Vacation rentals with a pool in Winter Park

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.

4.93 out of 5 average rating, 159 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, 148 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

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.

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.

4.88 out of 5 average rating, 246 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 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.

4.86 out of 5 average rating, 105 reviews

Cozy Mountain Studio Downtown Winter Park CO.

Come and enjoy our Cozy Mountain Studio in the Snow Blaze building. It is conveniently located in downtown Winter Park Colorado, at US 40 and Vasquez. Our condo is walking distance to shops and restaurants, and is on the free bus route. Pick up for the mountain is in front of our building. It is perfect for the adventure travelers who enjoys the outdoors, but want all of the conveniences of home. Our condo is clean and comfortable. It is an older building, with a great location.

A cozy living area is highlighted by a stone accent wall, featuring a decorative fireplace. Large windows allow natural light to fill the space, providing mountain views. A wooden dining table is set for meals, complemented by comfortable seating options around the room.

4.93 out of 5 average rating, 171 reviews

Peaceful place on river with great views

Amazing location in Winterpark; secluded by trees,mountains, river and pond in front of building with a peaceful wilderness surrounding. Leave your car and walk to restaurants, shops, market and activities. Next to Great trails for MTBiking, hiking, walking or snowshoe and cross country in the winter. This place has it all for easy convenience. Enjoy the new Recreational center with indoor pool, hot tubs, showers, pool table, exercise room and laundry facilities. Non-Smoking/Pet condo

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.

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.

A modern living area features a deep blue sofa adorned with decorative pillows, a glass coffee table, and a cozy textured rug. Natural light filters in through large windows, highlighting a dining area and a spiral staircase that leads to the loft space above.

4.89 out of 5 average rating, 152 reviews

Newly Renovated Mountain Modern Condo

This newly remodeled mountain modern condo features 1 bedroom (king size bed) plus an additional loft area with (queen size bed), making this condo sleep like a two bedroom. The condo features high end furnishings, vaulted ceilings with tons of natural light, fully updated kitchen, views of the mountain range, and spa-style bathroom with dual rainfall shower heads. Steps away from the free bus stop to Winter Park, clubhouse with year round hot tubs, pool, fitness center and laundry.

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.

4.94 out of 5 average rating, 104 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.

An open living area is featured, presenting a comfortable sectional sofa, a coffee table, and a dining area with bar stools. Natural light fills the space through high windows, illuminating the contemporary artwork on the wall. A kitchen is visible in the background, showcasing wood cabinetry.

4.86 out of 5 average rating, 114 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 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!

An aerial view showcases the condominium complex nestled alongside a flowing river, surrounded by lush greenery. The nearby trees enhance the natural setting, while the buildings feature a contemporary design with flat roofs and balconies overlooking the scenic landscape.

4.81 out of 5 average rating, 323 reviews

Michael’s Dream Condo #16, Winter Park

Located in Downtown WP, Condo 16, 3rd floor, awesome views, High Country Haus Condominiums. Lic#005206. Check out WP resort for exciting new activities. World class skiing, cross country, snowmobile, bike, hike, fish, restaurants, shops, Hideway Park (sledding hill, WALK TO Fireside Grocery Market, Great WiFi, Grand Park Rec Center. HCH Condos Rec center has pool/jacuzzi’s, billiards, gym. WP RESORTS FREE BUS pick up is across our parking lot.

4.87 out of 5 average rating, 415 reviews

A cozy seating area features a dark sofa adorned with soft pillows, positioned beside large windows with yellow curtains. A wooden coffee table is set with a plate of fruit and a book, while a warm light fixture hangs overhead, enhancing the inviting ambiance.

Condo in Granby

Cozy Studio~Mtn Views~Salt Water Pool & Hot-Tubs

Must be 21 or over, No Smoking, No Pets Resort was built in 1982, the common areas reflect that. Disinfecting professional housekeeping service. WalkOut Studio (one room) w/patio, Pond, fountain and Mtn views, 495 sq ft, fireplace, full kitchen, full bath, 55 inch FS TV, WiFi, and cable. Resort offering many amenities. Queen Murphy Bed and Queen Sofa Bed. Heated pool, hot tubs, Sauna, fitness center, RB, and tennis courts.

Popular amenities for Winter Park rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 7 reviews

A comfortable living area features a stone fireplace with a fire lit, complemented by a sectional sofa and a wooden coffee table. Large windows provide natural light and views of the outdoors, while a ceiling fan offers additional ventilation.

Home in Fraser

Meadowridge 30-2

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.

