Holiday 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.

0 of 0 items showing

1 of 3 pages

Guest favourite

Apartment in Winter Park

4.82 out of 5 average rating, 109 reviews

Cozy Condo on the Fraser River

Bright airy western sunset view with no obstructions looking down on Fraser river 25' in front of building. Walking distance to all of Winter Park. One year old new Rec Center with pool, hot tubs, pool table, Computer, guitar, great locker rooms with showers. Free town bus comes by hourly and pick up is right at our building. Car not really needed once your here. Winter Park is great Skiing with all the summertime activities as well. Sorry we are not pet friendly. We just installed a new stove.

Guest favourite

Condo in Fraser

4.89 out of 5 average rating, 102 reviews

Mountain Modern Cozyville

Remodeled with a high end modern flair for comfort and a classic mountain style A mountain-modern, warm, and cozy space that's conveniently located in a quiet mountain-view neighborhood with FREE recreation-center benefits right across the street and a FREE local bus system right out the front door to all local attractions. Safeway, coffee shops, ski/ride/hike stores less than 1-mile away. It really doesn't get any better than this! We will look forward to your feedback and adventure stories.

Guest favourite

Condo in Winter Park

4.96 out of 5 average rating, 143 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 favourite

Condo in Winter Park

4.93 out of 5 average rating, 125 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 favourite

Condo in Winter Park

4.87 out of 5 average rating, 220 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.

Guest favourite

Condo in Winter Park

4.97 out of 5 average rating, 144 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.

Top Guest favourite

Home in Winter Park

4.99 out of 5 average rating, 132 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 favourite

Condo in Granby

4.89 out of 5 average rating, 360 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 favourite

Condo in Winter Park

4.88 out of 5 average rating, 127 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.

Top Guest favourite

Condo in Winter Park

4.99 out of 5 average rating, 379 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.

Guest favourite

Condo in Granby

4.93 out of 5 average rating, 191 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.

Guest favourite

Condo in Winter Park

4.88 out of 5 average rating, 288 reviews

Walk to Downtown | Hot Tub | Near River | Private

Recently updated and located in a secluded setting with Fraser River on property, yet is walkable to all that downtown Winter Park has to offer! You will have a queen-size bed, new 2024 Article sofa sleeper, fully stocked kitchen, luxury bathroom, multiple hot tubs, patio & grassy front yard Walk to ski shuttle stop, hiking/biking trails, fishing, restaurants, grocery, bars, breweries & nightlife.