
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.

Ground floor 2 bedroom, at Hi Country Winter Park
Recently remodeled 2-bedroom GROUND floor condo is located on the Fraser River, one block away from the main strip of WP. The Hi Country complex features a newly remodeled clubhouse with indoor & outdoor hot tubs, large pool, fitness center, pool table, kids room, and an outdoor playground. In the winter, the free shuttle is located 45 steps behind our building and will whisk you to the ski area twice an hour. A 5-15 min walk to shops, restaurants, bars, movie theater, and the town park.

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! 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.

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.

Cozy Studio~Mtn Views~Salt Water Pool & Hot-Tubs
Must be 21 or over, No Smoking, No Pets Resort was built in 1982, the common areas reflect that. Disinfecting professional housekeeping service. WalkOut Studio (one room) w/patio, Pond, fountain and Mtn views, 495 sq ft, fireplace, full kitchen, full bath, 55 inch FS TV, WiFi, and cable. Resort offering many amenities. Queen Murphy Bed and Queen Sofa Bed. Heated pool, hot tubs, Sauna, fitness center, RB, and tennis courts.

Over the Rainbow Trout Inn - Granby Ranch
Enjoy a cabin in a condo! Clean, fully equipped, 1st floor, family friendly condo in Granby Ranch. Walk to hiking trails, 20 minutes drive to both Rocky Mountain National Park and Winter Park. So much to do close-by all year round; snowshoe, bike, golf, ski, hike, and more! This is a quiet condo complex ideal for anyone who is looking for relaxation. Enjoy spending family time in our cozy, comfortable, cabin-like condo!
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

Winterfell at Winter Park Resort

Alpine Vista Escape

REMI's River Retreat * FISH/SKI/HIKE/MtnLife*

Mountain Retreat with VIEW!

The Evangeline Haus *Dog Friendly
Apartment rentals with a pool

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

Ski-In/Ski-Out Studio-Newly Remodeled

Cozy 1 bedroom Granby Ranch condo

Mountain Adventure Condo in Fraser!

Mountain Delight Near Winter Park

Bear's Den

Luxurious Mountain Condo

The Rustic Moose
Other holiday rentals with a pool

Private Sauna, Covered Parking, Hot Tub, Pool!

Studio Downtown Winter Park

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

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

2-Bedroom Ski-In/Ski-Out Condo in Granby Ranch

Condo in Winter Park Ski and Mountain Views

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

1BR Condo in Winter Park, CO
When is the best time to visit Winter Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £162 | £162 | £168 | £98 | £104 | £103 | £124 | £120 | £126 | £137 | £128 | £171 |
| 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 £53 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 70 rentals that welcome pets

Rentals with dedicated workspaces
380 properties have a dedicated workspace

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




