5770+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Florida
  3. Sarasota
  4. Siesta Key

Siesta Key pickleball Stays, Resort Rentals, & Homes

About Siesta Key Vacation Rentals

Discover over 5770 amazing vacation rental options in Siesta Key with pickleball courts or nearby facilities. From resorts to hotels, villas to condos, PickleTrip connects you with a vast selection of pickleball-ready amenities at great prices, providing you with the perfect spot to base your next pickleball vacation. Stay and Play pickleball When You Travel and uncover great stays in Siesta Key.

Find exclusive last-minute deals on vacation rentals, resorts, and hotels with private courts and nearby facilities with PickleTrip™, whether you're traveling solo or with a group. Our platform offers a variety of stay options, from vacation rentals to Airbnb-style properties, all with private pickleball courts or nearby facilities. Compare options from multiple suppliers with a single click to find the perfect stay that fits your budget and style. Places to stay near pickleball courts are an average of 970.37 ft², with prices averaging US $586 per night.

With PickleTrip™, you can easily search for and book your next pickleball vacation rental with courts or nearby facilities. Our platform connects you with the ideal holiday rental to create a lifetime of travel memories. Prices listed are often discounted versus rack rates, so you can secure your perfect place to stay today and get ready to play pickleball in Siesta Key.

Show more
Show less

Things to Know Before You Visit Siesta Key

Siesta Key, a barrier island on Floridas West Coast, is a beach lovers paradise. Whether youre visiting for a week or just an afternoon, there are plenty of ways to enjoy the sights and sounds of this lively community. In fact ,there are so many possibilities that it can feel overwhelming as soon as you arrive at the Siesta Key beach.

To make it easy for you, here are 6 great things you should do while visiting Siesta Key.

  1. Greet the morning with a stroll on the beach.
  2. Take a yoga class on the beach or try out one of the other intown studios from something unique, like aerial yoga.
  3. Walk or run around Siesta Key Village to grab breakfast at one of the many cafu00e9s, restaurants, and coffee shops.
  4. Take a stroll along the bayside path to unwind. Rent rollerblades, bikes, or kayaks if youd a different way to get around. If youre not feeling active, walk through Roberts Bay Hammock Park instead. Its a lush oasis that will make you feel like youre somewhere else.
  5. Go beachcombing for shells and sand dollars at Roberts Bay Nature Park .
  6. Stroll down to the public beach access on Stickney Point Road before or after your Siesta Key sunset, which you wont want to miss! Then head over to one of the many outdoor dining options for food and drinks under the stars.
Show more
Show less

Top Pickleball-Ready Accommodation Types in Siesta Key

Type Count
Vacation Homes 1741
Holiday Apartments 558
Villas 376
Cottages 58

Use these Quick Filters to Find a Vacation Rental in Siesta Key

★ Pro Tip: PickleTrip™ is a travel platform, connecting avid pickleball players and enthusiasts with a variety of vacation rentals, resorts, and hotels featuring private pickleball courts or nearby facilities. We curate a vast selection of properties from trusted sources, providing you with unbeatable options and pricing to find the perfect pickleball getaway. Experience unforgettable pickleball matches in Siesta Key with PickleTrip™.

Weather in Siesta Key, FL

View the weather forecast for Siesta Key before booking your Siesta Key Vacation Rentals to confirm your best time to go.

December - February
High 79°F       Low 51°F
March - May
High 91°F       Low 53°F
June - August
High 92°F       Low 72°F
September - November
High 90°F       Low 57°F

Top Attractions Around Siesta Key, FL

PickleTrip offers a large selection of top attractions around Siesta Key . Research things to do on your vacation before you visit Siesta Key.


Siesta Key Beach
Turtle Beach
Crescent Beach
Siesta Key Marina
Point of Rocks
Shell Beach
St. Boniface Episcopal Church Labyrinth
Bay Island
Irma Beach
Jim Neville Marine Preserve
Lido Beach
Venice Beach
St. Armands Circle
IMG Academy
Nokomis Beach
Coquina Beach
Sarasota Jungle Gardens
Mote Marine Laboratory & Aquarium
Sarasota Memorial Hospital
John and Mable Ringling Museum of Art

Other Places to Stay in Siesta Key, FL


Siesta Key Marina 7,064 Properties
Crescent Beach 6,975 Properties
St. Boniface Episcopal Church Labyrinth 6,964 Properties
Point of Rocks 6,874 Properties
Siesta Key Beach 6,531 Properties
Irma Beach 5,863 Properties
Shell Beach 5,424 Properties
Siesta Key Village 4,042 Properties
Turtle Beach 3,684 Properties
Aloha Kai 92 Properties
Bay Island 40 Properties
Bay Isle 40 Properties

Frequently Asked Questions About Siesta Key?

What are the top vacation rentals, resorts, and hotels in Siesta Key with Courts?

Experience the ultimate pickleball vacation with PickleTrip™. We offer a variety of premium rental properties, resorts, and hotels with private pickleball courts or nearby facilities in Siesta Key. Whether you're a beginner or a seasoned player, we have the perfect destination for you to stay and play. Book now and discover the best pickleball vacation spots in Siesta Key!

How many pickleball-ready properties have private pools in Siesta Key?

Discover 919 accommodations with private or nearby pickleball courts in Siesta Key. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in Siesta Key is best for families looking for a pickleball-getaway?

Looking for a fun and active getaway with pickleball courts in Siesta Key? With PickleTrip™, you'll have access to a wide selection of top-rated properties that offer private pickleball courts or nearby facilities. Make the most of you getaway and ace your A-game while you travel.

How many PickleTrip vacation rentals or resorts are available in Siesta Key?

PickleTrip™ offers a diverse selection of properties with private pickleball courts or nearby facilities to enhance your pickleball experience on your next trip. With a combination of established great stays and new options in top locations, PickleTrip™ has over 5770 properties listed in Siesta Key in 2026, and the number only continues to grow. By consolidating listings from various providers, PickleTrip™ brings you the best luxury stays for a sporty, professional, and fun travel experience.

Nearby Neighborhood (4) 
Neighborhood Property Count
Siesta Key Village Vacation Rentals in Sarasota, Florida 4042
South Sarasota Vacation Rentals in Sarasota, Florida 118
Aloha Kai Vacation Rentals in Sarasota, Florida 92
Bay Isle Vacation Rentals in Sarasota, Florida 40

People Also Ask

There are 5770 Siesta Key, FL Vacation Rentals

Recently Booked Vacation Rentals in Siesta Key