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
Home in Orlando
4.94 out of 5 average rating, 126 reviewsThe Orlando Retreat.
Home in Maitland
4.94 out of 5 average rating, 148 reviewsOrlando area pool home in Maitland
Home in Mount Dora
4.95 out of 5 average rating, 111 reviewsModern Farmhouse & Pool in Mount Dora by Lake Ola
Home in Kissimmee
4.85 out of 5 average rating, 207 reviews3 bedroom Villa in Kissimmee
Home in Edgewood
4.93 out of 5 average rating, 151 reviewsTropical Paradise in the heart of Orlando
Home in Oviedo
4.92 out of 5 average rating, 285 reviews4 bedroom Modern pool home, close to UCF&Boombah
Home in Deltona
4.96 out of 5 average rating, 150 reviewsSt. John’s Luxury Pool Lake House
Home in Orlando
4.87 out of 5 average rating, 167 reviews*Lakefront Pool Home *paddleboard*kayak*game room*
Weekly house rentals
Home in Orlando
4.97 out of 5 average rating, 101 reviewsModern 3/1 in Ivanhoe Village - TrendyHome
Home in Sanford
4.97 out of 5 average rating, 213 reviewsClean, cozy home in a GREAT location
Home in Orlando
4.93 out of 5 average rating, 122 reviewsHidden Gem in SODO! - MCO ~16min
Home in Orlando
4.92 out of 5 average rating, 100 reviewsI'm On Vacation - Vibey, Fun, & Bright Dtown Spot
Home in Winter Park
4.84 out of 5 average rating, 103 reviewsModern 4 Bed Home in Winter Park (FullSail/UCF)
Home in Orlando
4.97 out of 5 average rating, 143 reviewsDowntown Orlando -The Modern Zen Studio w/Hot Tub
Home in Orlando
4.94 out of 5 average rating, 379 reviewsPet Welcome/Fully Fenced Backyard/Washer & Dryer
Home in Orlando
4.82 out of 5 average rating, 159 reviewsKing suite , Modern house perfect for vacation
Private house rentals
Home in Winter Park
5.0 out of 5 average rating, 11 reviewsNewly Renovated 2 Bed/2Bath, Fully Furnished Home
Home in Winter Park
4.97 out of 5 average rating, 34 reviewsCozy Winter Park Home
Home in Orlando
4.92 out of 5 average rating, 38 reviewsCity Charmer
Home in Orlando
4.98 out of 5 average rating, 52 reviewsMaison Luxe
Home in Orlando
4.96 out of 5 average rating, 24 reviewsColonialtown Bungalow
Home in Maitland
5.0 out of 5 average rating, 23 reviewsFern Park Retreat
Home in Casselberry
5.0 out of 5 average rating, 48 reviewsSpacious 3 BR Home Perfect for Orlando Getaway
Home in Orlando
4.97 out of 5 average rating, 36 reviewsCharming 2BR Cottage, Downtown Orlando
Quick stats about house rentals in Winter Park
Total rentals
190 properties
Rentals with dedicated workspaces
120 properties have a dedicated workspace
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
70 properties allow pets
Family-friendly rentals
130 properties are a good fit for families
Total number of reviews
4.6K reviews
Destinations to explore
- Orlando Vacation rentals
- Kissimmee Vacation rentals
- Tampa Vacation rentals
- Anna Maria Island Vacation rentals
- Sarasota Vacation rentals
- West Palm Beach Vacation rentals
- Boca Raton Vacation rentals
- Naples Vacation rentals
- Fort Lauderdale Vacation rentals
- Miami Beach Vacation rentals
- Miami Vacation rentals
- Key West Vacation rentals
- Lighthouse rentals United States
- Earth house rentals United States
- Townhouse rentals United States
- Guesthouse rentals United States
- House rentals United States
- Guesthouse rentals Orlando
- House rentals Orlando
- Tiny house rentals Orlando
- Townhouse rentals Orlando
- Lakehouse rentals Florida
- House rentals Florida
- Townhouse rentals Florida
- Guesthouse rentals Florida
- Tiny house rentals Florida
- Beach house rentals Florida
- Lakehouse rentals Florida
- House rentals Florida
- Townhouse rentals Florida
- Guesthouse rentals Florida
- Tiny house rentals Florida
- Beach house rentals Florida
- House rentals Kissimmee
- Tiny house rentals Kissimmee
- Guesthouse rentals Kissimmee
- Townhouse rentals Kissimmee
- Rentals with a patio Winter Park
- Rentals with pools Winter Park
- Rentals with a washer and dryer Winter Park
- Rentals with a fireplace Winter Park
- Private suite rentals Winter Park
- Rentals with an EV charger Winter Park
- Pet-friendly rentals Winter Park
- Fitness-friendly rentals Winter Park
- Rentals with outdoor seating Winter Park
- Guesthouse rentals Winter Park
- Apartment rentals Winter Park
- Monthly Rentals Winter Park
- Condo rentals Winter Park
- Rentals with a fire pit Winter Park
- Rentals with a hot tub Winter Park
- Kid-friendly rentals Winter Park
- Family-friendly rentals Winter Park
- Rentals with lake access Winter Park
- House rentals Orange County
- Townhouse rentals Orange County
- Guesthouse rentals Orange County
- Tiny house rentals Orange County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom