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Vacation rentals with a pool in Winter Park

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Winter Park

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite
The living area features a comfortable couch and armchair, accompanied by a wooden coffee table on a geometric-patterned rug. A 50-inch TV is visible, along with a fully equipped kitchen area at the back, highlighted by modern appliances and a dining table set for four.
Condo in Winter Park
4.89 out of 5 average rating, 268 reviews

Ground floor 2 bedroom, at Hi Country Winter Park

Recently remodeled 2-bedroom GROUND floor condo is located on the Fraser River, one block away from the main strip of WP. The Hi Country complex features a newly remodeled clubhouse with indoor & outdoor hot tubs, large pool, fitness center, pool table, kids room, and an outdoor playground. In the winter, the free shuttle is located 45 steps behind our building and will whisk you to the ski area twice an hour. A 5-15 min walk to shops, restaurants, bars, movie theater, and the town park.

Superhost
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.
Condo in Winter Park
4.91 out of 5 average rating, 162 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).

Guest favorite
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.
Condo in Winter Park
4.94 out of 5 average rating, 155 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

Guest favorite
Apartment in Winter Park
4.93 out of 5 average rating, 128 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.

Guest favorite
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.
Condo in Winter Park
4.88 out of 5 average rating, 249 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.

Top guest favorite
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.
Condo in Winter Park
4.95 out of 5 average rating, 154 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.

Guest favorite
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.
Condo in Winter Park
4.95 out of 5 average rating, 114 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

Top guest favorite
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.
Home in Winter Park
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.

Guest favorite
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.
Condo in Winter Park
4.87 out of 5 average rating, 106 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!

Guest favorite
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
4.89 out of 5 average rating, 158 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.

Superhost
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.
Condo in Granby
4.88 out of 5 average rating, 434 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.

Guest favorite
An aerial view showcases the condominium complex nestled alongside a flowing river, surrounded by lush greenery. The nearby trees enhance the natural setting, while the buildings feature a contemporary design with flat roofs and balconies overlooking the scenic landscape.
Condo in Winter Park
4.81 out of 5 average rating, 329 reviews

Michael’s Dream Condo #16, Winter Park

Located in Downtown WP, Condo 16, 3rd floor, awesome views, High Country Haus Condominiums. Lic#005206. Check out WP resort for exciting new activities. World class skiing, cross country, snowmobile, bike, hike, fish, restaurants, shops, Hideway Park (sledding hill, WALK TO Fireside Grocery Market, Great WiFi, Grand Park Rec Center. HCH Condos Rec center has pool/jacuzzi’s, billiards, gym. WP RESORTS FREE BUS pick up is across our parking lot.

Popular amenities for Winter Park rentals with a pool

When is the best time to visit Winter Park?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$44,725 GYDG$44,934 GYDG$46,396 GYDG$27,169 GYDG$28,841 GYDG$28,632 GYDG$34,275 GYDG$33,230 GYDG$34,902 GYDG$38,037 GYDG$35,320 GYDG$47,441 GYD
Avg. temp-7°C-7°C-3°C-1°C4°C9°C13°C12°C8°C2°C-3°C-7°C

Quick stats about vacation rentals with a pool in Winter Park

  • Total vacation rentals

    Explore 580 vacation rentals in Winter Park

  • Nightly prices starting at

    Winter Park vacation rentals start at G$14,630 GYD per night before taxes and fees

  • Verified guest reviews

    Over 17,660 verified reviews to help you choose

  • Family-friendly vacation rentals

    420 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    380 properties have a dedicated workspace

  • Wi-Fi availability

    570 of Winter Park vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winter Park rentals

  • 4.8 Average rating

    Winter Park stays are highly rated by guests—averaging 4.8 out of 5!

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