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

Vacation rentals in Winter Garden

Find 293 available house rentals from 9 partners
Anytime
Guests
Anytime
Guests

  • 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
    • Smoking allowed

  • Activities

    • Grill
    • Fishing

Top 15 Recommended vacation rentals in Winter Garden

Find your perfect vacation rental in Winter Garden from just $59 per night!

House Winter Garden
House ∙ 4 guests ∙ 2 bedrooms

Family-friendly vacation home

Winter Garden, Orange County, Florida, United States
from $225
per night
from $225
per night
View deal
House Winter Garden
House ∙ 6 guests ∙ 3 bedrooms

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

Winter Garden, Orange County, Florida, United States
from $145
per night
Outstanding(21 ratings)
from $145
per night
View deal
House Winter Garden
House ∙ 10 guests ∙ 4 bedrooms

Family-oriented vacation home with pool & grill

Winter Garden, Orange County, Florida, United States
from $159
per night
from $159
per night
View deal
Apartment Winter Garden
Apartment ∙ 2 guests ∙ 1 bedroom

Child-friendly pleasant apartment with garden, barbeque & patio | Suitable for remote work

Winter Garden, Orange County, Florida, United States
from $93
per night
Outstanding(3 ratings)
from $93
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 $342
per night
Outstanding(5 ratings)
from $342
per night
View deal
Apartment Winter Garden
Apartment ∙ 2 guests ∙ 1 bedroom

Rental apartment with yard | Perfect for remote work

Winter Garden, Orange County, Florida, United States
from $77
per night
Outstanding(16 ratings)
from $77
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
from $139
per night
Outstanding(4 ratings)
from $139
per night
View deal
House Winter Garden
House ∙ 2 guests ∙ 1 bedroom

Nice house with garden

Winter Garden, Orange County, Florida, United States
from $71
per night
Excellent(23 ratings)
from $71
per night
View deal
Condo Winter Garden
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with heated pool, hot tub & terrace

Winter Garden, Orange County, Florida, United States
from $192
per night
from $192
per night
View deal
Apartment Winter Garden
Apartment ∙ 3 guests ∙ 1 bedroom

Apartment with 1 room for 3 persons

Winter Garden, Orange County, Florida, United States
from $66
per night
Outstanding(4 ratings)
from $66
per night
View deal
Cottage Winter Garden
Cottage ∙ 7 guests ∙ 3 bedrooms

Cottage with 3 rooms for 7 persons

Winter Garden, Orange County, Florida, United States
from $178
per night
from $178
per night
View deal
Cottage Winter Garden
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage with terrace & yard | Good for workation

Winter Garden, Orange County, Florida, United States
from $184
per night
Outstanding(109 ratings)
from $184
per night
View deal
Cottage Winter Garden
Cottage ∙ 4 guests ∙ 1 bedroom

Family-oriented cottage with patio

Winter Garden, Orange County, Florida, United States
from $149
per night
Outstanding(26 ratings)
from $149
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
from $172
per night
Outstanding(96 ratings)
from $172
per night
View deal
House Winter Garden
House ∙ 4 guests ∙ 1 bedroom

House with terrace, yard & grill

Winter Garden, Orange County, Florida, United States
from $140
per night
Outstanding(122 ratings)
from $140
per night
View deal

Vacation rentals and apartments with air conditioning

Cottage Winter Garden
from $176
per night
Cottage ∙ 4 guests ∙ 3 bedrooms

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

4.8
Outstanding(109 ratings)
Winter Garden, Orange County, Florida, United States
Air conditioning
View deal
Cottage Winter Garden
from $156
per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage with patio

4.9
Outstanding(26 ratings)
Winter Garden, Orange County, Florida, United States
Air conditioning
View deal
House Winter Garden
from $131
per night
House ∙ 4 guests ∙ 2 bedrooms

