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Winter Park Vacation Rentals

Winter Park
Anytime
Guests
Winter Park
Anytime
Guests
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Best-rated vacation rentals in Winter Park

Discover vacation rentals with top-notch guest ratings

House Winter Park
$134 per night
House ∙ 5 guests ∙ 3 bedrooms
5.0
Outstanding (44 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
$201 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (1 rating)
Winter Park, Orange County, Florida, United States
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House Winter Park
$95 per night
House ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding (50 ratings)
Winter Park, Orange County, Florida, United States
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Pet-friendly rentals in Winter Park

Explore best dog-friendly accommodation offers and enjoy vacation with your pet

Apartment Winter Park
$127 per night
Apartment ∙ 6 guests ∙ 1 bedroom
5.0
Outstanding
Winter Park, Orange County, Florida, United States
Pet-friendly
Details
Vacasa
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House Winter Park
$294 per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding (32 ratings)
Winter Park, Orange County, Florida, United States
Pet-friendly
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House Winter Park
$107 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (1 rating)
Winter Park, Orange County, Florida, United States
Pet-friendly
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Accommodation with Internet in Winter Park

Choose your ideal rental with Internet and WiFi in Winter Park

House Winter Park
$160 per night
House ∙ 9 guests ∙ 3 bedrooms
5.0
Outstanding (2 ratings)
Winter Park, Orange County, Florida, United States
Internet
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House Winter Park
$207 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (2 ratings)
Winter Park, Orange County, Florida, United States
Internet
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House Winter Park
$145 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (7 ratings)
Winter Park, Orange County, Florida, United States
Internet
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Vacation rentals with pool in Winter Park

Discover best cabin and house rentals with pool in Winter Park

Apartment Winter Park
$100 per night
Apartment ∙ 8 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
Pool
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House Winter Park
$269 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (1 rating)
Winter Park, Orange County, Florida, United States
Pool
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House Winter Park
$376 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (5 ratings)
Winter Park, Orange County, Florida, United States
Pool
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Best vacation rental offers in Winter Park

Apartment Winter Park
$152 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
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House Winter Park
$147 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (2 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
$181 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (2 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
$105 per night
House ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
Details
HomeToGo
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House Winter Park
$279 per night
House ∙ 8 guests ∙ 4 bedrooms
4.4
Very good (12 ratings)
Winter Park, Orange County, Florida, United States
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Cottage Winter Park
$141 per night
Cottage ∙ 5 guests ∙ 2 bedrooms
4.9
Outstanding (32 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
$182 per night
Apartment ∙ 8 guests ∙ 2 bedrooms
4.5
Excellent (10 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
$144 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
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House Winter Park
$113 per night
House ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
$123 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
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House Winter Park
$282 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (4 ratings)
Winter Park, Orange County, Florida, United States
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Condo Winter Park
$433 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
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House Winter Park
$130 per night
House ∙ 8 guests ∙ 4 bedrooms
Winter Park, Orange County, Florida, United States
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House Winter Park
$227 per night
House ∙ 6 guests ∙ 4 bedrooms
Winter Park, Orange County, Florida, United States
Details
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House Winter Park
$161 per night
House ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
$144 per night
Apartment ∙ 3 guests ∙ 1 bedroom
5.0
Outstanding (4 ratings)
Winter Park, Orange County, Florida, United States
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Condo Winter Park
$135 per night
Condo ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding (2 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
$135 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (2 ratings)
Winter Park, Orange County, Florida, United States
Details
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House Winter Park
$161 per night
House ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
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House Winter Park
$176 per night
House ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
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House Winter Park
$157 per night
House ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding (35 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
$158 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (25 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
$131 per night
Apartment ∙ 6 guests ∙ 1 bedroom
5.0
Outstanding (21 ratings)
Winter Park, Orange County, Florida, United States
Details
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House Winter Park
$212 per night
House ∙ 12 guests ∙ 4 bedrooms
4.9
Outstanding (17 ratings)
Winter Park, Orange County, Florida, United States
Details
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Cottage Winter Park
$217 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (60 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
$272 per night
House ∙ 12 guests ∙ 4 bedrooms
5.0
Outstanding (31 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
$156 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (76 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
$143 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding (34 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
$182 per night
House ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding (14 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
$165 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding (30 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
$128 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (4 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
$107 per night
House ∙ 6 guests ∙ 2 bedrooms
4.8
Outstanding (8 ratings)
Winter Park, Orange County, Florida, United States
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Condo Winter Park
$284 per night
Condo ∙ 5 guests ∙ 2 bedrooms
4.9
Outstanding (39 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
$278 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (120 ratings)
Winter Park, Orange County, Florida, United States
Details
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House Winter Park
$135 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (6 ratings)
Winter Park, Orange County, Florida, United States
Details
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House Winter Park
$202 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (15 ratings)
Winter Park, Orange County, Florida, United States
Details
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Apartment Winter Park
$146 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (2 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
$186 per night
Apartment ∙ 8 guests ∙ 2 bedrooms
4.9
Outstanding (8 ratings)
Winter Park, Orange County, Florida, United States
Details
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House Winter Park
$135 per night
House ∙ 3 guests ∙ 1 bedroom
5.0
Outstanding (5 ratings)
Winter Park, Orange County, Florida, United States
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