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Winter Park vacation rentals
We found 2,030 vacation rentals — enter your dates for availability
Select from 287 houses, 386 condos, and other vacation rentals to find the perfect place for your stay in Winter Park. Vacation homes offer the best amenities for you and your friends, family, or even pets, like WiFi and cable TV. At the end of the day, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Winter Park
Showing deals for:Sep 4 - Sep 11
Image gallery for Large Upscale Retreat off Vasquez Rd. Sleeps 14

9.09.0 out of 10, Wonderful, (22 reviews)
Wonderful
(22 reviews)
Large Upscale Retreat off Vasquez Rd. Sleeps 14
Winter Park
13% off
Price is $854
$854
$5,976 for 7 nights
$5,976 for 7 nights
All fees included
Image gallery for Luxurious Townhome With 3 En-suites, Gorgeous Views and Private Hot Tub!

9.89.8 out of 10, Exceptional, (79 reviews)
Exceptional
(79 reviews)
Luxurious Townhome With 3 En-suites, Gorgeous Views and Private Hot Tub!
Winter Park
8% off
Price is $299
$299
$2,091 for 7 nights
$2,091 for 7 nights
All fees included
Image gallery for Luxury 4 bedroom Townhome in Lakota, across from resort, with stunning views!

9.89.8 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
Luxury 4 bedroom Townhome in Lakota, across from resort, with stunning views!
Winter Park
8% off
Price is $377
$377
$2,636 for 7 nights
$2,636 for 7 nights
All fees included
Image gallery for Ski-In/Ski-Out Zephyr 2BR - FRONT-ROW Gondola & Base VIEWS! - Walk Everywhere!

9.89.8 out of 10, Exceptional, (49 reviews)
Exceptional
(49 reviews)
Ski-In/Ski-Out Zephyr 2BR - FRONT-ROW Gondola & Base VIEWS! - Walk Everywhere!
Winter Park
6% off
Price is $248
$248
$1,738 for 7 nights
$1,738 for 7 nights
All fees included
Image gallery for Modern/Rustic 2-bedroom Townhouse + Bonus Loft

1010 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
Modern/Rustic 2-bedroom Townhouse + Bonus Loft
Winter Park
8% off
Price is $227
$227
$1,590 for 7 nights
$1,590 for 7 nights
All fees included
Image gallery for Walk to the base! Inside the WP gates! Complete Remodel w/private hot tub

1010 out of 10, Exceptional, (56 reviews)
Exceptional
(56 reviews)
Walk to the base! Inside the WP gates! Complete Remodel w/private hot tub
Winter Park
8% off
Price is $337
$337
$2,357 for 7 nights
$2,357 for 7 nights
All fees included
Image gallery for Spectacular Views! Luxury 3BR/2BA in Base Area Location - Trademark

9.89.8 out of 10, Exceptional, (47 reviews)
Exceptional
(47 reviews)
Spectacular Views! Luxury 3BR/2BA in Base Area Location - Trademark
Winter Park
11% off
Price is $390
$390
$2,732 for 7 nights
$2,732 for 7 nights
All fees included
Image gallery for A cozy non-smoking condo on the Fraser River in downtown Winter Park.

9.89.8 out of 10, Exceptional, (98 reviews)
Exceptional
(98 reviews)
A cozy non-smoking condo on the Fraser River in downtown Winter Park.
Winter Park
8% off
Price is $141
$141
$989 for 7 nights
$989 for 7 nights
All fees included
Image gallery for Modern Luxury Condo 3bed/2bath Ski In/Ski Out - Great for Families

1010 out of 10, Exceptional, (24 reviews)
Exceptional
(24 reviews)
Modern Luxury Condo 3bed/2bath Ski In/Ski Out - Great for Families
Winter Park
9% off
Price is $1,400
$1,400
$9,803 for 7 nights
$9,803 for 7 nights
All fees included
Image gallery for A Winter Park Gem - Reserve this Gorgeous Townhome Early

1010 out of 10, Exceptional, (84 reviews)
Exceptional
(84 reviews)
A Winter Park Gem - Reserve this Gorgeous Townhome Early
Winter Park
11% off
Price is $367
$367
$2,566 for 7 nights
$2,566 for 7 nights
All fees included
Image gallery for Top floor unit on The Corridor! Beautiful alpine views! 5 min. walk to WP Base!

9.89.8 out of 10, Exceptional, (33 reviews)
Exceptional
(33 reviews)
Top floor unit on The Corridor! Beautiful alpine views! 5 min. walk to WP Base!
Winter Park
8% off
Price is $113
$113
$792 for 7 nights
$792 for 7 nights
All fees included
Image gallery for Renovated, steps to restaurants, mountain views, on free bus route

1010 out of 10, Exceptional, (82 reviews)
Exceptional
(82 reviews)
Renovated, steps to restaurants, mountain views, on free bus route
Winter Park
8% off
Price is $249
$249
$1,743 for 7 nights
$1,743 for 7 nights
All fees included
Image gallery for Heart of Downtown - Private Hot Tub, Heated Garage, Fireplace & Washer/Dryer

