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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.

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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.
Condo 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.

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
Apartment 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.
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
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.
Condo in Winter Park
4.95 out of 5 average rating, 154 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 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
A bright living room features large windows that invite natural light and offers views of the outdoors. A spacious leather sectional sofa is positioned around a wooden coffee table, with a cozy area rug beneath. A modern fireplace and wall-mounted TV complete the inviting space.
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.

Guest favourite
A scenic mountainous landscape is showcased, with snow-covered peaks under a clear blue sky. The foreground features a line of trees and a snow-blanketed ground, while distant mountains create a dramatic backdrop.
Condo in Winter Park
4.94 out of 5 average rating, 107 reviews

Amazing Top Floor WP Getaway!

Beautiful condo with excellent access to all Winter Park has to offer! Relax by the wood burning fireplace after a day of the world's best skiing (the shuttle picks up right out front), hiking, mountain biking. 1/4 mile walking trail (or 3 minute drive) drops you right in the heart of Winter Park. Amazing views from three decks! Includes underground parking, ski locker, hot tubs, pool, exercise room, game room, bar, and restaurant within the building. Fully equipped kitchen.

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
4.77 out of 5 average rating, 286 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.

Top Guest favourite
A serene view from the deck showcases the expansive Fraser River, surrounded by lush greenery and trees. The space features a long bar-style counter, ideal for outdoor relaxation. A grass area leads down to the river where individuals can be seen enjoying the natural setting.
Cabin in Granby
4.97 out of 5 average rating, 134 reviews

Cozy Cabin! Ski Winter Pk & Granby Ranch

Amazing family-friendly cabin on the Fraser River and in the heart of Granby, CO. Ten minutes to the lodge at Granby Ranch or 25 minutes from Winter Park! Close to Rocky Mountain National Park, Sulphur Hot Springs, and the YMCA of the Rockies. River access and ponds on the property for fishing! This cabin is stocked with all you need (and more!). We host another cabin across the street. Message me about booking both for a larger group!

Guest favourite
A studio layout is presented, featuring a spacious bed with neutral bedding. A bunk bed is positioned nearby, and a set of skis is mounted on the wall. Two windows allow natural light to fill the space, complemented by a comfortable seating area with armchairs.
Condo in Winter Park
4.88 out of 5 average rating, 155 reviews

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.

Popular amenities for Winter Park rentals with a pool

When is the best time to visit Winter Park?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$372 NZD$374 NZD$386 NZD$226 NZD$240 NZD$238 NZD$285 NZD$277 NZD$290 NZD$317 NZD$294 NZD$395 NZD
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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 $122 NZD 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, 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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