
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).

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.

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

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.

Amazing Top Floor WP Getaway!
Beautiful condo with excellent access to all Winter Park has to offer! Relax by the wood burning fireplace after a day of the world's best skiing (the shuttle picks up right out front), hiking, mountain biking. 1/4 mile walking trail (or 3 minute drive) drops you right in the heart of Winter Park. Amazing views from three decks! Includes underground parking, ski locker, hot tubs, pool, exercise room, game room, bar, and restaurant within the building. Fully equipped kitchen.

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.

Cozy Cabin! Ski Winter Pk & Granby Ranch
Amazing family-friendly cabin on the Fraser River and in the heart of Granby, CO. Ten minutes to the lodge at Granby Ranch or 25 minutes from Winter Park! Close to Rocky Mountain National Park, Sulphur Hot Springs, and the YMCA of the Rockies. River access and ponds on the property for fishing! This cabin is stocked with all you need (and more!). We host another cabin across the street. Message me about booking both for a larger group!

Studio Condo in the Heart of Winter Park! lic#9602
You're steps from terrific shops, bars, and restaurants. Right outside the condo is the free bus stop to world-class skiing at Winter Park. It is a 3-minute bus ride and frequents every 15 minutes in the winter. Free covered parking is included on a first-come basis. All new kitchen appliances installed in February 2024! Note: There's no A/C in the unit, but there is an evaporative cooler to help keep the unit cool in summer.
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

Cozy mountain home w/ hot tub & fireplace

Summit Sanctuary @ MeadowRidge

Winterfell at Winter Park Resort

Luxury 3BR Winter Park | Hot Tub | Ski Shuttle

Alpine Vista Escape

REMI's River Retreat * FISH/SKI/HIKE/MtnLife*
Condo rentals with a pool

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

Studio~Ski Granby/Winter Park. Pool/Hot Tubs

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

Ski-In/Ski-Out Studio-Newly Remodeled

Ski-in Ski-out Cozy Condo

Cozy Studio Near RMNP – Pool & Hot Tubs

Mountain Delight Near Winter Park

Cozy Condo in Forest + Walk to Town!
Other holiday rentals with a pool

Studio Downtown Winter Park

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

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

Condo in Winter Park Ski and Mountain Views

8 min to WP! Hot Tubs, Pool, Pet-Friendly - 2B2B

1BR Condo in Winter Park, CO

Cabin Riverside• Fire Pit, Hot Tub, Pool, Fishing

Condo w/ Views, Bus Stop to Resort, Walk Downtown.
When is the best time to visit Winter Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $372 NZD | $374 NZD | $386 NZD | $226 NZD | $240 NZD | $238 NZD | $285 NZD | $277 NZD | $290 NZD | $317 NZD | $294 NZD | $395 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 580 holiday rentals in Winter Park

Nightly prices starting at
Winter Park holiday rentals start at $122 NZD per night before taxes and fees

Verified guest reviews
Over 17,660 verified reviews to help you choose

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

Pet-friendly accommodation
Find 70 rentals that welcome pets

Rentals with dedicated workspaces
380 properties have a dedicated workspace

Wi-Fi availability
570 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
- Center Village Resort Copper Mountain
- Winter Park Resort
- Arapahoe Basin Ski Area
- Keystone Resort
- Colorado Convention Center
- Ball Arena
- Empower Field at Mile High
- Granby Ranch
- City Park
- Loveland Ski Area
- Ski Cooper
- Fillmore Auditorium
- Pearl Street Mall
- Denver Zoo
- Elitch Gardens
- Denver Botanic Gardens
- Golden Gate Canyon State Park
- Water World




