
Vacation rentals with a pool in Winter Park
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Winter Park

Total vacation rentals
Explore 470 vacation rentals in Winter Park

Nightly prices starting at
Winter Park vacation rentals start at ﺩ.ﺇ220 per night before taxes and fees

Verified guest reviews
Over 16,730 verified reviews to help you choose

Family-friendly vacation rentals
310 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
270 properties have a dedicated workspace

Wi-Fi availability
470 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!
Top-rated rentals with a pool in Winter Park
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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.

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).

WP Mountain Retreat • 3BR/2BA • 3 Hot Tubs & Pool
Modern rustic condo nestled in the heart of Winter Park, CO. Completely remodeled, this charming retreat combines contemporary comfort with mountain elegance. The condo sleeps 9 comfortably with 3 cozy bedrooms, 2 full bathrooms, a fully-equipped kitchen with stainless steel appliances, and a warm living room area, perfect for relaxing after a day of mountain adventures. Enjoy easy access to local shops, dining, Lyft bus stop, and the resort. Ideal for families seeking a serene mountain getaway

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.

Cozy Condo - 20 miles to RMNP w/ Hot Tub & Firepit
Freshly remodeled in July 2025, Sundog Condo is your cozy ski-in/ski-out retreat at Granby Ranch – just 20 mins to Rocky Mountain National Park, Grand Lake & Winter Park. Enjoy a king bed with Brooklinen linens, fully stocked kitchen (Nespresso, quality cookware), gas fireplace, Roku TV, and patio with firepit. Year-round hot tub steps away; pool & gym access available. Walk to ski lifts; trails, golf, fishing, biking, hiking & skiing/Nordic trails right outside your door - adventure awaits!

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.

Charming 3BR Riverfront Cabin - Pet Friendly
Set along the Fraser River and backdropped by the majestic Rocky Mountains, this scenic spot is the Granby getaway for your small group! Come for the stunning alpine scenery and stick around for the abundant activities Grand County has in store. This charming mountain cabin is designed with families in mind, featuring a fully equipped kitchen and thoughtful kid-friendly touches. After a day of outdoor fun, unwind in comfort and enjoy the cozy atmosphere of your home away from home.

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.

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!

Peaceful Mountain Retreat & Clubhouse Access
Your mountain get away close to conveniences and activities with access to shared club hot tub. Located on a quiet street. 1/2 of a duplex on a 3/4 acre lot. Heated garage to keep you warm. A spacious entryway for gear, and parking for three cars. All beds, bedding and couches are new. Crib and high chair available. Large deck. 1.3 miles to Safeway 1.5 miles to restaurants and breweries in Fraser 3.5 miles to town of Winter Park 6 miles to Winter Park Resort Permit STR21-00011

Cozy Cabin on the Fraser River
Cozy & comfortable cabin located on the Fraser River. You can hear the peaceful river from the Master Bedroom or Living Room. The trout filled Frazer river is 50 feet away! You are twenty minutes from Winter Park or Grand Lake and ten minutes to Hot Sulfur Springs. Granby has a large grocery store a mile down the road and several nice restaurants and local shops. Granby Ranch has a fun ski resort in town to ski, board or tube. Short Term Rental Permit #006388

Cabin on the River- Pool, fly fishing & more
Amazing family-friendly cabin on the Fraser River and in the heart of Granby, CO. Ten minutes to the lodge at Granby Ranch or 25 minutes from Winter Park! Close to Rocky Mountain National Park, Sulphur Hot Springs, and the YMCA of the Rockies. River access and ponds on the property for fishing! This cabin is stocked with all you need (and more!). We host another cabin across the street. Message me about booking both for a larger group!
Popular amenities for Winter Park rentals with a pool
House rentals with a pool

Luxury Home with Stunning Views - Ski In/Ski Out!

Luxury Mountain Retreat with Hot Tub + Views!

Views, Ski, Golf! 6 BDR, 13 Beds, Hot Tub!

Winterfell at Winter Park Resort

Family Retreat | Pool + Hot Tubs Near Winter Park

Luxury 3BR Winter Park | Hot Tub | Ski Shuttle

Alpine Vista Escape

Mountain Retreat with VIEW!
Condo rentals with a pool

Grey Fox ~2 bed/2 BA Ski in/out Granby Ranch, RMNP

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

Cozy 1 bedroom Granby Ranch condo

FREE WP ski bus - King bed - pool & hot tubs @ rec

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

Mountain Studio | Pool & Hot Tubs + Pet Friendly

Cozy mountain retreat in downtown Winter Park

Granby Mountain Retreat
Other vacation rentals with a pool

Cozy & Close to Winter Park - Hot Tub & Pool

Ski in Ski out, One Bedroom Condo with Jacuzzi Tub

1BR Condo in Winter Park, CO

The Coop: Ski In/Ski Out Studio - Winter Park

Riverside Cabin • Hot Tub, Fire Pit, Pool, Fishing

Mini Moose Lodge

Mtn condo - hot tub, bus line, stocked kitchen

Panoramic Mountain & Fraser River Views
When is the best time to visit Winter Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ786 | ﺩ.ﺇ790 | ﺩ.ﺇ815 | ﺩ.ﺇ477 | ﺩ.ﺇ507 | ﺩ.ﺇ503 | ﺩ.ﺇ602 | ﺩ.ﺇ584 | ﺩ.ﺇ613 | ﺩ.ﺇ668 | ﺩ.ﺇ621 | ﺩ.ﺇ834 |
| Avg. temp | -7°C | -7°C | -3°C | -1°C | 4°C | 9°C | 13°C | 12°C | 8°C | 2°C | -3°C | -7°C |
Destinations to explore
- Durango Vacation rentals
- Denver Vacation rentals
- Breckenridge Vacation rentals
- Colorado Springs Vacation rentals
- Northern New Mexico Vacation rentals
- Aspen Vacation rentals
- Santa Fe Vacation rentals
- Vail Vacation rentals
- Steamboat Springs Vacation rentals
- Estes Park Vacation rentals
- Boulder Vacation rentals
- Moab Vacation rentals
- Rentals with lake access Winter Park
- Apartment rentals Winter Park
- Rentals with an accessible height toilet Winter Park
- House rentals Winter Park
- Family-friendly rentals Winter Park
- Cabin rentals Winter Park
- Rentals with a washer and dryer Winter Park
- Rentals with a fire pit Winter Park
- Rentals with a kayak Winter Park
- Rentals with a sauna Winter Park
- Rentals with an EV charger Winter Park
- Ski-in/ski-out rentals Winter Park
- Townhouse rentals Winter Park
- Fitness-friendly rentals Winter Park
- Chalet rentals Winter Park
- Rentals with a patio Winter Park
- Condo rentals Winter Park
- Rentals with a hot tub Winter Park
- Pet-friendly rentals Winter Park
- Rentals with outdoor seating Winter Park
- Rentals with a fireplace Winter Park
- Rentals with pools Grand County
- Rentals with pools Colorado
- Rentals with pools United States
- Breckenridge Ski Resort
- Rocky Mountain National Park
- Red Rocks Amphitheatre
- Beaver Creek Resort
- Coors Field
- Vail Ski Resort
- Center Village Resort Copper Mountain
- Winter Park Resort
- Arapahoe Basin Ski Area
- Colorado Convention Center
- Keystone Resort
- Ball Arena
- Empower Field at Mile High
- City Park
- Granby Ranch
- Loveland Ski Area
- Ski Cooper
- Fillmore Auditorium
- Pearl Street Mall
- Denver Zoo
- Elitch Gardens
- Denver Botanic Gardens
- Water World
- Golden Gate Canyon State Park




