19240+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Florida
  3. Port Richey
  4. Shady Hills

Shady Hills pickleball Stays, Resort Rentals, & Homes

About Shady Hills Vacation Rentals

Discover over 19240 amazing vacation rental options in Shady 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 Shady 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 941.2 ft², with prices averaging US $367 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 Shady Hills.

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Top Pickleball-Ready Accommodation Types in Shady Hills

Type Count
Vacation Homes 7354
Holiday Apartments 3259
Villas 899
Cottages 178

Use these Quick Filters to Find a Vacation Rental in Shady 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 Shady Hills with PickleTrip™.

Weather in Shady Hills, FL

View the weather forecast for Shady Hills before booking your Shady 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 Shady Hills, FL

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


Strong Tower Vineyard
Weeki Wachee Springs
Big Cat Rescue
Hudson Beach
Saint Leo University
Innisbrook Golf Club
Westfield Citrus Park
Lake Jovita Golf and Country Club
Tarpon Springs Sponge Docks
Tampa Premium Outlets
Green Key Beach
Sunset Beach
Saddlebrook Golf Course
Florida Hospital Wesley Chapel
Pine Island Beach Park
Tarpon Springs Aquarium
Giraffe Ranch
Tampa Palms Golf Course
Wesley Chapel District Park
World Woods Golf Club

Other Places to Stay in Shady Hills, FL


Florida 306,319 Properties
Highlands 13,611 Properties
Florida Central Atlantic Coast 6,226 Properties
Port Canaveral 924 Properties
Whitney Beach 831 Properties
Biggar 591 Properties
Survey Creek 503 Properties
Trailer Estates 470 Properties
Ludlam 407 Properties
Thomas Drive 402 Properties
Bearss Plaza 374 Properties
Braden River 359 Properties

Frequently Asked Questions About Shady Hills?

What are the top vacation rentals, resorts, and hotels in Shady 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 Shady 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 Shady Hills!

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

Discover 2731 accommodations with private or nearby pickleball courts in Shady Hills. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Shady 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 Shady 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 19240 properties listed in Shady 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.

Nearby Neighborhood (2) 
Neighborhood Property Count
Highlands Vacation Rentals in Port Richey, Florida 13611
Quail Ridge Vacation Rentals in Port Richey, Florida 31

People Also Ask

There are 19240 Shady Hills, FL Vacation Rentals

Recently Booked Vacation Rentals in Shady Hills