Holiday Rentals with Pools in Winter Park
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615 rentals in Winter Park.
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Fantastic townhouse in the heart of Downtown. Best in Red Quill Village
4 bedrooms
5 bathrooms
Sleeps 12
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Luxe Decor & More! | Room To Spread Out | Family Friendly | Bubbling Hot Tub!
3 bedrooms
4 bathrooms
Sleeps 8
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Lakota Reserve - Luxurious Six Bedroom Home Near Winter Park Resort
6 bedrooms
7 bathrooms
Sleeps 18
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Riverfront-Slopeside-Walk to Resort-On Bus Route
4 bedrooms
3 bathrooms
Sleeps 12
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Fabulous Slope-Side Lakota Townhome - Private Hot Tub & Magnificent Views
4 bedrooms
3 bathrooms
Sleeps 10
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Sophisticated Ski-In/Ski-Out Getaway – 1,471 Square Feet, Balcony & Fireplace
2 bedrooms
3 bathrooms
Sleeps 8
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Trailhead Lodges 512
1 bedroom
1 bathroom
Sleeps 4
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New listing! Cozy condo w/ shared pool & hot tub - easy access to town and ski
2 bedrooms
2 bathrooms
Sleeps 6
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Timber Ridge Lodge
5 bedrooms
5 bathrooms
Sleeps 17
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Rosie's Way
3 bedrooms
4 bathrooms
Sleeps 9
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Save time - get the best Winter Park rentals sent straight to your email!
One Block From All Restaurants And Shopping, Nightlife
1 bedroom
1 bathroom
Sleeps 5
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EXQUISITE MTN. HOME! PERF. FOR 2 FAMILIES! 2 Living Rms! MLK & a few wks left!
4 bedrooms
4 bathrooms
Sleeps 12
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Fantastic downtown townhouse. Perfect for 2 families or group.
3 bedrooms
4 bathrooms
Sleeps 11
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Ski in/out,2/2,hot tub,K & T/Q/T Bunk,memory foam Q couch/xbox/deck grill/sleep8
2 bedrooms
2 bathrooms
Sleeps 8
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❤ WP✦INCREDIBLE RIVER VIEWS✦Private Top Flr✦Hideaway Park✦Nightlife✦Cozy
2 bedrooms
2 bathrooms
Sleeps 8
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5th Floor With Beautiful views! Full-kitchen! Monthly booking is available!
1 bedroom
1 bathroom
Sleeps 4
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Beautifully Updated Luxury Condo at Affordable Price at Ideal Location!
2 bedrooms
2 bathrooms
Sleeps 6
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Oversized Zephyr Corner Unit, Walk Out Patio Entrance, Ski In/Out, 1 Bdrm/1 Bath
1 bedroom
1 bathroom
Sleeps 4
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Luxury 3 Bdrm, 3.5 Bath Townhome in Downtown WP
3 bedrooms
4 bathrooms
Sleeps 8
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Beautiful Winter Park Townhouse- Downtown, Great Mtn Views, Private Hot Tub!
3 bedrooms
4 bathrooms
Sleeps 8
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Beautiful two bedroom condo in Winter Park! Pool, hot tub, free transportation.
2 bedrooms
2 bathrooms
Sleeps 8
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Gorgeous Condo | Private Views from Balcony | Walk To The Best Restaurants
3 bedrooms
3 bathrooms
Sleeps 10
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A Real Ski-in Ski-Out Unit
1 bedroom
1 bathroom
Sleeps 4
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Luxury Estate- Close to Village- Well Stocked and Beautifully Furnished
5 bedrooms
6 bathrooms
Sleeps 18
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Heated Pool! Steps to dining & shops, sledding hill views!
3 bedrooms
3 bathrooms
Sleeps 8
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Spacious Retreat With Great Amenities!
3 bedrooms
3 bathrooms
Sleeps 8
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Booking for winter NOW! 3 Bed, 3 Bathroom, Sleeps 10 Hot Tub!
3 bedrooms
3 bathrooms
Sleeps 10
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Slopeside Paradise--3 BR, 2.5 Bath 2 Minute Shuttle Ride to the slopes!
3 bedrooms
3 bathrooms
Sleeps 14
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Large, Luxury Private Home in Downtown Winter Park on Vasquez Creek*
8 bedrooms
9 bathrooms
Sleeps 25
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Winter Park Founders Pointe Slope Side Studio Steps To Base Area
1 bedroom
1 bathroom
Sleeps 4
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PET-FRIENDLY | The Coolest & Newest: 4 Bedroom Downtown Condo w/ Views | Sleeps
4 bedrooms
3 bathrooms
Sleeps 10
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One block from all restaurans, shopping and nightlife.
2 bedrooms
2 bathrooms
Sleeps 6
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Family/ Pet Friendly Updated Downtown Winter Park Condo 3BD/2BA
3 bedrooms
2 bathrooms
Sleeps 10
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2BR/2BA **Just Read Our Reviews!** Beautiful Condo & Grt Value!
2 bedrooms
2 bathrooms
Sleeps 8
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Cozy, CLEAN Ski-in Ski-Out Top-Floor Studio at Iron Horse
0 bedrooms
1 bathroom
Sleeps 4
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Great Ski Condo Only 50 Ft Walk To The Lifts
1 bedroom
1 bathroom
Sleeps 6
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Large Glass Front with Beautiful Mountain Views
2 bedrooms
2 bathrooms
Sleeps 6
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Fantastic front corner 2BD/2BA Condo At Base Of Winter Park
2 bedrooms
2 bathrooms
Sleeps 6
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Zephyr Mountain Lodge/Slope Side Bldg True Ski/Bike in/ out with patio walk out
1 bedroom
1 bathroom
Sleeps 5
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New Luxury Unit: Downtown, On Ski Shuttle, Pool/HotTub, Pets OK, Back to Forest
3 bedrooms
2 bathrooms
Sleeps 8
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Luxury 5 br 4.5 bath 2 Masters! Across from Winter Park Ski Resort Sleeps 12
5 bedrooms
5 bathrooms
Sleeps 12
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Beautiful 3 Bedroom Townhome In Downtown Winter Park With Private Hot Tub!
3 bedrooms
3 bathrooms
Sleeps 10
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Five Bedroom Family Favorite -Sleeps 19!
5 bedrooms
5 bathrooms
Sleeps 19
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Awesome Views! Upgraded condo, Ski in ski out,views of slopes from every window
2 bedrooms
2 bathrooms
Sleeps 6
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Winter Park Mountain Views with Private Hot Tub
3 bedrooms
3 bathrooms
Sleeps 9
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Rated 'Exceptional','The Best Beaver Village Rental',Low Rates
2 bedrooms
2 bathrooms
Sleeps 6
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Creekside 3-br ski condo w/fireplace, scenic views, free shuttle to slopes
3 bedrooms
2 bathrooms
Sleeps 7
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Penthouse Sport Studio - Ski-In/out - Fireplace - Balcony - Iron Horse Resort
1 bedroom
1 bathroom
Sleeps 4
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Hi Country Haus - 10-18 Walk to Downtown and Free Shuttle to Winter Park! Hot Tu
2 bedrooms
2 bathrooms
Sleeps 7
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Elk Lodge
5 bedrooms
5 bathrooms
Sleeps 19
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