
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.

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).

WP Mountain Retreat • 3BR/2BA • 3 Hot Tubs & Pool
Modern rustic condo nestled in the heart of Winter Park, CO. Completely remodeled, this charming retreat combines contemporary comfort with mountain elegance. The condo sleeps 9 comfortably with 3 cozy bedrooms, 2 full bathrooms, a fully-equipped kitchen with stainless steel appliances, and a warm living room area, perfect for relaxing after a day of mountain adventures. Enjoy easy access to local shops, dining, Lyft bus stop, and the resort. Ideal for families seeking a serene mountain getaway

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

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.

Cozy DT condo mins from slopes
Welcome to your perfectly located ski getaway! This updated 2BD/2BA Beaver Village condo has its own shuttle line with the bus stop just a few steps from your door, bringing you directly to the Winter Park Ski Resort Village! The shops and restaurants of Cooper Creek and DT Winter Park are a short walk away. The well-equipped kitchen is upgraded with all new appliances, and fiber internet allows for remote work and streaming TV. Finally, warm your bones in the multiple hot tubs and sauna!

Riverfront Condo☆1st Floor☆Ski Bus☆Pool & Hot Tub
Recently remodeled 1st floor condo with views and sounds of Fraser River. Walking distance to downtown Winter Park grocery store, coffee shop, restaurants, breweries, retail stores, bars, movie theater, and bowling alley. Community amenities include an indoor pool, hot tubs, workout room, lounge with pool table, laundry facilities, and outdoor playground. Free bus to resort nearby. This riverfront condo is perfect for relaxing and unwinding after a full day of outdoor activities.

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 “Lift”bus/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!

Four-Season Winter Park Condo w/ Pool Access!
Seasonal recreation on world-class mountain trails awaits at this Winter Park vacation rental! Located in the Trailhead Lodges community - under a half-mile to the closest ski shuttle - this 2-bedroom, 2-bath condo offers all the at-home comforts in a premier mountain destination. Work remotely with beautiful views while also enjoying easy access to countless year-round outdoor activities for the whole group. You’ll also have access to a community pool, hot tub, clubhouse, and more!

Lone Eagle Luxe Mtn Home- Hot Tub + Gym/Peloton
Luxury mountain getaway located in the Granby Ranch ski resort, and golfing community. 4 bedrooms + loft, large deck with grill and fire pit, hot tub and gym featuring a peloton bike. Perfectly situated on the mountainside with views of the rocky mountains between Winter Park, and Grand Lake. 2 king suites, queen bedroom, bunk room and bunk loft with office. 5 minutes from Granby ranch ski resort, 30 minutes to winter park, grand lake and entrance of RMNP.

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.

Private sauna, amazing view, pool, hot tub!
Let the beauty of the Fraser Valley embrace you! Enjoy a breathtaking view of the entire valley while being steps away from beautiful hiking trails, the Lift (Winter Park’s free shuttle system), a shared community pool and hot tub, shared community rec room, and your own private sauna.

Beautifully Furnished Modern Condo In Downtown WP
In floor radiant heat, fireplace. Ceiling fans in each room. Three comfortable beds to sleep 6 people. We also supply a Pack and Play crib, High chair and a twin floor mattress.
Popular amenities for Winter Park rentals with a pool
House rentals with a pool

Meadowridge 30-2

Chill 301 | Pool | Hot Tub

Family Condo Near WP: Bike, Hike, Pool & Hot Tubs

Alpine Vista Escape

Family Ski Lodge | Sleeps 16 · Epic Views · Arcade

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

The Evangeline Haus *Dog Friendly

Ermine on the Black Line
Condo rentals with a pool

Cozy Studio~Mtn Views~Salt Water Pool & Hot-Tubs

On Fraser River - King bed - pool & hot tubs @ rec

Michael’s Dream Condo #15 Winter Park

Tall Timbers of the Rockies

Bear's Den

Newly Renovated Mountain Modern Condo

Cozy Condo - 20 miles to RMNP w/ Hot Tub & Firepit

Over the Rainbow Trout Inn - Granby Ranch
Other holiday rentals with a pool

3BR/3BA Penthouse Downtown, Htd Pool/Hot Tub

Studio Downtown Winter Park

POOL OPEN!! Mountain get away condo in Winter Park

Prime Location! Walk to Main St!

Hi Country Hideaway

Into the Ultimate Summer & Endless Discovery

3BR w/Views + Hot Tubs • Pool • Near Hiking/Biking

1BR Condo in Winter Park, CO
When is the best time to visit Winter Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $334 NZD | $333 NZD | $314 NZD | $217 NZD | $231 NZD | $229 NZD | $274 NZD | $266 NZD | $279 NZD | $304 NZD | $283 NZD | $380 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 470 holiday rentals in Winter Park

Nightly prices starting at
Winter Park holiday rentals start at $100 NZD per night before taxes and fees

Verified guest reviews
Over 16,730 verified reviews to help you choose

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

Pet-friendly accommodation
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
270 properties have a dedicated workspace

Wi-Fi availability
470 of Winter Park holiday 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
- Vail Ski Resort
- Colorado Convention Center
- Center Village Resort Copper Mountain
- Empower Field at Mile High
- Winter Park Resort
- Arapahoe Basin Ski Area
- Keystone Resort
- Ball Arena
- City Park
- Granby Ranch
- Pearl Street Mall
- Loveland Ski Area
- Ski Cooper
- Denver Zoo
- Fillmore Auditorium
- Denver Botanic Gardens
- University of Denver
- Elitch Gardens
- Golden Gate Canyon State Park





