Holiday rentals with a pool in Winter Park

Find and book unique homes with a pool on Airbnb

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Popular amenities for Winter Park rentals with a pool

House rentals with a pool

Superhost
Home in Granby
4.83 out of 5 average rating, 12 reviews

Spacious, Luxury Home with Views & Resort Access

AshleeRating, 5 stars5 months ago
This was a beautiful place to stay. It is definitely in great condition and looks brand new. The host is very responsive and super nice. We will definitely be back!
Guest favourite
Home in Granby
5 out of 5 average rating, 28 reviews

Modern Mtn Home @ Granby Ranch -Hot Tub, Mesh Wifi

MelissaRating, 5 stars2 weeks ago
The location is beautiful and the house was perfect for me and family staying for a high school graduation in town. Fully stocked with everything one could need. And it was great having two living areas for everyone to have their space.
Guest favourite
Home in Winter Park
5 out of 5 average rating, 5 reviews

Chill 301 | Pool + Hot Tub

ShabberRating, 5 stars3 months ago
I had a wonderful stay at this Airbnb! The place was easy to find and had a modern design with great amenities, including a relaxing hot tub. Everything was clean, comfortable, and well-equipped for a great getaway. One thing to note—while the ski-in/ski-out access was convenient, there were quite a few stairs to navigate, which might be challenging for some guests. Overall, though, it was a fantastic stay, and I would definitely recommend it for those looking for a well-appointed and comfortable retreat!
Guest favourite
Home in Winter Park
5 out of 5 average rating, 11 reviews

New Luxury Condo 2203 I Free Adventures Daily

Nancy and NedRating, 5 stars3 months ago
My son and I booked the condo for a late planned ski trip. The condo is very comfortable, clean and modern. It has an adequately stocked kitchen with plenty of utensils and spices for those that prefer to cook. It includes a drip coffee maker and a separate bean grinder (I never know what to buy before arriving). There is some ongoing new construction in the area (as of March 2025). I heard some trucks backing up in the morning, but it did not bother us as we were up each morning to ski. Overall, the place is very quiet with very minimal neighbor noise. There is no cable service, so be prepared to stream or cast from your own device using your own accounts. I was able to stream YouTube TV from my phone to the TV. We took the free shuttle service to the resort each day. It’s a quick walk to the bus stop, and we never waited more than a few minutes for a bus. We walked to the area restaurants and shops. Safeway is a quick drive down the street. We would book again.
Guest favourite
Home in Granby
5 out of 5 average rating, 36 reviews

Colorado's Coolest Ski In/Out Home

AaronRating, 5 stars3 months ago
Our stay was absolutely fantastic! From the moment we arrived, we were blown away by the breathtaking mountain views and well-appointed house. The home was spotless, beautifully decorated, and stocked with everything we needed for a comfortable stay. The hosts went above and beyond to ensure we had a seamless experience, providing clear instructions and thoughtful touches that made us feel right at home. Whether we were relaxing in the hot tub, sitting by the fireplace, or skiing the nearby trails, every moment was perfect. We can't recommend this place highly enough and will definitely be returning for another visit. Thank you for an unforgettable stay!
Guest favourite
Home in Fraser
5 out of 5 average rating, 26 reviews

Mountain Views: Hot Tub and Game Room

BrandonRating, 5 stars2 months ago
A great house for family trips. Plenty of space and the kids loved the game room in the basement. The kitchen was well equipped and everything was clean. The hosts were quick to respond. We had a maintenance request that they addressed very quickly. We'd stay here again!
Top guest favourite
Home in Winter Park
5 out of 5 average rating, 71 reviews

Cozy Modern Cabin w/ Hot Tub - Minutes to Ski Area

DarinRating, 5 stars1 month ago
We loved our stay! Kristen was a great host, very helpful and responsive. Really appreciated how clean and comfortable the place was!
Superhost
Home in Fraser
4.84 out of 5 average rating, 58 reviews

Alpine Vista Escape

JoshRating, 5 stars1 month ago
Elizabeth was super responsive and the area was beautiful. We encountered some minor issues with the community center but Elizabeth was super responsive and communicative to help remedy. The free ear plugs were a nice touch and needed. Would recommend staying here!

Apartment rentals with a pool

Guest favourite
Apartment in Winter Park
4.95 out of 5 average rating, 38 reviews

Escape to High Lonesome Haus in Winter Park

ÓliRating, 5 stars3 weeks ago
Great Stay in Winter Park I stayed here for about a week and really enjoyed it. The place was clean, cozy, and had everything I needed. The location was peaceful and convenient, and the host was friendly and easy to communicate with. Overall, it was a great experience and I’d definitely stay there again.
Guest favourite
Apartment in Winter Park
4.85 out of 5 average rating, 97 reviews

Cozy Mountain Studio Downtown Winter Park CO.

JohnRating, 5 stars4 months ago
Great spot for walking all over WP. right across the street from The Ditch, Hideaway, and the shuttle station to the hill. 10 out of 10 recommended.
Guest favourite
Apartment in Fraser
4.86 out of 5 average rating, 231 reviews

Beautiful Condo with Hot Tub on Ski Bus Route

SusanRating, 5 stars2 weeks ago
Trish was a wonderful host. Very accommodating for our needs. She was thorough in her check in and out instructions. The place was cozy and had all we need. It was located in walking distance to the rec room and a very short drive to Safeway. Awesome stay!
Guest favourite
Apartment in Fraser
4.9 out of 5 average rating, 135 reviews

Cozy 2 bed/2 bath with Hot Tub and Mountain View

MadisonRating, 5 stars6 days ago
Great location! Will definitely look into staying during winter!
Top guest favourite
Apartment in Winter Park
4.98 out of 5 average rating, 58 reviews

Elevation Station in Snowblaze condominiums

AustinRating, 5 stars2 months ago
It was everything we needed for our trip to Winter Park. The bus stop is nearby which was perfect for us to get to the mountain.
Superhost
Apartment in Winter Park
4.74 out of 5 average rating, 93 reviews

Winter Park Studio Condo - 5 Mins to Downtown!

NataliaRating, 5 stars2 months ago
Great place! Looked exactly like photos, had all the listed amenities. Great TV channels, walkable to downtown winter park and 5 minutes away from the mountain. Highly recommend!
Guest favourite
Apartment in Winter Park
4.89 out of 5 average rating, 233 reviews

Stay at Colorado Dreams|Resort Access, Indoor Pool

SusanRating, 5 stars3 months ago
Great location. Very comfortable and convenient. Amy was super responsive. Had a great stay.
Top guest favourite
Apartment in Winter Park
5 out of 5 average rating, 35 reviews

The Rustic Moose

GregoryRating, 5 stars1 week ago
This is a great place at Beaver Village. We've stayed at various units in this complex for many years so were aware of how nice the place was. This one has been remodeled really well, and it was great for our family of six. There was plenty of space and since we visited during what is kind of a mud season, it was very, very peaceful. Would for sure recommend this one!

Quick stats about holiday rentals with a pool in Winter Park

  • Total rentals

    620 properties

  • Nightly prices starting at

    ₹5,194 before taxes and fees

  • Total number of reviews

    18K reviews

  • Family-friendly rentals

    480 properties are a good fit for families

  • Pet-friendly rentals

    110 properties allow pets

  • Rentals with dedicated workspaces

    420 properties have a dedicated workspace

Destinations to explore