75+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Florida
  3. Leesburg
  4. Howey-in-the-Hills

Howey-in-the-Hills pickleball Stays, Resort Rentals, & Homes

About Howey-in-the-Hills Vacation Rentals

Discover over 75 amazing vacation rental options in Howey-in-the-Hills 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 Howey-in-the-Hills.

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 1028.5 ft², with prices averaging US $278 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 Howey-in-the-Hills.

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Top Pickleball-Ready Accommodation Types in Howey-in-the-Hills

Type Count
Vacation Homes 47
Villas 6
Holiday Apartments 4
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Howey-in-the-Hills

★ 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 Howey-in-the-Hills with PickleTrip™.

Weather in Howey-in-the-Hills, FL

View the weather forecast for Howey-in-the-Hills before booking your Howey-in-the-Hills 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

Top Attractions Around Howey-in-the-Hills, FL

PickleTrip offers a large selection of top attractions around Howey-in-the-Hills . Research things to do on your vacation before you visit Howey-in-the-Hills.


Mission Inn Golf Resort - El Campeon
Howey Estate
Wekiwa Springs State Park
The Villages Market Square
National Training Center
Kelly Park
Spanish Springs Town Square
Orange County National Golf Club
Webster Westside Flea Market
Lakeridge Winery
Lake Louisa State Park
Bella Collina Golf Club
Grand Oaks Resort and Carriage Musuem
Resurrection Catholic Church
Lake Dora
King's Landing
Lake Weir
Rock Springs Run
Hancock Park
Venetian Gardens

Other Places to Stay in Howey-in-the-Hills, FL


Mission Inn Golf Resort - El Campeon 116 Properties
Howey Estate 104 Properties

Frequently Asked Questions About Howey-in-the-Hills?

What are the top vacation rentals, resorts, and hotels in Howey-in-the-Hills 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 Howey-in-the-Hills. 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 Howey-in-the-Hills!

How many pickleball-ready properties have private pools in Howey-in-the-Hills?

Discover 2 accommodations with private or nearby pickleball courts in Howey-in-the-Hills. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Howey-in-the-Hills? 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 Howey-in-the-Hills?

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 75 properties listed in Howey-in-the-Hills 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.


People Also Ask

There are 75 Howey-in-the-Hills, FL Vacation Rentals

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