
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.

Ground floor 2 bedroom, at Hi Country Winter Park
Recently remodeled 2-bedroom GROUND floor condo is located on the Fraser River, one block away from the main strip of WP. The Hi Country complex features a newly remodeled clubhouse with indoor & outdoor hot tubs, large pool, fitness center, pool table, kids room, and an outdoor playground. In the winter, the free shuttle is located 45 steps behind our building and will whisk you to the ski area twice an hour. A 5-15 min walk to shops, restaurants, bars, movie theater, and the town park.

Hideaway Park! Hot tub,Pool,FitnessCtr&FreePrkg
BEST Location in Winter Park!!Trailhead condos offer a year-round heated pool, hot tub, fire pit, patio, clubhouse, large indoor lounge, fitness room & game room. Just steps to Fraser River trail, restaurants, shopping and free ski shuttle. *On Hideaway Park* Access to Summer concerts&festivals, playground, picnic area, fire pit, and skate park to entertain kids! Relax by the fire or private furnished covered deck. Top floor (w/elevator) corner unit w/views! Pets welcome! (w/add'l clean fee).

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

Sandy and Ryan's Granby Getaway!
The perfect getaway! Newly renovated with high end finishes and meticulously cared for, this cozy condo is waiting to be your home away from home! Ths cozy studio accommodates up to 4 people with a comfy king bed and sleeper sofa complete with a memory foam mattress for maximum comfort. Resort amenities include restaurant, game room, work station, salon, ski rental, swimming, sauna, hot tub, tennis, racquetball and ski shuttle. Rocky Mountain National Park, Grand Lake and Winter Park closeby.

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.

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.

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.

Newly Renovated Mountain Modern Condo
This newly remodeled mountain modern condo features 1 bedroom (king size bed) plus an additional loft area with (queen size bed), making this condo sleep like a two bedroom. The condo features high end furnishings, vaulted ceilings with tons of natural light, fully updated kitchen, views of the mountain range, and spa-style bathroom with dual rainfall shower heads. Steps away from the free bus stop to Winter Park, clubhouse with year round hot tubs, pool, fitness center and laundry.

Cozy Cabin! Ski Winter Pk & Granby Ranch
Amazing family-friendly cabin on the Fraser River and in the heart of Granby, CO. Ten minutes to the lodge at Granby Ranch or 25 minutes from Winter Park! Close to Rocky Mountain National Park, Sulphur Hot Springs, and the YMCA of the Rockies. River access and ponds on the property for fishing! This cabin is stocked with all you need (and more!). We host another cabin across the street. Message me about booking both for a larger group!

Studio Condo in the Heart of Winter Park! lic#9602
You're steps from terrific shops, bars, and restaurants. Right outside the condo is the free bus stop to world-class skiing at Winter Park. It is a 3-minute bus ride and frequents every 15 minutes in the winter. Free covered parking is included on a first-come basis. All new kitchen appliances installed in February 2024! Note: There's no A/C in the unit, but there is an evaporative cooler to help keep the unit cool in summer.

Winter Park Condo on the River: Walk to Downtown!
Welcome to Riverview where you will enjoy privacy and beautiful views of the Fraser River from this stylish retreat. This one-bedroom condo is equipped with a pillow soft queen-size bed, queen-size sofa sleeper, full kitchen, bathroom, electric fireplace, & patio. Located directly across from a ski shuttle stop and a short walk to Winter Park's Main St. lined with shops and dining.
Popular amenities for Winter Park rentals with a pool
House rentals with a pool

Luxury Home with Stunning Views - Ski In/Ski Out!

Meadowridge 30-2

Cozy mountain home w/ hot tub & fireplace

Summit Sanctuary @ MeadowRidge

Winterfell at Winter Park Resort

Luxury 3BR Winter Park | Hot Tub | Ski Shuttle

Alpine Vista Escape

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

Winter Park | Top-Floor | Pool & Hot Tub | Ski Bus

The Lodge

WP Mountain Retreat • 3BR/2BA • 3 Hot Tubs & Pool

1/2 Mile Walk to Town, Remodeled, Top-Floor Condo!

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

Ski-In/Ski-Out Studio-Newly Remodeled

Cozy 1 bedroom Granby Ranch condo

Mountain Delight Near Winter Park
Other vacation rentals with a pool

Private Sauna, Covered Parking, Hot Tub, Pool!

Studio Downtown Winter Park

Ski-in Ski-out Cozy Condo

Condo in Winter Park Ski and Mountain Views

Hot tubs & pool! Amazing views & free shuttle!

1BR Condo in Winter Park, CO

Trailhead Location! Hot tub,Pool, freePrkg,Sleeps9

Condo w/ Views, Bus Stop to Resort, Walk Downtown.
When is the best time to visit Winter Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$44,760 GYD | G$44,969 GYD | G$46,434 GYD | G$27,191 GYD | G$28,864 GYD | G$28,655 GYD | G$34,302 GYD | G$33,256 GYD | G$34,930 GYD | G$38,067 GYD | G$35,348 GYD | G$47,479 GYD |
| 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 G$14,641 GYD 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 & kid-friendly amenities

Pet-friendly vacation rentals
Find 70 rentals that welcome pets

Rentals with dedicated workspaces
380 properties have a dedicated workspace

Wi-Fi availability
570 of Winter Park vacation rentals include wi-fi 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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- Breckenridge Ski Resort
- Rocky Mountain National Park
- Red Rocks Amphitheatre
- Beaver Creek Resort
- Coors Field
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