Siesta Key Homes with Maintenance Amenities

Welcome to Siesta Key, Florida, a picturesque barrier island nestled within the stunning Sarasota County. Known for its powdery white sand beaches and vibrant sunsets, Siesta Key is a tropical paradise that offers a unique blend of relaxation and adventure. With a rich tapestry of local culture, an array of dining options, and outdoor activities, this charming island is a haven for families, retirees, and everyone in between.

Siesta Key boasts a diverse real estate market, featuring exquisite homes with maintenance amenities that cater to a carefree lifestyle. Imagine living in a beautifully designed residence where lawn care, pool maintenance, and exterior upkeep are handled for you, allowing you to focus on what truly matters—enjoying the sun, sand, and surf. Many of these homes are nestled within welcoming communities that offer additional perks such as clubhouses, fitness centers, and access to private beaches, making it easy to socialize and connect with neighbors.

The island's laid-back atmosphere is complemented by a host of recreational activities. From kayaking in the crystal-clear waters to exploring the lush nature trails, there's no shortage of ways to immerse yourself in the beauty of Siesta Key. Whether you’re savoring fresh seafood at a local eatery or basking in the sun at the world-renowned Siesta Beach, you'll find that every day feels like a vacation.

Discover the allure of Siesta Key and the exceptional homes available with maintenance amenities—your dream lifestyle awaits in this coastal gem!

Newest Siesta Key Homes with Maintenance Amenities

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

1130 W Peppertree Lane Unit 118, Sarasota image

1130 W Peppertree Lane Unit 118, Sarasota — 1130 $670,000

Live the Siesta Key lifestyle! This beautifully maintained 2-bedroom, 2-bath condo offers the perfect combination of island living, rental potential, and resort-style ame...

2 Beds
2 Baths
Peppertree 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

1300 N Portofino Drive Unit 103, Sarasota image

1300 N Portofino Drive Unit 103, Sarasota — Sailfish $449,500

Welcome to your own piece of paradise on world renowned Siesta Key! This beautifully updated and freshly painted 2 bedroom, 2 bathroom residence in the highly desirable S...

2 Beds
2 Baths
Siesta Harbor SubDv.
34242 Zip Code

915 Seaside Dr Unit 405, WEEKS 22-23, Sarasota image

915 Seaside Dr Unit 405, WEEKS 22-23, Sarasota — 405 $45,000

Fractional Ownership. FRACTIONAL OWNERSHIP **GUARANTEED GULF FRONT DELUXE UNIT** Imagine a perfect family retreat every year for Memorial Weekend on world famous Siest...

4 Beds
3 Baths
Siesta Key Beach Residences 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

5600 Beach Way Drive Unit 111, Sarasota image

5600 Beach Way Drive Unit 111, Sarasota — Beach Way Apts $689,000

Virtually Staged. Some photos have been virtually staged to illustrate the property's potential. Furnishings shown are for visualization purposes only and are not include...

2 Beds
2 Baths
Beachway Apts SubDv.
34242 Zip Code

5600 Beach Way Drive Unit 109, Sarasota image

5600 Beach Way Drive Unit 109, Sarasota — Beach Way Condominiums $689,000 ▼

Some photos have been virtually staged to illustrate the property's potential. Furnishings shown are for visualization purposes only and are not included in the sale. ...

2 Beds
2 Baths
Beachway Apts SubDv.
34242 Zip Code

5400 Ocean Boulevard Unit 15 1-4, Sarasota image

5400 Ocean Boulevard Unit 15 1-4, Sarasota — The Terrace $4,000,000

Perched 15 floors above the Gulf of Mexico within The Terrace—Frank Folsom Smith's iconic beach-front landmark on Siesta Key—two corner residences were combined to create...

2 Beds
3 Baths
Terrace SubDv.
34242 Zip Code