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Winter Park Vacation Rentals

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Choose from 163 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 $212 per night
House ∙ 6 guests ∙ 2 bedrooms

Family-friendly ample house with terrace & yard | Lake view | Good for workation | Dogs allowed

4.8
Outstanding(40 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $411 per night
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped pleasant vacation home with garden, jacuzzi & patio

5.0
Outstanding(19 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $299 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with hot tub, grill & terrace | Lake view | Suitable for remote work

5.0
Outstanding(10 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 $223 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with private pool, yard & terrace

4.1
Very good(30 ratings)
Winter Park, Orange County, Florida, United States
Pet-friendly
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House Winter Park
from $204 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with 3 bedrooms for 6 persons

Winter Park, Orange County, Florida, United States
Pet-friendly
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Apartment Winter Park
from $147 per night
Apartment ∙ 5 guests ∙ 2 bedrooms

Children-friendly holiday apartment with heated pool, BBQ & patio | City view | Suitable for remote work | Pets allowed

5.0
Outstanding(5 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 $190 per night
House ∙ 5 guests ∙ 3 bedrooms

House with BBQ, terrace & yard | Good for workation

5.0
Outstanding(46 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

House with terrace, garden & private pool | City view | Perfect for remote work

5.0
Outstanding(8 ratings)
Winter Park, Orange County, Florida, United States
Pool
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House Winter Park
from $342 per night
House ∙ 8 guests ∙ 4 bedrooms

Family-friendly vacation home with grill, private pool & patio | Pet-friendly

4.9
Outstanding(153 ratings)
Winter Park, Orange County, Florida, United States
Pool
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Best vacation rental offers in Winter Park

House Winter Park
from $118 per night
House ∙ 4 guests ∙ 2 bedrooms

Family-oriented house

4.9
Outstanding(57 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $176 per night
House ∙ 4 guests ∙ 2 bedrooms

House with yard & patio

4.8
Outstanding(37 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $291 per night
House ∙ 4 guests ∙ 2 bedrooms

Family-oriented big vacation home with barbecue, yard & terrace | Lake view | Suitable for remote work

5.0
Outstanding(4 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $71 per night
Apartment ∙ 3 guests ∙ 2 bedrooms

Rental apartment with garden | Pets allowed

4.7
Excellent(6 ratings)
Winter Park, Orange County, Florida, United States
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Cabin Winter Park
from $142 per night
Cabin ∙ 5 guests ∙ 2 bedrooms

Cottage with patio, BBQ & garden | City view

5.0
Outstanding(37 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $191 per night
House ∙ 4 guests ∙ 2 bedrooms

Family-friendly lovely vacation home with yard | City view | Pet-friendly

4.9
Outstanding(21 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $275 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Family-oriented apartment with pool | Nature view | Suitable for remote work | Pet-friendly

5.0
Outstanding(5 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $119 per night
House ∙ 4 guests ∙ 2 bedrooms

House with garden & patio | Dogs allowed

5.0
Outstanding(7 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $133 per night
Apartment ∙ 7 guests ∙ 3 bedrooms

Children-friendly wonderful holiday apartment

Winter Park, Orange County, Florida, United States
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House Winter Park
from $252 per night
House ∙ 8 guests ∙ 3 bedrooms

Family-oriented lovely vacation home with yard, patio & barbecue | City view | Dogs allowed

Winter Park, Orange County, Florida, United States
View deal
Apartment Winter Park
from $128 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Family-oriented pleasant holiday apartment with garden, heated pool & patio | City view | Suitable for remote work | Pets are welcome

5.0
Outstanding(1 rating)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $106 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Fully equipped lovely apartment with barbecue & terrace | Pets are welcome

5.0
Outstanding(2 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $176 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Rental apartment with BBQ, garden & heated pool | City view | Good for workation

4.0
Very good(2 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $150 per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with 2 bedrooms for 4 persons

4.6
Excellent(4 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $120 per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with 2 bedrooms for 4 persons

Winter Park, Orange County, Florida, United States
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House Winter Park
from $109 per night
House ∙ 4 guests ∙ 2 bedrooms

Family-friendly house | Suitable for remote work | Pets allowed

Winter Park, Orange County, Florida, United States
View deal
Apartment Winter Park
from $189 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Holiday apartment with terrace, heated pool & BBQ | City view | Suitable for remote work

5.0
Outstanding(4 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $148 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment with heated pool, terrace & barbecue

5.0
Outstanding(1 rating)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $335 per night
House ∙ 12 guests ∙ 4 bedrooms

House with barbecue & jacuzzi | City view

5.0
Outstanding(14 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $285 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with grill

4.3
Very good(7 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $277 per night
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped charming house with heated pool & garden | Good for workation | Pets are welcome

Winter Park, Orange County, Florida, United States
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Condo Winter Park
from $138 per night
Condo ∙ 2 guests ∙ 1 bedroom

Fully equipped condo with pool & patio | City view

5.0
Outstanding(1 rating)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $211 per night
House ∙ 4 guests ∙ 2 bedrooms

House with 2 bedrooms for 4 persons

Winter Park, Orange County, Florida, United States
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House Winter Park
from $180 per night
House ∙ 2 guests ∙ 1 bedroom

Fully equipped vacation home with terrace & jacuzzi

Winter Park, Orange County, Florida, United States
View deal
Apartment Winter Park
from $133 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Children-friendly lovely holiday apartment with heated pool | Perfect for remote work | Pet-friendly

5.0
Outstanding(1 rating)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $709 per night
House ∙ 6 guests ∙ 3 bedrooms

House with 3 bedrooms for 6 persons

Winter Park, Orange County, Florida, United States
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House Winter Park
from $618 per night
House ∙ 10 guests ∙ 5 bedrooms

House with 5 bedrooms for 10 persons

Winter Park, Orange County, Florida, United States
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Apartment Winter Park
from $160 per night
Apartment ∙ 4 guests ∙ 3 bedrooms

Family-friendly rental apartment with yard & terrace | Nature view | Good for workation

5.0
Outstanding(150 ratings)
Winter Park, Orange County, Florida, United States
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Villa Winter Park
from $96 per night
Villa ∙ 4 guests ∙ 2 bedrooms

Villa with 2 bedrooms for 4 persons

3.5
Good(4 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
from $130 per night
House ∙ 2 guests ∙ 1 bedroom

Charming vacation home with garden

Winter Park, Orange County, Florida, United States
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Show all 167 apartments in Winter Park

And we love our apartments

Family-oriented house
House with yard & patio
Family-oriented big vacation home with barbecue, yard & terrace | Lake view | Suitable for remote work
Rental apartment with garden | Pets allowed
Cottage with patio, BBQ & garden | City view
Show all 167 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 51 rentals
🌙 Minimum price starting at $56
🐾 Pet friendly vacation homes 78 rentals
🏡 Rentals available 163 rentals

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