Holiday rentals with a pool in Winter Park

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.

4.97 out of 5 average rating, 116 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.

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, 152 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.

A stone fireplace is centered in the room, flanked by a television mounted on the wall. A dining table with two red dishes sits in front of the fireplace, while a photo of a bear adorns the wall above. Warm tones create a cozy setting.

4.9 out of 5 average rating, 128 reviews

Bear's Den

New! Kick back and relax in this beautifully remodeled, ground level studio. Fully equipped kitchen, stone fireplace, queen size bed and pull out sofa. Large covered patio too with mountain views! Ski Granby Ranch or Winter Park, visit Grand Lake, Hot Sulphur Springs, Rocky Mountain National Park and more! Horseback riding, Sleigh rides, Tubing, Snowmobiling, Boating, Kayaking, Paddle boarding, Fishing, Golf, Swimming. It's all here! Check in is at 4:00 pm and check out is at 10:00 am.

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.

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.

4.86 out of 5 average rating, 114 reviews

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.

Apartment in Fraser

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!

4.88 out of 5 average rating, 130 reviews

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

This top-floor 1BR condo is a short, free shuttle ride or 10 min drive to Winter Park Resort. You'll be skiing in no time! Enjoy community amenities like an indoor pool, indoor/outdoor hot tub, playground, laundry facilities, game room, & grill area. Includes ski storage. Sleeps 4 comfortably. Off-season activities are also close - The Fraser River and Rendezvous Trails are just outside the front door. Walking distance to restaurants and bars!

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.

4.87 out of 5 average rating, 415 reviews

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.

The living area features a stone fireplace as its focal point, complemented by a cozy leather sofa and a vintage wooden coffee table. Large windows provide natural light, while a wall-mounted TV sits on a wooden console. A textured area rug adds warmth to the space.

4.98 out of 5 average rating, 406 reviews

Winter Park Studio: On the River~ Walk Downtown!

Fireside Haven is a cozy studio located on a secluded spot RIGHT on the Fraser River, yet is walkable to all that downtown Winter Park has to offer. Dine-out, shop, enjoy coffee at a café, cocktails at happy hour, hike/bike and catch the ski shuttle all within a five-minute walk from your front door! You will have a king-size bed, queen-size sofa sleeper, full kitchen, bathroom, fireplace, private patio & ski closet.

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, 41 reviews

Home in Granby

Luxury Mountain Retreat with Hot Tub + Views!

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

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.

5 out of 5 average rating, 20 reviews

Winterfell at Winter Park Resort

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

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

Apartment rentals with a pool

4.79 out of 5 average rating, 217 reviews

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.

Apartment in Fraser

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

4.86 out of 5 average rating, 237 reviews

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.

Apartment in Fraser

Beautiful Condo with Hot Tub on Ski Bus Route

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

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

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, 53 reviews

Hi Country Hideaway

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, 556 reviews

Granby Mountain Retreat

Lush green pine trees surround a winding road that leads to the exterior of the condominium. The clear blue sky is dotted with clouds, and the scenery captures a tranquil mountain environment typical of the Winter Park area.

4.82 out of 5 average rating, 82 reviews

Ski-in / Ski-out Studio Condo

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!

Other holiday rentals with a pool

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!

A spacious studio is depicted, featuring a comfortable sofa paired with a small round table. Large windows allow natural light to fill the space, while a cozy bed is positioned against a wall. A television is mounted opposite, enhancing the functional layout.

4.84 out of 5 average rating, 91 reviews

Studio Downtown Winter Park

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 spacious living area is presented, featuring a comfortable gray sofa adorned with patterned cushions. A wooden coffee table occupies the center, surrounded by neatly arranged chairs. A stone fireplace serves as a focal point, while large windows allow natural light to illuminate the space.

4.86 out of 5 average rating, 28 reviews

Mountain Escape and Adventure at Winter Park

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

4.91 out of 5 average rating, 45 reviews

Updated Ski-in / Ski/Out Condo at Winter Park

Two colorful blankets are neatly folded and placed on a wooden table, displaying intricate patterns. A modern electric fireplace with glowing embers is visible in the background, providing a cozy ambiance to the space.