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 Fraser
4.78 out of 5 average rating, 27 reviewsPanoramic Mountain Views
Aug 18 – 25
Home in Winter Park
5.0 out of 5 average rating, 39 reviewsRendezvous Winter Park Cabin / Private Hot Tub
May 18 – 25
Home in Fraser
5.0 out of 5 average rating, 6 reviewsLuxury Condo G301 - $500 Free Activities Daily
Jun 4 – 11
Home in Winter Park
4.85 out of 5 average rating, 13 reviewsThe Evangeline Haus
Oct 6 – 13
Home in Granby
5.0 out of 5 average rating, 23 reviewsColorado's Coolest Ski In/Out Home
Apr 11 – 18
Home in Granby
4.82 out of 5 average rating, 84 reviewsGranby Ranch Ski in/ski out family cabin
May 12 – 19
Home in Granby
5.0 out of 5 average rating, 39 reviewsBeautiful Granby Ranch home close to ski hill.
Aug 28 – Sep 4
Home in Granby
5.0 out of 5 average rating, 37 reviewsGorgeous 4bd/4ba Ski-in/out on Main Lift at GR
Oct 23 – 30
Condo rentals with a pool
Condo in Granby
4.83 out of 5 average rating, 299 reviewsCozy 1 bedroom Granby Ranch condo
Feb 2 – 9
Condo in Granby
4.89 out of 5 average rating, 206 reviewsQueen Studio~Resort Amenities~19 Mls to West RMNP
Sep 1 – 8
Condo in Fraser
4.95 out of 5 average rating, 101 reviewsMountain Delight Near Winter Park
May 15 – 22
Condo in Winter Park
4.86 out of 5 average rating, 233 reviewsWalk to Downtown | Hot Tub | Near River | Private
Oct 15 – 22
Condo in Winter Park
4.91 out of 5 average rating, 148 reviewsHi Country Haus Hideaway - Great Location!
Jul 23 – 30
Condo in Fraser
4.91 out of 5 average rating, 121 reviewsCozy 2 bed/2 bath with Hot Tub and Mountain View
Aug 18 – 25
Condo in Granby
4.87 out of 5 average rating, 494 reviewsGranby Mountain Retreat
Jun 9 – 16
Condo in Granby
4.86 out of 5 average rating, 180 reviewsSandy and Ryan's Granby Getaway!
Jan 19 – 26
Quick stats about vacation 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
$50 before taxes and fees
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