Siesta Key Homes with Pickleball Court(s) Amenities

Welcome to Siesta Key, Florida—a stunning barrier island renowned for its powdery white sand beaches and vibrant coastal lifestyle. Nestled in Sarasota County, Siesta Key is not only a tropical paradise but also a community rich in charm and recreational opportunities. With its inviting atmosphere, it’s no wonder that Siesta Key has become a sought-after destination for beach lovers, families, and retirees alike.

One of the unique features of Siesta Key is its commitment to active living, and what better way to embrace that lifestyle than with homes that offer pickleball court amenities? As the fastest-growing sport in America, pickleball is a perfect blend of tennis, badminton, and ping-pong, making it enjoyable for all ages. Imagine waking up in your beautiful Siesta Key home and stepping outside to enjoy a friendly match with family or neighbors, all while basking in the warm Florida sun.

Homes equipped with pickleball courts not only provide a space for recreation but also foster a sense of community and connection. Whether you’re a seasoned player or just starting, these properties offer a unique opportunity to engage with your surroundings and make lasting memories.

In addition to the courts, Siesta Key boasts an array of amenities, including world-class dining, boutique shopping, and breathtaking sunsets that paint the sky in hues of orange and pink. With its idyllic atmosphere and active lifestyle options, Siesta Key is the perfect place to call home. Experience the magic of coastal living and elevate your lifestyle with a home that embraces both relaxation and recreation!

Newest Siesta Key Homes with Pickleball Court(s) Amenities

8701 Midnight Pass Road Unit 304A, Sarasota image

8701 Midnight Pass Road Unit 304A, Sarasota — 8701 $649,000

Experience the ultimate Bayfront lifestyle on Siesta Key in this turnkey furnished 2BR/2BA residence at Turtle Bay. Tucked away on the serene south end of the island, thi...

2 Beds
2 Baths
Turtle Bay SubDv.
34242 Zip Code

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

6265 Midnight Pass Road Unit 102, Sarasota image

6265 Midnight Pass Road Unit 102, Sarasota — Excelsior Beach To Bay 8 $675,000 ▼

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

7740 Sanderling Road, Sarasota $22,000,000

Pre-Construction. To be built. Architectural Rendering Of What Could Be Built Are For Planning Purposes Only. An Extraordinary Gulf-Front Estate Opportunity! There ...

6 Beds
8 Baths
Siesta Properties Inc SubDv.
34242 Zip Code

1600 Cove Ii Place Unit 412, Sarasota image

1600 Cove Ii Place Unit 412, Sarasota — 4 $580,000

Welcome to your Siesta Key getaway at Midnight Cove II! This desirable first-floor condominium offers a wonderful combination of coastal living, resort-style amenities, a...

2 Beds
2 Baths
Midnight Cove Ii 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

1141 W Peppertree Drive Unit 1141, Sarasota image

1141 W Peppertree Drive Unit 1141, Sarasota — 36 $669,000

Discover effortless Siesta Key living in this beautifully updated and fully furnished 2-bedroom, 2-bath condo in the highly desirable Peppertree Bay community. Located on...

2 Beds
2 Baths
Peppertree Bay 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

8764 Midnight Pass Road Unit A201, Sarasota image

8764 Midnight Pass Road Unit A201, Sarasota — Island Reef I $629,900 ▼

Ready to Enjoy the Great Life? Welcome to your own piece of paradise at Island Reef, one of Siesta Key's most sought-after Gulf-to-Bay Communities. Perfectly positioned i...

2 Beds
2 Baths
Island Reef SubDv.
34242 Zip Code

8911 Midnight Pass Road Unit 409, Sarasota image

8911 Midnight Pass Road Unit 409, Sarasota — 8911 $519,000 ▼

Move-in ready, turnkey furnished, and perfect for your winter retreat or next investment! Ideally located on the south end of Siesta Key, directly across from the free Si...

2 Beds
2 Baths
Sunrise Cove SubDv.
34242 Zip Code

7740 Sanderling Road, Sarasota $8,000,000

An Extraordinary Gulf-Front Estate Opportunity There are few opportunities remaining to create a legacy estate directly on the Gulf of Mexico. At 7740 Sanderling Road, ...

Siesta Properties Inc SubDv.
34242 Zip Code