
Holiday rentals with a pool in Winter Park
Find and book unique homes with a pool on Airbnb
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 $106 NZD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
270 properties have a dedicated workspace

Wi-Fi availability
470 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!
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.

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.

Perfect ski Condo
My place (Snow Blaze) in town, perfect for 2 . Pool, 2 hot tub, saunas, gym and a fire pit. Short walk to shops, bars, restaurants and music venues. The free bus stops every 15-20 minutes, 40 yards down from the driveway. Only 5 minute drive to the Resort. We have a parking garage under the building with additional outside parking. An elevator to bring you to the 2nd floor unit. The pool house/gym is easily accessed from out the back door of the first floor. In unit cable T.V. and internet.

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!

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

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!

Riverfront Condo☆1st Floor☆Ski Bus☆Pool & Hot Tub
Recently remodeled 1st floor condo with views and sounds of Fraser River. Walking distance to downtown Winter Park grocery store, coffee shop, restaurants, breweries, retail stores, bars, movie theater, and bowling alley. Community amenities include an indoor pool, hot tubs, workout room, lounge with pool table, laundry facilities, and outdoor playground. Free bus to resort nearby. This riverfront condo is perfect for relaxing and unwinding after a full day of outdoor activities.

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!
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

Winterfell at Winter Park Resort

Luxury 3BR Winter Park | Hot Tub | Ski Shuttle

Family Ski Lodge | Sleeps 16 · Epic Views · Arcade

The Evangeline Haus *Dog Friendly

Ermine on the Black Line
Condo rentals with a pool

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

Winter Park 2bd/2ba (Sleeps 6) - Ideal Location!

Cozy Studio~Mtn Views~Salt Water Pool & Hot-Tubs

On Fraser River - King bed - pool & hot tubs @ rec

Newly Renovated Mountain Modern Condo

Cozy Condo - 20 miles to RMNP w/ Hot Tub & Firepit

Mtn condo - hot tub, bus line, stocked kitchen

Mountain Modern Cozyville
Other holiday rentals with a pool

Modern Mountain Condo in WP

Studio Downtown Winter Park

Best location - Incredible access

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

Into the Ultimate Summer & Endless Discovery

1BR Condo in Winter Park, CO

The Coop: Trestle Bike Park +Ski In Ski Out Studio

Cozy Wint. Park Condo 2 BR 2 Ba Downtwn on Bus Rt.
When is the best time to visit Winter Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $354 NZD | $353 NZD | $333 NZD | $230 NZD | $245 NZD | $243 NZD | $291 NZD | $282 NZD | $296 NZD | $323 NZD | $299 NZD | $402 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 |
Destinations to explore
- Fitness-friendly rentals Winter Park
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- Rentals with outdoor seating Winter Park
- Rentals with a washing machine and dryer Winter Park
- Rentals with a fire pit Winter Park
- Apartment rentals Winter Park
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- Family-friendly rentals Winter Park
- Rentals with a kayak Winter Park
- Rentals with a fireplace Winter Park
- Rentals with an accessible height toilet Winter Park
- House rentals Winter Park
- Ski-in/ski-out rentals Winter Park
- Townhouse rentals Winter Park
- Rentals with a sauna Winter Park
- Luxury rentals Winter Park
- Chalet rentals Winter Park
- Rentals with lake access Winter Park
- Cabin rentals Winter Park
- Rentals with a patio Winter Park
- Condo rentals Winter Park
- Rentals with a hot tub Winter Park
- Pet-friendly rentals Winter Park
- Rentals with pools Grand County
- Rentals with pools Colorado
- Rentals with pools United States
- Rocky Mountain National Park
- Red Rocks Amphitheatre
- Breckenridge Ski Resort
- Coors Field
- Empower Field at Mile High
- Arapahoe Basin Ski Area
- Vail Ski Resort
- Keystone Resort
- Colorado Convention Center
- City Park
- Ball Arena
- Beaver Creek Resort
- Winter Park Resort
- Loveland Ski Area
- Pearl Street Mall
- Ski Cooper
- Granby Ranch
- Denver Zoo
- University of Denver
- Fillmore Auditorium
- Golden Gate Canyon State Park
- St. Mary's Glacier
- Denver Botanic Gardens
- Elitch Gardens





