Home rentals with a pool near Winter Park Resort

An indoor swimming pool is showcased with crystal-clear water, surrounded by large windows that invite natural light. Lounge chairs are arranged along the edges, and colorful pool toys float on the surface. The ceiling features exposed beams, emphasizing the spaciousness of the area.

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 spacious living area is highlighted by a stone fireplace and a large mounted TV. Comfortable seating includes a plush sofa and an accent chair. A rustic area rug beneath a coffee table and a contemporary dining area are visible, with natural light streaming in from sliding glass doors.

4.99 out of 5 average rating, 132 reviews

The Adventure Loft-modern luxury in Winter Park!

The Adventure Loft is in a premier top-floor location in Trailhead Lodges. It is within walking distance to Hideaway Park, breweries, and bakeries in Winter Park! The free shuttle bus picks up right down the street. The wrap-around deck offers views of the Rocky Mountains and peek-a-boo views of the Rendezvous Music Stage. This modern luxury loft with high vaulted ceilings and a gourmet kitchen awaits you for the perfect mountain getaway! We welcome pets for a $75 fee PER PET. Two pet maximum.

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.

4.87 out of 5 average rating, 230 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.

4.98 out of 5 average rating, 120 reviews

Granby Ranch Ski-In/Out – Hot Tub & Firepit

Freshly remodeled in July 2025, Sundog Condo is your cozy ski-in/ski-out retreat at Granby Ranch – just 20 mins to Rocky Mountain National Park, Grand Lake & Winter Park. Enjoy a king bed with Brooklinen linens, fully stocked kitchen (Nespresso, quality cookware), gas fireplace, Roku TV, and patio with firepit. Year-round hot tub steps away; pool & gym access available. Walk to ski lifts; trails, golf, fishing, biking, hiking & skiing/Nordic trails right outside your door - adventure awaits!

A cozy living area features a black leather sofa and an armchair positioned near a wooden coffee table. A fireplace is framed by decorative tile, while large windows provide natural light. An accent wall displays a piece of art, adding a touch of character to the space.

4.95 out of 5 average rating, 22 reviews

Ski-In/Ski-Out Studio

Step into comfort at this ski-in/ski-out studio at Iron Horse Condominiums in Winter Park. This first-floor condo features patio access to a heated pool, hot tubs, and grill. Perfect for families or couples, the light-filled space has cozy sleeping options, a full kitchen with a crock pot, and resort-style amenities, including a gym and game room. Enjoy garage parking, Wi-Fi, and proximity to trails, Winter Park Village, and the gondola. Relax and recharge after every mountain adventure!

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.

4.86 out of 5 average rating, 101 reviews

Four-Season Winter Park Condo w/ Pool Access!

Seasonal recreation on world-class mountain trails awaits at this Winter Park vacation rental! Located in the Trailhead Lodges community - under a half-mile to the closest ski shuttle - this 2-bedroom, 2-bath condo offers all the at-home comforts in a premier mountain destination. Work remotely with beautiful views while also enjoying easy access to countless year-round outdoor activities for the whole group. You’ll also have access to a community pool, hot tub, clubhouse, and more!

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, 100 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.

4.97 out of 5 average rating, 34 reviews

Slopeside Studio

Ski-in/ski-out studio at Iron Horse Condominiums with direct access to Winter Park Resort via skybridge. Hit the slopes in winter or explore scenic trails and bike paths in summer—all just steps away. Enjoy a fireplace, full kitchen, patio, and access to hot tubs, pool, & gym. Ideal for small families, couples or solo travelers seeking year-round adventure with resort comfort. Minutes from Winter Park Village...ski, walk, or bus to the village easily from the complex!

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.

4.9 out of 5 average rating, 404 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.

An outdoor heated pool is featured alongside two hot tubs, surrounded by a scenic landscape of snow-covered trees and mountains. The area is paved with a spacious deck for relaxation, with clear skies above enhancing the serene atmosphere of the retreat.

4.93 out of 5 average rating, 183 reviews

Ski-in/Ski-out, Luxury amenities +Free parking

Discover the perfect mountain retreat! Enjoy seamless ski-in/ski-out access, a first-floor location, and unwind in the indoor/outdoor heated pool and new hot tubs. Stay fit in our on-site fitness center, park hassle-free, and explore with a free local shuttle at your doorstep. With custom queen and bunk murphy beds, this cozy escape offers comfort and convenience. Your mountain getaway awaits – embrace the charm, relax, and make unforgettable memories!

