
Vacation rentals with a pool in Winter Park
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Top-rated rentals with a pool in Winter Park
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Entire Condo In The Heart of Winter Park
Roomy studio sleeps 4, wood, tile and granite floors. Full kitchen with dishwasher, queen size Murphy bed(recesses into wall ) and queen sleeper sofa, bathroom with tub and shower. Separate vanity sink area. Top floor and great views!! Full access to indoor swimming pool , gym, yoga room, hot and dry sauna, and both indoor/outdoor jacuzzis. Free parking is available. Free Ski slope bus stop right in front of condominiums. Great location right in the heart of Winter Park!!!TOWP STR Permit #6104

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.

Walk to Town, Front Door Ski Shuttle Pick-up!
Located in the heart of Winter Park, this stylish top floor condo is a 2 bedroom 2 bath that's perfectly situated to meet all your vacation needs. Convenient front door ski shuttle pickup/drop-off! The condo is tucked away on a beautiful hillside, allowing for privacy and panoramic views, only a couple of blocks away from restaurants/bars. It includes two queen size beds, a sofa sleeper, fully-stocked kitchen, wood-burning fire place, spacious private patio, skylights, and new furniture.

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.

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.

Cozy 1 bedroom Granby Ranch condo
Welcome to our Granby Ranch condo! Great access to skiing, hiking, biking, fishing and golf. Guests also have access to the outdoor pool and hot tub at the base of the ski mountain (small fee required)as well as a free tub in our complex. Unit has a master bedroom with a queen sized bed. FYI-I don’t accept any reservation requests without confirming the cleaning arrangements first. Our STR permit # is 006840.
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

Winterfell at Winter Park Resort

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

Alpine Vista Escape

REMI's River Retreat * FISH/SKI/HIKE/MtnLife*
Condo rentals with a pool

Walkout King Suite | Pet Friendly + Hot Tubs

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

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

Pine in the Sky Condo, Cozy + Close to GR/WP/RMNP

Bear's Den

The Rustic Moose

Ski-in / Ski-out Studio Condo

Winter Park Riverside Retreat WP ST Reg#005544
Other vacation rentals with a pool

Private Sauna, Covered Parking, Hot Tub, Pool!

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

Ski-In/Ski-Out Winter Park Condo w/ Pool Access!

Ski-In/Ski-Out Cozy Studio Retreat

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

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

Renovated Condo- Perfect for a Family Getaway!

Cozy DT condo mins from slopes
When is the best time to visit Winter Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $293 CAD | $294 CAD | $304 CAD | $178 CAD | $189 CAD | $187 CAD | $224 CAD | $217 CAD | $228 CAD | $249 CAD | $231 CAD | $310 CAD |
| 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 vacation rentals with a pool in Winter Park

Total vacation rentals
Explore 580 vacation rentals in Winter Park

Nightly prices starting at
Winter Park vacation rentals start at $96 CAD per night before taxes and fees

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

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

Pet-friendly vacation rentals
Find 70 rentals that welcome pets

Rentals with dedicated workspaces
380 properties have a dedicated workspace

Wifi availability
570 of Winter Park vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, 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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