
Home rentals with a pool near Winter Park Resort
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool near Winter Park Resort
Guests agree: these stays are highly rated for location, cleanliness and more.

Mountain Modern Cozyville
Remodeled with a high end modern flair for comfort and a classic mountain style A mountain-modern, warm, and cozy space that's conveniently located in a quiet mountain-view neighborhood with FREE recreation-center benefits right across the street and a FREE local bus system right out the front door to all local attractions. Safeway, coffee shops, ski/ride/hike stores less than 1-mile away. It really doesn't get any better than this! We will look forward to your feedback and adventure stories.

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

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.

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!

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.

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!

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.

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.

Ski-in/Ski-out, Luxury amenities +Free parking
Discover the perfect mountain retreat! Enjoy seamless ski-in/ski-out access, a first-floor location, and unwind in the indoor/outdoor heated pool and new hot tubs. Stay fit in our on-site fitness center, park hassle-free, and explore with a free local shuttle at your doorstep. With custom queen and bunk murphy beds, this cozy escape offers comfort and convenience. Your mountain getaway awaits – embrace the charm, relax, and make unforgettable memories!
Popular amenities for rentals with a pool near Winter Park Resort
House rentals with a pool

Luxury Mountain Retreat with Hot Tub + Views!

Meadowridge 30-2

Chill 301 | Pool + Hot Tub

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

Peaceful Mountain Retreat & Clubhouse Access
Condo rentals with a pool

Entire Condo In The Heart of Winter Park

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

Private Sauna, Covered Parking, Hot Tub, Pool!

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

Mountain Delight Near Winter Park

Bear's Den

Walk to Town, Front Door Ski Shuttle Pick-up!

Ski-in / Ski-out Studio Condo
Other holiday rentals with a pool

Studio Downtown Winter Park

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

Hi Country Hideaway

Ski-In/Ski-Out Cozy Studio Retreat

Condo in Winter Park Ski and Mountain Views

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

1BR Condo in Winter Park, CO

Mini Moose Lodge
Quick stats about rentals with a pool near Winter Park Resort

Total holiday rentals
Explore 120 holiday rentals in Winter Park Resort

Nightly prices starting at
Winter Park Resort holiday rentals start at $201 NZD per night before taxes and fees

Verified guest reviews
Over 2,990 verified reviews to help you choose

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

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
120 of Winter Park Resort holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winter Park Resort rentals

4.8 Average rating
Winter Park Resort stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Rentals with a fire pit Winter Park Resort
- Ski-in/ski-out rentals Winter Park Resort
- Rentals with an EV charger Winter Park Resort
- Condo rentals Winter Park Resort
- Rentals with a kayak Winter Park Resort
- Pet-friendly rentals Winter Park Resort
- Rentals with a fireplace Winter Park Resort
- Rentals with a washing machine and dryer Winter Park Resort
- Rentals with a patio Winter Park Resort
- Rentals with a hot tub Winter Park Resort
- Rentals with outdoor seating Winter Park Resort
- Family-friendly rentals Winter Park Resort
- Fitness-friendly rentals Winter Park Resort
- House rentals Winter Park Resort
- Townhouse rentals Winter Park Resort
- Rentals with a sauna Winter Park Resort
- Rentals with lake access Winter Park Resort
- Apartment rentals Winter Park Resort
- Rentals with pools Winter Park
- Rentals with pools Grand County
- Rentals with pools Colorado
- Rentals with pools United States
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