Holiday 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.
Holiday 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
5.0 out of 5 average rating, 20 reviewsMountain Cabin 44 - $500 Free Activities Daily
5–12 Sep
Home in Fraser
4.78 out of 5 average rating, 27 reviewsPanoramic Mountain Views
2–9 Nov
Home in Winter Park
4.85 out of 5 average rating, 13 reviewsThe Evangeline Haus
25 Sep – 2 Oct
Home in Winter Park
5.0 out of 5 average rating, 39 reviewsRendezvous Winter Park Cabin / Private Hot Tub
21–28 Mar
Home in Granby
5.0 out of 5 average rating, 23 reviewsColorado's Coolest Ski In/Out Home
3–10 May
Home in Granby
4.82 out of 5 average rating, 84 reviewsGranby Ranch Ski in/ski out family cabin
27 Jul – 3 Aug
Home in Granby
5.0 out of 5 average rating, 17 reviewsGranby Ski & Golf Getaway - Pank's Peak
12–19 Nov
Home in Granby
4.92 out of 5 average rating, 13 reviewsNew Lux Mtn Home, Skiing, Two Family Rooms
29 Oct – 5 Nov
Condo rentals with a pool
Condo in Granby
4.93 out of 5 average rating, 178 reviewsPine in the Sky Condo, Cozy & Contemporary + Views
3–10 Jul
Condo in Winter Park
4.93 out of 5 average rating, 110 reviewsWinter Park Riverside Retreat WP ST Reg#005544
22–29 May
Condo in Fraser
4.79 out of 5 average rating, 190 reviewsGreat Views/bus route 1 bed & loft sleep 6 hot tub
4–11 Oct
Condo in Winter Park
4.81 out of 5 average rating, 135 reviewsWinter Park 2bd/2ba (Sleeps 6) - Ideal Location!
23–30 Aug
Condo in Granby
4.89 out of 5 average rating, 204 reviewsQueen Studio~Resort Amenities~19 Mls to West RMNP
17–24 Sep
Condo in Winter Park
4.89 out of 5 average rating, 194 reviewsGround floor 2 bedroom, at Hi Country Winter Park
21–28 Aug
Condo in Winter Park
5.0 out of 5 average rating, 303 reviewsWinter Park Studio: On the River~ Walk Downtown!
12–19 Jun
Condo in Granby
4.86 out of 5 average rating, 180 reviewsSandy and Ryan's Granby Getaway!
22–29 Mar
Quick stats about holiday rentals with a pool in Winter Park
Total rentals
570 properties
Rentals with dedicated workspaces
420 properties have a dedicated workspace
Pet-friendly rentals
90 properties allow pets
Family-friendly rentals
420 properties are a good fit for families
Total number of reviews
15K reviews
Nightly prices starting at
$84 NZD before taxes and fees
Destinations to explore
- Aspen Holiday rentals
- Colorado Springs Holiday rentals
- Breckenridge Holiday rentals
- Vail Holiday rentals
- Boulder Holiday rentals
- Nederland Holiday rentals
- Steamboat Springs Holiday rentals
- Estes Park Holiday rentals
- Downtown Denver Holiday rentals
- Fort Collins Holiday rentals
- Aurora Holiday rentals
- Denver Holiday rentals
- Rentals with pools United States
- Rentals with pools Denver
- Rentals with pools Colorado
- Rentals with pools Colorado
- Rentals with pools Aspen
- Rentals with an EV charger Winter Park
- Waterfront rentals Winter Park
- Monthly Rentals Winter Park
- Rentals with a fireplace Winter Park
- Pet-friendly rentals Winter Park
- Rentals with a hot tub Winter Park
- Townhouse rentals Winter Park
- Family-friendly rentals Winter Park
- Rentals with a fire pit Winter Park
- Rentals with lake access Winter Park
- Kid-friendly rentals Winter Park
- House rentals Winter Park
- Rentals with outdoor seating Winter Park
- Apartment rentals Winter Park
- Rentals with a kayak Winter Park
- Rentals with a patio Winter Park
- Cabin rentals Winter Park
- Rentals with a sauna Winter Park
- Rentals with a washing machine and dryer Winter Park
- Condo rentals Winter Park
- Fitness-friendly rentals Winter Park
- Rentals with pools Grand 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