Vacation rentals with a pool in Winter Park

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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

Condo in Granby

4.94 out of 5 average rating, 166 reviews

Modern Condo in the heart of Grand County

Stay in our beautiful and newly remodeled studio condo in the heart of Grand County, close to all this area has to offer. Located within the Inn at Silvercreek, which backs up to Granby Ranch, our condo offers a modern, yet cozy getaway complete with a fireplace, first floor patio with a beautiful view of Granby Ranch and condominium-style lodging full of amenities. Minutes from skiing, hiking and boating, our condo is the perfect spot for year round adventures in Colorado's beautiful mountains.

Sep 28 – Oct 5

G$23,238 GYD per night

Guest favorite

Condo in Winter Park

4.86 out of 5 average rating, 177 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 fifteen 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.

Oct 20 – 27

G$22,681 GYD per night

Guest favorite

Condo in Granby

4.93 out of 5 average rating, 178 reviews

Pine in the Sky Condo, Cozy & Contemporary + Views

Our renovated condo is located in Granby, CO—just a 10-minute drive to Granby Lake for premium fishing, boating, and paddleboarding, a 25-minute drive to historic Grand Lake and nearby Rocky Mountain National Park, where wildlife and outdoor recreation abound, and a 15-minute drive from Winter Park and the town of Fraser. Enjoy a smaller ski hill nearby, located at Granby Ranch, and the Fraser-Granby Trail is steps away (open seasonally). Includes WiFi, a smart TV, snacks, and a walk-in shower.

Jul 23 – 30

G$23,997 GYD per night

Guest favorite

Condo in Winter Park

4.93 out of 5 average rating, 123 reviews

Peaceful place on river with great views

Amazing location in Winterpark; secluded by trees,mountains, river and pond in front of building with a peaceful wilderness surrounding. Leave your car and walk to restaurants, shops, market and activities. Next to Great trails for MTBiking, hiking, walking or snowshoe and cross country in the winter. This place has it all for easy convenience. Enjoy the new Recreational center with indoor pool, hot tubs, showers, game/ kids room, exercise room and laundry facilities. Non-Smoking/Pet condo

Jan 15 – 22

G$26,943 GYD per night

Superhost

Condo in Winter Park

4.81 out of 5 average rating, 135 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.

Sep 7 – 14

G$26,176 GYD per night

Superhost

Condo in Winter Park

4.88 out of 5 average rating, 138 reviews

Ski-In Ski-Out Studio with Desirable Amenities

This updated studio is situated in one of the best locations at Iron Horse Condominiums. A cozy unit close to amenities, yet in a private location; just walk out the sliding glass door to deck just steps from hot tubs and pool. The studio has a full kitchen, queen Murphy Bed with a new memory foam mattress that folds up for extra space, a 49-inch high definition smart TV with Netflix, Xfinity on demand, and HBO. Enjoy your favorite shows and sports after a day out on the mountain!

Nov 17 – 24

G$28,731 GYD per night

Guest favorite

Condo in Winter Park

4.87 out of 5 average rating, 323 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 fire, relax, and unwind after a full day of outdoor activities.

Oct 11 – 18

G$24,940 GYD per night

Guest favorite

Condo in Fraser

4.9 out of 5 average rating, 121 reviews

Remodeled Condo w/ Hot Tub, Pool & Prime Location

Enjoy all the year round adventures Winter Park has to offer in our quaint condo. Just steps outside your front door is access to an outdoor, year-round heated pool and 2 oversized hot tubs. This 1 bed, 1 bath home is perfect for couples or families, and comes with 2 beds, 1 fold out couch, and a fully equipped kitchen. On the free bus to town and the ski resort and less than a 5 minute drive to restaurants, bars, grocery stores, and countless outdoor activities!

Oct 18 – 25

G$22,908 GYD per night

Superhost

Condo in Winter Park

4.78 out of 5 average rating, 238 reviews

Michael’s Dream Views in Winter Park, CO condo #15

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.

Sep 22 – 29

G$22,769 GYD per night

Guest favorite

Condo in Winter Park

4.88 out of 5 average rating, 212 reviews

Winter Park Studio: Resort Access, Mountain Charm

Experience elevated comfort at our upgraded studio condo within Snowblaze Resort, just minutes away from downtown Winter Park and the ski resort. Accommodating 2 to 4 guests, this retreat offers access to community swimming pools and relaxing hot tubs. Enjoy the convenience of covered on-site parking. Whether you're a skier or an adventure finder our condo serves as the perfect base. Secure your spot now for an unforgettable Winter Park adventure!

Aug 18 – 25

G$24,116 GYD per night

Guest favorite

Condo in Granby

4.85 out of 5 average rating, 117 reviews

Studio~Ski Winter Park. Near RMNP w/ Pool/Hot Tub

This 2nd floor studio is located at the Inn at Silvercreek in Granby Ranch. It is 495 sq ft. Inside the studio has been updated and is stylish and cozy. The resort offers many amenities including pool, hot tubs, an arcade, a gym and even a barber shop. The location is about 5 min from the Granby Ski area, 20 min to Grand Lake and 30 min to either RMNP or Winter Park. There is a free “Lift” shuttle to Winter Park during the ski season.

May 2 – 9

G$14,324 GYD per night

Guest favorite

Condo in Winter Park

5.0 out of 5 average rating, 304 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.

Oct 2 – 9

G$32,195 GYD per night