
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.

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).

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.

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.

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!

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!

Cozy Cabin on the Fraser River
Cozy & comfortable cabin located on the Fraser River. You can hear the peaceful river from the Master Bedroom or Living Room. The trout filled Frazer river is 50 feet away! You are twenty minutes from Winter Park or Grand Lake and ten minutes to Hot Sulfur Springs. Granby has a large grocery store a mile down the road and several nice restaurants and local shops. Granby Ranch has a fun ski resort in town to ski, board or tube. Short Term Rental Permit #006388

Lone Eagle Luxury 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.
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

Chill 301 | Pool | Hot Tub

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

Winterfell at Winter Park Resort

Family Retreat | Pool + Hot Tubs Near Winter Park

Luxury 3BR Winter Park | Hot Tub | Ski Shuttle

Alpine Vista Escape
Apartment rentals with a pool

Grey Fox ~2 bed/2 BA Ski in/out Granby Ranch, RMNP

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

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

Mountain Delight Near Winter Park

Tall Timbers of the Rockies

Granby Mountain Retreat

Hotel-Style Studio | Near RMNP | Pool & Hot Tubs

Perfect ski Condo
Other holiday rentals with a pool

Studio Downtown Winter Park

Cozy & Close to Winter Park - Hot Tub & Pool

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

Ski in / Ski out at Winter Park - pool & hot tub

Condo in Winter Park Ski and Mountain Views

1BR Condo in Winter Park, CO

The Coop: Ski In/Ski Out Studio - Winter Park

Mtn condo - hot tub, bus line, stocked kitchen
When is the best time to visit Winter Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £150 | £149 | £141 | £98 | £104 | £103 | £123 | £119 | £125 | £137 | £127 | £170 |
| 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 £45 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
270 properties have a dedicated workspace

Wifi availability
470 of Winter Park holiday 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
- Red Rocks Amphitheatre
- Beaver Creek Resort
- Coors Field
- Vail Ski Resort
- Center Village Resort Copper Mountain
- Colorado Convention Center
- Winter Park Resort
- Arapahoe Basin Ski Area
- Keystone Resort
- Empower Field at Mile High
- Ball Arena
- City Park
- Granby Ranch
- Pearl Street Mall
- Loveland Ski Area
- Ski Cooper
- Fillmore Auditorium
- Denver Zoo
- Denver Botanic Gardens
- Elitch Gardens
- University of Denver
- Water World





