Vacation 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 favorite
A modern living area is shown featuring a comfortable sectional sofa adorned with a cozy throw. A sleek gas fireplace is positioned beneath a flat screen TV. Large windows frame expansive mountain views, while a dining area with stylish chairs and a round table is visible.
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 favorite
A modern living area features a spacious sectional sofa and two accent chairs. A stone fireplace with changing flame colors serves as a focal point. Large windows provide natural light and offer views of the surrounding snowy landscape.
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 favorite
An outdoor swimming pool is surrounded by lounge chairs in various colors. The pool area is framed by aspen trees, with a mountain backdrop and a modern building visible in the distance.
Home in Granby
5 out of 5 average rating, 36 reviews

Colorado's Coolest Ski In/Out Home

AaronRating, 5 stars4 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 favorite
A spacious living area features high ceilings, a stone fireplace, and large glass doors that provide access to a scenic outdoor view. A cozy sofa is paired with a coffee table, while a vibrant piece of artwork adorns the wall above the fireplace.
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 favorite
A modern mountain home is presented under clear blue skies, with a snow-covered roof and driveway leading to a spacious 2-car garage. The backdrop features the majestic slopes of Winter Park Resort, blanketed in fresh snow, surrounded by evergreen trees glistening in winter light.
Home in Winter Park
5 out of 5 average rating, 12 reviews

Winterfell at Winter Park Resort

KristenRating, 5 stars2 weeks ago
We had a amazing stay here at Winter Park. We had 11 family members and didn't feel like we were right ontop of each other with its 3 stories and its open concept. The house had every amenitie that we needed plus some. The views are spectacular in this home which was a added bonus. The house was immaculate upon arrival it looked like nobody had ever lived in it. Tim was very responsive to any questions we had and made staying there just so easy! You wont regret booking this house!!
Superhost
The modern mountain home is showcased against a clear blue sky, featuring large windows that allow for ample natural light. A spacious deck extends from the upper level, equipped with comfortable seating. A private hot tub is positioned on the ground level, surrounded by a landscaped area.
Home in Granby
4.86 out of 5 average rating, 21 reviews

Lux Mtn Home, Hot Tub, Ski&Golf, A/C split, VIEWS

LindsayRating, 5 stars10 months ago
We loved Aaron and Katie’s home! Their home was beautiful and the views were breathtaking! It was a great place to stay with lots of kids! Their management texted us to check in on us and were very helpful with everything we needed!!
Top guest favorite
A modern living room features a gas fireplace framed by a sleek black tile surround. A large television is mounted above. Natural light floods the space through expansive glass doors that open to a serene outdoor view. Unique seating is complemented by a rustic coffee table made from natural wood.
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!

Condo rentals with a pool

Guest favorite
The exterior of the building showcases a four-story structure with a mix of red and stone finishes. Lush greenery surrounds a stone fire pit and seating area, while mountains are visible in the background under a partly cloudy sky.
Condo in Winter Park
4.82 out of 5 average rating, 146 reviews

Winter Park 2bd/2ba (Sleeps 6) - Ideal Location!

RossRating, 5 stars3 months ago
We had a great time in Winter Park. Skied 9 days. Billy's condo was right on the Lift Bus Route--very convenient. The hot tubs were great! Everything was as advertised. We would stay there again.
Guest favorite
An aerial view showcases the Club Meadowridge complex, highlighting a centrally located clubhouse with a heated outdoor pool and two tennis courts. Surrounding mountains and lush greenery create a scenic backdrop, while nearby lodgings are visible in the distance.
Condo 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 favorite
A cozy living room features a comfortable armchair with an ottoman, a wooden TV stand with decorative elements, and a fireplace set against a textured wood wall. Natural light filters through sheer curtains, highlighting a vintage artwork depicting Winter Park.
Condo in Fraser
4.9 out of 5 average rating, 135 reviews

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

MadisonRating, 5 stars1 week ago
Great location! Will definitely look into staying during winter!
Superhost
A serene outdoor heated pool is framed by lush trees and autumn-colored foliage. Surrounding lounge chairs and tables provide a relaxing space for guests. Steps lead up to the building, enhancing the inviting atmosphere of the pool area.
Condo in Winter Park
4.84 out of 5 average rating, 70 reviews

Ski-In/Ski-Out Studio Mtn View-Free Heated Parking

KaraRating, 5 stars4 weeks ago
We had a great stay. Perfect room — clean with a great view. The game room in the building was a huge plus for my son. Shawn’s detailed instructions on parking and checking into the building were perfect. We were confused at first but then realized it’s all laid out with photos and videos. Thanks so much for letting us stay!
Top guest favorite
A studio condo showcases a spacious layout featuring a queen bed and a pull-out sleeper sofa. Large windows provide natural light, while artistic decor and a cozy throw blanket enhance the inviting atmosphere. A dining table and a patterned area rug complete the living space.
Condo 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
An outdoor swimming pool is surrounded by a sunlit deck featuring multiple lounge chairs. The building is designed with a contemporary style, showcasing covered balconies on the upper level and large windows that provide views of the pool area.
Condo in Granby
4.9 out of 5 average rating, 295 reviews

Queen Studio~Hot Tubs~Pool~RMNP

LaurenRating, 5 stars2 weeks ago
Krista and Scott had a lovely place at the Inn which was exactly as described. Our kids loved access to the pool and the Murphy bed made the small place feel much bigger during the day. The communication was excellent and we were informed of all the necessary check in and check out info as well as local events/attractions. We highly recommend the nearby train museum for littles!
Guest favorite
The exterior entrance of the condo features a covered porch with a wooden sign displaying the property name. Steps lead up to the door, surrounded by lush trees and vibrant autumn foliage, reflecting the natural beauty of the area.
Condo in Winter Park
4.95 out of 5 average rating, 40 reviews

Hi Country Hideaway

AdriaRating, 5 stars2 months ago
Perfect place for our ski trip! Walkable and beautiful location with easy access to free shuttle to the resort. Kelly was friendly and provided great information. Would recommend!
Top guest favorite
The kitchen features light wood cabinetry and modern appliances, including a black stove and refrigerator. A large island with granite countertops provides seating with three wooden stools. A welcoming entry area is visible, complemented by a textured rug and a decorative door.
Condo in Winter Park
5 out of 5 average rating, 35 reviews

The Rustic Moose

GregoryRating, 5 stars2 weeks 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 vacation rentals with a pool in Winter Park

  • Total rentals

    620 properties

  • Nightly prices starting at

    G$12,553 GYD 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

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