645+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Florida
  3. Fort Walton Beach - Destin
  4. Seaside

Seaside pickleball Stays, Resort Rentals, & Homes

About Seaside Vacation Rentals

Discover over 645 amazing vacation rental options in Seaside 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 Seaside.

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 1747.26 ft², with prices averaging $987 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 Seaside.

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Top Pickleball-Ready Accommodation Types in Seaside

Type Count
Vacation Homes 548
Cottages 22
Holiday Apartments 5
Villas 1

Use these Quick Filters to Find a Vacation Rental in Seaside

★ 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 Seaside with PickleTrip™.

Weather in Seaside, FL

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

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Other Places to Stay in Seaside, FL


Newbill Collection by the Sea 5,760 Properties
Seaside Repertory Theatre 5,758 Properties
Sundog Books 5,755 Properties
Central Square 5,715 Properties
Fusion Art Glass Gallery 5,666 Properties
Seaside Beach 5,287 Properties

Frequently Asked Questions About Seaside?

What are the top vacation rentals, resorts, and hotels in Seaside 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 Seaside. 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 Seaside!

How many pickleball-ready properties have private pools in Seaside?

Discover 19 accommodations with private or nearby pickleball courts in Seaside. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in ? 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 Seaside?

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 645 properties listed in Seaside in 2025, 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
Seagrove Beach Vacation Rentals in Florida 3237
Watercolor Vacation Rentals in Florida 731
Cottage District Vacation Rentals in Florida 33
Seagrove Beach West Vacation Rentals in Florida 4974

People Also Ask

There are 645 Seaside, FL Vacation Rentals

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