
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.

Cozy mountain retreat in downtown Winter Park
Lovingly remodeled Hi Country Haus 1 bedroom 1 bathroom condo central to downtown Winter Park. Use our Tiny Mountain Retreat as a launchpad to all the local access Winter Park has to offer or as a space for rejuvenation in this beautiful mountain town. Incredible access to local trail running, mountain biking, backpacking, fly-fishing, hiking and skiing. Grand Lake and Rocky Mountain National Park are easily and often visited from our spot as well. WP Short-term rental registration #019404

Sleeper@SnowBlaze! Great Location! Hot Tubs/Pool!
Town of Winter Park license (007884) Newly renovated studio in Snowblaze Condominiums! Perfect location in the Town of Winter Park, close to Winter Park Resort and bus stop outside the front door, and walking distance from all the shops, restaurants, and bars in town! Super comfy Queen size bed in a large studio apartment, large couch and ottoman with huge TV! Updated amenities for the community! Pool has been refinished, new outdoor fire pit area, access to gym and community areas included.

Homebase Snowblaze
Enjoy the magic of the Fraser River Valley and charm of downtown Winter Park from our well-equipped, completely remodeled studio. Only an hour and thirty minute drive from Denver International Airport. Walking distance to Winter Park's Main St. lined with shops and dining and a quick 5 minute drive to the world class slopes of Winter Park resort. Take advantage of the free "Lift" bus, with a stop right out front of the building and a ride to the resort in less than 5 minutes. WP STR # 009036.

Condo Overlooking River in Town of Winter Park
Our Condo overlooks the beautiful Fraser River close to downtown Winter Park in the heart of the Rocky Mountains. Just a few minute walk to restaurants, pubs, shops, hiking trails, and all that Winter Park has to offer! Soak in one of the hot tubs at the nearby clubhouse after a full ski day or cool off in the indoor pool after adventuring out on a hike or bike ride. Enjoy the convenience of the winter ski shuttle (Blue line) behind the building for a 15-minute ride to Winter Park Ski Resort.

Mountian Views | Near Winter Park | Pets Stay Free
Situated in the stunning Fraser Valley, this mountain retreat has everything you need to rest and relax. Soak in the mountain views at the clubhouse hot tubs or curly up by the fireplace with a drink. Near Winter Park Resort and Rocky Mountain National with easy access to snowshoeing, Mtn biking, hiking, fishing, cross-country skiing and more! ✔ Two ♛ King Beds ✔Pets Stay Free ✔ Private Balcony ✔ Well Equipped Kitchen ✔ Fireplace ✔ High-Speed Wi-Fi ✔ Clubhouse Access Book your stay today!

King & Bunkbeds 5 min to Base of Granby Ski Area!
Enjoy the very best Colorado has to offer! This 2Br 2Ba condo is the perfect place to stay year-round! We are located 1 mile from downtown Granby, and 5 minute drive from Granby Ranch Ski Resort. Granby is located at the heart of Grand County, amidst so many of Colorado’s best destinations for outdoor exploration and fun! The condo is a short drive to Winter Park, Snow Mountain Ranch, Grand Lake, and Rocky Mountain National Park! Grand County Short Term Rental License/Permit No: 007640

Cozy Mountain Studio Downtown Winter Park CO.
Come and enjoy our Cozy Mountain Studio in the Snow Blaze building. It is conveniently located in downtown Winter Park Colorado, at US 40 and Vasquez. Our condo is walking distance to shops and restaurants, and is on the free bus route. Pick up for the mountain is in front of our building. It is perfect for the adventure travelers who enjoys the outdoors, but want all of the conveniences of home. Our condo is clean and comfortable. It is an older building, with a great location.

Luxury Mtn Cabin/Free Shuttle/ Views/Garage
Escape to Mountain Flower Cabin located in the Rendezvous community just a short walk to downtown Winter Park and a 4 mile shuttle ride (free) to Winter Park Ski Resort. Our 3BR cabin is well appointed with custom furniture, modern amenities, and breathtaking mtn views. Nestled within the Rendezvous Trail System, alongside the Fraser River, you'll find miles of hiking, biking, fishing and cross country skiing right outside your door. The free shuttle to WP is steps from the cabin.

Great View, pool & hot tub, 1 bed & loft sleeps 6
Beautifully remodeled 700 sq ft. condo with 1 bedroom and a loft, that sleeps 6. It has a full kitchen and amazing views of Winter Park, the Continental Divide and Byers Peak. The Clubhouse, which is across the parking lot, has 2 outdoor hot tubs a heated pool, fitness center 2 racquetball courts, a ping pong table, laundry facilities, a conference room that is available for rent, massage, and ski tuning. It is only 2.5 miles from Winter park and right on the free bus route.

