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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Guest favourite
A cozy living area is showcased with a spacious sofa, a coffee table, and a prominent linear electric fireplace framed in travertine stone. In the background, a modern dining table sits adjacent to a well-equipped kitchen, with bar stools positioned at the counter.
Apartment in Fraser
4.89 out of 5 average rating, 131 reviews

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.

Guest favourite
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.
Apartment in Winter Park
4.91 out of 5 average rating, 164 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
A welcoming living area features a stone fireplace with a modern fire display. A large sectional couch and coffee table are arranged around a colorful braided rug. A flat-screen TV is mounted on the wall, with a view of nature through the window. A cozy front door leads to the outside.
Apartment in Winter Park
4.88 out of 5 average rating, 104 reviews

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

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.
Apartment in Winter Park
4.94 out of 5 average rating, 156 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
Flat in Winter Park
4.93 out of 5 average rating, 129 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.

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.
Apartment in Winter Park
4.88 out of 5 average rating, 251 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
Home in Winter Park
4.99 out of 5 average rating, 148 reviews

Luxury WP Mtn Cabin, Free Shuttle, Views & Garage

Rendezvous Neighborhood | 1 Mi to Dtwn Bites & Brews | 4 Mi to WP Resort Adventure begins just outside your door at this Winter Park vacation rental, where alpine trails and fresh air set the stage for an unforgettable stay. Spend your days skiing, biking, or hiking through scenic terrain, then return to a beautiful cabin thoughtfully designed with custom furniture, modern amenities, and epic views. The bright, cozy space invites you to relax and unwind. This is mountain living at its best!

Top guest favourite
A cozy living space is highlighted by a large sectional sofa positioned against a brick fireplace. Natural light fills the room through a skylight and glass door that opens to a private deck. A desk with a chair adds a functional touch to the layout.
Apartment in Winter Park
4.95 out of 5 average rating, 155 reviews

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.

Guest favourite
The cozy living area features a comfortable sofa adorned with patterned cushions, complemented by a rustic coffee table. A modern kitchen with wooden cabinetry and bar stools is visible, along with a bright, inviting atmosphere enhanced by natural light from the ceiling fixtures.
Apartment in Winter Park
4.87 out of 5 average rating, 119 reviews

In Town and on the River

Our condo is a cozy escape from the city, centered around a huge stone fireplace. The condo has a main bedroom with a queen bed and half bath. The second bedroom has a double bed and a bunk bed and we just remodeled the bathroom for a luxurious experience. Being a first floor, corner unit, our condo offers walk up access and is just a few blocks away from all the shops and eats. There is also a pool, laundry, hot tubs, and a work out area for use in the clubhouse just down the street.

Guest favourite
Apartment in Fraser
4.86 out of 5 average rating, 117 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!

Guest favourite
A community pool area features a clear blue water pool surrounded by a sun deck. Several lounge chairs are positioned alongside the pool, with a wooden clubhouse visible in the background, providing a spacious area for relaxation and gatherings.
Apartment in Winter Park
4.87 out of 5 average rating, 106 reviews

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!

Top guest favourite
The cabin's exterior is showcased, featuring multiple levels and a spacious deck. A large flat stone patio includes several seating options. Nearby, the landscape is landscaped with gravel and grass, surrounded by a community of similar structures.
Cabin in Granby
4.97 out of 5 average rating, 118 reviews

Cozy Cabin on the Fraser River

Cozy & comfortable cabin located on the Fraser River. You can hear the peaceful river from the Master Bedroom or Living Room. The trout filled Frazer river is 50 feet away! You are twenty minutes from Winter Park or Grand Lake and ten minutes to Hot Sulfur Springs. Granby has a large grocery store a mile down the road and several nice restaurants and local shops. Granby Ranch has a fun ski resort in town to ski, board or tube. Short Term Rental Permit #006388

Popular amenities for Winter Park rentals with a pool

When is the best time to visit Winter Park?

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Avg. price€ 171€ 171€ 161€ 111€ 118€ 117€ 141€ 136€ 143€ 156€ 145€ 195
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Quick stats about holiday rentals with a pool in Winter Park

  • Total holiday rentals

    Explore 470 holiday rentals in Winter Park

  • Nightly prices starting at

    Winter Park holiday rentals start at € 51 per night before taxes and fees

  • Verified guest reviews

    Over 16,730 verified reviews to help you choose

  • Family-friendly holiday rentals

    310 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    270 properties have a dedicated workspace

  • Wifi availability

    470 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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