Updating...

Enter dates for more accurate prices

Winter Park Rentals with Pools

Filter

Winter Park Rentals with Pools

347 vacation rentals

New Downtown Winter Park Villa On A Pond - FREE Activities/Great View/Hot Tub

Winter Park villa

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 3 hours 7 minutes

Price per night from

$179

1 / 39

Ski In/Out Resort Village #4283 - FREE Activities/Great Views/Pool Sized Hot Tub

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 8

“Nothing Negative to Say!” This condo was GREAT! The location is excellent, within walking distance of shops and restaurants, and an unbelievable view! The inside of the condo was very well maintained, all kitchen equipment was provided, decor was nice

Responds fast! avg. 3 hours 7 minutes

Price per night from

$99

1 / 29

Winter Park Home w/Ski Hill Views, Sauna & Hot Tub

Winter Park house

5 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 55 minutes

Price per night from

$400

1 / 29

Iron Horse Resort 3094

Winter Park apartment

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 18 minutes

Price per night from

$211

1 / 32

Snowblaze Condominiums B22

Winter Park apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 18 minutes

Price per night from

$118

1 / 20

Winter Park Condo w/Views & Ski-In/Ski-Out Access!

Winter Park apartment

1 bedroom / 1 bathroom / sleeps 5

Responds fast! avg. 55 minutes

Price per night from

$85

1 / 24

Ski In/Out Resort Village #3307 - FREE Activities/Great Views/Pool Sized Hot Tub

Winter Park condo

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 7 minutes

Price per night from

$79

1 / 34

Iron Horse Resort 3084

Winter Park studio

Studio / 1 bathroom / sleeps 4

Responds fast! avg. 18 minutes

Price per night from

$102

1 / 29

Slopeside 3 Story Luxury Villa - FREE Activities/Fantastic Views/Ski Shuttle

Winter Park villa

3 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 7 minutes

Price per night from

$149

1 / 43

Snowblaze Condominiums C14

Winter Park apartment

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 18 minutes

Price per night from

$118

1 / 39

New Downtown Winter Park Luxury Villa - FREE Activities/Great View/Hot Tub/Wifi

Winter Park house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 hours 7 minutes

Price per night from

$149

1 / 40

Special Rates for Springtime!

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 58 minutes

Price per night from

$140

1 / 18

Ski In/Out Resort Village #3301 - FREE Activities/Great Views/Pool Sized Hot Tub

Winter Park house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 7 minutes

Price per night from

$99

1 / 32

Ski In/Out Resort Village #3133 - FREE Activities/Great Views/Pool Sized Hot Tub

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 7 minutes

Price per night from

$99

1 / 32

Trailhead Lodges 512

Winter Park house

1 bedroom / 1 bathroom / sleeps 4

“happy” everything we needed, comfy and content! Great location, loved the area, we had one problem with the cable and they came right over, I would stay again

Price per night from

$118

1 / 35

NEW! 1BR Winter Park Condo w/ Unrivaled Amenities!

Winter Park apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 55 minutes

Price per night from

$95

1 / 24

Trailhead Lodges 323

Winter Park house

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$189

1 / 32

Inviting Winter Park Condo w/ Shuttle & Mtn Views!

Winter Park apartment

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 55 minutes

Price per night from

$165

1 / 24

Bright, Updated Top Floor Unit With Great Views

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$130

1 / 18

Snowblaze Condominiums 211

Winter Park studio

Studio / 1 bathroom / sleeps 2

“SNowblaze Spring Break” Fresh look. Great little studio. I'd stay here again! Perfect for a single our couple, though you can sleep 4.

Responds fast! avg. 18 minutes

Price per night from

$85

1 / 26

Cozy, Family-Friendly, End Unit

Winter Park apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 19 minutes

Price per night from

$120

1 / 17

Newly remodeled Winter Park condo

Winter Park condo

1 bedroom / 1 bathroom / sleeps 5

“well situated” This condo is very well situated in the heart of Winter Park, walking distance to the convenience store and bakery as well to the recreation center. The condo is perfectly suited for a couple or 3 adults. TV and wifi worked perfectly, t

Price per night from

$65

1 / 9

Timber Lake 341 (************)

Winter Park house

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$225

1 / 16

Ski In/Out Resort Village #3235 - FREE Activities/Great Views/Pool Sized Hot Tub

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 7 minutes

Price per night from

$99

1 / 31

Snowblaze C24

Winter Park house

2 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$143

1 / 38

Iron Horse Resort 5064

Winter Park studio

Studio / 1 bathroom / sleeps 4

Responds fast! avg. 18 minutes

Price per night from

$102

1 / 22

Winter Park CO from $65.00 per Ski Season night !!

Winter Park villa

/ 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 1 minutes

Price per night from

$50

1 / 14

2 Bedroom End Unit at Beaver Village-Views, Pool, Hot Tubs

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 3 hours 2 minutes

Price per night from

$150

1 / 20

2BR Ground-Floor w/ Granite Kitchen, Pool, & Hot Tub - Shuttle to Slopes

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$121

1 / 24

Ski In/Out Resort Village #4474 - FREE Activities/Great Views/Pool Sized Hot Tub

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 7 minutes

Price per night from

$99

1 / 30

Trailhead Lodges 432

Winter Park house

2 bedrooms / 2 bathrooms / sleeps 8

“Summertime in Winter Park” Outstanding from the first phone call to Winter Park Lodging till the day we left our unit, Trailhead Lodge 432. Crystal & Meg were fantastic in answering all questions and taking care of any concerns that we had.

Price per night from

$177

1 / 26

Trailhead Lodges 524

Winter Park townhouse

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 38 minutes

Price per night from

$179

1 / 40

Hi Country Haus 21-15

Winter Park apartment

3 bedrooms / 2 bathrooms / sleeps 8

“Spacey and cozy” This newly remodeled and newly furnished condo was very comfortable for my family with kids. New furniture made a lot of difference.

Responds fast! avg. 18 minutes

Price per night from

$153

1 / 39

Trailhead Lodges 734

Winter Park house

2 bedrooms / 2 bathrooms / sleeps 8

“Spring Ski” It was a beautiful condo with everything you need for a relaxing vacation stay! It would be great for entertaining! The location had easy access to restaurants and shops.

Price per night from

$182

1 / 29

Ski In/Out Resort Village #3302 - FREE Activities/Great Views/Pool Sized Hot Tub

Winter Park apartment

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 7 minutes

Price per night from

$99

1 / 30

Ski In/Out Resort Village #3129 - FREE Activities/Great Views/Pool Sized Hot Tub

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 7 minutes

Price per night from

$99

1 / 37

Trailhead Lodges 723

Winter Park house

3 bedrooms / 3 bathrooms / sleeps 8

“Comfortable and great location.” Checking in late was easy and a great convenience for us. The condo was clean and great decor. It was quite roomy. We had eight people including six teenagers. There was plenty of room to relax after skiing all day. Th

Price per night from

$189

1 / 26

Newly Remodeled Studio/Think Snow!

Winter Park studio

Studio / 1 bathroom / sleeps 3

Price per night from

$125

1 / 16
Viewing 38 of 347
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more