Vacation Rentals with Pool in Winter Park

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

Filtering by: Swimming pool

401 vacation rentals

(8) Excellent 

29

Ski In/Out Resort Village #3313 - FREE Activities/Resort Discounts/Views/Hot Tub

Grand County / Winter Park

Winter Park condo

1 6 min stay varies

  • 1 bedroom
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$95

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$95

20

Snowblaze Condominiums B22

Grand County / Winter Park

Winter Park apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$152

Responds fast!
avg. 2 hours 5 minutes

Price per night from

$152

(7) Excellent 

31

Ski In/Out Resort Village #3301 - FREE Activities/Resort Discounts/Views/Hot Tub

Grand County / Winter Park

Winter Park house

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$119

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$119

(11) Excellent 

37

Ski In/Out Resort Village #3129 - FREE Activities/Resort Discounts/Views/Hot Tub

Grand County / Winter Park

Winter Park condo

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$119

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$119

(7) Excellent 

31

Ski In/Out Resort Village #3307 - FREE Activities/Resort Discounts/Views/Hot Tub

Grand County / Winter Park

Winter Park condo

1 6 min stay varies

  • 1 bedroom
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$95

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$95

24

Winter Park Condo w/ Amenities - Mins to Slopes!

Grand County / Winter Park

Winter Park apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$95

Responds fast!
avg. 22 minutes

Price per night from

$95

(1) Excellent 

38

Snowblaze C24

Grand County / Winter Park

Winter Park house

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$190

Price per night from

$190

(8) Excellent 

32

Ski In/Out Resort Village #3133 - FREE Activities/Resort Discounts/Views/Hot Tub

Grand County / Winter Park

Winter Park condo

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$119

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$119

24

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

Grand County / Winter Park

Winter Park apartment

1 5 min stay varies

  • 1 bedroom
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$85

Responds fast!
avg. 10 minutes

Price per night from

$85

(1) Excellent 

18

Bright, Updated Top Floor Unit With Great Views

Grand County / Winter Park

Winter Park condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$150

Price per night from

$150

29

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

Grand County / Winter Park

Winter Park house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$401

Responds fast!
avg. 22 minutes

Price per night from

$401

24

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

Grand County / Winter Park

Winter Park apartment

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$95

Responds fast!
avg. 22 minutes

Price per night from

$95

(4) Excellent 

38

New Downtown Winter Park Villa - FREE Activities/Resort Discounts/FREE Shuttle

Grand County / Winter Park

Winter Park villa

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$216

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$216

24

Inviting Winter Park Condo w/ Shuttle & Mtn Views!

Grand County / Winter Park

Winter Park apartment

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$165

Responds fast!
avg. 22 minutes

Price per night from

$165

(2) Excellent 

43

Slopeside Luxury Villa - FREE Activities/Resort Discounts/Views/FREE Shuttle

Grand County / Winter Park

Winter Park villa

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$179

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$179

31

Winter Park Condo Only 2 Miles from Ski Lifts!

Grand County / Winter Park

Winter Park apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$99

Responds fast!
avg. 22 minutes

Price per night from

$99

(1) Very Good 

32

Iron Horse Resort 3094

Grand County / Winter Park

Winter Park apartment

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$273

Responds fast!
avg. 2 hours 5 minutes

Price per night from

$273

(4) Very Good 

14

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

Grand County / Winter Park

Winter Park villa

4 min stay varies

  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$50

Responds fast!
avg. 2 hours 7 minutes

Price per night from

$50

(12) Excellent 

29

Ski In/Out Resort Village #4283 - FREE Activities/Resort Discounts/Views/Hot Tub

Grand County / Winter Park

Winter Park condo

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly
“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
…see more

Price per night from

$119

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$119

(1) Very Good 

25

NEW! Downtown Winter Park Condo w/ Balcony!

Grand County / Winter Park

Winter Park apartment

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$125

Responds fast!
avg. 22 minutes

Price per night from

$125

(2) Excellent 

30

Ski In/Out Resort Village #3235 - FREE Activities/Resort Discounts/Views/Hot Tub

Grand County / Winter Park

Winter Park condo

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$119

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$119

39

New Downtown Winter Park Villa - FREE Activities/Resort Discounts/Free Shuttle

Grand County / Winter Park

Winter Park house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$179

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$179

(1) Excellent 

34

Trailhead Lodges 323

Grand County / Winter Park

Winter Park house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$275

Price per night from

$275

30

Trailhead Lodges 822

Grand County / Winter Park

Winter Park condo

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$231

Price per night from

$231

(4) Excellent 

28

Ski In/Out Resort Village #3509 - FREE Activities/Resort Discounts/Views/Hot Tub

Grand County / Winter Park

Winter Park condo

1 6 min stay varies

  • 1 bedroom
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$95

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$95

(5) Very Good 

39

Hi Country Haus 21-15

Grand County / Winter Park

Winter Park apartment

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
“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.
…see more

Price per night from

$155

Responds fast!
avg. 2 hours 5 minutes

Price per night from

$155

26

New! 2BR Winter Park Condo - 4 Mins to Ski Area!

Grand County / Winter Park

Winter Park apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$100

Responds fast!
avg. 22 minutes

Price per night from

$100

29

Iron Horse Resort 3084

Grand County / Winter Park

Winter Park studio

Studio 4 min stay varies

  • Studio
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$131

Responds fast!
avg. 2 hours 5 minutes

Price per night from

$131

(2) Excellent 

32

Trailhead Lodges 432

Grand County / Winter Park

Winter Park house

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
“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.
…see more

Price per night from

$231

Price per night from

$231

(1) Excellent 

33

Ski In/Out Resort Village #3425 - FREE Activities/Resort Discounts/Views/Hot Tub

Grand County / Winter Park

Winter Park house

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$119

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$119

14

2 Bedroom Condo on River

Grand County / Winter Park

Winter Park condo

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$85

Price per night from

$85

(2) Excellent 

18

Winter Wonderland in WP!!!

Grand County / Winter Park

Winter Park condo

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Swimming pool
  • Child Friendly

Price per night from

$141

Responds fast!
avg. 42 minutes

Price per night from

$141

(2) Very Good 

39

Snowblaze Condominiums C14

Grand County / Winter Park

Winter Park apartment

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$152

Responds fast!
avg. 2 hours 5 minutes

Price per night from

$152

(1) Very Good 

24

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

Grand County / Winter Park

Winter Park condo

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$184

Price per night from

$184

27

Trailhead Lodges 424

Grand County / Winter Park

Winter Park house

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$227

Price per night from

$227

25

Winter Park Condo w/Sauna Near Skiing & Hiking!

Grand County / Winter Park

Winter Park apartment

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$175

Responds fast!
avg. 22 minutes

Price per night from

$175

(3) Very Good 

20

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

Grand County / Winter Park

Winter Park condo

2 7 2 nights min

  • 2 bedrooms
  • sleeps 7
  • 2 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$149

Responds fast!
avg. 2 hours 14 minutes

Price per night from

$149

(24) Excellent 

26

Trailhead Lodges 723

Grand County / Winter Park

Winter Park house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
“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
…see more

Price per night from

$275

Price per night from

$275