
Holiday rentals with a pool in Sumter County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Sumter County
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Sumter County rentals with a pool
House rentals with a pool

StJohns is a great area for golf, hiking, Kayaking

2 Minute Stroll to Pools and Rec Center, Golf Cart

4 Bedroom Dade City Home

The Villages - Sunshine and pickleball

Renovated! Between Two Squares with Golf Cart !

Central Villages w/ Golf Cart

New, private pool getaway in The Villages, FL

Brooksville Oasis! 3 Bedroom, Heated Pool Home
Other holiday rentals with a pool

PATIO VILLA W/GOLF CART 1M TO SQ-NO XTRA GUEST FEE

Heated Pool, Dog Friendly, Golf Cart Included

Villages - Htd. Pool 3BR/2BA, Conv. Loc., pet +

Beautiful House and free tickets to Mirada Lagoon!

Safari themed private addition with pool/hot tub.

Welcome to the Villages

Fabulous Courtyard Villa close to Sumter Landing

Charming Villages Retreat
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- Universal Studios Florida
- Orange County Convention Center
- Universal's Volcano Bay
- Universal Orlando Resort
- Old Town Kissimmee
- Discovery Cove
- SeaWorld Orlando
- Disney's Animal Kingdom Theme Park
- Disney Springs
- Busch Gardens Tampa Bay
- ESPN Wide World of Sports
- Magic Kingdom Park
- Amway Center
- Epcot
- Aquatica
- Island H2O Water Park
- Rainbow Springs State Park
- Disney's Hollywood Studios
- ChampionsGate Golf Club
- Kissimmee Lakefront Park
- ICON Park
- Universal CityWalk
- Southern Dunes Golf and Country Club
- Fort Island Beach