Vacation rentals in Winter Garden - HomeToGo base64Hash Vacation rentals in Winter Garden - HomeToGo

Vacation rentals in Winter Garden

Browse 261 available vacation homes and compared across 9 trusted partners
Anytime
Guests
Anytime
Guests

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • House
    • Apartment
    • Bed and breakfast

  • Distance to center

    • 1 mi
    • 2 mi
    • 3 mi

  • Rating

    • 4.5+
    • 4+

  • Booking Options

    • Instant Booking

  • Services

    • Pool
    • Air conditioning
    • WiFi
    • Kitchen
    • Washing machine
    • TV
    • Parking
    • Microwave
    • Balcony/patio
    • Dishwasher
    • Yard
    • Hot tub
    • Fireplace
    • Crib
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • Wheelchair access
    • No pets

  • Activities

    • Grill
    • Fishing

Top 15 most Recommended Vacation Rentals in Winter Garden

Discover your ideal Winter Garden vacation rental with real-time comparisons of 263 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Winter Garden
House ∙ 4 guests ∙ 2 bedrooms

Vacation home | Good for workation

Winter Garden, Orange County, Florida, United States
from $309
per night
from $309
per night
View deal
House Winter Garden
House ∙ 10 guests ∙ 3 bedrooms

Vacation home with garden | Suitable for remote work

Winter Garden, Orange County, Florida, United States
from $172
per night
from $172
per night
View deal
Apartment Winter Garden
Apartment ∙ 6 guests ∙ 2 bedrooms

Holiday apartment with terrace, barbecue & yard | Lake view | Suitable for remote work

Winter Garden, Orange County, Florida, United States
from $164
per night
Outstanding(21 ratings)
from $164
per night
View deal
Apartment Winter Garden
Apartment ∙ 4 guests ∙ 1 bedroom

Fully equipped beautiful rental apartment with pool | Nature view

Winter Garden, Orange County, Florida, United States
from $128
per night
Outstanding(1 rating)
from $128
per night
View deal
Apartment Winter Garden
Apartment ∙ 3 guests ∙ 1 bedroom

Holiday apartment for 3 persons

Winter Garden, Orange County, Florida, United States
from $81
per night
Outstanding(1 rating)
from $81
per night
View deal
House Winter Garden
House ∙ 4 guests ∙ 2 bedrooms

Fully equipped lovely house | Good for workation

Winter Garden, Orange County, Florida, United States
from $200
per night
from $200
per night
View deal
Apartment Winter Garden
Apartment ∙ 2 guests ∙ 1 bedroom

Holiday apartment for 2 persons

Winter Garden, Orange County, Florida, United States
from $82
per night
from $82
per night
View deal
House Winter Garden
House ∙ 2 guests ∙ 1 bedroom

House with 1 room for 2 persons

Winter Garden, Orange County, Florida, United States
from $149
per night
from $149
per night
View deal
Apartment Winter Garden
Apartment ∙ 4 guests ∙ 2 bedrooms

Family-oriented lovely rental apartment with pool | City view | Perfect for remote work

Winter Garden, Orange County, Florida, United States
from $204
per night
Outstanding(1 rating)
from $204
per night
View deal
House Winter Garden
House ∙ 6 guests ∙ 2 bedrooms

House with barbeque

Winter Garden, Orange County, Florida, United States
from $235
per night
Outstanding(1 rating)
from $235
per night
View deal
Villa Winter Garden
Villa ∙ 8 guests ∙ 3 bedrooms

Family-oriented spacious villa with barbecue, patio & hot tub | Pets allowed

Winter Garden, Orange County, Florida, United States
from $150
per night
Outstanding(28 ratings)
from $150
per night
View deal
Apartment Winter Garden
Apartment ∙ 3 guests ∙ 1 bedroom

Family-oriented charming rental apartment with garden | Suitable for remote work | Pet-friendly

Winter Garden, Orange County, Florida, United States
from $123
per night
Outstanding(14 ratings)
from $123
per night
View deal
House Winter Garden
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with yard & patio

Winter Garden, Orange County, Florida, United States
from $250
per night
Excellent(15 ratings)
from $250
per night
View deal
House Winter Garden
House ∙ 4 guests ∙ 2 bedrooms

Family-friendly big vacation home with terrace, garden & grill | Nature view | Suitable for remote work | Pets are welcome

Winter Garden, Orange County, Florida, United States
from $171
per night
Outstanding(32 ratings)
from $171
per night
View deal
House Winter Garden
House ∙ 4 guests ∙ 2 bedrooms

Wonderful house with 2 rooms for 4 persons

Winter Garden, Orange County, Florida, United States
from $212
per night
Outstanding(2 ratings)
from $212
per night
View deal

