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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.

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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
4.73 out of 5 average rating, 292 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
Condo in Granby
4.81 out of 5 average rating, 340 reviews

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

📸 ❤️ Add us on the Gram First! : @moosetrackscondo You will be able to watch videos and pics of Guests and so much more! ❤️ STUNNING MOUNTAIN VIEWS! Sought after valley side condo on the slopes of Granby Ranch Ski Resort. 8 person hot tub in the Second bedroom. Floor to ceiling windows allow for breathtaking views of Granby Ranch golf course and peaks of Rocky Mountain Natl Park. Perfectly located between Winter Park, Grand Lake, Ski-in/Ski-out Mountain Bike In/Out unit is ready for fun 🤩

Superhost
An open-concept living area presents a stone fireplace and vaulted wooden ceiling. A dining table with black chairs is positioned beside a fully equipped kitchen featuring stainless appliances and granite countertops. Natural light filters in through large windows, highlighting the cozy seating area.
Condo in Winter Park
4.91 out of 5 average rating, 162 reviews

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).

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, 155 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
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, 249 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
The exterior of the corner unit loft showcases a welcoming entrance with wooden steps leading to a covered porch. Lush greenery surrounds the building, complemented by slender aspen trees and meticulously maintained landscaping that enhances the natural setting.
Loft in Granby
4.99 out of 5 average rating, 195 reviews

Beautiful Spacious 2 BR & Loft Mountain Condo

Welcome to your perfect mountain escape! From breathtaking views through the large windows & private deck, to easy access to the slopes. Our condo has so much to offer. Located right in the middle of all things Rocky Mountains. You're just 30 minutes from Grand Lake/Rocky Mountain National Park/Winter Park and 2 mins from skiing, fishing, golf, and mountain biking at Granby Ranch. This corner unit is very spacious. The condo is able to sleep 5. We only allow 4 guests-with special exceptions.

Guest favourite
The kitchen features rich wooden cabinets and granite countertops. An under-mount sink is positioned at the island, with a view of the stainless-steel stove and microwave. Stone accents add texture to the space, while shelves display decorative items and dishware.
Condo in Winter Park
4.95 out of 5 average rating, 114 reviews

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

Top guest favourite
Cabin in Granby
4.95 out of 5 average rating, 170 reviews

Charming 3BR Riverfront Cabin - Pet Friendly

Set along the Fraser River and backdropped by the majestic Rocky Mountains, this scenic spot is the Granby getaway for your small group! Come for the stunning alpine scenery and stick around for the abundant activities Grand County has in store. This charming mountain cabin is designed with families in mind, featuring a fully equipped kitchen and thoughtful kid-friendly touches. After a day of outdoor fun, unwind in comfort and enjoy the cozy atmosphere of your home away from home.

Top guest favourite
An illustrated representation of Mountain Flower Cabin features a modern two-story structure set against a mountainous backdrop. Elements such as trees and a bicycle are detailed, along with the sun and stars, conveying a serene connection to nature in Winter Park, Colorado.
Home in Winter Park
4.99 out of 5 average rating, 148 reviews

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.

Top guest favourite
Home in Fraser
4.94 out of 5 average rating, 108 reviews

Peaceful Mountain Retreat & Clubhouse Access

Your mountain get away close to conveniences and activities with access to shared club hot tub. Located on a quiet street. 1/2 of a duplex on a 3/4 acre lot. Heated garage to keep you warm. A spacious entryway for gear, and parking for three cars. All beds, bedding and couches are new. Crib and high chair available. Large deck. 1.3 miles to Safeway 1.5 miles to restaurants and breweries in Fraser 3.5 miles to town of Winter Park 6 miles to Winter Park Resort Permit STR21-00011

Superhost
A spacious king bed is dressed in soft, neutral linens, complemented by decorative pillows. A window offers mountain views, while a small dining area with a table for two and a light fixture above adds functionality. A television occupies the corner, enhancing the cozy ambiance.
Condo in Granby
4.88 out of 5 average rating, 434 reviews

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.

Guest favourite
An outdoor heated pool is featured alongside two hot tubs, surrounded by a scenic landscape of snow-covered trees and mountains. The area is paved with a spacious deck for relaxation, with clear skies above enhancing the serene atmosphere of the retreat.
Condo in Winter Park
4.93 out of 5 average rating, 189 reviews

Ski-in/Ski-out, Luxury amenities +Free parking

Discover the perfect mountain retreat! Enjoy seamless ski-in/ski-out access, a first-floor location, and unwind in the indoor/outdoor heated pool and new hot tubs. Stay fit in our on-site fitness center, park hassle-free, and explore with a free local shuttle at your doorstep. With custom queen and bunk murphy beds, this cozy escape offers comfort and convenience. Your mountain getaway awaits – embrace the charm, relax, and make unforgettable memories!

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 vacation rentals with a pool in Winter Park

  • Total vacation rentals

    Explore 580 vacation rentals in Winter Park

  • Nightly prices starting at

    Winter Park vacation rentals start at $96 CAD per night before taxes and fees

  • Verified guest reviews

    Over 17,660 verified reviews to help you choose

  • Family-friendly vacation rentals

    420 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    380 properties have a dedicated workspace

  • Wifi availability

    570 of Winter Park vacation 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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