
Holiday rentals with a pool in Winter Park
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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.

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

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.

Riverfront Cabin! Skiing • Fly-Fishing • Hiking
If you're seeking a relaxing family-friendly getaway, look no further than this 3-bed, 2.5-bath vacation rental cabin! Located in the Edgewater community and sitting right on the Fraser River, this cozy cabin offers sleeping arrangements for 7. Spend your days skiing at Granby Ranch, only 5 minutes away or Winter Park, 25 minutes away. Enjoy the thrill of downhill tubing or snowmobiling within 20 minutes. This cabin is centrally located to enjoy a vacation filled with outdoor adventure!

Granby Mountain Retreat
Hiking, golfing, biking, fishing within 5 minutes! 20 minutes to the West Entry of RMNP, 20 minutes to Hot Sulphur Springs, 20 minutes to Winter Park, 20 minutes to Grand Lake! Out of door mountain biking, minutes to cross country skiing, fishing and golfing! Perfect for a solo traveler looking to relax, a romantic getaway for a couple, a group of friends interested in exploring the surrounding mountains, or a full family, looking to enjoy the onsite amenities and surrounding activities!

The Mountainside at Granby Ranch
This is truly mountainside living with trail & ski access right out the door! We remodeled over 4 months & added a 14 ft live edge bar, 100 year old hardwood vanities and many other touches to make the mountainside a memorable Colorado experience. While staying you can enjoy all that Granby Ranch has to offer in every season or access Winter Park or Grand Lake in quick 20 minute drives. A grocery store and gas station are only 5 minutes away and Granby is right around the corner. Enjoy!

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.

Great View, pool & hot tub, 1 bed & loft sleeps 6
Beautifully remodeled 700 sq ft. condo with 1 bedroom and a loft, that sleeps 6. It has a full kitchen and amazing views of Winter Park, the Continental Divide and Byers Peak. The Clubhouse, which is across the parking lot, has 2 outdoor hot tubs a heated pool, fitness center 2 racquetball courts, a ping pong table, laundry facilities, a conference room that is available for rent, massage, and ski tuning. It is only 2.5 miles from Winter park and right on the free bus route.

Cozy K-Suite~Mtn Views~ Salt Water Pool & Hot-Tubs
Must be 21 or over. No pets, No Smoking. Resort was built in 1982 the commons reflect that. Professional Housekeeping Service. 1st floor walkout Mountain Views of pond & fountain, 300 Sq Ft, Studio Style K-Suite, coffee maker, micro/mini fridge, dining for two, patio w/seating, full size Bathroom w/large tub/shower, double sinks. TV, WiFi, cable, Heated Pool, HotTubs, Sauna. Skiing/boarding, trails and fishing. Grnd Lake, RMNP and Hot Sulphur Springs and Winter Park.

FREE WP ski bus - King bed - pool & hot tubs @ rec
1st Floor - Hi Country Haus Condos in Winter Park, Colorado. On the Fraser River and steps away from WP Ski Bus pick-up. Our cozy condo offers a King bed, full/double bed and twin/single bed. Walking distance to groceries at Fireside Market. Restaurants = Hernando’s, Randi’s, Namaste, Carver’s, Fontenot’s, The Perk, Wake-n-Bacon, Domino’s & more! NOTE - the recreation center will be unavailable from 11/2/25 - 11/8/25 for fall cleaning.

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.

Winter Park Studio: On the River~ Walk Downtown!
Fireside Haven is a cozy studio located on a secluded spot RIGHT on the Fraser River, yet is walkable to all that downtown Winter Park has to offer. Dine-out, shop, enjoy coffee at a café, cocktails at happy hour, hike/bike and catch the ski shuttle all within a five-minute walk from your front door! You will have a king-size bed, queen-size sofa sleeper, full kitchen, bathroom, fireplace, private patio & ski closet.
Popular amenities for Winter Park rentals with a pool
House rentals with a pool

Meadowridge 30-2

Private Hot Tub! Stunning Luxury Home, Ski-In/Out

Colorado's Coolest Ski In/Out Home

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

Cozy Modern Cabin w/ Hot Tub - Minutes to Ski Area

Alpine Vista Escape

Rooftop Loft 21 I HotTub I Discounted Attractions

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

Beautiful Condo with Hot Tub on Ski Bus Route

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

Pine in the Sky Condo, Cozy + Close to GR/WP/RMNP

Mountain Delight Near Winter Park

Walk to Town, Front Door Ski Shuttle Pick-up!

Newly Renovated Mountain Modern Condo

❤️ NEW PRIVATE 8 Person *HOTTUB* ROCKY Mnt Park 🏞❤️

The Adventure Loft-Views of the Music Stage!
Other holiday rentals with a pool

Ski-In/Ski-Out Studio Mtn View-Free Heated Parking

Elevation Station in Snowblaze condominiums

Ski-in / Ski-out Studio Condo

The Rustic Moose

Amazing Top Floor WP Getaway!

Meadowridge Mountain View Condo

Mountain getaway near great trails/hot tub access

Rare King Bed Mtn Retreat Hot Tub Fireplace Views
Quick stats about holiday rentals with a pool in Winter Park
Total rentals
580 properties
Nightly prices starting at
$77 AUD before taxes and fees
Total number of reviews
18K reviews
Family-friendly rentals
440 properties are a good fit for families
Pet-friendly rentals
90 properties allow pets
Rentals with dedicated workspaces
400 properties have a dedicated workspace
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- Breckenridge Ski Resort
- Rocky Mountain National Park
- Beaver Creek Resort
- Coors Field
- Vail Ski Resort
- Red Rocks Park and Amphitheatre
- Winter Park Resort
- Keystone Resort
- Granby Ranch
- Arapahoe Basin Ski Area
- Denver Zoo
- Elitch Gardens
- Fillmore Auditorium
- City Park
- Pearl Street Mall
- Water World
- Denver Botanic Gardens
- Golden Gate Canyon State Park
- Ogden Theatre
- Loveland Ski Area
- Ski Cooper
- Arrowhead Golf Course
- Downtown Aquarium
- St. Mary's Glacier