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

Vacation rentals in Winter Garden

Browse 211 available vacation homes and compared across 8 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+

  • 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 213 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Mobile home Winter Garden
Mobile home ∙ 5 guests ∙ 2 bedrooms

Mobile home with 2 rooms for 5 persons

Winter Garden, Orange County, Florida, United States
This RV rental in Winter Garden accommodates five guests and offers a unique way to explore the area's outdoor adventures.
from $137
per night
from $137
per night
View deal
Cabin Winter Garden
Cabin ∙ 4 guests ∙ 1 bedroom

Cottage with patio & garden

Winter Garden, Orange County, Florida, United States
This Winter Garden cabin offers a kitchen, yard, and parking, perfect for a family getaway with space for four guests.
from $141
per night
Outstanding(81 ratings)
from $141
per night
View deal
House Winter Garden
House ∙ 4 guests ∙ 2 bedrooms

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

Winter Garden, Orange County, Florida, United States
This Winter Garden house rental features a kitchen, yard, and parking, perfect for a family getaway with pets.
from $155
per night
Outstanding(33 ratings)
from $155
per night
View deal
Apartment Winter Garden
Apartment ∙ 3 guests ∙ 1 bedroom

Holiday apartment for 3 persons

Winter Garden, Orange County, Florida, United States
This Winter Garden apartment rental features a kitchen and parking, perfect for a getaway with friends or family.
from $92
per night
Outstanding(5 ratings)
from $92
per night
View deal
House Winter Garden
House ∙ 4 guests ∙ 2 bedrooms

Fully equipped house

Winter Garden, Orange County, Florida, United States
This house rental in Winter Garden features a kitchen and parking, perfect for a getaway with family or friends.
from $164
per night
Excellent(8 ratings)
from $164
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
This house rental in Winter Garden features a kitchen, yard, and parking, perfect for hosting up to 10 guests.
from $266
per night
from $266
per night
View deal
Villa Winter Garden
Villa ∙ 5 guests ∙ 2 bedrooms

Villa with barbecue, yard & patio | Suitable for remote work

Winter Garden, Orange County, Florida, United States
This villa in Winter Garden features a kitchen, fireplace, yard, and parking, perfect for families and pets alike.
from $143
per night
Outstanding(8 ratings)
from $143
per night
View deal
Apartment Winter Garden
Apartment ∙ 6 guests ∙ 2 bedrooms

Apartment with pool

Winter Garden, Orange County, Florida, United States
This Winter Garden apartment rental features a pool, kitchen, balcony, and parking, perfect for a getaway with family or friends.
from $216
per night
Outstanding(6 ratings)
from $216
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
This Winter Garden apartment rental features a pool, parking, and space for four, perfect for a fun-filled getaway.
from $165
per night
Outstanding(16 ratings)
from $165
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
This Winter Garden house rental offers a perfect retreat for four, blending comfort with easy access to local attractions.
from $186
per night
Outstanding(10 ratings)
from $186
per night
View deal
Apartment Winter Garden
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment | City view

Winter Garden, Orange County, Florida, United States
This Winter Garden apartment rental features a kitchen and parking, perfect for a cozy getaway for two.
from $87
per night
Outstanding(4 ratings)
from $87
per night
View deal
House Winter Garden
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with yard & patio

Winter Garden, Orange County, Florida, United States
This house rental in Winter Garden features a kitchen, family-friendly spaces, and a yard, perfect for gatherings of up to 10.
from $369
per night
Excellent(22 ratings)
from $369
per night
View deal
Cabin Winter Garden
Cabin ∙ 4 guests ∙ 1 bedroom

Family-oriented cottage with patio & yard

Winter Garden, Orange County, Florida, United States
This Winter Garden cabin features a kitchen, parking, and family-friendly space for up to four guests to relax and unwind.
from $148
per night
Outstanding(81 ratings)
from $148
per night
View deal
House Winter Garden
House ∙ 4 guests ∙ 2 bedrooms

Child-friendly vacation home with terrace, yard & barbeque | Perfect for remote work

Winter Garden, Orange County, Florida, United States
This cozy house rental in Winter Garden features a kitchen, yard, and parking, perfect for a family getaway of up to four.
from $175
per night
Outstanding(195 ratings)
from $175
per night
View deal
Apartment Winter Garden
Apartment ∙ 4 guests ∙ 1 bedroom

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

Winter Garden, Orange County, Florida, United States
This Winter Garden apartment rental features a pool, kitchen, balcony, and parking, perfect for a family getaway for four.
from $196
per night
Outstanding(4 ratings)
from $196
per night
View deal