4.96 out of 5 average rating, 103 reviews

Cozy Condo in Forest + Walk to Town!

Forest Retreat Near Winter Park 🌲 Walk to Main Street + just 10 min to the ski resort (free shuttle from the lot!). Bright + cozy with updated baths, gas fireplace, and balcony views of the forest. Spacious enough for 8 to sleep + hang. Relax after your day at the clubhouse with heated indoor pool + multiple hot tubs. Frisbee golf + trails right outside your door. The perfect mountain getaway! Winter Park License for Short Term Rental #020932

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, 394 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 rentals with a pool near Winter Park Resort

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A modern two-story retreat is displayed, featuring a covered patio with multiple large windows. Stone accents complement the sleek exterior. A private hot tub is visible on the lower level, with ample outdoor seating areas and views of the surrounding landscape.

5 out of 5 average rating, 36 reviews

Modern Mtn Home @ Granby Ranch -Hot Tub, Mesh Wifi

5 out of 5 average rating, 5 reviews

Home in Winter Park

Slopeside Villa 125 I Discounted Attractions

5 out of 5 average rating, 5 reviews

Private Hot Tub! Stunning Luxury Home, Ski-In/Out

A modern custom home features a mix of stone and wood exteriors, framed by a gently sloping driveway. The design highlights large windows and slanted roofs, with solar panels visible on the roof. Surrounding natural landscaping adds to the mountain setting.

5 out of 5 average rating, 38 reviews

Colorado's Coolest Ski In/Out Home

4.97 out of 5 average rating, 29 reviews

Home in Fraser

Mountain retreat w/ hot tub & game room

A modern mountain home is presented with a combination of stone and wooden elements, showcasing large windows and a spacious driveway. Snow blankets the surrounding landscape, and the entrance features a covered porch that leads into the inviting interiors.

4.92 out of 5 average rating, 37 reviews

Views, Ski, Golf! 6 BDR, 13 Beds, Hot Tub!

5 out of 5 average rating, 82 reviews

Home in Winter Park

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

4.85 out of 5 average rating, 62 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

Condo rentals with a pool

Superhost

4.88 out of 5 average rating, 125 reviews

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

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.

4.94 out of 5 average rating, 155 reviews

Hideaway Park! Hot tub,Pool,FitnessCtr&FreePrkg

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, 463 reviews

Cozy 1 bedroom Granby Ranch condo

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, 139 reviews

Cozy mountain retreat in downtown Winter Park

Superhost

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, 273 reviews

Michael’s Dream Condo #15 Winter Park

A cozy living area is highlighted by a stone fireplace and wooden accents. A sectional sofa faces a coffee table adorned with decorative items. A dining table for four is visible, set against the backdrop of a well-equipped kitchen with modern appliances.

4.86 out of 5 average rating, 236 reviews

Sandy and Ryan's Granby Getaway!

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, 552 reviews

Granby Mountain Retreat

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, 148 reviews

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

Other vacation rentals with a 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, 59 reviews

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

A studio kitchen area features wooden cabinetry, stainless steel appliances, and a mosaic backsplash. A comfortable brown couch is positioned in the living space, complemented by a decorative lamp and a coffee table. An orange accent wall adds a vibrant touch to the room.

4.94 out of 5 average rating, 88 reviews

Ski-in/out Condo

A modern living room features a large sectional sofa facing a stone fireplace and mounted TV. Large windows provide views of the snowy trees outside. Two armchairs and a side table complete the seating area, enhancing the cozy ambiance.

4.92 out of 5 average rating, 37 reviews

Chill 303 | Pool + Hot Tub

5 out of 5 average rating, 5 reviews

Condo in Winter Park Ski and Mountain Views

Superhost

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.

4.83 out of 5 average rating, 29 reviews

Ski-In/Ski-Out Cozy Studio Retreat

4.98 out of 5 average rating, 49 reviews

The exterior of the condo is framed by lush greenery, with a warm wooden entrance leading to the front door. Large windows are visible on the upper levels, and a covered porch features a seating area, inviting guests to enjoy the surrounding nature.

Townhouse in Granby

Ski In/Out, Hike, Play, Granby Colorado

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.

4.95 out of 5 average rating, 22 reviews

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

A cozy living area features a large sectional sofa in muted blue, positioned near a gas fireplace. A wooden coffee table rests in front, while a flat-screen TV is mounted above the fireplace. Natural light enters through a window, enhancing the inviting ambiance.