Vacation rentals with a pool in Winter Park
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Winter Park
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 Park rentals with a pool
House rentals with a pool
Home in Winter Park
4.87 out of 5 average rating, 104 reviewsComfy 3 Bedrooms - 2 Bathrooms home with pool.
Jul 27 – Aug 3
Home in Mount Dora
4.94 out of 5 average rating, 109 reviewsModern Farmhouse & Pool in Mount Dora by Lake Ola
Aug 12 – 19
Home in Oviedo
4.92 out of 5 average rating, 284 reviews4 bedroom Modern pool home, close to UCF&Boombah
Oct 21 – 28
Home in Orlando
4.87 out of 5 average rating, 166 reviews*Lakefront Pool Home *paddleboard*kayak*game room*
Jul 7 – 14
Home in Orlando
4.83 out of 5 average rating, 137 reviewsPrivate Luxury Pool / Swim up bar / Smart-home
Sep 13 – 20
Home in Edgewood
4.93 out of 5 average rating, 150 reviewsTropical Paradise in the heart of Orlando
Nov 17 – 24
Home in Kissimmee
4.84 out of 5 average rating, 205 reviews3 bedroom Villa in Kissimmee
Oct 30 – Nov 6
Home in Orlando
4.95 out of 5 average rating, 314 reviews*HALF HOME* (read desc) Pool/Disney/Universal
Jun 20 – 27
Condo rentals with a pool
Condo in Orlando
4.82 out of 5 average rating, 108 reviewsDesigner Orlando Retreat near UCF & Outdoor Space
Sep 10 – 17
Condo in Orlando
4.91 out of 5 average rating, 184 reviewsDeluxe Studio:Lakeview, parking, pool
Jun 4 – 11
Condo in Orlando
4.89 out of 5 average rating, 152 reviewsHuge/Terrace Studio. Universal Studios Area.
Dec 27 – Jan 3
Condo in Kissimmee
4.98 out of 5 average rating, 291 reviewsGorgeous❤️ Pool & Lake View Condo near Disney Parks
Dec 12 – 19
Condo in Orlando
4.87 out of 5 average rating, 200 reviewsAirbnb's Choice- Best at Blue Heron- Stunning View
Jun 9 – 16
Condo in Kissimmee
4.98 out of 5 average rating, 163 reviewsRemodeled, Stylish and Affordable Close to Disney
Aug 16 – 23
Condo in Kissimmee
4.94 out of 5 average rating, 186 reviewsLakeview Escape close to Disney&retail therapy
Apr 24 – May 1
Condo in Orlando
4.82 out of 5 average rating, 397 reviewsModern Studio with Private Terrace near Universal
Feb 24 – Mar 3
Home rentals with a private pool
Townhouse in Kissimmee
4.82 out of 5 average rating, 192 reviewsBeach House with Private Pool and Clubhouse near Disney
Sep 10 – 17
Townhouse in Kissimmee
4.88 out of 5 average rating, 128 reviewsStellar Five Bedroom Townhome Under Ten Minutes to Disney
Sep 16 – 23
Home in Davenport
4.97 out of 5 average rating, 97 reviewsAiry, Stylish Home with Pool Heat Included in Davenport
Apr 6 – 13
Villa in Kissimmee
5.0 out of 5 average rating, 13 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
Apr 21 – 28
Villa in Kissimmee
4.79 out of 5 average rating, 224 reviewsVisit Disney World from a Sunny Home with a Pool
Dec 10 – 17
Home in Davenport
4.61 out of 5 average rating, 23 reviewsSolterra Resort 7br Family Home Pool Near Disney
Oct 13 – 20
Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
Jul 11 – 18
Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
Jan 8 – 15
Quick stats about vacation rentals with a pool in Winter Park
Total rentals
110 properties
Wifi availability
110 properties include access to wifi
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
3.4K 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
- Rentals with pools United States
- Rentals with pools Orlando
- Rentals with pools Florida
- Rentals with pools Florida
- Rentals with pools Kissimmee
- Condo rentals Winter Park
- Rentals with outdoor seating Winter Park
- Family-friendly rentals Winter Park
- Rentals with lake access Winter Park
- Guesthouse rentals Winter Park
- Private suite rentals Winter Park
- Rentals with a patio Winter Park
- Rentals with an EV charger Winter Park
- Rentals with a washer and dryer Winter Park
- Fitness-friendly rentals Winter Park
- Rentals with a hot tub Winter Park
- Monthly Rentals Winter Park
- Apartment rentals Winter Park
- Kid-friendly rentals Winter Park
- Rentals with a fireplace Winter Park
- Rentals with a fire pit Winter Park
- Pet-friendly rentals Winter Park
- House rentals Winter Park
- Rentals with pools 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