
House holiday rentals in Winter Haven
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Top-rated house rentals in Winter Haven
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter Haven house rentals
House rentals with a pool

Lake Whistler Beach House with lakefront pool

Hollingsworth Pool Home

Lakefront House w/ Private Pool, Beach & Dock

Kid-friendly Home w/ Pool & BBQ

Costa Legoland | 5BDR Private Resort | LEGO Theme

*Luxurious Paradise Mansion: Pool, Spa & Cinema

Little Castle on the canal on lake Arietta

Family & Pet Friendly near Disney & Legoland. Pool
Weekly house rentals

Bright Home Near Legoland & Lake

Winter Haven Legoland Retreat

Lakefront Home on the Winter Haven Chain O’Lakes!

Tranquil Haven, Near Disney

Perfect retreat for the family near Legoland!

Arcade+Pingpong + 10 guests + 11 mil to Lego Land!

Magnolia Farmhouse- Cozy with a Perfect Patio

Newly remodeled House 3BR/2BA
Private house rentals

"Elohim Cozy House" In Winter Haven

Sweet vacation home.

Encanto At Auburndale

Cozy Lakefront Home w/ Pool -7 mins from Legoland

Overlook Joy

Escape Comfort Property

House near Legoland Lake Eva Park Bok Tower Garden

Lakefront Cabin Oasis
Quick stats about house rentals in Winter Haven
Total rentals
300 properties
Total number of reviews
11K reviews
Family-friendly rentals
210 properties are a good fit for families
Pet-friendly rentals
100 properties allow pets
Rentals with a pool
90 properties have a pool
Rentals with dedicated workspaces
170 properties have a dedicated workspace
Destinations to explore
- Central Florida Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
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- Seminole Holiday rentals
- Saint Johns River Holiday rentals
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- Private suite rentals Winter Haven
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- Guesthouse rentals Winter Haven
- Rentals with lake access Winter Haven
- Villa rentals Winter Haven
- Rentals with pools Winter Haven
- Rentals with a washing machine and dryer Winter Haven
- Kid-friendly rentals Winter Haven
- Apartment rentals Winter Haven
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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
- Raymond James Stadium
- Busch Gardens Tampa Bay
- ESPN Wide World of Sports
- Amalie Arena
- Amway Center
- Magic Kingdom Park
- Epcot
- Aquatica
- Walt Disney World Resort Golf
- Reunion West
- Island H2O Water Park
- ChampionsGate Golf Club
- Disney's Hollywood Studios
- Kissimmee Lakefront Park
- ICON Park