Vacation 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, 147 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

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, 115 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, 151 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 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

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.

4.79 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 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

⸻ Get ready for mountain magic! This third-floor Rustic Cabin Feel getaway at the Inn at Silver Creek sits right at the entrance to Granby Ranch Ski Resort, surrounded by epic Colorado Rocky Mountain views. Nestled between Rocky Mountain National Park and Winter Park, it’s the perfect launchpad for skiing, hiking, biking, or spontaneous scenic drives. After a day of adventure, kick back, get cozy, and soak in the views—this is mountain living done right!

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, 473 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.

A cozy sleeping area features a spacious bed adorned with large check-patterned pillows and a textured accent pillow. A scenic mountain landscape photograph hangs above the bed, reflecting vibrant colors from a sunset over a tranquil lake.

4.94 out of 5 average rating, 221 reviews

Mountain Escape Condo-Pool/Hot Tub RMNP WinterPark

YOUR MOUNTAIN GETAWAY AWAITS! This cozy studio resort condo is newly renovated and has everything you need for your mountain stay. Featuring comfy, queen-sized murphy and sofa beds. Free shuttle to Winter Park. Short drive to Sky Granby Ranch, Rocky Mountain National Park, Grand Lake, fishing, golf, hiking, biking, skiing and other activities. Free Wifi and cable, full kitchen, and single-cup coffee maker.

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!

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

Superhost

5 out of 5 average rating, 3 reviews

Summit Sanctuary @ MeadowRidge

5 out of 5 average rating, 20 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

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*

4.93 out of 5 average rating, 40 reviews

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.

Home in Winter Park

The Evangeline Haus *Dog Friendly

4.94 out of 5 average rating, 114 reviews

Peaceful Mountain Retreat & Clubhouse Access

Condo 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!

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 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

4.87 out of 5 average rating, 89 reviews

Ski-In/Ski-Out Studio-Newly Remodeled

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

4.89 out of 5 average rating, 323 reviews

Cozy Mountain Studio | Pet Friendly + Hot Tubs

4.91 out of 5 average rating, 141 reviews

Tall Timbers of the Rockies

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.

4.87 out of 5 average rating, 104 reviews

Four-Season Winter Park Condo w/ Pool Access!

Other vacation rentals with a pool

4.86 out of 5 average rating, 37 reviews

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.

Apartment in Winter Park

Ski-In/Ski-Out Cozy Studio Retreat

4.94 out of 5 average rating, 17 reviews

Apartment in Granby

Kate’s studio condo in the Rocky Mountains

4.88 out of 5 average rating, 26 reviews

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.

Apartment in Winter Park

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

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.

4.97 out of 5 average rating, 95 reviews

Mtn condo - hot tub, bus line, stocked kitchen

4.91 out of 5 average rating, 45 reviews

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

4.84 out of 5 average rating, 31 reviews

A light-filled living area features a comfortable light gray sofa next to a wooden coffee table. Framed artwork depicting mountains and a sun adorns the wall. The dining area with wooden chairs and a table is visible, providing a cozy space for meals. A well-equipped kitchen is seen in the background.

Apartment in Fraser

Meadowridge Mountain View Condo

Superhost

An outdoor pool is framed by a modern building with multiple floors. Surrounding trees add greenery, while a deck with wooden planks offers lounging options. The pool's clear blue water reflects the sky, and a hot tub is positioned nearby for relaxation.

4.77 out of 5 average rating, 56 reviews

Bike the Trails, Swim at Winter Park Resort

A cozy living area features a stone fireplace, providing warmth and comfort. Large windows reveal scenic mountain views, while soft seating is arranged around a wooden coffee table. Natural light enhances the inviting atmosphere, with curtains framing the view.