Holiday rentals with a pool in Winter Park

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.

4.9 out of 5 average rating, 115 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.

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.

4.94 out of 5 average rating, 154 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).

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.

4.94 out of 5 average rating, 139 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

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.

4.87 out of 5 average rating, 230 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.

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.

4.95 out of 5 average rating, 148 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.

4.99 out of 5 average rating, 141 reviews

A spacious living area features large windows allowing ample natural light. A large leather sectional is positioned near a gas fireplace, complemented by two modern chairs. A flat-screen TV is mounted on the wall opposite, and a coffee table sits on a decorative rug.

Home in Winter Park

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.

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.

4.86 out of 5 average rating, 101 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!

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.

4.94 out of 5 average rating, 146 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

The living area features a spacious sectional sofa arranged around a light-colored area rug. Nearby, a dining space with high-top wooden stools complements the modern kitchen, equipped with stainless steel appliances and white cabinetry. Natural light flows in through large windows, enhancing the inviting atmosphere.

4.97 out of 5 average rating, 110 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 free ski shuttle behind the building for a 15-minute ride to Winter Park Ski Resort.

Superhost

A bright living area features wood-paneled walls and modern decor. A comfortable sofa is arranged with two decorative pillows. A round dining table with four white chairs offers space for meals. Large windows provide views of the outdoors, enhancing the inviting atmosphere.

Loft in Granby

4.83 out of 5 average rating, 328 reviews

Cozy Mtn. Condo | Ski, Hike, Fish + Hot Tub & Pool

Relax and enjoy our cozy updated mountain condo in the heart of the Rockies! Perfect for year-round adventure—ski, snowshoe, hike, bike, fish, boat, and explore all that Granby has to offer. Just 20 min to Winter Park, 20 min to Grand Lake, and 5 min to downtown Granby! Our private 615 sq. ft. unit sleeps 4 with two queen beds in the open loft. Unwind on the private balcony or enjoy shared amenities: 2 indoor hot tubs, 2 outdoor hot tubs, sauna, and outdoor heated pool.

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.

4.9 out of 5 average rating, 401 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.

4.78 out of 5 average rating, 273 reviews

Michael’s Dream Views in Winter Park, CO condo #15

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.

Popular amenities for Winter Park rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A modern two-story retreat is displayed, featuring a covered patio with multiple large windows. Stone accents complement the sleek exterior. A private hot tub is visible on the lower level, with ample outdoor seating areas and views of the surrounding landscape.

5 out of 5 average rating, 35 reviews

Modern Mtn Home @ Granby Ranch -Hot Tub, Mesh Wifi

5 out of 5 average rating, 5 reviews

Private Hot Tub! Stunning Luxury Home, Ski-In/Out

5 out of 5 average rating, 5 reviews

A modern living area is shown featuring a comfortable sectional sofa adorned with a cozy throw. A sleek gas fireplace is positioned beneath a flat screen TV. Large windows frame expansive mountain views, while a dining area with stylish chairs and a round table is visible.

Home in Winter Park

Chill 301 | Pool + Hot Tub

A modern custom home features a mix of stone and wood exteriors, framed by a gently sloping driveway. The design highlights large windows and slanted roofs, with solar panels visible on the roof. Surrounding natural landscaping adds to the mountain setting.

5 out of 5 average rating, 38 reviews

Colorado's Coolest Ski In/Out Home

4.97 out of 5 average rating, 29 reviews

Home in Fraser

Mountain-view cabin w/ hot tub & deck

A modern mountain home is presented with a combination of stone and wooden elements, showcasing large windows and a spacious driveway. Snow blankets the surrounding landscape, and the entrance features a covered porch that leads into the inviting interiors.

4.91 out of 5 average rating, 34 reviews

Views, Ski, Golf! 6 BDR, 13 Beds, Hot Tub!

5 out of 5 average rating, 17 reviews

A modern mountain home is presented under clear blue skies, with a snow-covered roof and driveway leading to a spacious 2-car garage. The backdrop features the majestic slopes of Winter Park Resort, blanketed in fresh snow, surrounded by evergreen trees glistening in winter light.

Home in Winter Park

Winterfell at Winter Park Resort

4.85 out of 5 average rating, 62 reviews

Two chairs are positioned on a patio, facing a scenic view of expansive meadows and distant mountains. The sky displays soft pastel colors as the sun sets, creating a serene backdrop for relaxation.

Home in Fraser

Alpine Vista Escape

Apartment rentals with a pool

Superhost

The living area features a comfortable seating arrangement with wooden chairs and a coffee table. A television is mounted above a fireplace, while a clock and books are displayed on a shelf. Large sliding glass doors provide access to outdoor views.

