Home rentals with a pool near Winter Park Resort

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Top-rated rentals with a pool near Winter Park Resort

Guests agree: these stays are highly rated for location, cleanliness and more.

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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, 142 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
An indoor swimming pool is showcased with crystal-clear water, surrounded by large windows that invite natural light. Lounge chairs are arranged along the edges, and colorful pool toys float on the surface. The ceiling features exposed beams, emphasizing the spaciousness of the area.
Flat 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 spacious living area is highlighted by a stone fireplace and a large mounted TV. Comfortable seating includes a plush sofa and an accent chair. A rustic area rug beneath a coffee table and a contemporary dining area are visible, with natural light streaming in from sliding glass doors.
Apartment in Winter Park
4.99 out of 5 average rating, 133 reviews

The Adventure Loft-modern luxury in Winter Park!

The Adventure Loft is in a premier top-floor location in Trailhead Lodges. It is within walking distance to Hideaway Park, breweries, and bakeries in Winter Park! The free shuttle bus picks up right down the street. The wrap-around deck offers views of the Rocky Mountains and peek-a-boo views of the Rendezvous Music Stage. This modern luxury loft with high vaulted ceilings and a gourmet kitchen awaits you for the perfect mountain getaway! We welcome pets for a $75 fee PER PET. Two pet maximum.

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, 235 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
Apartment in Winter Park
4.97 out of 5 average rating, 112 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.

Top guest favourite
Apartment in Granby
4.98 out of 5 average rating, 119 reviews

Granby Ranch Condo - Ski-In/Out, Hot Tub & Firepit

Freshly remodeled in July 2025, Sundog Condo is your cozy ski-in/ski-out retreat at Granby Ranch – just 20 mins to Rocky Mountain National Park, Grand Lake & Winter Park. Enjoy a king bed with Brooklinen linens, fully stocked kitchen (Nespresso, quality cookware), gas fireplace, Roku TV, and patio with firepit. Year-round hot tub steps away; pool & gym access available. Walk to ski lifts; trails, golf, fishing, biking, hiking & skiing/Nordic trails right outside your door - adventure awaits!

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, 150 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
A modern studio condo is depicted, featuring a king-sized bed with decorative bedding. A dining table is visible beside the kitchen area with navy cabinetry. Outdoor amenities are shown, including a blue pool surrounded by a wooden deck. A bathroom features dual sinks and a tub.
Apartment in Granby
4.94 out of 5 average rating, 152 reviews

Sexy King bed Retreat, Hot tub Fireplace Pool More

Nestled a mountain resort, this stylish modern studio condo offers a perfect sanctuary for adventure seekers and nature lovers. The sleek and contemporary design provides a cozy yet luxurious escape. During the day, the resort's inviting pool and hot tubs beckon with their warm embrace, after a day of thrilling skiing or mountain adventure. A cozy retreat or a launching pad for alpine adventures, this studio condo promises the perfect blend of modern comfort and outdoor excitement

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.
Apartment in Winter Park
4.94 out of 5 average rating, 103 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.

Top guest favourite
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.
Apartment in Granby
4.9 out of 5 average rating, 411 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.

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.
Apartment in Winter Park
4.78 out of 5 average rating, 277 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
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.
Apartment in Winter Park
4.93 out of 5 average rating, 184 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 rentals with a pool near Winter Park Resort

Quick stats about rentals with a pool near Winter Park Resort

  • Total holiday rentals

    Explore 110 holiday rentals in Winter Park Resort

  • Nightly prices starting at

    Winter Park Resort holiday rentals start at £37 per night before taxes and fees

  • Verified guest reviews

    Over 2,890 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    110 of Winter Park Resort holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winter Park Resort rentals

  • 4.8 Average rating

    Winter Park Resort stays are highly rated by guests – averaging 4.8 out of 5!