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.

4.92 out of 5 average rating, 169 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).

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, 325 reviews

View • Fireplace • Hot Tub • Sauna • Pool

Welcome to our favorite place in the mountains We've been sharing our family getaway with guests for years; there's nothing we love more than hearing that someone watched the sunrise with a cup of coffee on the deck, came back from skiing to relax by the fireplace, or spent the evening laughing around the table together We hope you'll feel right at home here And yes...we're dog people🐾 We know vacations are better when the whole family comes along, so well-behaved dogs are warmly welcomed

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.

4.88 out of 5 average rating, 112 reviews

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

Modern rustic condo nestled in the heart of Winter Park, CO. Completely remodeled, this charming retreat combines contemporary comfort with mountain elegance. The condo sleeps 9 comfortably with 3 cozy bedrooms, 2 full bathrooms, a fully-equipped kitchen with stainless steel appliances, and a warm living room area, perfect for relaxing after a day of mountain adventures. Enjoy easy access to local shops, dining, Lyft bus stop, and the resort. Ideal for families seeking a serene mountain getaway

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, 157 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, 130 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, 254 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.

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, 151 reviews

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

Well furnished 2 bedroom, 2 bath unit at Silverado II, sleeps 6 comfortably with the sleeper sofa in the living room. Enjoy the indoor pool, jacuzzi, sauna, game room, and underground parking on site. Dedicated free wifi available in our unit. The ski area is a free shuttle ride away and town is just a short walk down the mountain. In winter, enjoy world class alpine skiing, cross-country skiing, tubing and ice skating. In summer, experience mountain biking, alpine slide and horseback riding.

4.99 out of 5 average rating, 150 reviews

Pool Access & Mtn View! Luxe WP Cabin, Near Trails

Rendezvous Neighborhood | 1 Mi to Dtwn Bites & Brews | Walk to Fraser River Adventure begins right out your door at this Winter Park vacation rental, where alpine trails and fresh air set the stage for an unforgettable stay. Hike and bike through scenic terrain, or take advantage of Club MeadowRidge amenities just a short drive away. Then return to unwind in a beautiful cabin thoughtfully designed with custom furniture, modern amenities, and epic views. This is mountain living at its best!

The kitchen features rich wooden cabinets and granite countertops. An under-mount sink is positioned at the island, with a view of the stainless-steel stove and microwave. Stone accents add texture to the space, while shelves display decorative items and dishware.

4.95 out of 5 average rating, 117 reviews

Walk to town! Indoor pool, sauna, hot tubs.

Enjoy this spacious (1000sqft) 2 bedroom/ 2 bath. Beautifully updated kitchen and baths with granite counter tops and rustic reclaimed barnwood. 1-2 block stroll to nearly 2 dozen restaurants and bars. Heated indoor pool, workout room, hot tubs and sauna in the clubhouse. Free shuttle bus to ski resort. Equipped with all kitchen amenities you might need. 1 Queen and 2 twins, covered parking, living room, dining room, no air conditioning. 4p check in/10a check WP STR Registration #4481

A serene outdoor space features smooth stones lining the banks of a gentle stream. Two wooden Adirondack chairs are positioned on the grass, offering views of the water. Lush greenery and trees frame the scene, contributing to a peaceful natural setting.

4.89 out of 5 average rating, 392 reviews

Riverfront Condo☆1st Floor☆Ski Bus☆Pool & Hot Tub

Recently remodeled 1st floor condo with views and sounds of Fraser River. Walking distance to downtown Winter Park grocery store, coffee shop, restaurants, breweries, retail stores, bars, movie theater, and bowling alley. Community amenities include an indoor pool, hot tubs, workout room, lounge with pool table, laundry facilities, and outdoor playground. Free bus to resort nearby. This riverfront condo is perfect for relaxing and unwinding after a full day of outdoor activities.

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.

