Winter Garden Vacation Rentals - HomeToGo base64Hash Winter Garden Vacation Rentals - HomeToGo

Winter Garden Vacation Rentals

Find 261 available offers from 8 partners
Anytime
1 guest
Anytime
1 guest

  • Price per night

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

  • Accommodation types

    • Condo
    • House
    • Apartment

  • Distance to center

    • 1 km
    • 2 km
    • 5 km

  • 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

Recommended vacation rentals in Winter Garden

Find your perfect vacation rental in Winter Garden from just $54 per night!

House Winter Garden
-59%
Mar 1 - Mar 8
House ∙ 4 guests ∙ 2 bedrooms

House with Grill, Patio & Yard

Winter Garden, Orange County, Florida, United States
$274$149
per night
Outstanding(118 ratings)
$274$149
per night
View deal
Bed and breakfast Winter Garden
-25%
Mar 22 - Mar 29
Bed and breakfast ∙ 8 guests ∙ 1 bedroom

Nice Bed & Breakfast with Yard & Terrace

Winter Garden, Orange County, Florida, United States
$235$176
per night
Excellent
$235$176
per night
View deal
Resort Winter Garden
-33%
Jan 4 - Jan 11
Resort ∙ 127 guests ∙ 2 bedrooms

Lovely Resort with Pool, Patio & Jacuzzi

Winter Garden, Orange County, Florida, United States
$169$124
per night
Good
$169$124
per night
View deal
Resort Winter Garden
-64%
Feb 24 - Mar 3
Resort ∙ 127 guests ∙ 1 bedroom

Resort with Hot Tub, Pool & Sauna

Winter Garden, Orange County, Florida, United States
$1,044$191
per night
Excellent
$1,044$191
per night
View deal
Resort Winter Garden
Jan 9 - Jan 16
Resort ∙ 127 guests ∙ 1 bedroom

Resort with Terrace, Pool & Hot Tub

Winter Garden, Orange County, Florida, United States
$678
per night
Excellent
$678
per night
View deal
House Winter Garden
Apr 26 - May 3
House ∙ 7 guests ∙ 3 bedrooms

House with Patio, Pool & Grill | Perfect for Remote Work

Winter Garden, Orange County, Florida, United States
$186
per night
Outstanding(3 ratings)
$186
per night
View deal
Cottage Winter Garden
Apr 22 - Apr 29
Cottage ∙ 5 guests ∙ 2 bedrooms

Cottage with Pool & Barbeque | Lake View

Winter Garden, Orange County, Florida, United States
$112
per night
Outstanding(57 ratings)
$112
per night
View deal
Condo Winter Garden
-57%
Jan 11 - Jan 18
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with Jacuzzi, Pool & Barbecue

Winter Garden, Orange County, Florida, United States
$248$116
per night
Very good
$248$116
per night
View deal
Cottage Winter Garden
-55%
Feb 1 - Feb 8
Cottage ∙ 4 guests ∙ 1 bedroom

Child-Friendly Cottage with Patio

Winter Garden, Orange County, Florida, United States
$279$140
per night
Outstanding(26 ratings)
$279$140
per night
View deal
Cottage Winter Garden
-59%
Jan 9 - Jan 16
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage with Terrace

Winter Garden, Orange County, Florida, United States
$258$148
per night
Outstanding(26 ratings)
$258$148
per night
View deal
House Winter Garden
-53%
Apr 26 - May 3
House ∙ 4 guests ∙ 3 bedrooms

Family-Oriented Wonderful House with Terrace, Grill & Garden | Perfect for Remote Work

Winter Garden, Orange County, Florida, United States
$334$182
per night
Outstanding(97 ratings)
$334$182
per night
View deal
Cottage Winter Garden
-56%
Sep 13 - Sep 20
Free cancellation
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage with Garden & Patio | Good for Workation

Winter Garden, Orange County, Florida, United States
$366$181
per night
Outstanding(104 ratings)
$366$181
per night
View deal
House Winter Garden
-55%
Feb 8 - Feb 15
Free cancellation
House ∙ 4 guests ∙ 2 bedrooms