House with yard, patio & barbeque

5.0
Outstanding(122 ratings)
Winter Garden, Orange County, Florida, United States
Air conditioning
View deal
See all offers

Vacation rentals with a balcony

Villa Winter Garden
from $406
per night
Villa ∙ 8 guests ∙ 2 bedrooms

Villa with pool

Winter Garden, Orange County, Florida, United States
Balcony
View deal
Apartment Winter Garden
from $156
per night
Apartment ∙ 5 guests ∙ 8 bedrooms

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

Winter Garden, Orange County, Florida, United States
Balcony
View deal
Apartment Winter Garden
from $158
per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Lovely rental apartment with pool | City view

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

Vacation Rentals With Fireplaces

House Winter Garden
from $164
per night
House ∙ 4 guests ∙ 3 bedrooms

Family-friendly lovely vacation home with grill, garden & patio | Good for workation

4.9
Outstanding(96 ratings)
Winter Garden, Orange County, Florida, United States
Fireplace
View deal
House Winter Garden
from $178
per night
House ∙ 3 guests ∙ 1 bedroom

Charming vacation home with barbecue, yard & terrace | Lake view

5.0
Outstanding(8 ratings)
Winter Garden, Orange County, Florida, United States
Fireplace
View deal
House Winter Garden
from $226
per night
House ∙ 6 guests ∙ 1 bedroom

Vacation home with pool | City view | Pets are welcome

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

Budget-friendly Vacation Rentals in Winter Garden

Find Fantastic yet Inexpensive Offers

House Winter Garden
from $145
per night
House ∙ 2 guests ∙ 1 bedroom

House with 1 room for 2 persons

Winter Garden, Orange County, Florida, United States
View deal
House Winter Garden
from $272
per night
House ∙ 4 guests ∙ 2 bedrooms

Beautiful vacation home with 2 rooms for 4 persons

Winter Garden, Orange County, Florida, United States
View deal
Apartment Winter Garden
from $101
per night
Apartment ∙ 2 guests ∙ 1 bedroom

Rental apartment with 1 room for 2 persons

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

Bed and breakfast Winter Garden
from $150
per night
Bed and breakfast ∙ 8 guests ∙ 1 bedroom

Lovely bed & breakfast with patio & garden

4.6
Excellent
Winter Garden, Orange County, Florida, United States
View deal
Bed and breakfast Winter Garden
from $157
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with terrace & garden

4.7
Excellent(273 ratings)
Winter Garden, Orange County, Florida, United States
View deal
Bed and breakfast Winter Garden
from $159
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with yard & patio

4.7
Excellent(273 ratings)
Winter Garden, Orange County, Florida, United States
View deal

Customer ratings and reviews

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
Cottage Winter Garden
from $182
per night
HomeToGo
Cottage ∙ 4 guests ∙ 2 bedrooms
4.8
Outstanding(109 ratings)
Winter Garden, Orange County, Florida, United States
View deal

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Popular Rental Amenities in Winter Garden

  • Pet-friendly (103)
  • Pool (173)
  • Air conditioning (275)
  • WiFi (280)
  • Kitchen (199)
  • Washing machine (130)
  • TV (250)
  • Parking (15)
  • Microwave (223)
  • Balcony/patio (74)
  • Dishwasher (151)
  • Yard (86)

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, 42 of them are located within 2 miles of water.

Information about vacation rentals in Winter Garden

🏡 Vacation rentals available 293 rentals
💳 Possible discounts up to 79%
🌙 Nightly prices starting at $59
⭐ Popular amenities Pets allowed, Pool and Air conditioning
🐾 Pet friendly homes 107 homes
🏊 Vacation rentals with pools 173 homes
203,154 reviews
Winter Garden vacation rentals have an average rating of 4.5/5 on 203,154 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 $59. Nightly prices for house rentals are $271 on average. Apartment rentals in Winter Garden cost $164 per night on average.

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

There are currently 293 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 173 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 - 37% of vacation homes are pet-friendly.

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