5 out of 5 average rating, 6 reviews

Chill 301 | Pool + Hot Tub

5 out of 5 average rating, 4 reviews

Home in Fraser

Summit Sanctuary @ MeadowRidge

5 out of 5 average rating, 90 reviews

Cozy Modern Cabin w/ Hot Tub - Minutes to Ski Area

4.87 out of 5 average rating, 69 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

5 out of 5 average rating, 3 reviews

The open-concept living area features a high, sloped wood-paneled ceiling and large windows that frame the scenic views. A modern kitchen island with bar seating is positioned near the cozy seating arrangement around a stone fireplace, creating a welcoming space for relaxation and gathering.

Home in Tabernash

Chalet Ski Retreat w/Scenic Views/Private hot tub

4.94 out of 5 average rating, 82 reviews

A cozy living area is highlighted by natural wood paneling and a light-colored ceiling. Comfortable seating includes a spacious gray sectional and a textured armchair. Decorative accessories complement a patterned area rug, and the bar-style seating offers a view of the well-equipped kitchen.

Home in Granby

REMI's River Retreat * FISH/SKI/HIKE/MtnLife*

A cozy living area showcases a light grey sectional sofa adorned with decorative pillows. Above the sofa, two framed prints of bears complement the soft tones. A round wooden coffee table and a small bookshelf add functional charm to the space, with sunlight filtering through the window.

4.93 out of 5 average rating, 41 reviews

The Evangeline Haus *Dog Friendly

Condo rentals with a pool

4.88 out of 5 average rating, 130 reviews

Winter Park | Top-Floor | Pool & Hot Tub | Ski Bus

The living room features a modern gas fireplace framed by stone tiles, with a large window offering views of trees outside. Comfortable couches are arranged around a wooden coffee table, while a flat-screen TV is mounted above the fireplace.

5 out of 5 average rating, 43 reviews

Private Sauna, Covered Parking, Hot Tub, Pool!

The studio features a fully equipped kitchen with granite countertops and modern stainless steel appliances. A seating area is arranged with a small dining table and chairs next to large windows, allowing natural light and a view of the outdoor landscape.

4.97 out of 5 average rating, 66 reviews

Remodeled Ski In/Out Condo. 30 Sec Walk To Slope!

A private balcony features a round table surrounded by four wicker chairs, offering expansive views of the Fraser Valley and mountains. Sunlight illuminates the area, and the nearby river reflects the clear sky.

4.98 out of 5 average rating, 311 reviews

Private sauna, amazing view, pool, hot tub!

The exterior of the building showcases a four-story structure with a mix of red and stone finishes. Lush greenery surrounds a stone fire pit and seating area, while mountains are visible in the background under a partly cloudy sky.

4.82 out of 5 average rating, 148 reviews

Winter Park 2bd/2ba (Sleeps 6) - Ideal Location!

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, 315 reviews

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

4.93 out of 5 average rating, 241 reviews

Condo in Granby

Pine in the Sky Condo, Cozy + Close to GR/WP/RMNP

4.91 out of 5 average rating, 141 reviews

Tall Timbers of the Rockies

Other vacation rentals with a pool

A spacious living area features a large sectional sofa adorned with red and neutral pillows. A coffee table sits in front of the sofa, complemented by a dining table set for four. Sunlight filters through a skylight and large windows, revealing snow-covered scenery outside.

4.71 out of 5 average rating, 35 reviews

Ski-In/Ski-Out Winter Park Condo w/ Pool Access!

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.

4.95 out of 5 average rating, 21 reviews

Cozy mtn getaway! 2 blocks from Main Street

5 out of 5 average rating, 11 reviews

Condo in Winter Park Ski and Mountain Views

A cozy studio condo is displayed, featuring a queen Murphy bed in the foreground. Twin bunk beds and a seating area with a sofa are positioned in the background. A large window provides natural light, with a TV mounted above a fireplace.

4.84 out of 5 average rating, 38 reviews

Ski-In/Ski-Out Cozy Studio Retreat

An aerial view showcases a landscape blanketed in snow, with mountains in the background featuring ski trails. Pine trees dot the hillside, and clusters of rustic buildings are nestled within the forest, highlighting the serene mountain setting.

4.88 out of 5 average rating, 26 reviews

Winter Park Ski-In/Out Studio | Hot Tubs + Views

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.

5 out of 5 average rating, 37 reviews

1BR Condo in Winter Park, CO

The kitchen features light wood cabinetry and modern appliances, including a black stove and refrigerator. A large island with granite countertops provides seating with three wooden stools. A welcoming entry area is visible, complemented by a textured rug and a decorative door.

5 out of 5 average rating, 55 reviews

The Rustic Moose

A modern living space is showcased, featuring two dark leather sofas with decorative pillows, a coffee table, and a simple area rug. The kitchen area includes white cabinets, stainless steel appliances, and a small wood island, all illuminated by recessed lighting.