361+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. California
  3. San Simeon
  4. Happy Hill

Happy Hill pickleball Stays, Resort Rentals, & Homes

About Happy Hill Vacation Rentals

Discover over 361 amazing vacation rental options in Happy Hill 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 Happy Hill.

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 899.05 ft², with prices averaging US $396 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 Happy Hill.

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Top Pickleball-Ready Accommodation Types in Happy Hill

Type Count
Vacation Homes 286
Cottages 16
Holiday Apartments 7
Villas 1

Use these Quick Filters to Find a Vacation Rental in Happy Hill

★ 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 Happy Hill with PickleTrip™.

Weather in Happy Hill, CA

View the weather forecast for Happy Hill before booking your Happy Hill 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 Happy Hill, CA

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


Hearst Castle
Cayucos State Beach
Moonstone Beach Park
Elephant Seal Rookery
Justin Vineyards and Winery
San Simeon State Park
Morro Strand State Beach
San Simeon Pier
Lake San Antonio
Piedras Blancas Lighthouse
Cambria Center for the Arts
Fiscalini Ranch Preserve
Nitt Witt Ridge
Cayucos Pier
Hearst Ranch Winery
Leffingwell Landing
Brown Butter Cookie Company
Jade Cove
Silver Peak Wilderness
William Randolph Hearst State Park

Frequently Asked Questions About Happy Hill?

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

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

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

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 361 properties listed in Happy Hill 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 361 Happy Hill, CA Vacation Rentals

Recently Booked Vacation Rentals in Happy Hill