
House vacation rentals in Winter Haven
Find and book unique houses on Airbnb
Top-rated house rentals in Winter Haven
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation 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

Cozy, Relaxing & Fun Gateway!

15% Off Florida Summer Vacation Rentals

Lakefront House w/ Private Pool, Beach & Dock

Executive home on private lake.

Stunning 4BR home w/Pool

4/2 New Spacious Pool Home

Heated Pool | Luxury Design | Disney | Golf Course

Legoland Poolside Paradise
Family-friendly house rentals

Luxury near Disney Large extended private pool/spa

Welcoming fully equipped villa in Davenport

Private Pool & Spa, Close Disney, Disney Playhouse

3 bedroom Villa in Kissimmee

The Old Haven - An Enduring Piece of Nostalgia

Disney World Area Villa Orlando * Pool * Sleeps 10

Beautiful 5 Bed Home With Rear Conservation Views

Amazing 4 bed home, large pool, Disney 12 miles!
House rentals with a hot tub

Modern 3br home

PRIVATE Pool Villa - Family Holiday Getaway

No Airbnb Fees! Pvt Pool & SPA / Game Room 272951!

Awesome Vacation Home w/ Private Heated Pool/Spa

Luxurious Golf Front Oasis: Pool, Spa, View&Cinema

There is no other place you want to be than here.

Southern Dunes Lakeview Poolhome

Stunning and modern 4 bedroom home with pool
Quick stats about house rentals in Winter Haven
Total rentals
290 properties
Total number of reviews
10K 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
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- Fitness-friendly rentals Winter Haven
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- Universal Studios Florida
- Orange County Convention Center
- Universal's Volcano Bay
- Old Town Kissimmee
- Discovery Cove
- Disney's Animal Kingdom Theme Park
- Universal Orlando Resort
- SeaWorld Orlando
- Disney Springs
- Raymond James Stadium
- ESPN Wide World of Sports
- Busch Gardens Tampa Bay
- Amalie Arena
- Amway Center
- Epcot
- Magic Kingdom Park
- Reunion West
- Aquatica
- ChampionsGate Golf Club
- Disney's Hollywood Studios
- Kissimmee Lakefront Park
- Walt Disney World Resort Golf
- Island H2O Water Park
- ICON Park