
House vacation rentals in Winter Park
Find and book unique houses on Airbnb
Top-rated house rentals in Winter Park
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 Park house rentals
House rentals with a pool

The Cypress House

Quiet Place, convenient to everything!

Private pool home near Downtown

Private Pool 4/2 Waterfront Oasis Weekly Discounts

Cozy 4/2, King Beds, Pergola, Hot Tub & Pool

Pool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney

Year around Heated Pool 7 min from Airport!

3 bedroom Modern pool home,close to UCF&Boombah
Weekly house rentals

10 min to Winter Park, Games, Gym, King bd, Coffee

Luxurious 5,778 Sq Ft Estate · Helipad · 3+ Acres

Winter Park - Cozy retreat near Lake Killarney

Charming Retreat In Winter Park

Charming Bungalow in Winter Park

Cozy home 5min to Park Ave and Downtown Orlando

The Winter Park Experience

King/Queen Quiet Vibey Bungalow
Private house rentals

NEW! ☀Bungalow+Patio+FirePit! Close to Everything!

Casa Winter Park

Turtle Lake House

Newly Renovated 2 Bed/2Bath, Fully Furnished Home

Lake Front Home near Winter Park!

Luxurious and modern cottage near UCF

Stunning Modern 2/2 Home in Hip Enclave near DT

Modern Relaxing Retreat w/ Pool, Firepit, Gameroom
Quick stats about house rentals in Winter Park
Total rentals
170 properties
Total number of reviews
5.1K reviews
Family-friendly rentals
120 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
110 properties have a dedicated workspace
Destinations to explore
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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
- Playalinda Beach
- ESPN Wide World of Sports
- Amway Center
- Titusville Beach
- Epcot
- Magic Kingdom Park
- Daytona International Speedway
- Aquatica
- Reunion West
- Walt Disney World Resort Golf
- ChampionsGate Golf Club
- Island H2O Water Park
- Kissimmee Lakefront Park
- Disney's Hollywood Studios
- Blue Spring State Park
- Things to do Winter Park
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- Art and culture United States