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, 141 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

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.

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 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.

4.88 out of 5 average rating, 235 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.

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, 149 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.

4.89 out of 5 average rating, 118 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 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, 385 reviews

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

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. It is a great place to curl up next to the electric fireplace, relax, and unwind after a full day of outdoor activities.

4.9 out of 5 average rating, 145 reviews

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.

Condo in Fraser

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.

A modern studio condo is depicted, featuring a king-sized bed with decorative bedding. A dining table is visible beside the kitchen area with navy cabinetry. Outdoor amenities are shown, including a blue pool surrounded by a wooden deck. A bathroom features dual sinks and a tub.

4.94 out of 5 average rating, 148 reviews

Sexy King bed Retreat, Hot tub Fireplace Pool More

Nestled a mountain resort, this stylish modern studio condo offers a perfect sanctuary for adventure seekers and nature lovers. The sleek and contemporary design provides a cozy yet luxurious escape. During the day, the resort's inviting pool and hot tubs beckon with their warm embrace, after a day of thrilling skiing or mountain adventure. A cozy retreat or a launching pad for alpine adventures, this studio condo promises the perfect blend of modern comfort and outdoor excitement.

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, 102 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.

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, 274 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.

A studio layout is presented, featuring a spacious bed with neutral bedding. A bunk bed is positioned nearby, and a set of skis is mounted on the wall. Two windows allow natural light to fill the space, complemented by a comfortable seating area with armchairs.

4.89 out of 5 average rating, 141 reviews

Studio Condo in the Heart of Winter Park! lic#9602

You're steps from terrific shops, bars, and restaurants. Right outside the condo is the free bus stop to world-class skiing at Winter Park. It is a 3-minute bus ride and frequents every 15 minutes in the winter. Free covered parking is included on a first-come basis. All new kitchen appliances installed in February 2024! Note: There's no A/C in the unit, but there is an evaporative cooler to help keep the unit cool in summer.

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, 5 reviews

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

5 out of 5 average rating, 5 reviews

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.

Home in Winter Park

Chill 301 | Pool + Hot Tub

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

5 out of 5 average rating, 19 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

4.86 out of 5 average rating, 63 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

A cozy living room features a gas fireplace surrounded by stone, with a mounted television above. Two large windows provide natural light, and a leather sofa is accompanied by a round table and a rustic coffee table, complemented by decorative art and soft throw pillows.

4.83 out of 5 average rating, 41 reviews

Mountain Retreat with VIEW!

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.

4.94 out of 5 average rating, 77 reviews

REMI's River Retreat * FISH/SKI/HIKE/MtnLife*

Condo rentals with a pool

A cozy living area features a stone fireplace with a wooden mantle. A flat-screen TV is positioned on an oak cabinet. Light filters through sheer curtains, illuminating a comfortable green armchair and a patterned sofa, accompanied by a wooden coffee table at the center.

4.86 out of 5 average rating, 117 reviews

Beaver Village in Winter Park - 2br/2bath Condo

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, 405 reviews

Cozy Studio~Mtn Views~Salt Water Pool & Hot-Tubs

4.9 out of 5 average rating, 143 reviews

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.

Condo in Fraser

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

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, 205 reviews

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

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, 467 reviews

Cozy 1 bedroom Granby Ranch condo

A living area is showcased with a comfortable gray sofa and a warm electric fireplace. A large television is mounted on the stone wall. Natural light illuminates the space through windows, complemented by colorful wall accents and a cozy rug underneath.

4.88 out of 5 average rating, 308 reviews

Walk to Downtown | Hot Tub | Near River | Private

4.95 out of 5 average rating, 124 reviews

A spacious bedroom is furnished with a wooden king bed, layered with a white comforter and a brown throw. Two bedside tables with lamps flank the bed. A colorful autumn-themed artwork adorns the wall above, complementing the warm tones of the decor.

Condo in Fraser

Mountain Delight Near Winter Park

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

Other vacation rentals with a pool

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.

4.94 out of 5 average rating, 47 reviews

Escape to High Lonesome Haus in Winter Park

4.84 out of 5 average rating, 32 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

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, 47 reviews

Hi Country Hideaway

5 out of 5 average rating, 34 reviews

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.

Apartment in Winter Park

1BR Condo in Winter Park, CO

Superhost

The living room features a large sectional couch equipped with three recliners, providing ample seating space. A wood-burning fireplace, framed by natural stone, serves as a focal point. A flat-screen cable TV is positioned on a stand, with sliding glass doors leading to a balcony.

4.81 out of 5 average rating, 59 reviews

Condo w/ Views, Bus Stop to Resort, Walk Downtown.

Superhost

The living room features two comfortable gray sofas positioned opposite a wooden coffee table. A stone fireplace serves as a focal point beneath a mounted television, while natural light streams through large windows adorned with wooden blinds. Artwork is displayed on the walls.

4.88 out of 5 average rating, 48 reviews

Trailhead 721 Pet Friendly pool hot tub

4.86 out of 5 average rating, 29 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

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.