Holiday Rentals with Pools in Winter Park
List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Bedrooms
Any
Bathrooms
Any
Amenities
Show more
Suitability
Show more
Property type
Show more
Distinctive Features
Show more
Distance from
1 km
332 rentals in Winter Park.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order. Learn more.
❤ WP✦INCREDIBLE RIVER VIEWS✦Private Top Flr✦Hideaway Park✦Nightlife✦Cozy
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check-in
Check-out
One block from all restaurans, shopping and nightlife.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check-in
Check-out
Gorgeous Condo | Private Views from Balcony | Walk To The Best Restaurants
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
Check-in
Check-out
Luxury 3 Bdrm, 3.5 Bath Townhome in Downtown WP
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check-in
Check-out
Beautiful two bedroom condo in Winter Park! Pool, hot tub, free transportation.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check-in
Check-out
Heated Pool! Steps to dining & shops, sledding hill views!
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check-in
Check-out
Family/ Pet Friendly Updated Downtown Winter Park Condo 3BD/2BA
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check-in
Check-out
PET-FRIENDLY | The Coolest & Newest: 4 Bedroom Downtown Condo w/ Views | Sleeps
Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
Check-in
Check-out
Luxury Condo at Standard Pricing. 2 Bed 2 Bath with Divide and River Views!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check-in
Check-out
Beautiful Winter Park Townhouse- Downtown, Great Mtn Views, Private Hot Tub!
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check-in
Check-out
Save time - get the best Winter Park rentals sent straight to your email!
New Luxury Unit: Downtown, On Ski Shuttle, Pool/HotTub, Pets OK, Back to Forest
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check-in
Check-out
Winter Park Ski Condo.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, All pools
More info
Check-in
Check-out
Boutique hotel style in a family-friendly 2-bed condo, free shuttles to Resort
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, All pools
More info
Check-in
Check-out
2BR/2BA **Just Read Our Reviews!** Beautiful Condo & Grt Value!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check-in
Check-out
Fresh & clean platinum-rated condo, W&D, pool, in-town, fast internet, 3 HDTVs.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Check-in
Check-out
FREE Activities Daily, WiFi & Shuttle - Slopeside Luxury Villa #136/Great Ski Vi
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
Check-in
Check-out
FREE Activities Daily, WiFi & Shuttle - Luxury Villa #190 Next To Resort/Hot Tub
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, All pools
More info
Check-in
Check-out
Luxury in Downtown Winter Park CO
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, All pools
More info
Check-in
Check-out
Rated 'Exceptional','The Best Beaver Village Rental',Low Rates
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check-in
Check-out
Ski-in Ski-Out One Bedroom Condo at the Iron Horse
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, All pools
More info
Check-in
Check-out
Winter Park 2 bdrm, Beautifully Updated, Walk2town, Summer Getaway!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check-in
Check-out
Luxurious 2 Masters, 2 Family Rooms, Hot Tub & WiFi
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, All pools
More info
Check-in
Check-out
Penthouse Sport Studio - Ski-In/out - Fireplace - Balcony - Iron Horse Resort
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
Check-in
Check-out
Winter Park Condo on Bus Route, 2 Blocks to Dtwn!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check-in
Check-out
Beautifully Updated Luxury Condo at Affordable Price at Ideal Location!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check-in
Check-out
Enjoy the outdoor beauty Winter Park offers with reduced rates!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check-in
Check-out
NEW! Cozy Ski Condo w/Hot Tubs, 3 Mi to WP Resort!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, All pools
More info
Check-in
Check-out
The Perfect 'Base Camp' for All Your Winter Park Adventures!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check-in
Check-out
FREE Activities Daily & WiFi - Base Village Ski In/Out Luxury Condo #3325/Pool S
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check-in
Check-out
SLEIGH BELZ: Book this super clean, roomy condo for ski season NOW!
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check-in
Check-out
FREE Activities Daily, WiFi & Shuttle - Slopeside Luxury Chalet On River/Hot Tub
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
Check-in
Check-out
Cozy 1-bed, 1-bath condo on the Fraser river in downtown Winter Park, Colorado
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
Check-in
Check-out
A Real Ski-in Ski-Out Unit
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
Check-in
Check-out
Cozy large studio condo.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
Check-in
Check-out
Newly remodeled. Bright and Spacious with Views, Pool, Hot Tub, Wifi.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check-in
Check-out
New! Luxury condo, Pool and Hot Tub, Ski Shuttle, Downtown, Close to All!
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check-in
Check-out
Riverfront Condo In The Heart Of Winter Park
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check-in
Check-out
Cozy, CLEAN Ski-in Ski-Out Top-Floor Studio at Iron Horse
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
Check-in
Check-out
Remodeled, Ground Level, Family Friendly Mountain Haven Flexible cancellation
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
Check-in
Check-out
Ski-in Ski-Out: Iron Horse Resort :DISCOUNT LIFT TICKETS; 2+BR/2BA; King; Quiet
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check-in
Check-out
Creekside 3-br ski condo w/fireplace, scenic views, free shuttle to slopes
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, All pools
More info
Check-in
Check-out
FREE Activities Daily & WiFi - Base Village Ski In/Out Luxury Condo #3129/Pool S
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check-in
Check-out
Luxury 1 Bedroom- 1 Bathroom Condo at Trailhead Lodges- Sleeps up to 6 guests
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, All pools
More info
Check-in
Check-out
Cozy Mountain Escape / Ski In+Out / Family Friendly / Pool & Hot Tub
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check-in
Check-out
FREE Activities Daily & WiFi - Base Village Ski In/Out Luxury Condo #4475/Pool S
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check-in
Check-out
Comfy condo near Winter Park w/ shared pool, hot tub & ski shuttle!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
More info
Check-in
Check-out
Walk to town, walk to free shuttle to Winter Park resort
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps, All pools
More info
Check-in
Check-out
Upscale 3BR In Town with Pool, Walking Distance To Shops/Restaurants/Park
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check-in
Check-out
FREE Activities Daily & WiFi - Mountaintop Luxury Villa/Incredible Views/Hot Tub
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, All pools
More info
Check-in
Check-out
Reduced Feb! Ski-In, Ski-Out Luxury, Corner. Sleeps 6. Hot Tubs, Pool, 55' TV
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
Check-in
Check-out
1234567