1010 out of 10, Exceptional, (17 reviews)
Exceptional
(17 reviews)
Heart of Downtown - Private Hot Tub, Heated Garage, Fireplace & Washer/Dryer
Winter Park
9% off
Price is $196
$196
$1,375 for 7 nights
$1,375 for 7 nights
All fees included
Image gallery for WP Base! Zephyr Mtn Ldge 1BR Ski In/Out, Smart TVs, solo WiFi, NEW BATH

1010 out of 10, Exceptional, (143 reviews)
Exceptional
(143 reviews)
WP Base! Zephyr Mtn Ldge 1BR Ski In/Out, Smart TVs, solo WiFi, NEW BATH
Winter Park
7% off
Price is $153
$153
$1,072 for 7 nights
$1,072 for 7 nights
All fees included
Image gallery for Updated Condo at Winter Park and Trestle Bike Park

9.89.8 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Updated Condo at Winter Park and Trestle Bike Park
Winter Park
8% off
Price is $273
$273
$1,913 for 7 nights
$1,913 for 7 nights
All fees included
Image gallery for Penthouse Cozy Condo in the heart of Downtown Winter Park

1010 out of 10, Exceptional, (27 reviews)
Exceptional
(27 reviews)
Penthouse Cozy Condo in the heart of Downtown Winter Park
Winter Park
9% off
Price is $355
$355
$2,483 for 7 nights
$2,483 for 7 nights
All fees included
Image gallery for Modern Condo at Iron Horse - Ski In / Ski Out, Sleeps 4

9.69.6 out of 10, Exceptional, (15 reviews)
Exceptional
(15 reviews)
Modern Condo at Iron Horse - Ski In / Ski Out, Sleeps 4
Winter Park
9% off
Price is $430
$430
$3,012 for 7 nights
$3,012 for 7 nights
All fees included
Image gallery for Ski-in Ski-out studio

9.49.4 out of 10, Exceptional, (144 reviews)
Exceptional
(144 reviews)
Ski-in Ski-out studio
Winter Park
8% off
Price is $112
$112
$781 for 7 nights
$781 for 7 nights
All fees included
Image gallery for Luxury condo, Pool and Hot Tub, Ski Shuttle, Downtown, Close to All!

1010 out of 10, Exceptional, (81 reviews)
Exceptional
(81 reviews)
Luxury condo, Pool and Hot Tub, Ski Shuttle, Downtown, Close to All!
Winter Park
8% off
Price is $399
$399
$2,794 for 7 nights
$2,794 for 7 nights
All fees included
Image gallery for Cozy, 1 bedroom Condo, 2 Blocks from Downtown, on Ski Bus Route

9.09.0 out of 10, Wonderful, (57 reviews)
Wonderful
(57 reviews)
Cozy, 1 bedroom Condo, 2 Blocks from Downtown, on Ski Bus Route
Winter Park
11% off
Price is $124
$124
$868 for 7 nights
$868 for 7 nights
All fees included
Image gallery for Zephyr Mountain Lodge - Beautifully Renovated

1010 out of 10, Exceptional, (30 reviews)
Exceptional
(30 reviews)
Zephyr Mountain Lodge - Beautifully Renovated
Winter Park
8% off
Price is $260
$260
$1,818 for 7 nights
$1,818 for 7 nights
All fees included
Image gallery for Beautiful Ski In/Ski Out Studio Condo NO CLEANING FEES

9.89.8 out of 10, Exceptional, (120 reviews)
Exceptional
(120 reviews)
Beautiful Ski In/Ski Out Studio Condo NO CLEANING FEES
Winter Park
9% off
Price is $167
$167
$1,166 for 7 nights
$1,166 for 7 nights
All fees included
Image gallery for Cozy 1-bed, 1-bath condo on the Fraser river in downtown Winter Park, Colorado

9.49.4 out of 10, Exceptional, (106 reviews)
Exceptional
(106 reviews)
Cozy 1-bed, 1-bath condo on the Fraser river in downtown Winter Park, Colorado
Winter Park
11% off
Price is $121
$121
$846 for 7 nights
$846 for 7 nights
All fees included
Image gallery for Penthouse Studio Ski In-Out- Easy Access Resort; Sauna Pool Gym Hot Tub Views

9.69.6 out of 10, Exceptional, (179 reviews)
Exceptional
(179 reviews)
Penthouse Studio Ski In-Out- Easy Access Resort; Sauna Pool Gym Hot Tub Views
Winter Park
6% off
Price is $161
$161
$1,126 for 7 nights
$1,126 for 7 nights
All fees included
Find spaces that suit your style
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Find properties near top attractions in Winter Park
Map Attractions

3
Winter Park Visitor Center
Find the best place to stay - Winter Park
Trestle House | Ski Out Your Back Door | WP's Most Stunning Home INSTAGRAM FAMOUS!
Sleeps 12 · 5 bedrooms · 4+ bathrooms
1010 out of 10
Exceptional
exceptional
13 reviews
(13 reviews)
Luxury Downtown Condo - Private Hot Tub! Walk to Dining and Ski Bus...
Sleeps 12 · 5 bedrooms · 4+ bathrooms
9.89.8 out of 10
Exceptional
exceptional
93 reviews
(93 reviews)
Beautiful Condo - Riverfront-Slopeside-Walk to Resort-On Bus Route
Sleeps 10 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptional
exceptional
118 reviews
(118 reviews)





