
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.

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

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.

Pool Access & Mtn View! Luxe WP Cabin, Near Trails
Rendezvous Neighborhood | 1 Mi to Dtwn Bites & Brews | Walk to Fraser River Adventure begins right out your door at this Winter Park vacation rental, where alpine trails and fresh air set the stage for an unforgettable stay. Hike and bike through scenic terrain, or take advantage of Club MeadowRidge amenities just a short drive away. Then return to unwind in a beautiful cabin thoughtfully designed with custom furniture, modern amenities, and epic views. This is mountain living at its best!

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!

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.

Cozy Winter Park Riverfront Studio~ Walk Downtown
Riverside Rendezvous is a stylish studio nestled right on the Fraser River. This tranquil location is walkable to all the amenities one would desire in town. You will have a queen-size bed, queen-size sofa sleeper, full kitchen, bathroom, fireplace, private patio & ski closet. Walk to ski shuttle stop, miles of hiking/biking trails, fishing, restaurants, grocery store, bars, breweries & nightlife.

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.
Popular amenities for Winter Park rentals with a pool
House rentals with a pool

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

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

The Evangeline Haus *Dog Friendly

Ermine on the Black Line

Peaceful Mountain Retreat & Clubhouse Access
Condo rentals with a pool

Come to WP-30% off nightly rate for 6 night stay!

Walk to town! Indoor pool, sauna, hot tubs.

Cozy K-Suite~Mtn Views~ Salt Water Pool & Hot-Tubs

Michael’s Dream Condo #15 Winter Park

Tall Timbers of the Rockies

Bear's Den

Mtn condo - hot tub, bus line, stocked kitchen

Cozy Condo - 20 miles to RMNP w/ Hot Tub & Firepit
Other vacation rentals with a pool

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

Studio Downtown Winter Park

Cozy & Close to Winter Park - Hot Tub & Pool

Prime Location! Walk to Main St!

Ski-in Ski-out Cozy Condo

Hi Country Hideaway

Into the Ultimate Summer & Endless Discovery

3BR w/Views + Hot Tubs • Pool • Near Hiking/Biking
When is the best time to visit Winter Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 172 | € 171 | € 161 | € 112 | € 118 | € 118 | € 141 | € 136 | € 143 | € 156 | € 145 | € 195 |
| 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 470 vacation rentals in Winter Park

Nightly prices starting at
Winter Park vacation rentals start at € 52 per night before taxes and fees

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

Family-friendly vacation rentals
310 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
270 properties have a dedicated workspace

Wi-Fi availability
470 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
- 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
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- Ski Cooper
- Denver Zoo
- Fillmore Auditorium
- Denver Botanic Gardens
- University of Denver
- Elitch Gardens
- Golden Gate Canyon State Park