Vacation rentals with a balcony

Apartment Winter Garden
from $152
per night
Apartment ∙ 5 guests ∙ 7 bedrooms

Rental apartment with BBQ, garden & patio | Lake view | Good for workation

3.5
Good(2 ratings)
Winter Garden, Orange County, Florida, United States
Balcony
View deal
Apartment Winter Garden
from $268
per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Family-oriented spacious holiday apartment with pool | City view | Suitable for remote work

Winter Garden, Orange County, Florida, United States
Balcony
View deal
Apartment Winter Garden
from $296
per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment with pool | City view | Perfect for remote work

Winter Garden, Orange County, Florida, United States
Balcony
View deal
See all offers

Vacation Rentals With Fireplaces

Lodge Winter Garden
from $185
per night
Lodge ∙ 4 guests ∙ 1 bedroom

Lodge with barbeque

Winter Garden, Orange County, Florida, United States
Fireplace
View deal
House Winter Garden
from $318
per night
House ∙ 4 guests ∙ 2 bedrooms

Beautiful vacation home with 2 rooms for 4 persons

Winter Garden, Orange County, Florida, United States
Fireplace
View deal
Mobile home Winter Garden
from $150
per night
Mobile home ∙ 4 guests ∙ 1 bedroom

Mobile home with barbecue

Winter Garden, Orange County, Florida, United States
Fireplace
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Winter Garden offering exceptional value for money

Apartment Winter Garden
from $103
per night
Apartment ∙ 2 guests ∙ 1 bedroom

Rental apartment with patio

Winter Garden, Orange County, Florida, United States
View deal
Apartment Winter Garden
from $223
per night
Apartment ∙ 5 guests ∙ 1 bedroom

Beautiful rental apartment with 1 room for 5 persons

Winter Garden, Orange County, Florida, United States
View deal
House Winter Garden
from $183
per night
House ∙ 4 guests ∙ 1 bedroom

Vacation home with 1 room for 4 persons

Winter Garden, Orange County, Florida, United States
View deal

Top-Rated Vacation rentals in Winter Garden

Book the highest-rated Winter Garden vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Winter Garden
from $227
per night
House ∙ 10 guests ∙ 4 bedrooms

House with garden & barbeque

4.7
Excellent(28 ratings)
Winter Garden, Orange County, Florida, United States
View deal
House Winter Garden
from $123
per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with pool

4.8
Outstanding(14 ratings)
Winter Garden, Orange County, Florida, United States
View deal
House Winter Garden
from $211
per night
House ∙ 20 guests ∙ 4 bedrooms

Fully equipped wonderful vacation home

5.0
Outstanding(12 ratings)
Winter Garden, Orange County, Florida, United States
View deal

Discover real guest reviews to help you choose the perfect stay in Winter Garden

How are reviews collected?
MARSHA S.
Guest verified by HomeToGo

Great little cottage in a wonderful location. It was fine for two people. We were comfortable and it was clean and decorated just as the pictures showed. Only issue was the double bed.

Reviewed on 4/7/2025 | Couple
Cabin Winter Garden
from $191
per night
Cabin ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding(219 ratings)
Winter Garden, Orange County, Florida, United States
View deal

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Find your dream stay

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Popular Features & Amenities in Winter Garden

  • Pet-friendly (103)
  • Pool (186)
  • Air conditioning (252)
  • WiFi (260)
  • Kitchen (189)
  • Washing machine (141)
  • TV (231)
  • Parking (17)
  • Microwave (213)
  • Balcony/patio (66)
  • Dishwasher (155)
  • Yard (74)

You will find a great selection of properties to compare and choose from if you are looking for a vacation rental including a pool in Winter Garden. Additionally, more Apartment rental have pools than any other property type. They are an excellent choice if you go in a group of 5, as that is the number of people they can usually accommodate. Among these properties, 43 of them are located within 2 miles of water.

Information about vacation rentals in Winter Garden

🏡 Vacation rentals available 263 rentals
🌙 Nightly prices starting at $83
⭐ Popular amenities Pets allowed, Pool and Air conditioning
🐾 Pet friendly homes 103 homes
🏊 Vacation rentals with pools 187 homes

Frequently Asked Questions

What is the average nightly price for a vacation home in Winter Garden?

The price of a night's stay in Winter Garden starts at $83. $180 is the average nightly price for apartment rentals in Winter Garden. House rentals in Winter Garden cost $264 per night on average.

How many vacation rentals are available for booking in Winter Garden?

There are currently 263 vacation homes to choose from for your vacation.

What amenities are most popular for vacation rentals in Winter Garden?

Travelers look for Pets allowed, Pool, and Air conditioning when booking a vacation rental in Winter Garden.

How many vacation homes with a pool are there in Winter Garden?

There are 187 rentals across 9 providers in Winter Garden.

Are pets allowed in vacation rentals in Winter Garden?

Finding a rental in Winter Garden that allows pets is definitely possible, with 103 pet-friendly available.

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