
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.

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

❤️ NEW PRIVATE 8 Person *HOTTUB* ROCKY Mnt Park 🏞❤️
📸 ❤️ Add us on the Gram First! : @moosetrackscondo You will be able to watch videos and pics of Guests and so much more! ❤️ STUNNING MOUNTAIN VIEWS! Sought after valley side condo on the slopes of Granby Ranch Ski Resort. 8 person hot tub in the Second bedroom. Floor to ceiling windows allow for breathtaking views of Granby Ranch golf course and peaks of Rocky Mountain Natl Park. Perfectly located between Winter Park, Grand Lake, Ski-in/Ski-out Mountain Bike In/Out unit is ready for fun 🤩

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

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.

Beautiful Spacious 2 BR & Loft Mountain Condo
Welcome to your perfect mountain escape! From breathtaking views through the large windows & private deck, to easy access to the slopes. Our condo has so much to offer. Located right in the middle of all things Rocky Mountains. You're just 30 minutes from Grand Lake/Rocky Mountain National Park/Winter Park and 2 mins from skiing, fishing, golf, and mountain biking at Granby Ranch. This corner unit is very spacious. The condo is able to sleep 5. We only allow 4 guests-with special exceptions.

Walk to town! Indoor pool, sauna, hot tubs.
Enjoy this spacious (1000sqft) 2 bedroom/ 2 bath. Beautifully updated kitchen and baths with granite counter tops and rustic reclaimed barnwood. 1-2 block stroll to nearly 2 dozen restaurants and bars. Heated indoor pool, workout room, hot tubs and sauna in the clubhouse. Free shuttle bus to ski resort. Equipped with all kitchen amenities you might need. 1 Queen and 2 twins, covered parking, living room, dining room, no air conditioning. 4p check in/10a check WP STR Registration #4481

Charming 3BR Riverfront Cabin - Pet Friendly
Set along the Fraser River and backdropped by the majestic Rocky Mountains, this scenic spot is the Granby getaway for your small group! Come for the stunning alpine scenery and stick around for the abundant activities Grand County has in store. This charming mountain cabin is designed with families in mind, featuring a fully equipped kitchen and thoughtful kid-friendly touches. After a day of outdoor fun, unwind in comfort and enjoy the cozy atmosphere of your home away from home.

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.

Peaceful Mountain Retreat & Clubhouse Access
Your mountain get away close to conveniences and activities with access to shared club hot tub. Located on a quiet street. 1/2 of a duplex on a 3/4 acre lot. Heated garage to keep you warm. A spacious entryway for gear, and parking for three cars. All beds, bedding and couches are new. Crib and high chair available. Large deck. 1.3 miles to Safeway 1.5 miles to restaurants and breweries in Fraser 3.5 miles to town of Winter Park 6 miles to Winter Park Resort Permit STR21-00011

Cozy K-Suite~Mtn Views~ Salt Water Pool & Hot-Tubs
Must be 21 or over. No pets, No Smoking. Resort was built in 1982 the commons reflect that. Professional Housekeeping Service. 1st floor walkout Mountain Views of pond & fountain, 300 Sq Ft, Studio Style K-Suite, coffee maker, micro/mini fridge, dining for two, patio w/seating, full size Bathroom w/large tub/shower, double sinks. TV, WiFi, cable, Heated Pool, HotTubs, Sauna. Skiing/boarding, trails and fishing. Grnd Lake, RMNP and Hot Sulphur Springs and Winter Park.

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 Winter Park rentals with a pool
House rentals with a pool

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

Luxury Mountain Retreat with Hot Tub + Views!

Meadowridge 30-2

Cozy mountain home w/ hot tub & fireplace

Winterfell at Winter Park Resort

Views, Ski, Golf! 6 BDR, 13 Beds, Hot Tub!

Luxury 3BR Winter Park | Hot Tub | Ski Shuttle

Alpine Vista Escape
Condo rentals with a pool

Ski-In/Ski-Out Studio-Newly Remodeled

Cozy 1 bedroom Granby Ranch condo

Ski in Ski out, One Bedroom Condo with Jacuzzi Tub

Mountain Studio Suite - Pool & Hot Tubs

Bear's Den

Cozy Condo - Walk To Ski Lifts - Hot Tub & Firepit

In Town and on the River

Mountian Views | Near Winter Park | Pets Stay Free
Other vacation rentals with a pool

Ski in ski out Gby ranch King bed pvt hot tub! 52

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

Ski-In/Out | Hot Tub | Stunning Mountain Views

Ski-in Ski-out Cozy Condo

Condo in Winter Park Ski and Mountain Views

Winter Park 3BR/3.5BA | Pool, Hot Tubs, Bus Route

1BR Condo in Winter Park, CO

Mountainside Ski in/out Bike-in/out updated Condo
When is the best time to visit Winter Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $294 CAD | $296 CAD | $305 CAD | $179 CAD | $190 CAD | $188 CAD | $226 CAD | $219 CAD | $230 CAD | $250 CAD | $233 CAD | $312 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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- Breckenridge Ski Resort
- Rocky Mountain National Park
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