Holiday rentals with a pool in Winter Park

4.9 out of 5 average rating, 109 reviews

Apartment in Fraser

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.

4.95 out of 5 average rating, 152 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).

4.93 out of 5 average rating, 135 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

4.87 out of 5 average rating, 227 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.

4.88 out of 5 average rating, 549 reviews

Granby Mountain Retreat

Hiking, golfing, biking, fishing within 5 minutes! 20 minutes to the West Entry of RMNP, 20 minutes to Hot Sulphur Springs, 20 minutes to Winter Park, 20 minutes to Grand Lake! Out of door mountain biking, minutes to cross country skiing, fishing and golfing! Perfect for a solo traveler looking to relax, a romantic getaway for a couple, a group of friends interested in exploring the surrounding mountains, or a full family, looking to enjoy the onsite amenities and surrounding activities!

Superhost

4.86 out of 5 average rating, 129 reviews

Mountain Loft-Views-Pool-Hot tub-Near RMNP&WP

Experience mountain living in this stunning Vaulted Loft Condo with top-floor mountain views. Boasting a full kitchen, balcony, new smart TV, WiFi, cable, and shared heated pool & hot tubs. With year-round activities, such as skiing, hiking, biking, and fishing nearby, there's something for everyone. Located conveniently near RMNP, Granby Ranch, Winter Park, Snow Mtn Ranch, Grand Lake, and Hot Sulphur Springs. NO PETS, NO SMOKING, with Professional Housekeeping Service for a worry-free stay.

4.94 out of 5 average rating, 233 reviews

Pine in the Sky Condo, Cozy + Close to GR/WP/RMNP

Our renovated condo is located in Granby, CO—just a 10-minute drive to Lake Granby for premium fishing, boating, and paddleboarding, a 20-minute drive to historic Grand Lake and nearby RMNP, where wildlife and outdoor recreation abound, and a 20-minute drive from Winter Park. Enjoy a smaller ski hill nearby, Granby Ranch, and the Fraser-Granby Trail is just steps away (open seasonally). Includes WiFi, a smart TV, snacks, kitchen essentials, a walk-in shower, toys, games, and books for kids.

4.89 out of 5 average rating, 111 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.

4.91 out of 5 average rating, 176 reviews

The Mountainside at Granby Ranch

This is truly mountainside living with trail & ski access right out the door! We remodeled over 4 months & added a 14 ft live edge bar, 100 year old hardwood vanities and many other touches to make the mountainside a memorable Colorado experience. While staying you can enjoy all that Granby Ranch has to offer in every season or access Winter Park or Grand Lake in quick 20 minute drives. A grocery store and gas station are only 5 minutes away and Granby is right around the corner. Enjoy!

4.89 out of 5 average rating, 385 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.

4.89 out of 5 average rating, 136 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.