Holiday 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).

4.93 out of 5 average rating, 126 reviews

Apartment in Winter Park

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, 245 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 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.

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.

4.79 out of 5 average rating, 216 reviews

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

Beautifully remodeled 700 sq ft. condo with 1 bedroom and a loft, that sleeps 6. It has a full kitchen and amazing views of Winter Park, the Continental Divide and Byers Peak. The Clubhouse, which is across the parking lot, has 2 outdoor hot tubs a heated pool, fitness center 2 racquetball courts, a ping pong table, laundry facilities, a conference room that is available for rent, massage, and ski tuning. It is only 2.5 miles from Winter park and right on the free bus route.

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, 113 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!

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.

4.89 out of 5 average rating, 419 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.

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, 280 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.

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, 210 reviews

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

This 2nd floor studio is located at the Inn at Silvercreek in Granby Ranch. It is 495 sq ft. Inside the studio has been updated and is stylish and cozy. The resort offers many amenities including pool, hot tubs, an arcade, a gym and even a barber shop. The location is about 5 min from the Granby Ski area, 20 min to Grand Lake and 30 min to either RMNP or Winter Park. There is a free “Lift” shuttle to Winter Park during the ski season.

A spacious living area features a red seating arrangement with a comfortable sofa and armchair, complemented by light streaming through multiple windows. A kitchen island with a sink is visible, alongside a dining area that includes four chairs. A stone fireplace adds a touch of warmth to the space.

4.85 out of 5 average rating, 474 reviews

Cozy 1 bedroom Granby Ranch condo

Welcome to our Granby Ranch condo! Great access to skiing, hiking, biking, fishing and golf. Guests also have access to the outdoor pool and hot tub at the base of the ski mountain (small fee required)as well as a free tub in our complex. Unit has a master bedroom with a queen sized bed. FYI-I don’t accept any reservation requests without confirming the cleaning arrangements first. Our STR permit # is 006840.

Popular amenities for Winter Park rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

5 out of 5 average rating, 6 reviews

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, 3 reviews

Summit Sanctuary @ MeadowRidge

5 out of 5 average rating, 89 reviews

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

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.

4.87 out of 5 average rating, 68 reviews

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

A two-story townhome is featured, surrounded by snow-covered trees. The entrance showcases a red door and large windows. The driveway is visible, lined with snow, leading to the property amidst a serene winter landscape.

5 out of 5 average rating, 7 reviews

Ermine on the Black Line

Condo rentals with a pool

A cozy living room features a comfortable armchair with an ottoman, a wooden TV stand with decorative elements, and a fireplace set against a textured wood wall. Natural light filters through sheer curtains, highlighting a vintage artwork depicting Winter Park.

4.9 out of 5 average rating, 147 reviews

Cozy 2 bed/2 bath with Hot Tub and Mountain View

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

4.91 out of 5 average rating, 141 reviews

Tall Timbers of the Rockies

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, 555 reviews

Granby Mountain Retreat

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, 126 reviews

Bear's Den

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 cozy bedroom features a spacious bed with a patterned quilt and bright accent pillows. A circular mirror reflects the inviting space. A small dining area with a table and two chairs is adjacent to the kitchenette, enhancing the functional layout of the unit.

4.73 out of 5 average rating, 198 reviews

Classy studio room with a mountain view

A balcony view overlooks a lush green area with a picnic table situated beside a gently flowing river. Towering trees provide shade, while shrubs line the water's edge, creating a serene outdoor space that invites relaxation.

4.91 out of 5 average rating, 140 reviews

Winter Park Riverside Retreat WP ST Reg#005544

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, 42 reviews

Private Sauna, Covered Parking, Hot Tub, Pool!

4.67 out of 5 average rating, 9 reviews

A modern kitchen features wooden cabinets with a contrasting stone island. Stainless steel appliances include a refrigerator, microwave, and oven. Soft lighting highlights the space, while a dining area with four high-backed chairs is visible near a sliding glass door leading to the private balcony.

Apartment in Winter Park

Remodeled Condo: Ski-In/Out, Hot Tub & Pool Access

A welcoming living area features a stone fireplace with a modern fire display. A large sectional couch and coffee table are arranged around a colorful braided rug. A flat-screen TV is mounted on the wall, with a view of nature through the window. A cozy front door leads to the outside.

4.86 out of 5 average rating, 92 reviews

WP Mountain Retreat • 3BR/2BA • 3 Hot Tubs & Pool

A combined living and dining area features a cozy couch, a coffee table, and a mounted television. A brick fireplace adds warmth to the space, complemented by a dining table with seating for four. Light-colored cabinets and countertops enhance the inviting atmosphere.

4.77 out of 5 average rating, 66 reviews

Best location - Incredible access

4.87 out of 5 average rating, 89 reviews

Ski-In/Ski-Out Studio-Newly Remodeled

A cluster of condos is nestled in a snowy landscape, showcasing multiple balconies with wooden railings. The building's exterior is highlighted by its muted tones against a clear blue sky, while snow blankets the ground and clings to the edges of the structure.

5 out of 5 average rating, 38 reviews

Mountain Adventure Condo in Fraser!

An aerial view captures the surrounding mountainous landscape, featuring peaks with snow-capped summits. The expansive green valley is dotted with clusters of buildings, showcasing the compatibility of nature and development. A winding stream is visible in the distance, bordered by trees and open space.

4.86 out of 5 average rating, 37 reviews

Hideaway Park Escape: Shuttle, Pool, and Views

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.