Cozy Mtn. Condo | Ski, Hike, Fish + Hot Tub & Pool
Relax and enjoy our cozy updated mountain condo in the heart of the Rockies! Perfect for year-round adventure—ski, snowshoe, hike, bike, fish, boat, and explore all that Granby has to offer. Just 20 min to Winter Park, 20 min to Grand Lake, and 5 min to downtown Granby! Our private 615 sq. ft. unit sleeps 4 with two queen beds in the open loft. Unwind on the private balcony or enjoy shared amenities: 2 indoor hot tubs, 2 outdoor hot tubs, sauna, and outdoor heated pool.

Mountain Getaway Condo w/ Pool and Hot Tub
Freshly Updated- 2 Bedroom, 1 Bath Meadow Ridge Condo with space for the whole family or your favorite group to enjoy a mountain getaway! Located right on the FREE shuttle route to Winter Park Ski Resort, adventure awaits in every direction from this perfectly located condo. Start hiking or biking right out the front door. Guests have access to all the amenities at Club MeadowRidge, located steps away from the condo. Stay, Play, Relax at our wonderful Mountain Getaway!

Michael’s Dream Condo #15 Winter Park
Located in Downtown WP, Condo 15, top floor, awesome views, in Hi Country Haus Condominiums, Lic#009357. Check out WP resort website for exciting improvements. World class skiing, biking, hike, fish, restaurants, shops, breweries, Hideway Park (sledding hill, Concerts, skateboard). WALK TO Fireside Grocery Market, Foundry Movies/Bowling/Pizza, Grand Park Rec Center and more. HCH has exclusive Rec center. WP RESORTS FREE BUS, pick up across our parking lot.
Popular amenities for Winter Park rentals with a pool
House rentals with a pool

Luxury Mountain Retreat with Hot Tub + Views!

Meadowridge 30-2

Chill 301 | Pool + Hot Tub

Summit Sanctuary @ MeadowRidge

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

Alpine Vista Escape

REMI's River Retreat * FISH/SKI/HIKE/MtnLife*

The Evangeline Haus *Dog Friendly
Condo rentals with a pool

Private sauna, amazing view, pool, hot tub!

Best location - Incredible access

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

Studio~Ski Granby/Winter Park. Pool/Hot Tubs

FREE WP ski bus - King bed - pool & hot tubs @ rec

Cozy Mountain Studio | Pet Friendly + Hot Tubs

Hi Country Hideaway

Bear's Den
Other holiday rentals with a pool

Studio Downtown Winter Park

Remodeled Ski In/Out Condo. 30 Sec Walk To Slope!

Remodeled Condo: Ski-In/Out, Hot Tub & Pool Access

Ski-In/Ski-Out Cozy Studio Retreat

Winter Park Ski-In/Out Studio | Hot Tubs + Views

The Rustic Moose

Updated Ski-in / Ski/Out Condo at Winter Park

Meadowridge Mountain View Condo
When is the best time to visit Winter Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $354 NZD | $356 NZD | $368 NZD | $215 NZD | $228 NZD | $227 NZD | $271 NZD | $263 NZD | $276 NZD | $301 NZD | $280 NZD | $376 NZD |
| Avg. temp | -7°C | -7°C | -3°C | -1°C | 4°C | 9°C | 13°C | 12°C | 8°C | 2°C | -3°C | -7°C |
Quick stats about holiday rentals with a pool in Winter Park

Total holiday rentals
Explore 580 holiday rentals in Winter Park

Nightly prices starting at
Winter Park holiday rentals start at $116 NZD per night before taxes and fees

Verified guest reviews
Over 17,660 verified reviews to help you choose

Family-friendly holiday rentals
420 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 70 rentals that welcome pets

Rentals with dedicated workspaces
380 properties have a dedicated workspace

Wi-Fi availability
570 of Winter Park holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Winter Park rentals

4.8 Average rating
Winter Park stays are highly rated by guests—averaging 4.8 out of 5!
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- Breckenridge Ski Resort
- Rocky Mountain National Park
- Beaver Creek Resort
- Red Rocks Amphitheatre
- Vail Ski Resort
- Center Village Resort Copper Mountain
- Winter Park Resort
- Keystone Resort
- Coors Field
- Arapahoe Basin Ski Area
- Colorado Convention Center
- Ball Arena
- Granby Ranch
- Empower Field at Mile High
- Loveland Ski Area
- Ski Cooper
- Fillmore Auditorium
- City Park
- Pearl Street Mall
- Denver Zoo
- Elitch Gardens
- Denver Botanic Gardens
- Water World
- Ogden Theatre