Vacation houses with Balconies or Patios

Apartment Winter Garden
from $196
per night
Apartment ∙ 4 guests ∙ 1 bedroom

Apartment with pool | City view | Perfect for remote work

5.0
Outstanding(2 ratings)
Winter Garden, Orange County, Florida, United States
Balcony/Patio
View deal
Apartment Winter Garden
from $187
per night
Apartment ∙ 4 guests ∙ 1 bedroom

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

4.4
Very good(3 ratings)
Winter Garden, Orange County, Florida, United States
Balcony/Patio
View deal
Apartment Winter Garden
from $83
per night
Apartment ∙ 2 guests ∙ 1 bedroom

Rental apartment with patio

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

Vacation rentals and apartments with air conditioning

House Winter Garden
from $229
per night
House ∙ 4 guests ∙ 2 bedrooms

Family-friendly vacation home

4.6
Excellent(25 ratings)
Winter Garden, Orange County, Florida, United States
Air conditioning
View deal
House Winter Garden
from $121
per night
House ∙ 4 guests ∙ 1 bedroom

House with yard, patio & barbeque

5.0
Outstanding(237 ratings)
Winter Garden, Orange County, Florida, United States
Air conditioning
View deal
Cabin Winter Garden
from $180
per night
Cabin ∙ 4 guests ∙ 2 bedrooms

Family-friendly pleasant cottage with yard & patio | Suitable for remote work

4.8
Outstanding(224 ratings)
Winter Garden, Orange County, Florida, United States
Air conditioning
View deal
See all offers

Vacation rentals with a balcony

Villa Winter Garden
from $267
per night
Villa ∙ 11 guests ∙ 5 bedrooms

Family-oriented villa with yard, heated pool & barbecue | Pets are welcome

Winter Garden, Orange County, Florida, United States
Balcony
View deal
House Winter Garden
from $226
per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with barbeque & garden | Suitable for remote work

4.9
Outstanding(19 ratings)
Winter Garden, Orange County, Florida, United States
Balcony
View deal
House Winter Garden
from $130
per night
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped house with garden

5.0
Outstanding(1 rating)
Winter Garden, Orange County, Florida, United States
Balcony
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 $81
per night
Apartment ∙ 2 guests ∙ 1 bedroom

Holiday apartment for 2 persons

Winter Garden, Orange County, Florida, United States
View deal
Apartment Winter Garden
from $84
per night
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment for 2 persons

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

Nice rental apartment with 1 room for 2 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

Cabin Winter Garden
from $95
per night
Cabin ∙ 4 guests ∙ 1 bedroom

Cottage with terrace, yard & grill | Lake view | Good for workation

5.0
Outstanding(2 ratings)
Winter Garden, Orange County, Florida, United States
View deal
House Winter Garden
from $58
per night
House ∙ 2 guests ∙ 1 bedroom

Vacation home with hot tub, private pool & garden

4.8
Outstanding(42 ratings)
Winter Garden, Orange County, Florida, United States
View deal
Villa Winter Garden
from $112
per night
Villa ∙ 5 guests ∙ 2 bedrooms

Child-friendly villa with yard & heated pool

4.7
Excellent(22 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 $189
per night
Cabin ∙ 4 guests ∙ 2 bedrooms
4.8
Outstanding(224 ratings)
Winter Garden, Orange County, Florida, United States
View deal

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Popular Features & Amenities in Winter Garden

  • Pet-friendly (103)
  • Pool (175)
  • Air conditioning (246)
  • WiFi (246)
  • Kitchen (198)
  • Washing machine (127)
  • TV (230)
  • Parking (15)
  • Microwave (203)
  • Balcony/patio (65)
  • Dishwasher (159)
  • Yard (63)

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 7, as that is the number of people they can usually accommodate. Among these properties, 30 of them are located within 2 miles of water.

Information about vacation rentals in Winter Garden

🏡 Vacation rentals available 213 rentals
🌙 Nightly prices starting at $81
⭐ Popular amenities Pets allowed, Pool and Air conditioning
🐾 Pet friendly homes 79 homes
🏊 Vacation rentals with pools 138 homes
2 reviews
Winter Garden vacation rentals have an average rating of 4/5 on 2 reviews left by travelers.

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 $81. $194 is the average nightly price for apartment rentals in Winter Garden. House rentals in Winter Garden cost $279 per night on average.

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

There are currently 213 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 138 rentals across 8 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 79 pet-friendly available.

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