
Vacation rentals with a pool in Winter Haven
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Winter Haven
Guests agree: these homes with a pool 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 rentals with a pool
House rentals with a pool

Lake Whistler Beach House with lakefront pool

Hollingsworth Pool Home

Lakefront House w/ Private Pool, Beach & Dock

Costa Legoland | 5BDR Private Resort | LEGO Themed

Stylish Lakehome w.HUGE Pool/Arcade/Theater

Escape Comfort Property

4/2 New Spacious Pool Home

Southern Dunes Villa - Pool - Golf - near Disney
Condo rentals with a pool

The Mouse Pad: Luxury Condo near Walt Disney World

Maria Luz Studio-Huge Terrace/Universal area.

Orlando Spacious 2-Suites & Resort-Style Pool

Disney & Epic Free Shuttle, Kitchen

*Sunset Perch: Views, Reunion Resort, XBox, 2Pools

Luxury 2B2B APT Near Convention Center, Universal

Lakefront Resort Condo near Disney & Universal

1-101 Legacy Dunes, Gym, Tennis, Close To Disney!
Home rentals with a private pool

Disney's Championsgate: Private Pool & Arcade Fun!

Minniehaha Castle Retreat

Beautiful 9 Br Pool Home In the Solterra Resort!

Airy, Stylish Home with Pool Heat Included in Davenport

Visit Disney World from a Sunny Home with a Pool

Family Retreat Near Disney with Pool & Hot Tub!

New! 209mcv - Balmoral Resort

The Manors at Westridge Home W/ Private Pool
Quick stats about vacation rentals with a pool in Winter Haven
Total rentals
140 properties
Total number of reviews
5K reviews
Family-friendly rentals
100 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
90 properties have a dedicated workspace
Wifi availability
140 properties include access to wifi
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- Universal Studios Florida
- Orange County Convention Center
- Universal's Volcano Bay
- Old Town Kissimmee
- Universal Orlando Resort
- Discovery Cove
- SeaWorld Orlando
- Disney's Animal Kingdom Theme Park
- Disney Springs
- Raymond James Stadium
- ESPN Wide World of Sports
- Busch Gardens Tampa Bay
- Amalie Arena
- Amway Center
- Epcot
- Magic Kingdom Park
- Aquatica
- Reunion West
- Walt Disney World Resort Golf
- ChampionsGate Golf Club
- Island H2O Water Park
- Kissimmee Lakefront Park
- Disney's Hollywood Studios
- ICON Park