Family-Friendly Vacation Home with Garden, Barbeque & Terrace | Perfect for Remote Work

Winter Garden, Orange County, Florida, United States
$334$172
per night
Outstanding(97 ratings)
$334$172
per night
View deal
Cottage Winter Garden
-59%
Jan 11 - Jan 18
Cottage ∙ 7 guests ∙ 3 bedrooms

Cottage with 3 Rooms for 7 Persons

Winter Garden, Orange County, Florida, United States
$402$200
per night
$402$200
per night
View deal
House Winter Garden
-50%
Mar 8 - Mar 15
Free cancellation
House ∙ 4 guests ∙ 2 bedrooms

Family-Friendly Vacation Home

Winter Garden, Orange County, Florida, United States
$393$221
per night
$393$221
per night
View deal

Vacation homes and rentals with a yard

House Winter Garden
May 3 - May 10
-56%
$354
$172
per night
House ∙ 5 guests ∙ 2 bedrooms

House with Garden

5.0
Outstanding(3 ratings)
Winter Garden, Orange County, Florida, United States
Free cancellation
Yard
View deal
Studio flat Winter Garden
Jan 7 - Jan 14
-50%
$124
$68
per night
Studio flat ∙ 4 guests ∙ 1 bedroom

Studio with Garden, Pool & Jacuzzi

Winter Garden, Orange County, Florida, United States
Free cancellation
Yard
View deal
House Winter Garden
Jan 27 - Feb 3
$400
per night
House ∙ 10 guests ∙ 5 bedrooms

Child-Friendly Vacation Home with Barbeque, Terrace & Private Pool | Near Harry Potter and the Forbidden Journey

3.8
Good(19 ratings)
Winter Garden, Orange County, Florida, United States
Yard
View deal
See all offers

Apartments With Balconies or Patios

Private room Winter Garden
Dec 28 - Jan 4
$92
per night
Private room ∙ 2 guests ∙ 1 bedroom

Private Room with Grill & Patio

Winter Garden, Orange County, Florida, United States
Balcony/Patio
View deal
Apartment Winter Garden
Jan 27 - Feb 3
$175
per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Holiday Apartment with Pool

4.6
Excellent(22 ratings)
Winter Garden, Orange County, Florida, United States
Balcony/Patio
View deal
Condo Winter Garden
Jan 14 - Jan 21
$107
per night
Condo ∙ 3 guests ∙ 1 bedroom

Children-Friendly Pleasant Condo with Patio, Heated Pool & Yard | Lake View | Good for Workation

4.3
Very good(8 ratings)
Winter Garden, Orange County, Florida, United States
Balcony/Patio
View deal
See all offers

Best vacation rentals with a balcony

Condo Winter Garden
Mar 1 - Mar 8
-22%
$203
$150
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Lovely Condo with Yard & Heated Pool | Lake View | Pets Are Welcome

4.0
Very good(13 ratings)
Winter Garden, Orange County, Florida, United States
Balcony
View deal
Apartment Winter Garden
Jun 14 - Jun 21
$145
per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Rental Apartment with Pool

4.7
Excellent(9 ratings)
Winter Garden, Orange County, Florida, United States
Balcony
View deal
Apartment Winter Garden
Jan 4 - Jan 11
-35%
$138
$97
per night
Apartment ∙ 4 guests ∙ 1 bedroom

Pleasant Holiday Apartment with Heated Pool, Patio & Garden | City View

4.2
Very good(18 ratings)
Winter Garden, Orange County, Florida, United States
Balcony
View deal
See all offers

Best Vacation Home Deals in Winter Garden

Save up to 75%

House Winter Garden
Jan 11 - Jan 18
-75%
$330
$83
per night
House ∙ 2 guests ∙ 3 bedrooms

Child-Friendly Spacious House

Winter Garden, Orange County, Florida, United States
View deal
Condo Winter Garden
Jan 26 - Feb 2
-41%
$170
$100
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with Pool | Lake View

Winter Garden, Orange County, Florida, United States
View deal
Apartment Winter Garden
Feb 8 - Feb 15
-71%
$353
$101
per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Apartment with Pool

5.0
Outstanding(2 ratings)
Winter Garden, Orange County, Florida, United States
Free cancellation
View deal

Choose a welcoming vacation home for as little as $54 per night by exploring the 261 rentals featured in Winter Garden. With HomeToGo, you can instantaneously search and compare the offers of each listed rental to discover the best deal and save up to 76%.

