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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
from $108 per night
House ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding (51 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $106 per night
House ∙ 6 guests ∙ 2 bedrooms
4.8
Outstanding (8 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $169 per night
House ∙ 9 guests ∙ 3 bedrooms
5.0
Outstanding (2 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

House Winter Park
from $268 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (4 ratings)
Winter Park, Orange County, Florida, United States
Pet-friendly
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House Winter Park
from $138 per night
House ∙ 5 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
Pet-friendly
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House Winter Park
from $151 per night
House ∙ 8 guests ∙ 4 bedrooms
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
from $68 per night
House ∙ 2 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
Internet
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HomeToGo
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House Winter Park
from $112 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
from $207 per night
House ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding (30 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

House Winter Park
from $258 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (4 ratings)
Winter Park, Orange County, Florida, United States
Pool
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House Winter Park
from $230 per night
House ∙ 8 guests ∙ 4 bedrooms
4.0
Very good (1 rating)
Winter Park, Orange County, Florida, United States
Pool
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House Winter Park
from $323 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (117 ratings)
Winter Park, Orange County, Florida, United States
Pool
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Best vacation rental offers in Winter Park

House Winter Park
from $116 per night
House ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
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Bed and breakfast Winter Park
from $124 per night
Bed and breakfast ∙ 5 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
Details
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House Winter Park
from $89 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (2 ratings)
Winter Park, Orange County, Florida, United States
Details
HomeToGo
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Cottage Winter Park
from $186 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (59 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $128 per night
Apartment ∙ 6 guests ∙ 1 bedroom
5.0
Outstanding
Winter Park, Orange County, Florida, United States
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Vacasa
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Apartment Winter Park
from $179 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (103 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $176 per night
House ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding (36 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $278 per night
House ∙ 12 guests ∙ 4 bedrooms
5.0
Outstanding (37 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $122 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
from $361 per night
House ∙ 8 guests ∙ 4 bedrooms
4.9
Outstanding (133 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $391 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (8 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $405 per night
House ∙ 10 guests ∙ 4 bedrooms
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $170 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding (35 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $221 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (8 ratings)
Winter Park, Orange County, Florida, United States
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Cottage Winter Park
from $147 per night
Cottage ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding (33 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $186 per night
Apartment ∙ 8 guests ∙ 2 bedrooms
4.5
Excellent (13 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $176 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding (31 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $152 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $152 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (4 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $126 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
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House Winter Park
from $238 per night
House ∙ 6 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
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House Winter Park
from $186 per night
House ∙ 6 guests ∙ 2 bedrooms
4.8
Outstanding (21 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $146 per night
Apartment ∙ 3 guests ∙ 1 bedroom
5.0
Outstanding (4 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $347 per night
House ∙ 8 guests ∙ 4 bedrooms
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $190 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
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House Winter Park
from $183 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (2 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $200 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding (9 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $149 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
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House Winter Park
from $179 per night
House ∙ 6 guests ∙ 3 bedrooms
3.0
(3 ratings)
Winter Park, Orange County, Florida, United States
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Condo Winter Park
from $295 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
from $330 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (4 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $235 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
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House Winter Park
from $122 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (7 ratings)
Winter Park, Orange County, Florida, United States
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Condo Winter Park
from $438 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
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House Winter Park
from $192 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (25 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $133 per night
House ∙ 6 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
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House Winter Park
from $154 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (2 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $147 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
4.7
Excellent (6 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $292 per night
House ∙ 8 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
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View all 177 apartments in Winter Park

And we love our apartments

102 m² House
Winter Park charm
82 m² House
93 m² Cottage
60 m² Apartment
View all 177 apartments in Winter Park

Features of Winter Park vacation rentals

💳 Discounts up to 10%
⭐ Popular amenities Pets allowed, Pool and Internet
🏊  Vacation rentals with a pool 50 rentals
🌙 Minimum price starting at $80
🐾 Pet friendly vacation homes 63 rentals
🏡 Rentals available 176 rentals

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