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Winter Park Vacation Rentals

Anytime
Guests
Anytime
Guests
Choose from 170 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 $225 per night
House ∙ 10 guests ∙ 4 bedrooms

204 m² House

5.0
Outstanding(115 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $255 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 $210 per night
House ∙ 4 guests ∙ 2 bedrooms

167 m² House

4.9
Outstanding(36 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 $99 per night
House ∙ 4 guests ∙ 2 bedrooms

82 m² House

4.8
Outstanding(7 ratings)
Winter Park, Orange County, Florida, United States
Pet-friendly
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House Winter Park
from $257 per night
8 guests ∙ 3 bedrooms

House

4.5
Excellent(41 ratings)
Winter Park, Orange County, Florida, United States
Pet-friendly
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House Winter Park
from $266 per night
House ∙ 8 guests ∙ 4 bedrooms

209 m² House

4.2
Very good(19 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

Condo Winter Park
from $138 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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House Winter Park
from $383 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 $279 per night
8 guests ∙ 4 bedrooms

House

Winter Park, Orange County, Florida, United States
Pool
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See all offers with pool

Best vacation rental offers in Winter Park

House Winter Park
from $115 per night
House ∙ 6 guests ∙ 2 bedrooms

260 m² House

4.5
Excellent(12 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $160 per night
4 guests ∙ 2 bedrooms

Apartment

5.0
Outstanding(139 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $191 per night
House ∙ 5 guests ∙ 3 bedrooms

151 m² House

5.0
Outstanding(46 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $301 per night
House ∙ 6 guests ∙ 3 bedrooms

195 m² House

5.0
Outstanding(10 ratings)
Winter Park, Orange County, Florida, United States
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Condo Winter Park
from $289 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 $159 per night
6 guests ∙ 2 bedrooms

House

4.7
Excellent(41 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $180 per night
6 guests ∙ 3 bedrooms

House

5.0
Outstanding(30 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $686 per night
6 guests ∙ 3 bedrooms

House

Winter Park, Orange County, Florida, United States
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House Winter Park
from $408 per night
12 guests ∙ 4 bedrooms

House

5.0
Outstanding(6 ratings)
Winter Park, Orange County, Florida, United States
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Cabin Winter Park
from $95 per night
2 guests ∙ 1 bedroom

Cabin

Winter Park, Orange County, Florida, United States
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House Winter Park
from $177 per night
2 guests ∙ 1 bedroom

House

Winter Park, Orange County, Florida, United States
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Condo Winter Park
from $446 per night
4 guests ∙ 2 bedrooms

Condo

Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $108 per night
2 guests ∙ 1 bedroom

Apartment

5.0
Outstanding(1 rating)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $96 per night
Apartment ∙ 3 guests ∙ 2 bedrooms

84 m² Apartment

4.6
Excellent(5 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $149 per night
4 guests ∙ 2 bedrooms

House

5.0
Outstanding(3 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $128 per night
House ∙ 4 guests ∙ 2 bedrooms

79 m² House

5.0
Outstanding(8 ratings)
Winter Park, Orange County, Florida, United States
View deal
House Winter Park
from $358 per night
House ∙ 8 guests ∙ 3 bedrooms

139 m² House

3.0
(1 rating)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $177 per night
House ∙ 4 guests ∙ 2 bedrooms

143 m² House

Winter Park, Orange County, Florida, United States
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Cabin Winter Park
from $141 per night
Cabin ∙ 5 guests ∙ 2 bedrooms

93 m² Cabin

5.0
Outstanding(36 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $217 per night
House ∙ 5 guests ∙ 3 bedrooms

1049 m² House

4.9
Outstanding(18 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $331 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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Apartment Winter Park
from $211 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

181 m² Apartment

5.0
Outstanding(8 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $327 per night
House ∙ 8 guests ∙ 4 bedrooms

186 m² House

4.7
Excellent(23 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $179 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

104 m² Apartment

4.0
Very good(2 ratings)
Winter Park, Orange County, Florida, United States
View deal
House Winter Park
from $228 per night
4 guests ∙ 2 bedrooms

House

4.9
Outstanding(19 ratings)
Winter Park, Orange County, Florida, United States
View deal
House Winter Park
from $167 per night
4 guests ∙ 2 bedrooms

House

5.0
Outstanding(2 ratings)
Winter Park, Orange County, Florida, United States
View deal
House Winter Park
from $120 per night
4 guests ∙ 2 bedrooms

House

4.9
Outstanding(57 ratings)
Winter Park, Orange County, Florida, United States
View deal
Apartment Winter Park
from $165 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

88 m² Apartment

4.7
Excellent(6 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $130 per night
Apartment ∙ 2 guests ∙ 1 bedroom

84 m² Apartment

Winter Park, Orange County, Florida, United States
View deal
House Winter Park
from $177 per night
4 guests ∙ 2 bedrooms

House

4.8
Outstanding(37 ratings)
Winter Park, Orange County, Florida, United States
View deal
Show all 171 apartments in Winter Park

And we love our apartments

260 m² House
Apartment
151 m² House
195 m² House
102 m² Condo
Show all 171 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 49 rentals
🌙 Minimum price starting at $95
🐾 Pet friendly vacation homes 83 rentals
🏡 Rentals available 170 rentals

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