Old Town pickleball Stays, Resort Rentals, & Homes
About Old Town Vacation Rentals
Discover over 3536 amazing vacation rental options in Old Town 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 Old Town.
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 770.03 ft², with prices averaging US $740 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 Old Town.
Top Pickleball-Ready Accommodation Types in Old Town
| Type | Count |
|---|---|
| Vacation Homes | 1713 |
| Holiday Apartments | 398 |
| Cottages | 90 |
| Villas | 37 |
Use these Quick Filters to Find a Vacation Rental in Old Town
★ 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 Old Town with PickleTrip™.
Weather in Old Town, FL
View the weather forecast for Old Town before booking your Old Town Vacation Rentals to confirm your best time to go.
Other Places to Stay in Old Town, FL
Frequently Asked Questions About Old Town?
What are the top vacation rentals, resorts, and hotels in Old Town 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 Old Town. 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 Old Town!
- Sunrise Condo at Seaside - KEY WEST!
- 3 bedroom with living room and sitting room and a pool just 2 blocks from Higgs beach
- SOUL OF THE SEA ~ Charming 3 BR, 3 Ba Home w/Pool and Parking!
- Key West Butterfly Garden Flat - Minutes from Beach & Old Town Perfect for Couples
- ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/Pool, Fitness Area & Beach!
- ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking
- A Duval Street Oasis with balcony overlooking Duval
- GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/Pool and Ocean Views!
- Key West Private Pool Garden Villa - 2 Blocks from Beach
- Old Town Key West classic with private saltwater pool & enclosed patio- by shops
How many pickleball-ready properties have private pools in Old Town?
Discover 600 accommodations with private or nearby pickleball courts in Old Town. Some of the best destinations to stay and play pickleball are:
- Everything Key West has to offer @ Mango Cottage
- Perfect Pineapple by AvantStay Pet Friendly w Pool Month Long Stays Only
- Parking, Heated Pool, Pet Friendly - Seagate House
- Key West Oasis, Seperate Cottage, Very Private Pool and Back Yard
Which vacation rentals, resorts, or hotels in Old Town is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Old Town? 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.
- Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- Duval Street Suite w kitchen and shared heated pool
- Capmar House by Brightwild Huge Home Pool
How many PickleTrip vacation rentals or resorts are available in Old Town?
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 3536 properties listed in Old Town 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 (11)
| Neighborhood | Property Count |
|---|---|
| Key West Historic District Vacation Rentals in Key West, Florida | 2276 |
| Downtown Vacation Rentals in Key West, Florida | 928 |
| Uptown - Upper Duval Vacation Rentals in Key West, Florida | 725 |
| Historic Seaport Vacation Rentals in Key West, Florida | 366 |
| Truman Annex Vacation Rentals in Key West, Florida | 329 |
| Meadows Vacation Rentals in Key West, Florida | 107 |
| The Meadows Vacation Rentals in Key West, Florida | 107 |
| Bahama Village Vacation Rentals in Key West, Florida | 84 |
| Midtown Vacation Rentals in Key West, Florida | 48 |
| White St. Gallery Vacation Rentals in Key West, Florida | 3797 |
| White Street Gallery District Vacation Rentals in Key West, Florida | 3796 |
