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Winter Park Holiday Rentals

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1661 rentals in Winter Park.
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The Cottage on Lake Fairview, Orlando.
3 bedrooms
2 bathrooms
Sleeps 6
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1 other traveller has booked this property
Championsgate 58 - villa with pool, game room and theater room near Disney
8 bedrooms
5 bathrooms
Sleeps 20
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Winter Park-College Park-Orlando-1
1 bedroom
1 bathroom
Sleeps 2
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6 other travellers have booked this property
Winter Park-College Park-Orlando -2
1 bedroom
1 bathroom
Sleeps 2
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3 other travellers have booked this property
'Lakeside' in old Winter Park (exclusive 32789zip)
4 bedrooms
4 bathrooms
Sleeps 8
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2 other travellers have booked this property
2br - 1000ft2 - Winter Park House
2 bedrooms
2 bathrooms
Sleeps 5
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3 other travellers have booked this property
Casa Aloma - Elegant Winter Park House with Great Pool and Huge Backyard!!
3 bedrooms
3 bathrooms
Sleeps 9
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Casa Justine
3 bedrooms
3 bathrooms
Sleeps 9
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Walk to Park Ave Shops, Restaurants, LiveTheater, Farmers Mrkt, & Lakefront walk
2 bedrooms
2 bathrooms
Sleeps 5
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A Rare Jewel - Steps to Park Ave, Shops, Restaurants, Rollins college, Farmers m
3 bedrooms
2 bathrooms
Sleeps 6
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Just Like Home... With A Pool!
3 bedrooms
2 bathrooms
Sleeps 6
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Mid-Century Modern Gem
2 bedrooms
1 bathroom
Sleeps 6
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Mid Century Luxury, 1 block from Park Ave (#3)
2 bedrooms
1 bathroom
Sleeps 5
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Stroll to Park Avenue from Vintage Lake-View House
2 bedrooms
2 bathrooms
Sleeps 6
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Fantastically Exclusive - Temporarily Reduced
2 bedrooms
2 bathrooms
Sleeps 6
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Family home with flexible schedule
3 bedrooms
2 bathrooms
Sleeps 5
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Beautiful Retreat in the Heart of Winter Park - Office, Patio, Hammock & More!
2 bedrooms
2 bathrooms
Sleeps 4
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Charming, Historic Spanish Mission Cottage in heart of Winter Park
2 bedrooms
2 bathrooms
Sleeps 4
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Mid Century Luxury, 1 block from Park Ave (#2)
2 bedrooms
1 bathroom
Sleeps 5
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Cute bungalow minutes walk from Park Avenue.
2 bedrooms
2 bathrooms
Sleeps 4
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Luxury vacation place in Winter Park Garden
2 bedrooms
3 bathrooms
Sleeps 4
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SPACIOUS CONDO CLOSE TO UCF, FULL SAIL & ROLLINS
2 bedrooms
1 bathroom
Sleeps 4
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$ Picasso Villa $ Ultra Luxurious Abstract Villa
4 bedrooms
3 bathrooms
Sleeps 10
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Vista Cay Luxury Condo 3 bed/2 bath (#3030)
3 bedrooms
2 bathrooms
Sleeps 8
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1 other traveller has booked this property
Vista Cay Luxury Condo 3 bed/2 bath (#3015)
3 bedrooms
2 bathrooms
Sleeps 6
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3 other travellers have booked this property
Vista Cay Standard Condo 3 bed/2 bath (#3040)
3 bedrooms
2 bathrooms
Sleeps 6
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Vista Cay Townhome..Luxury Resort..Great Location!
3 bedrooms
4 bathrooms
Sleeps 8
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11 other travellers have booked this property
3 Bed Condo - WQRrentals - Disney just 1 Mile - from $100/nt
3 bedrooms
2 bathrooms
Sleeps 6
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58 other travellers have booked this property
Exceptional Vista Cay Townhouse Close to OCCC/SeaWorld and Universal
3 bedrooms
4 bathrooms
Sleeps 6
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4 other travellers have booked this property
Wheelchair Accessible Home, with Pool and Spa
Highlands Reserve
5 bedrooms
3 bathrooms
Sleeps 10
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15 other travellers have booked this property
Lakefront Townhouse 5 Star LOCATION
2 bedrooms
2 bathrooms
Sleeps 6
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15 other travellers have booked this property
Magnificent Central Condo - Disney/Universal/OCCC
3 bedrooms
2 bathrooms
Sleeps 8
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16 other travellers have booked this property
Villa Sogna Vista Cay Lakefront/Penthouse Condo O
3 bedrooms
2 bathrooms
Sleeps 8
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5 other travellers have booked this property
Villa Bella Vista Cay Penthouse/Lakefront Condo Overlooking the Pool & Lake Cay
3 bedrooms
2 bathrooms
Sleeps 8
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Luxurious
3 bedrooms
4 bathrooms
Sleeps 8
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1 other traveller has booked this property
Vista Cay Luxury Condo 3 bed/2 bath (#3068)
3 bedrooms
2 bathrooms
Sleeps 10
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4 other travellers have booked this property
Vista Cay Luxury 3 bedroom condo #3066
3 bedrooms
2 bathrooms
Sleeps 8
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1 other traveller has booked this property
Secluded Pool, hot tub and backyard for privacy
5 bedrooms
4 bathrooms
Sleeps 12
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20 other travellers have booked this property
Luxurious, Lakefront, Poolside Condo @ Vista Cay
3 bedrooms
2 bathrooms
Sleeps 8
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2 Bed Condo - WQRrentals - Disney just 1 Mile - from $90/nt
2 bedrooms
2 bathrooms
Sleeps 4
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49 other travellers have booked this property
Fantastic Designer Townhome Vista Cay Orlando
3 bedrooms
4 bathrooms
Sleeps 7
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44 other travellers have booked this property
EXECTIVE PLUS BLUELAKEVIEW with Private Pool & Spa with Conservation Views
4 bedrooms
3 bathrooms
Sleeps 8
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12 other travellers have booked this property
Tuscan Hills
4 bedrooms
3 bathrooms
Sleeps 8
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38 other travellers have booked this property
Beautiful Luxury Lakeside Penthouse Vista Cay
3 bedrooms
2 bathrooms
Sleeps 6
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49 other travellers have booked this property
Beautiful Outstanding Luxury Vista Cay Villa
3 bedrooms
4 bathrooms
Sleeps 6
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35 other travellers have booked this property
Luxury Condo at Hotel prices - Isles of Cay Commons
3 bedrooms
2 bathrooms
Sleeps 8
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5 other travellers have booked this property
4 Bed Kissimmee Orlando House in Resort - Disney
4 bedrooms
3 bathrooms
Sleeps 10
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African Paradise-Vista Cay-Lake/Pool/Disney/Univer
4 bedrooms
2 bathrooms
Sleeps 8
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Most Beautiful Oustanding 3/BR Condo Orlando
3 bedrooms
2 bathrooms
Sleeps 6
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28 other travellers have booked this property
Superb Florida Villa: 7 Beds 5min from Disney
7 bedrooms
5 bathrooms
Sleeps 16
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3 other travellers have booked this property
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