4.8 out of 5 average rating, 215 reviews

Great View, pool & hot tub, 1 bed & loft sleeps 6

A spacious living area features a modern sectional sofa and a dark stone fireplace, creating a cozy focal point. A large flat-screen TV is mounted on the wall above the fireplace. Light filters in through the high ceilings, enhancing the open layout.

4.86 out of 5 average rating, 233 reviews

Beautiful Condo with Hot Tub on Ski Bus Route

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.

4.85 out of 5 average rating, 200 reviews

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

A modern kitchen setup features a granite countertop with bar seating for four. Stainless steel appliances, including a refrigerator and oven, complement the tile backsplash. A coffee maker is visible, along with pantry items organized on shelves.

4.91 out of 5 average rating, 313 reviews

FREE WP ski bus - King bed - pool & hot tubs @ rec

A living area is showcased with a comfortable gray sofa and a warm electric fireplace. A large television is mounted on the stone wall. Natural light illuminates the space through windows, complemented by colorful wall accents and a cozy rug underneath.

4.88 out of 5 average rating, 305 reviews

Walk to Downtown | Hot Tub | Near River | Private

A spacious bedroom is furnished with a wooden king bed, layered with a white comforter and a brown throw. Two bedside tables with lamps flank the bed. A colorful autumn-themed artwork adorns the wall above, complementing the warm tones of the decor.

4.95 out of 5 average rating, 122 reviews

Mountain Delight Near Winter Park

A dining area showcases a table set for four, complemented by green placemats and glassware. A flat-screen TV is mounted on a wood-paneled wall, while a stone fireplace adds warmth to the space. A nature-themed artwork enhances the atmosphere.

4.88 out of 5 average rating, 552 reviews

Granby Mountain Retreat

A spacious private hot tub is positioned against a vibrant mural featuring a moose, complemented by geometric mountain patterns. The space is designed with wood paneling and provides an inviting atmosphere for relaxation.

4.81 out of 5 average rating, 325 reviews

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

Other holiday rentals with a pool

A spacious living area features a large brown leather sectional sofa and a wooden coffee table, with a gas fireplace central to the room. A flat-screen TV is mounted above the fireplace, while large sliding glass doors offer access to a private balcony. Natural light fills the space.

4.89 out of 5 average rating, 28 reviews

Trailhead 232 pool, hot tub, clubhouse

A spacious studio is furnished with a large bed and two sofas, one featuring decorative pillows. Antique skis hang on the walls, while a small coffee table occupies the center. Natural light is filtered through the window, enhancing the room's inviting ambiance.

4.85 out of 5 average rating, 99 reviews

Cozy Mountain Studio Downtown Winter Park CO.

5 out of 5 average rating, 18 reviews

A cozy living area features a large stone fireplace as the focal point, with a comfortable sofa and armchair arrangement. A wooden coffee table sits centrally, and a 65" TV is mounted on the wall opposite, while natural light enters through a skylight and sliding glass doors.

Flat in Winter Park

Cozy mtn getaway! 2 blocks from Main Street

The exterior entrance of the condo features a covered porch with a wooden sign displaying the property name. Steps lead up to the door, surrounded by lush trees and vibrant autumn foliage, reflecting the natural beauty of the area.

4.94 out of 5 average rating, 47 reviews

Hi Country Hideaway

5 out of 5 average rating, 30 reviews

A living area features a comfortable dark sofa paired with a vibrant yellow chair. A coffee table sits in front, with a rug underfoot. Natural light enters through large windows, and a door leads to the outside. Decorative artwork adorns the walls.

Flat in Winter Park

1BR Condo in Winter Park, CO

4.89 out of 5 average rating, 18 reviews

A welcoming living area features a comfortable sofa and armchair, arranged around a wooden coffee table. Large windows provide natural light and showcase the surrounding mountains, while a wooden entertainment center holds a television.

Flat in Winter Park

Mini Moose Lodge

An inviting studio space features warm wooden walls and modern furnishings. A fully equipped kitchen is complemented by a dining bar with three stools. An electric fireplace adds ambiance, while a round coffee table sits comfortably in the living area, perfect for relaxation.

4.92 out of 5 average rating, 38 reviews

Studio condo in the heart of Winter Park

A skier navigates through untouched snow on a mountain slope, surrounded by tall evergreen trees blanketed in fresh snow. A subtle hint of sunlight peeks through cloudy skies, creating a serene winter atmosphere.