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Holiday Rentals in Winter Park

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382 rentals in Winter Park.
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Winter Park Cabin - Walk to Main Street & Downtown, holiday rental in Winter Park

Winter Park Cabin - Walk to Main Street & Downtown

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Home w/ Hot Tub < 1 Mile to Winter Park Resort!, holiday rental in Winter Park

Home w/ Hot Tub < 1 Mile to Winter Park Resort!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Awesome Views! Upgraded condo, Ski in ski out,views of slopes from every window, holiday rental in Winter Park

Awesome Views! Upgraded condo, Ski in ski out,views of slopes from every window

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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One Block From All Restaurants And Shopping, Nightlife, holiday rental in Winter Park

One Block From All Restaurants And Shopping, Nightlife

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Fantastic downtown townhouse. Perfect for 2 families or group., holiday rental in Winter Park

Fantastic downtown townhouse. Perfect for 2 families or group.

3 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Beautiful two bedroom condo in Winter Park! Pool, hot tub, free transportation., holiday rental in Winter Park

Beautiful two bedroom condo in Winter Park! Pool, hot tub, free transportation.

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Gorgeous Condo | Private Views from Balcony | Walk To The Best Restaurants, holiday rental in Winter Park

Gorgeous Condo | Private Views from Balcony | Walk To The Best Restaurants

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Winter Park Townhouse- Downtown, Great Mtn Views, Private Hot Tub!, holiday rental in Winter Park

Beautiful Winter Park Townhouse- Downtown, Great Mtn Views, Private Hot Tub!

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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5th Floor With Beautiful views! Full-kitchen! Monthly booking is available!, holiday rental in Winter Park

5th Floor With Beautiful views! Full-kitchen! Monthly booking is available!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Slopeside Paradise--3 BR, 2.5 Bath 2 Minute Shuttle Ride to the slopes!, holiday rental in Winter Park

Slopeside Paradise--3 BR, 2.5 Bath 2 Minute Shuttle Ride to the slopes!

3 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Heated Pool! Steps to dining & shops, sledding hill views!, holiday rental in Winter Park

Heated Pool! Steps to dining & shops, sledding hill views!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautifully Updated Luxury Condo at Affordable Price at Ideal Location!, holiday rental in Winter Park

Beautifully Updated Luxury Condo at Affordable Price at Ideal Location!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ski in/out,2/2,hot tub,K & T/Q/T Bunk,memory foam Q couch/xbox/deck grill/sleep8, holiday rental in Winter Park

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
Match: Sleeps
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New Luxury Unit: Downtown, On Ski Shuttle, Pool/HotTub, Pets OK, Back to Forest, holiday rental in Winter Park

New Luxury Unit: Downtown, On Ski Shuttle, Pool/HotTub, Pets OK, Back to Forest

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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❤ WP✦INCREDIBLE RIVER VIEWS✦Private Top Flr✦Hideaway Park✦Nightlife✦Cozy, holiday rental in Winter Park

❤ WP✦INCREDIBLE RIVER VIEWS✦Private Top Flr✦Hideaway Park✦Nightlife✦Cozy

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxury 3 Bdrm, 3.5 Bath Townhome in Downtown WP, holiday rental in Winter Park

Luxury 3 Bdrm, 3.5 Bath Townhome in Downtown WP

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Estate- Close to Village- Well Stocked and Beautifully Furnished, holiday rental in Winter Park

Luxury Estate- Close to Village- Well Stocked and Beautifully Furnished

5 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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Rated 'Exceptional','The Best Beaver Village Rental',Low Rates, holiday rental in Winter Park

Rated 'Exceptional','The Best Beaver Village Rental',Low Rates

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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PET-FRIENDLY | The Coolest & Newest: 4 Bedroom Downtown Condo w/ Views | Sleeps, holiday rental in Winter Park

PET-FRIENDLY | The Coolest & Newest: 4 Bedroom Downtown Condo w/ Views | Sleeps

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Large, Luxury Private Home in Downtown Winter Park on Vasquez Creek*, holiday rental in Winter Park

Large, Luxury Private Home in Downtown Winter Park on Vasquez Creek*

8 bedrooms
9 bathrooms
Sleeps 25
Match: Sleeps
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Zephyr Mountain Lodge/Slope Side Bldg True Ski/Bike in/ out with patio walk out, holiday rental in Winter Park

Zephyr Mountain Lodge/Slope Side Bldg True Ski/Bike in/ out with patio walk out

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Oversized Zephyr Corner Unit, Walk Out Patio Entrance, Ski In/Out, 1 Bdrm/1 Bath, holiday rental in Winter Park

Oversized Zephyr Corner Unit, Walk Out Patio Entrance, Ski In/Out, 1 Bdrm/1 Bath

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Zephyr Mtn Lodge Slopeside - True ski-in / ski-out at WP base - UPGRADES 2017-18, holiday rental in Winter Park

Zephyr Mtn Lodge Slopeside - True ski-in / ski-out at WP base - UPGRADES 2017-18

2 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Borders National Forest Trail Head For Amazing Winter and Summer Activities, holiday rental in Winter Park

Borders National Forest Trail Head For Amazing Winter and Summer Activities

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Winter Park Mountain Views with Private Hot Tub, holiday rental in Winter Park

Winter Park Mountain Views with Private Hot Tub

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Creekside 3-br ski condo w/fireplace, scenic views, free shuttle to slopes, holiday rental in Winter Park

Creekside 3-br ski condo w/fireplace, scenic views, free shuttle to slopes

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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One block from all restaurans, shopping and nightlife., holiday rental in Winter Park

One block from all restaurans, shopping and nightlife.

