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Winter Park Vacation Rentals

Anytime
Guests
Anytime
Guests
Choose from 198 vacation rentals and homes for your trip!

Best-rated vacation rentals in Winter Park

Discover vacation rentals with top-notch guest ratings

House Winter Park
from $192 per night
House ∙ 10 guests ∙ 4 bedrooms

204 m² House

5.0
Outstanding(117 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $95 per night
4 guests ∙ 2 bedrooms

House

4.9
Outstanding(55 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $162 per night
4 guests ∙ 2 bedrooms

House

4.8
Outstanding(37 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 $97 per night
House ∙ 4 guests ∙ 2 bedrooms

82 m² House

5.0
Outstanding(2 ratings)
Winter Park, Orange County, Florida, United States
Pet-friendly
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House Winter Park
from $222 per night
House ∙ 8 guests ∙ 4 bedrooms

209 m² House

4.3
Very good(16 ratings)
Winter Park, Orange County, Florida, United States
Pet-friendly
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House Winter Park
from $146 per night
House ∙ 4 guests ∙ 2 bedrooms

125 m² House

4.9
Outstanding(31 ratings)
Winter Park, Orange County, Florida, United States
Pet-friendly
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See all pet-friendly offers

Vacation rentals with pool in Winter Park

Discover best cabin and house rentals with pool in Winter Park

House Winter Park
from $384 per night
House ∙ 6 guests ∙ 3 bedrooms

233 m² House

5.0
Outstanding(8 ratings)
Winter Park, Orange County, Florida, United States
Pool
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House Winter Park
from $212 per night
House ∙ 5 guests ∙ 3 bedrooms

151 m² House

5.0
Outstanding(46 ratings)
Winter Park, Orange County, Florida, United States
Pool
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Condo Winter Park
from $139 per night
Condo ∙ 2 guests ∙ 1 bedroom

73 m² Condo

5.0
Outstanding(2 ratings)
Winter Park, Orange County, Florida, United States
Pool
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Best vacation rental offers in Winter Park

House Winter Park
from $233 per night
4 guests ∙ 2 bedrooms

House

4.9
Outstanding(18 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $263 per night
House ∙ 6 guests ∙ 2 bedrooms

232 m² House

4.8
Outstanding(40 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $253 per night
8 guests ∙ 4 bedrooms

House

Winter Park, Orange County, Florida, United States
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House Winter Park
from $241 per night
House ∙ 6 guests ∙ 3 bedrooms

195 m² House

5.0
Outstanding(5 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $196 per night
6 guests ∙ 3 bedrooms

House

5.0
Outstanding(27 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $256 per night
House ∙ 5 guests ∙ 3 bedrooms

1049 m² House

4.8
Outstanding(15 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $122 per night
House ∙ 2 guests ∙ 1 bedroom

88 m² House

Winter Park, Orange County, Florida, United States
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Cabin Winter Park
from $154 per night
Cabin ∙ 5 guests ∙ 2 bedrooms

93 m² Cabin

5.0
Outstanding(33 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $151 per night
4 guests ∙ 2 bedrooms

House

5.0
Outstanding(3 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $166 per night
4 guests ∙ 2 bedrooms

Apartment

5.0
Outstanding(128 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $259 per night
House ∙ 7 guests ∙ 3 bedrooms

93 m² House

Winter Park, Orange County, Florida, United States
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House Winter Park
from $97 per night
House ∙ 4 guests ∙ 2 bedrooms

83 m² House

5.0
Outstanding(6 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $292 per night
House ∙ 4 guests ∙ 2 bedrooms

181 m² House

5.0
Outstanding(4 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $197 per night
6 guests ∙ 3 bedrooms

House

Winter Park, Orange County, Florida, United States
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House Winter Park
from $166 per night
4 guests ∙ 2 bedrooms

House

5.0
Outstanding(2 ratings)
Winter Park, Orange County, Florida, United States
View deal
Condo Winter Park
from $259 per night
Condo ∙ 5 guests ∙ 2 bedrooms

102 m² Condo

5.0
Outstanding(40 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $245 per night
House ∙ 6 guests ∙ 3 bedrooms

139 m² House

Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $169 per night
Apartment ∙ 5 guests ∙ 2 bedrooms

74 m² Apartment

5.0
Outstanding(37 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $166 per night
4 guests ∙ 2 bedrooms

House

Winter Park, Orange County, Florida, United States
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House Winter Park
from $126 per night
8 guests ∙ 4 bedrooms

House

Winter Park, Orange County, Florida, United States
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House Winter Park
from $355 per night
10 guests ∙ 3 bedrooms

House

5.0
Outstanding(30 ratings)
Winter Park, Orange County, Florida, United States
View deal
Apartment Winter Park
from $170 per night
Apartment ∙ 5 guests ∙ 2 bedrooms

74 m² Apartment

5.0
Outstanding(32 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $206 per night
6 guests ∙ 3 bedrooms

House

Winter Park, Orange County, Florida, United States
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House Winter Park
from $184 per night
6 guests ∙ 3 bedrooms

House

3.0
(4 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $268 per night
10 guests ∙ 3 bedrooms

House

Winter Park, Orange County, Florida, United States
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House Winter Park
from $152 per night
8 guests ∙ 3 bedrooms

House

Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $81 per night
Apartment ∙ 3 guests ∙ 2 bedrooms

84 m² Apartment

4.5
Excellent(4 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $167 per night
6 guests ∙ 2 bedrooms

House

4.8
Outstanding(36 ratings)
Winter Park, Orange County, Florida, United States
View deal
House Winter Park
from $253 per night
8 guests ∙ 3 bedrooms

House

Winter Park, Orange County, Florida, United States
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House Winter Park
from $178 per night
2 guests ∙ 1 bedroom

House

Winter Park, Orange County, Florida, United States
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Show all 195 apartments in Winter Park

And we love our apartments

House
232 m² House
House
195 m² House
House
Show all 195 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 52 rentals
🌙 Minimum price starting at $81
🐾 Pet friendly vacation homes 82 rentals
🏡 Rentals available 198 rentals

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