172+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Florida
  3. Port Richey
  4. Brooksville

Brooksville pickleball Stays, Resort Rentals, & Homes

About Brooksville Vacation Rentals

Discover over 172 amazing vacation rental options in Brooksville 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 Brooksville.

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 1346.14 ft², with prices averaging US $222 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 Brooksville.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Brooksville

Type Count
Vacation Homes 113
Cottages 18
Holiday Apartments 15
Villas 4

Use these Quick Filters to Find a Vacation Rental in Brooksville

★ 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 Brooksville with PickleTrip™.

Weather in Brooksville, FL

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

December - February
High 75°F       Low 53°F
March - May
High 86°F       Low 55°F
June - August
High 91°F       Low 71°F
September - November
High 89°F       Low 59°F

Top Attractions Around Brooksville, FL

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


World Woods Golf Club
Brooksville Country Club
Withlacoochee Trail State Park
Withlacoochee State Forest
Boyett's Grove
HerNonedo Oaks Golf and Country Club
Sherman Hills Golf & Country Club
Chassahowitzka Wildlife Reserve
HerNonedo Heritage Museum
Rivard Golf Club
The Dunes Golf Club
Train Depot Museum
Bayfront Health Brooksville
Oak Hill Hospital
Weeki Wachee Springs
Hudson Beach
Homosassa Springs Wildlife State Park
Saint Leo University
Three Sisters Springs
Lake Jovita Golf and Country Club

Other Places to Stay in Brooksville, FL


Hernando County 874 Properties
Woodland Waters 425 Properties
Oak Hill Hospital 123 Properties
Hernando Oaks Golf and Country Club 118 Properties
Rivard Golf Club 107 Properties
The Dunes Golf Club 105 Properties
Avis Oaks 102 Properties
Masaryktown 99 Properties
High Point 84 Properties
North Weeki Wachee 64 Properties
Nobleton 28 Properties
Brookridge 28 Properties

Frequently Asked Questions About Brooksville?

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

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

Discover 10 accommodations with private or nearby pickleball courts in Brooksville. Some of the best destinations to stay and play pickleball are:

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

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

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 172 properties listed in Brooksville 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
Weeki Wachee Vacation Rentals in Port Richey, Florida 266
Avis Oaks Vacation Rentals in Port Richey, Florida 102
Woodland Waters Vacation Rentals in Port Richey, Florida 425
High Point Vacation Rentals in Port Richey, Florida 84

People Also Ask

There are 172 Brooksville, FL Vacation Rentals

Recently Booked Vacation Rentals in Brooksville