living in this beautifully updated one-bedroom, one-bath condominium on Siesta Key. This inv...

1 Beds
1 Baths
Casa Mar SubDv.
34242 Zip Code

5955 Midnight Pass Road Unit 21E, Sarasota image

5955 Midnight Pass Road Unit 21E, Sarasota — Sea Club 2,Phase 1, #21e $729,500

Sea Club II -Only those looking for a relaxing, quiet and tranquil get-away with an "Old Florida" feel. Sea Club II has private access to Siesta Key beach sand and the Gu...

2 Beds
2 Baths
Contntls Sea Club SubDv.
34242 Zip Code

5770 Midnight Pass Road Unit 301, Sarasota image

5770 Midnight Pass Road Unit 301, Sarasota — 5770 $1,099,000

Welcome to Gulf & Bay, Siesta Key’s premier GATED condominium complex. If you are looking for a great investment or the perfect place to call home, look no further. Loca...

2 Beds
2 Baths
Gulf & Bay Club SubDv.
34242 Zip Code