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Winter Park Luxury Vacation Rentals

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    Travellers to Winter Park are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    133 Matching Rentals in Winter ParkView all 887 rentals
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    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Iron Horse C2093: Ski In / Ski Out Studio Condo;1 / 19
    (75)Very good
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Winter Park Modern Riverfront-Free Shuttle-Pool/Hot Tubs-Rec Center-Walk to Town1 / 26
    (28)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Affordable, Large, in Town - Pool, Hot Tubs, Great Views, Wi-Fi1 / 29
    (66)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    True SKI IN/OUT&GREAT VIEW of slopes, gondola from every window & bed & balcony!1 / 25
    (77)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Spacious Retreat With Great Amenities!1 / 18
    (29)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Steps from the new gondola!  True ski-in, ski-out.1 / 29
    (20)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Large Upscale Retreat off Vasquez Rd.1 / 20
    (8)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Winter Park, Grand County 80482
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 16
    Beautifully Updated Luxury Condo Affordable Price & Great Location1 / 32
    (104)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautiful Winter Park Townhouse- Downtown, Great Mtn Views, Private Hot Tub!1 / 50
    (46)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Skiing: Property Is In A Ski Resort
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    Winter Park, Grand County 80482
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Oversized Zephyr Corner Unit, Walk Out Patio Entrance, Ski In/Out, 1 Bdrm/1 Bath1 / 19
    (90)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Beautifully Upgraded Downtown Winter Park Condo With DirecTV(HD) and Wi-Fi1 / 24
    (47)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Popular 3 bedroom Remodel in best HCH building1 / 22
    (44)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Upscale Condo Overlooking Hideaway Park1 / 24
    (49)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Washer/Dryer INSIDE condo/Amazing Base Views  (Xmas & New Year still available)1 / 11
    (24)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Avoid parking stress - use free ski shuttle bus. Kitchen remodel in Oct. '191 / 19
    (21)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 9
    Winter Park 2 bdrm, Beautifully Updated, Walk2town, New Pool and Rec Center!1 / 25
    (39)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Winter Park Condo Pool, HotTub 10% Discount If Booked Before  3/311 / 24
    (24)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2BR/2BA  **Just Read Our Reviews!**  Beautiful Condo & Grt Value!1 / 24
    (51)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Remodeled, Ground Level, Family Friendly Mountain Retreat1 / 24
    (72)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Downtown Winter Park Condo1 / 7
    (27)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Prime Location!  Free Winter Park Shuttle Stop Right Outside The Door!!1 / 41
    (8)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
    Cozy Log Home,3 min to slopes  sleeps 10-11, Free shuttle steps away. location!!1 / 45
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Winter Park, Grand County 80482
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    2BR in Winter Park- In town near restaurants! Resort shuttle out the front door!1 / 34
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 9
    Streamside townhome, on shuttle route, sleeps 6, in heart of Winter Park1 / 20
    (10)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Winter Park, Grand County 80482
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Opening Day November 2nd!  Snow is falling!1 / 30
    (54)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Beautiful!  Family friendly,  2 bedroom/3 bath condo in downtown Winter Park!1 / 34
    (10)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 8
    Large Beautiful Townhome, Private Hot Tub, On Shuttle Route, In Town, WIFI1 / 20
    (25)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Winter Park, Grand County 80482
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 7
    Cozy Winter Park condo, free wifi, minutes from the ski mountain1 / 35
    (16)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Cozy large studio condo.1 / 13
    (17)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Walk to Downtown and Free Shuttle to Winter Park! Hot Tub and Club house. Pets W1 / 22
    (51)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    WALK to downtown from this Top Floor Unit with amazing views and sunlight Beaver1 / 33
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 7
    Hi Country Haus 13-15, Cozy Downtown WP 1BR, Walk to Everything!1 / 22
    (10)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Walk Right Out To Lifts | Ski In/Ski Out * Founders Pointe | Great Amenities! |1 / 31
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Walk To Festivals | Couples Retreat | Downtown | RARE Pool!1 / 37
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Location! Downtown Winter Park with private Hot Tub. Walk to everything!1 / 49
    (2)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Winter Park, Grand County 80482
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    2 Bed 2 Bath w/ Mountain Views and Garage Parking #KingsCrossing1 / 27
    (11)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    New 2BR + Loft Winter Park Condo w/ Serene Forest and Creek Views!1 / 19
    (27)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Winter Park, Grand County 80446
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Amazing Decor | Two Lounges | Private Hot Tub | Slope Views1 / 38
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Winter Park, Grand County 80482
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Retreat in ♥ of Downtown WP | Pet-Friendly | Pool + Hot Tub | Views of the Park!1 / 34
    (5)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Winter Park, Grand County 80482
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Mtn Modern Cabin | 1 Mile To Resort | 2 Lounge Areas | Sleeps 11 | Lots to Love1 / 37
    (6)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Winter Park, Grand County 80482
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 11
    Family Luxury | Stunning Mtn Views | Theater Room | Pets Welcome!1 / 43
    (4)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Winter Park, Grand County 80482
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    Modern Downtown Condo | See The Park | Pool + Hot Tub | One Level1 / 42
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Cozy condo w/ shared hot tubs, pool, sauna, gym, and game room1 / 31
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 7
    Joanna Gaines Would Want to Stay Here: Barnwood, High End Touches, Super Chic, V1 / 40
    (18)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Gorgeous Condo | Private Views from Balcony | Pool + Hot Tub + Clubhouse!1 / 38
    (53)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Winter Park, Grand County 80482
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Family-friendly condo w/private hot tub & fireplace - near skiing1 / 32
    (5)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Modern Pet Friendly Townhome | Downtown | Private Hot Tub | Steps from Shops & M1 / 34
    (3)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 9
    Above Downtown WP | Huge Deck & Hot Tub | Mtn Furnishings | Sleeps 81 / 23
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Spacious 3Bd Townhome | Ski In\Ski Out | Base Area Amenities | Views of Divide1 / 38
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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