
Holiday rentals in Winter Park
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Top-rated holiday rentals in Winter Park
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter Park holiday rentals
Other great holiday rentals in Winter Park
Top guest favourite

Bungalow in Maitland
4.88 out of 5 average rating, 564 reviewsMaitland-Orlando Area, FL. Pool House Bungalow
Top guest favourite

Home in Altamonte Springs
5 out of 5 average rating, 11 reviewsLuxurious 5,778 Sq Ft Estate · Helipad · 3+ Acres
Guest favourite

Home in Winter Park
4.89 out of 5 average rating, 75 reviewsWinter Park Guest Suite near UCF/FullSail/Rollins!
Guest favourite

Home in Winter Park
4.88 out of 5 average rating, 26 reviewsWinter Park - Cozy retreat near Lake Killarney
Guest favourite

Home in Orlando
4.98 out of 5 average rating, 48 reviewsCharming Bungalow in Winter Park
Guest favourite

Home in Maitland
4.91 out of 5 average rating, 81 reviewsLake Front Home near Winter Park!
Guest favourite

Home in Winter Park
4.91 out of 5 average rating, 54 reviewsLakefront Paradise Near Attractions
Top guest favourite

Home in Orlando
5 out of 5 average rating, 20 reviewsModern Relaxing Retreat w/ Pool, Firepit, Gameroom
Quick stats about holiday rentals in Winter Park
Total rentals
380 properties
Total number of reviews
19K reviews
Family-friendly rentals
190 properties are a good fit for families
Pet-friendly rentals
120 properties allow pets
Rentals with a pool
110 properties have a pool
Rentals with dedicated workspaces
220 properties have a dedicated workspace
Destinations to explore
- Orlando Holiday rentals
- Kissimmee Holiday rentals
- Four Corners Holiday rentals
- Saint Johns River Holiday rentals
- Central Florida Holiday rentals
- Tampa Holiday rentals
- Tampa Bay Holiday rentals
- St Petersburg Holiday rentals
- Seminole Holiday rentals
- Fort Lauderdale Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Waterfront rentals Winter Park
- Rentals with an EV charger Winter Park
- Rentals with a fireplace Winter Park
- Rentals with pools Winter Park
- Rentals with a firepit Winter Park
- Rentals with outdoor seating Winter Park
- Guest house rentals Winter Park
- Rentals with a hot tub Winter Park
- Rentals with lake access Winter Park
- Family-friendly rentals Winter Park
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- Rentals with a washing machine and dryer Winter Park
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- Flat rentals Winter Park
- Rentals with a patio Winter Park
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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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