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Boutique hotel style in a family-friendly 2-bed condo, free shuttles to Resort, holiday rental in Winter Park

Boutique hotel style in a family-friendly 2-bed condo, free shuttles to Resort

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Large Glass Front with Beautiful Mountain Views, holiday rental in Winter Park

Large Glass Front with Beautiful Mountain Views

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury 5 br 4.5 bath 2 Masters! Across from Winter Park Ski Resort Sleeps 12, holiday rental in Winter Park

Luxury 5 br 4.5 bath 2 Masters! Across from Winter Park Ski Resort Sleeps 12

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Family/ Pet Friendly Updated Downtown Winter Park Condo 3BD/2BA, holiday rental in Winter Park

Family/ Pet Friendly Updated Downtown Winter Park Condo 3BD/2BA

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Zephyr Lodge Riverside Ski in/Ski Out 1 BR/1 BA King Bed, holiday rental in Winter Park

Zephyr Lodge Riverside Ski in/Ski Out 1 BR/1 BA King Bed

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Top Floor with Beautiful Views! Great reviews!  Monthly booking is available!!!, holiday rental in Winter Park

Top Floor with Beautiful Views! Great reviews! Monthly booking is available!!!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Remodeled, Ground Level, Family Friendly Mountain Haven   Flexible cancellation, holiday rental in Winter Park

Remodeled, Ground Level, Family Friendly Mountain Haven Flexible cancellation

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Winter Park Founders Pointe Slope Side Studio Steps To Base Area, holiday rental in Winter Park

Winter Park Founders Pointe Slope Side Studio Steps To Base Area

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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3 BR  with Private Hot Tub and views of the slopes in prestigious Lakota!!, holiday rental in Winter Park

3 BR with Private Hot Tub and views of the slopes in prestigious Lakota!!

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
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Riverfront Condo In The Heart Of Winter Park, holiday rental in Winter Park

Riverfront Condo In The Heart Of Winter Park

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Lakota Reserve - Luxurious Six Bedroom Home Near Winter Park Resort, holiday rental in Winter Park

Lakota Reserve - Luxurious Six Bedroom Home Near Winter Park Resort

6 bedrooms
7 bathrooms
Sleeps 18
Match: Sleeps
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Ski-in Ski-Out: Iron Horse Resort :DISCOUNT LIFT TICKETS;  2+BR/2BA; King; Quiet, holiday rental in Winter Park

Ski-in Ski-Out: Iron Horse Resort :DISCOUNT LIFT TICKETS; 2+BR/2BA; King; Quiet

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Fantastic front corner 2BD/2BA Condo At Base Of Winter Park, holiday rental in Winter Park

Fantastic front corner 2BD/2BA Condo At Base Of Winter Park

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2BR/2BA  **Just Read Our Reviews!**  Beautiful Condo & Grt Value!, holiday rental in Winter Park

2BR/2BA **Just Read Our Reviews!** Beautiful Condo & Grt Value!

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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2 Bedroom -Great Ski Area Views, Reasonable Rates, holiday rental in Winter Park

2 Bedroom -Great Ski Area Views, Reasonable Rates

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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PERFECT Cabin set in the Mtns. Infrared Sauna Hot tub GREAT for families!, holiday rental in Winter Park

PERFECT Cabin set in the Mtns. Infrared Sauna Hot tub GREAT for families!

4 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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Newly renovated, steps to restaurants, mountain views, on free bus route, holiday rental in Winter Park

Newly renovated, steps to restaurants, mountain views, on free bus route

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Great Ski Condo Only 50 Ft Walk To The Lifts, holiday rental in Winter Park

Great Ski Condo Only 50 Ft Walk To The Lifts

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Penthouse Sport Studio - Ski-In/out - Fireplace - Balcony - Iron Horse Resort, holiday rental in Winter Park

Penthouse Sport Studio - Ski-In/out - Fireplace - Balcony - Iron Horse Resort

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The 'Serenity Mountain House' nestled in the trees, holiday rental in Winter Park

The 'Serenity Mountain House' nestled in the trees

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Cozy large studio condo., holiday rental in Winter Park

Cozy large studio condo.

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious Retreat With Great Amenities!, holiday rental in Winter Park

Spacious Retreat With Great Amenities!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Gorgeous Rocky Mountain home w/ a full kitchen, shared tennis, & amazing views, holiday rental in Winter Park

Gorgeous Rocky Mountain home w/ a full kitchen, shared tennis, & amazing views

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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