Budget-friendly Vacation Rentals in Winter Garden

Find Fantastic yet Inexpensive Offers

Apartment Winter Garden
Feb 15 - Feb 22
$162
per night
Apartment ∙ 3 guests ∙ 1 bedroom

Rental Apartment with 1 Room for 3 Persons

Winter Garden, Orange County, Florida, United States
View deal
Apartment Winter Garden
Feb 15 - Feb 22
$109
per night
Apartment ∙ 3 guests ∙ 2 bedrooms

Rental Apartment | Suitable for Remote Work

4.6
Excellent(10 ratings)
Winter Garden, Orange County, Florida, United States
View deal
House Winter Garden
Mar 22 - Mar 29
$800
per night
House ∙ 8 guests ∙ 5 bedrooms

Children-Friendly Big House with Yard, Barbecue & Patio | Lake View | Good for Workation | Pet-Friendly

5.0
Outstanding(21 ratings)
Winter Garden, Orange County, Florida, United States
View deal

Top-Rated Rentals and Accommodations in Winter Garden

Book Vacation Rental Offers with the Highest User Rating

House Winter Garden
Jan 25 - Feb 1
-48%
$561
$221
per night
House ∙ 10 guests ∙ 3 bedrooms

Vacation Home with Terrace & Private Pool | Perfect for Remote Work

4.9
Outstanding(80 ratings)
Winter Garden, Orange County, Florida, United States
Free cancellation
View deal
House Winter Garden
Feb 8 - Feb 15
$211
per night
House ∙ 8 guests ∙ 4 bedrooms

House with Garden, Private Pool & Patio | Perfect for Remote Work

4.8
Outstanding(43 ratings)
Winter Garden, Orange County, Florida, United States
View deal
House Winter Garden
Feb 15 - Feb 22
$178
per night
House ∙ 5 guests ∙ 2 bedrooms

House with Pool

4.8
Outstanding(14 ratings)
Winter Garden, Orange County, Florida, United States
Free cancellation
View deal

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Find your dream stay

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

Popular Rental Amenities in Winter Garden

  • Pet-friendly (83)
  • Pool (149)
  • Air conditioning (246)
  • WiFi (256)
  • Kitchen (174)
  • Washing machine (122)
  • TV (223)
  • Parking (15)
  • Microwave (199)
  • Balcony/patio (58)
  • Dishwasher (127)
  • Yard (92)

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 House rental have pools than any other property type. They are an excellent choice if you go in a group of 9, as that is the number of people they can usually accommodate. Among these properties, 49 of them are located within 2 miles of water.

Information about vacation rentals in Winter Garden

🏡 Vacation rentals available 261 rentals
💳 Possible discounts up to 76%
🌙 Nightly prices starting at $54
⭐ Popular amenities Pets allowed, Pool and Air conditioning
🐾 Pet friendly homes 82 homes
🏊 Vacation rentals with pools 147 homes
169,311 reviews
Winter Garden vacation rentals have an average rating of 4.5/5 on 169,311 reviews left by travelers.

Frequently Asked Questions

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

The price of a night's stay in Winter Garden starts at $54. Nightly prices for house rentals are $251 on average. Apartment rentals in Winter Garden cost $188 per night on average.

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

There are currently 261 vacation homes to choose from for your next trip.

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

Three most popular amenities for vacation rentals in Winter Garden include accommodations that have: Pets allowed, Pool, and Air conditioning.

How many vacation rentals with a pool are in Winter Garden?

There are 147 rentals from 8 providers in Winter Garden.

Are pets allowed in vacation homes in Winter Garden?

If you are traveling with a dog in Winter Garden - 31% of vacation homes are pet-friendly.

Find the perfect Winter Garden home to match your style

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