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Winter Park Rentals with Pools

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178 villas in Winter Park with pools

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

Winter Park house

5 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 4 minutes

Match: Swimming pool

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Price per night from

$378

Snowblaze C24

Winter Park house

2 bedrooms / 2 bathrooms / sleeps 7

Match: Swimming pool

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Price per night from

$176

Bright, Updated Top Floor Unit With Great Views

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$201

Cozy condo w/ shared hot tubs, pool, sauna, gym, and game room

Winter Park house

2 bedrooms / 2 bathrooms / sleeps 7

Match: Swimming pool

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Price per night from

$158

Winter Park Condo w/ Hot Tubs, 3 Mi to Ski Resort!

Winter Park apartment

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 4 minutes

Match: Swimming pool

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Price per night from

$148

Trailhead Lodges 323

Winter Park house

3 bedrooms / 3 bathrooms / sleeps 10

Match: Swimming pool

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Price per night from

$242

Cozy Winter Park Condo Only 2 Miles from Ski Lifts

Winter Park apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 18 minutes

Match: Swimming pool

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Price per night from

$118

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

Winter Park villa

/ 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 23 minutes

Match: Swimming pool

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Price per night from

$58

Trailhead Lodges 822

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$219

Winter Wonderland in WP!!!

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 7 minutes

Match: Swimming pool

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Price per night from

$161

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.

Match: Swimming pool

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Price per night from

$219

Trailhead Lodges 424

Winter Park house

2 bedrooms / 2 bathrooms / sleeps 7

Match: Swimming pool

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Price per night from

$215

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. The convenience to the slopes and downtown was great. We could walk to several stores and eating establishments. Or we could use the bus transportation to anywhere we needed including the slopes. The kitchen was great and well equipped for evening snacks or meals.It had a washer and dryer that came in handy.Oh and the sledding hill across the street was a great asset. Winter Park ski slopes were excellent as usual. We were also able to print our boarding passes at the Winter Park Lodging main office which was a great convenience also.We had a great stay.

Match: Swimming pool

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Price per night from

$242

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

Winter Park house

3 bedrooms / 4 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$285

Newly Remodeled Studio/Think Snow!

Winter Park studio

Studio / 1 bathroom / sleeps 3

Match: Swimming pool

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Price per night from

$201

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

Match: Swimming pool

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Price per night from

$152

3BR Upscale Penthouse with Largest Deck at Base with Amazing View

Winter Park condo

3 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$574

Winter Park Condo on Bus Route, 2 Blocks to Dwntwn

Winter Park apartment

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 4 minutes

Match: Swimming pool

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Price per night from

$131

Trailhead Lodges 514

Winter Park condo

3 bedrooms / 3 bathrooms / sleeps 10

Match: Swimming pool

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Price per night from

$284

Trailhead Lodges 524

Winter Park townhouse

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 34 minutes

Match: Swimming pool

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Price per night from

$172

Trailhead Lodges 134

Winter Park house

3 bedrooms / 3 bathrooms / sleeps 10

Match: Swimming pool

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Price per night from

$316

Winter Park Area Family Cabin w/Mtn View & Hot Tub

Winter Park house

3 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 57 minutes

Match: Swimming pool

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Price per night from

$237

Downtown Winter Park Condo - Steps to Ski Shuttle!

Winter Park apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 4 minutes

Match: Swimming pool

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Price per night from

$142

Cozy Winter Park Studio w/Views-Walk to Downtown!

Winter Park studio

Studio / 1 bathroom / sleeps 6

Responds fast! avg. 4 minutes

Match: Swimming pool

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Price per night from

$91

Winter Park Condo w/ Amenities - Walk to Town!

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 4 minutes

Match: Swimming pool

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Price per night from

$131

Hi Country House 1909

Winter Park house

2 bedrooms / 2 bathrooms / sleeps 6

“So nice I wish I could give it 5 stars!!!” The purpose for our visit to Winter Park was to do something special for my nearly 90-year-old in-laws. It was about them, so we gave them the master bedroom, from which room the river could be heard...gorgeous room and bathroom. Top notch. My husband and I took the bedroom with twin beds. The beds were very comfortable and worked fine for us (married 38 years). We spent more time at the condo than away because of the age of my in-laws, otherwise it wouldn't have been so bothersome to hear the heavy construction (earth moving equipment?) just across from our bedroom window. Then on the second night, some partyers were making noise past 1:00 am. This is no fault of Winter Park Lodging Company (who are the most friendly, stand-up, service-oriented company I've ever worked with). But I was asked for an absolutely honest review. The company will be giving us a discount on our next stay because of the partyers. We will definitely be back, but will choose a different unit if the construction is still going on in a noisy way.

Match: Swimming pool

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Price per night from

$176

NEW! Cozy Ski Condo w/Hot Tubs, 3 Mi to WP Resort!

Winter Park condo

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 26 minutes

Match: Swimming pool

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Price per night from

$84

Remodeled Riverside Getaway w/ Hot Tubs, Pool, Clubhouse & Shuttle to Slopes

Winter Park condo

1 bedroom / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$89

Ski-In/Ski-Out Winter Park Condo w/Hot Tub Access!

Winter Park condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 4 minutes

Match: Swimming pool

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Price per night from

$82

Comfy condo near Winter Park w/ shared pool, hot tub & ski shuttle!

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 5

Match: Swimming pool

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Price per night from

$125

Sophisticated Ski-In/Ski-Out Winter Park Getaway w/ Balcony & Gas Fireplace

Winter Park condo

2 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$109

Trailhead Lodges 812

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 1 hour 34 minutes

Match: Swimming pool

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Price per night from

$160

Trailhead Lodges 133

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 7

Match: Swimming pool

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Price per night from

$235

Trailhead Lodges 212

Winter Park condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 34 minutes

Match: Swimming pool

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Price per night from

$133

Charming Condo w/ Hot Tub & Heated Pool -- Walk to Downtown, Near Ski Shuttle

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$99

Trailhead Lodges 811

Winter Park house

1 bedroom / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$152

Iron Horse 5044-Ski in/Ski Out Access Level!

Winter Park studio

Studio / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$104

Iron Horse Studio w/Pool, Hot Tub, Walk to WP

Winter Park studio

Studio / 1 bathroom / sleeps 4

Responds fast! avg. 26 minutes

Match: Swimming pool

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Price per night from

$54

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