4.83 out of 5 average rating, 100 reviews

Studio Downtown Winter Park

Pet-friendly. Do NOT book if you have pet allergies. On the bus route to the resort and within a 3-minute walk to Cooper Creek shopping and restaurants, Hideaway Park and the Visitor's Center. Our well-appointed studio sleeps 4 comfortably and has amazing amenities including 2 hot tubs, a heated lap pool, an outdoor fire pit. There is a complimentary parking space in the covered garage, along with a secure ski locker to store your gear at the end of a long day. STR License #021860

Superhost

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, 163 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.

Popular amenities for Winter Park rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 45 reviews

Home in Granby

Luxury Mountain Retreat with Hot Tub + Views!

4.91 out of 5 average rating, 11 reviews

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

4.92 out of 5 average rating, 13 reviews

A newly constructed townhome features a blend of stone and siding exteriors. A covered balcony extends from the second floor, and snow-covered ground reflects the nearby mountainous landscape under a clear blue sky.

Home in Fraser

Amazing new Luxury corner townhome!

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, 22 reviews

Winterfell at Winter Park Resort

5 out of 5 average rating, 97 reviews

Luxury 3BR Winter Park | Hot Tub | Ski Shuttle

5 out of 5 average rating, 5 reviews

Home in Granby

Family Ski Lodge | Sleeps 16 · Epic Views · Arcade

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, 44 reviews

The Evangeline Haus *Dog Friendly

Apartment rentals with a pool

4.92 out of 5 average rating, 154 reviews

The exterior of the Grey Fox Condo features a charming wooden design with a welcoming entrance. Decorative flower pots and a well-maintained pathway invite guests inside. Two chairs are positioned on the patio, offering a spot to relax and take in the surroundings.

Apartment in Granby

Grey Fox ~2 bed/2 BA Ski in/out Granby Ranch, RMNP

A panoramic view showcases the majestic mountains, framed by a landscape of rolling hills and dotted with trees. The seasonal colors reveal golden foliage alongside patches of green, while a serene sky provides a dramatic backdrop with soft, cloud-covered tones.

4.9 out of 5 average rating, 151 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, 320 reviews

On Fraser River - King bed - pool & hot tubs @ rec

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, 155 reviews

Walk to Town, Front Door Ski Shuttle Pick-up!

4.98 out of 5 average rating, 142 reviews

Apartment in Granby

Cozy Condo - 20 miles to RMNP w/ Hot Tub & Firepit

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, 101 reviews

Mtn condo - hot tub, bus line, stocked kitchen

An indoor swimming pool is surrounded by large windows that allow natural light to fill the space. The clear water reflects the overhead beams and sunlight, while lounge chairs are positioned nearby for relaxation.

4.77 out of 5 average rating, 149 reviews

Perfect ski Condo

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, 136 reviews

Mountain Modern Cozyville

Other holiday rentals with a pool

4.97 out of 5 average rating, 122 reviews

The cabin's exterior is showcased, featuring multiple levels and a spacious deck. A large flat stone patio includes several seating options. Nearby, the landscape is landscaped with gravel and grass, surrounded by a community of similar structures.

Cabin in Granby

Cozy Cabin on the Fraser River

An entrance view reveals a newly updated kitchen and seating area. Light wood cabinetry and modern appliances are visible, while a dining table is set for four. A comfortable gray sectional couch with decorative pillows and a patterned rug adds warmth to the living space.

4.93 out of 5 average rating, 58 reviews

Come to WP-30% off nightly rate for 6 night stay!

5 out of 5 average rating, 47 reviews

Mountain Adventure Condo in Fraser!

5 out of 5 average rating, 12 reviews

Ski in / Ski out at Winter Park - pool & hot tub

5 out of 5 average rating, 20 reviews

Into the Ultimate Summer & Endless Discovery

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, 45 reviews

1BR Condo in Winter Park, CO

5 out of 5 average rating, 12 reviews

The Coop: Trestle Bike Park +Ski In Ski Out Studio

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.