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

Vacation rentals in Winter Garden

Browse 135 available vacation homes and compared across 6 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 135 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Apartment Winter Garden
Apartment ∙ 4 guests ∙ 1 bedroom

Fully equipped beautiful rental apartment with yard & 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 $149
per night
Outstanding(31 ratings)
from $149
per night
View deal
Mobile home Winter Garden
Mobile home ∙ 5 guests ∙ 2 bedrooms

Mobile home with 2 bedrooms 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 $94
per night
from $94
per night
View deal
Cabin Winter Garden
Cabin ∙ 6 guests ∙ 3 bedrooms

Family-friendly nice cottage with garden

Winter Garden, Orange County, Florida, United States
This Winter Garden cabin features a kitchen, yard, and parking, perfect for a family getaway with space for six guests.
from $190
per night
Outstanding(23 ratings)
from $190
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
This villa in Winter Garden features a hot tub, fireplace, and a yard, perfect for family gatherings and pets.
from $121
per night
Outstanding(28 ratings)
from $121
per night
View deal
House Winter Garden
House ∙ 6 guests ∙ 3 bedrooms

Child-friendly charming vacation home with terrace, yard & barbecue | City view | Good for workation | Pets allowed

Winter Garden, Orange County, Florida, United States
This Winter Garden house rental features a yard, fireplace, and kitchen, perfect for families and pets, accommodating up to six guests.
from $172
per night
Outstanding(25 ratings)
from $172
per night
View deal
Villa Winter Garden
Villa ∙ 8 guests ∙ 2 bedrooms

Villa with jacuzzi & pool

Winter Garden, Orange County, Florida, United States
This Winter Garden villa features a pool, kitchen, balcony, and parking, accommodating up to 8 guests for a perfect getaway.
from $394
per night
from $394
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 $265
per night
Excellent(23 ratings)
from $265
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 $147
per night
Outstanding(8 ratings)
from $147
per night
View deal
House Winter Garden
House ∙ 6 guests ∙ 2 bedrooms

House with barbeque & garden

Winter Garden, Orange County, Florida, United States
This Winter Garden house rental offers parking and welcomes pets, making it the perfect retreat for up to six guests.
from $209
per night
Outstanding(9 ratings)
from $209
per night
View deal
House Winter Garden
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly nice house with garden, grill & private pool | Perfect for remote work | Pets allowed

Winter Garden, Orange County, Florida, United States
This waterfront house rental in Winter Garden features a kitchen, fireplace, yard, and balcony, perfect for family gatherings.
from $417
per night
Outstanding(50 ratings)
from $417
per night
View deal
Apartment Winter Garden
Apartment ∙ 6 guests ∙ 2 bedrooms

Holiday apartment with barbecue & yard | Suitable for remote work

Winter Garden, Orange County, Florida, United States
This waterfront apartment in Winter Garden features a kitchen, yard, and balcony, perfect for families and pets alike.
from $133
per night
Outstanding(39 ratings)
from $133
per night
View deal
House Winter Garden
House ∙ 5 guests ∙ 2 bedrooms

Vacation home with BBQ & garden | Good for workation

Winter Garden, Orange County, Florida, United States
This waterfront apartment in Winter Garden features a kitchen, fireplace, and balcony, perfect for families and pets alike.
from $150
per night
Excellent(19 ratings)
from $150
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 $241
per night
Outstanding(6 ratings)
from $241
per night
View deal
House Winter Garden
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped house | Dogs allowed

Winter Garden, Orange County, Florida, United States
This Winter Garden house rental offers a kitchen, parking, and pet-friendly space for up to 8 guests looking to unwind.
from $264
per night
Outstanding(4 ratings)
from $264
per night
View deal
House Winter Garden
House ∙ 4 guests ∙ 2 bedrooms

Wonderful house with 2 bedrooms 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 $210
per night
Outstanding(15 ratings)
from $210
per night
View deal

Vacation rentals and apartments with air conditioning

Apartment Winter Garden
from $241
per night
Apartment ∙ 4 guests ∙ 1 bedroom

Family-friendly apartment with pool | City view | Suitable for remote work

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

Vacation home | City view

Winter Garden, Orange County, Florida, United States
Air conditioning
View deal
House Winter Garden
from $125
per night
House ∙ 3 guests ∙ 1 bedroom

Vacation home | City view

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

Vacation Rentals With Saunas

Condo Winter Garden
from $322
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with sauna, garden & patio | Nature view

3.9
Good(24 ratings)
Winter Garden, Orange County, Florida, United States
Sauna
View deal
Condo Winter Garden
from $155
per night
Condo ∙ 7 guests ∙ 2 bedrooms

Family-oriented wonderful condo with barbecue, private pool & patio | Lake view | Suitable for remote work

3.0
(1 rating)
Winter Garden, Orange County, Florida, United States
Sauna
View deal
Condo Winter Garden
from $140
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with hot tub, sauna & grill

4.0
Very good(2 ratings)
Winter Garden, Orange County, Florida, United States
Sauna
View deal
See all offers

Apartments and vacation rentals with a kitchen

House Winter Garden
from $162
per night
House ∙ 5 guests ∙ 2 bedrooms

Vacation home with pool

4.8
Outstanding(46 ratings)
Winter Garden, Orange County, Florida, United States
Kitchen
View deal
House Winter Garden
from $258
per night
House ∙ 10 guests ∙ 3 bedrooms

Fully equipped house with terrace & private pool | Good for workation

4.7
Excellent(79 ratings)
Winter Garden, Orange County, Florida, United States
Kitchen
View deal
House Winter Garden
from $102
per night
House ∙ 4 guests ∙ 2 bedrooms

House with garden & terrace | Suitable for remote work

5.0
Outstanding(31 ratings)
Winter Garden, Orange County, Florida, United States
Kitchen
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 $107
per night
Apartment ∙ 2 guests ∙ 1 bedroom

Nice rental apartment with 1 bedroom for 2 persons

Winter Garden, Orange County, Florida, United States
View deal
Bed and breakfast Winter Garden
from $156
per night
Bed and breakfast ∙ 5 guests ∙ 1 bedroom

Wonderful bed and breakfast with yard & pool

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(52 ratings)
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 $158
per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with grill & garden | City view

4.6
Excellent(25 ratings)
Winter Garden, Orange County, Florida, United States
View deal
Villa Winter Garden
from $106
per night
Villa ∙ 5 guests ∙ 2 bedrooms

Child-friendly villa with yard & heated pool

4.8
Outstanding(24 ratings)
Winter Garden, Orange County, Florida, United States
View deal
House Winter Garden
from $103
per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with pool

4.9
Outstanding(21 ratings)
Winter Garden, Orange County, Florida, United States
View deal

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Verified reviews

Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

Price clarity, no surprises

Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

Smart search made simple

Transform vacation planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

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 13, as that is the number of people they can usually accommodate. Among these properties, 20 of them are located within 2 miles of water.

Information about vacation rentals in Winter Garden

🏡 Vacation rentals available 135 rentals
🌙 Nightly prices starting at $92
⭐ Popular amenities Pets allowed, Pool and Air conditioning
🐾 Pet friendly homes 64 homes
🏊 Vacation rentals with pools 66 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 $92. $236 is the average nightly price for apartment rentals in Winter Garden. House rentals in Winter Garden cost $262 per night on average.

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

There are currently 135 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 66 rentals across 6 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 64 pet-friendly available.

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