
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.

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.

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.

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!

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.

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!
Popular amenities for Winter Park rentals with a pool
House rentals with a pool

Luxury Mountain Retreat with Hot Tub + Views!

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

Beautiful Condo with Pool, Hot Tub and Rec Room

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

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

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

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

Michael’s Dream Condo #15 Winter Park

Bear's Den

Newly Renovated Mountain Modern Condo
Other vacation rentals with a pool

Ski-In/Out & Trestle Access | Pool

3BR/3BA Penthouse Downtown, Htd Pool/Hot Tub

Cozy & Close to Winter Park - Hot Tub & Pool

Prime Location! Walk to Main St!

Enjoy the Mountains! - 2 bedroom condo unit

Hi Country Hideaway

3BR w/Views + Hot Tubs • Pool • Near Hiking/Biking

Riverfront Cabin • Hot Tub • Pool • Lakes • Park
When is the best time to visit Winter Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$41,839 GYD | G$41,629 GYD | G$39,328 GYD | G$27,195 GYD | G$28,869 GYD | G$28,659 GYD | G$34,308 GYD | G$33,262 GYD | G$34,935 GYD | G$38,073 GYD | G$35,354 GYD | G$47,487 GYD |
| 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 470 vacation rentals in Winter Park

Nightly prices starting at
Winter Park vacation rentals start at G$12,552 GYD per night before taxes and fees

Verified guest reviews
Over 16,730 verified reviews to help you choose

Family-friendly vacation rentals
310 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
270 properties have a dedicated workspace

Wi-Fi availability
470 of Winter Park vacation 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
- Colorado Convention Center
- Empower Field at Mile High
- Winter Park Resort
- Arapahoe Basin Ski Area
- Keystone Resort
- Ball Arena
- City Park
- Pearl Street Mall
- Loveland Ski Area
- Ski Cooper
- Denver Zoo
- Fillmore Auditorium
- Denver Botanic Gardens
- Granby Ranch
- Elitch Gardens
- University of Denver
- Golden Gate Canyon State Park
- Fraser Tubing Hill





