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.

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Superhost
A welcoming living area features a dark sofa adorned with decorative pillows. Two wide windows with wooden blinds frame serene views of the surrounding mountains, while a rustic wooden table complements the space. Soft natural light highlights the cozy interior.
Condo in Winter Park
4.72 out of 5 average rating, 289 reviews

Entire Condo In The Heart of Winter Park

Roomy studio sleeps 4, wood, tile and granite floors. Full kitchen with dishwasher, queen size Murphy bed(recesses into wall ) and queen sleeper sofa, bathroom with tub and shower. Separate vanity sink area. Top floor and great views!! Full access to indoor swimming pool , gym, yoga room, hot and dry sauna, and both indoor/outdoor jacuzzis. Free parking is available. Free Ski slope bus stop right in front of condominiums. Great location right in the heart of Winter Park!!!TOWP STR Permit #6104

Guest favourite
The welcoming living area showcases a spacious sectional sofa adorned with a colorful throw. A stone accent wall complements the large flat-screen smart TV. Natural light enters through expansive windows, illuminating the area, while a modern counter separates the kitchen from the living space.
Condo in Winter Park
4.94 out of 5 average rating, 149 reviews

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

Guest favourite
Apartment in Winter Park
4.93 out of 5 average rating, 126 reviews

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.

Top Guest favourite
A modern studio is presented, featuring a well-equipped kitchen with bar stools at the counter. Two armchairs sit on a patterned area rug, and a spacious bed is visible in the foreground. The design incorporates neutral tones and textured wall tiles.
Condo in Winter Park
4.88 out of 5 average rating, 246 reviews

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.

Top Guest favourite
Condo in Winter Park
4.97 out of 5 average rating, 119 reviews

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.

Guest favourite
The image showcases four distinct views of the condo. A bright living area features comfortable leather sofas and a stone fireplace. The outdoor hot tub offers scenic mountain views. A modern kitchen is equipped with stainless steel appliances, and the dining area is illuminated by stylish lighting.
Condo in Fraser
4.87 out of 5 average rating, 153 reviews

Mountian Views | Near Winter Park | Pets Stay Free

Situated in the stunning Fraser Valley, this mountain retreat has everything you need to rest and relax. Soak in the mountain views at the clubhouse hot tubs or curly up by the fireplace with a drink. Near Winter Park Resort and Rocky Mountain National with easy access to snowshoeing, Mtn biking, hiking, fishing, cross-country skiing and more! ✔ Two ♛ King Beds ✔Pets Stay Free ✔ Private Balcony ✔ Well Equipped Kitchen ✔ Fireplace ✔ High-Speed Wi-Fi ✔ Clubhouse Access Book your stay today!

Guest favourite
Condo in Granby
4.95 out of 5 average rating, 192 reviews

King & Bunkbeds 5 min to Base of Granby Ski Area!

Enjoy the very best Colorado has to offer! This 2Br 2Ba condo is the perfect place to stay year-round! We are located 1 mile from downtown Granby, and 5 minute drive from Granby Ranch Ski Resort. Granby is located at the heart of Grand County, amidst so many of Colorado’s best destinations for outdoor exploration and fun! The condo is a short drive to Winter Park, Snow Mountain Ranch, Grand Lake, and Rocky Mountain National Park! Grand County Short Term Rental License/Permit No: 007640

Top Guest favourite
A serene outdoor space features smooth stones lining the banks of a gentle stream. Two wooden Adirondack chairs are positioned on the grass, offering views of the water. Lush greenery and trees frame the scene, contributing to a peaceful natural setting.
Condo in Winter Park
4.89 out of 5 average rating, 385 reviews

Riverfront Condo☆1st Floor☆Ski Bus☆Pool & Hot Tub

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. It is a great place to curl up next to the electric fireplace, relax, and unwind after a full day of outdoor activities.

Guest favourite
Condo in Fraser
4.86 out of 5 average rating, 114 reviews

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!

Superhost
A sign indicating the various snow depth measurements at Winter Park is partially buried in snow, with visible markers at six-inch intervals up to 18 inches. The forest backdrop is lined with snow-covered trees, creating a peaceful winter scene.
Condo in Winter Park
4.78 out of 5 average rating, 280 reviews

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.

Guest favourite
The studio accommodates a cozy sleeping area with a queen Murphy bed and a queen pull-out couch. Large windows provide natural light, and rustic wooden accents enhance the interior. A small table and comfortable seating complete the inviting atmosphere.
Condo in Granby
4.85 out of 5 average rating, 212 reviews

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

This 2nd floor studio is located at the Inn at Silvercreek in Granby Ranch. It is 495 sq ft. Inside the studio has been updated and is stylish and cozy. The resort offers many amenities including pool, hot tubs, an arcade, a gym and even a barber shop. The location is about 5 min from the Granby Ski area, 20 min to Grand Lake and 30 min to either RMNP or Winter Park. There is a free “Lift” shuttle to Winter Park during the ski season.

Guest favourite
A spacious living area features a red seating arrangement with a comfortable sofa and armchair, complemented by light streaming through multiple windows. A kitchen island with a sink is visible, alongside a dining area that includes four chairs. A stone fireplace adds a touch of warmth to the space.
Condo in Granby
4.85 out of 5 average rating, 478 reviews

Cozy 1 bedroom Granby Ranch condo

Welcome to our Granby Ranch condo! Great access to skiing, hiking, biking, fishing and golf. Guests also have access to the outdoor pool and hot tub at the base of the ski mountain (small fee required)as well as a free tub in our complex. Unit has a master bedroom with a queen sized bed. FYI-I don’t accept any reservation requests without confirming the cleaning arrangements first. Our STR permit # is 006840.

Popular amenities for Winter Park rentals with a pool

When is the best time to visit Winter Park?

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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 $99 AUD 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, Wi-Fi 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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