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

Vacation rentals in Winter Garden

Find 266 available vacation homes
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
    • Fireplace
    • Crib
    Show more

  • Accommodation type

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

  • Activities

    • Grill
    • Fishing

Top 15 Recommended vacation rentals in Winter Garden

Find your perfect vacation rental in Winter Garden from just $64 per night!

Mobile home Winter Garden
Mobile home ∙ 4 guests ∙ 1 bedroom

Mobile home with barbecue

Winter Garden, Orange County, Florida, United States
from $177
per night
from $177
per night
View deal
House Winter Garden
House ∙ 4 guests ∙ 2 bedrooms

Vacation home | Good for workation

Winter Garden, Orange County, Florida, United States
from $256
per night
from $256
per night
View deal
Apartment Winter Garden
Apartment ∙ 2 guests ∙ 1 bedroom

Holiday apartment with garden & terrace | Good for workation

Winter Garden, Orange County, Florida, United States
from $86
per night
from $86
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 $64
per night
Outstanding(5 ratings)
from $64
per night
View deal
House Winter Garden
House ∙ 8 guests ∙ 2 bedrooms

Fully equipped wonderful house with pool & jacuzzi

Winter Garden, Orange County, Florida, United States
from $287
per night
from $287
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 $232
per night
Outstanding(31 ratings)
from $232
per night
View deal
House Winter Garden
House ∙ 4 guests ∙ 2 bedrooms

Fully equipped house

Winter Garden, Orange County, Florida, United States
from $168
per night
from $168
per night
View deal
House Winter Garden
House ∙ 5 guests ∙ 2 bedrooms

Children-friendly lovely vacation home

Winter Garden, Orange County, Florida, United States
from $153
per night
Outstanding(3 ratings)
from $153
per night
View deal
House Winter Garden
House ∙ 4 guests ∙ 2 bedrooms

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

Winter Garden, Orange County, Florida, United States
from $157
per night
Outstanding(98 ratings)
from $157
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 $141
per night
Outstanding(14 ratings)
from $141
per night
View deal
Cabin Winter Garden
Cabin ∙ 7 guests ∙ 3 bedrooms

Family-friendly nice cottage with garden | Pets allowed

Winter Garden, Orange County, Florida, United States
from $168
per night
Outstanding(21 ratings)
from $168
per night
View deal
Apartment Winter Garden
Apartment ∙ 3 guests ∙ 1 bedroom

Holiday apartment | Perfect for remote work

Winter Garden, Orange County, Florida, United States
from $76
per night
Outstanding(18 ratings)
from $76
per night
View deal
House Winter Garden
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly nice house with garden, terrace & grill | Lake view | Perfect for remote work | Pets allowed

Winter Garden, Orange County, Florida, United States
from $464
per night
Outstanding(43 ratings)
from $464
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 $198
per night
from $198
per night
View deal
House Winter Garden
House ∙ 4 guests ∙ 2 bedrooms

Family-friendly vacation home

Winter Garden, Orange County, Florida, United States
from $223
per night
from $223
per night
View deal

Vacation rentals and apartments with air conditioning

Cabin Winter Garden
from $179
per night
Cabin ∙ 7 guests ∙ 3 bedrooms

Cottage with 3 rooms for 7 persons

Winter Garden, Orange County, Florida, United States
Air conditioning
View deal
House Winter Garden
from $135
per night
House ∙ 4 guests ∙ 1 bedroom

House with yard, patio & barbeque

5.0
Outstanding(126 ratings)
Winter Garden, Orange County, Florida, United States
Air conditioning
View deal
Cabin Winter Garden
from $144
per night
Cabin ∙ 4 guests ∙ 1 bedroom

Cottage with patio

5.0
Outstanding(29 ratings)
Winter Garden, Orange County, Florida, United States
Air conditioning
View deal
See all offers

Vacation houses with Balconies or Patios

Villa Winter Garden
from $375
per night
Villa ∙ 8 guests ∙ 2 bedrooms

Villa with pool

Winter Garden, Orange County, Florida, United States
Balcony/Patio
View deal
Apartment Winter Garden
from $172
per night
Apartment ∙ 5 guests ∙ 7 bedrooms

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

Winter Garden, Orange County, Florida, United States
Balcony/Patio
View deal
House Winter Garden
from $179
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
Balcony/Patio
View deal
See all offers

Vacation Rentals With Fireplaces

House Winter Garden
from $176
per night
House ∙ 4 guests ∙ 1 bedroom

Pleasant vacation home | Dogs allowed

Winter Garden, Orange County, Florida, United States
Fireplace
View deal
House Winter Garden
from $160
per night
House ∙ 4 guests ∙ 1 bedroom

House | Perfect for remote work | Pets are welcome

Winter Garden, Orange County, Florida, United States
Fireplace
View deal
House Winter Garden
from $164
per night
House ∙ 4 guests ∙ 1 bedroom

Lovely house 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 $222
per night
House ∙ 7 guests ∙ 3 bedrooms

House with 3 rooms for 7 persons

Winter Garden, Orange County, Florida, United States
View deal
House Winter Garden
from $149
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 $186
per night
House ∙ 4 guests ∙ 2 bedrooms

Wonderful house with 2 rooms for 4 persons

5.0
Outstanding(1 rating)
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 $154
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with terrace & garden

4.7
Excellent(274 ratings)
Winter Garden, Orange County, Florida, United States
View deal
Bed and breakfast Winter Garden
from $191
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Charming bed and breakfast with garden & terrace

4.7
Excellent(274 ratings)
Winter Garden, Orange County, Florida, United States
View deal
Apartment Winter Garden
from $76
per night
Apartment ∙ 3 guests ∙ 1 bedroom

Holiday apartment | Suitable for remote work

4.8
Outstanding(10 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
Cabin Winter Garden
from $184
per night
HomeToGo
Cabin ∙ 4 guests ∙ 2 bedrooms
4.8
Outstanding(109 ratings)
Winter Garden, Orange County, Florida, United States
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 (31)
  • Pool (25)
  • Air conditioning (117)
  • WiFi (118)
  • Kitchen (83)
  • Washing machine (63)
  • TV (109)
  • Parking (3)
  • Microwave (85)
  • Balcony/patio (50)
  • Dishwasher (57)
  • Yard (52)

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 10, 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 266 rentals
🌙 Nightly prices starting at $64
⭐ Popular amenities Pets allowed, Pool and Air conditioning
🐾 Pet friendly homes 102 homes
🏊 Vacation rentals with pools 161 homes

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 $64. Nightly prices for house rentals are $270 on average. Apartment rentals in Winter Garden cost $167 per night on average.

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

There are currently 266 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 161 rentals from 9 providers in Winter Garden.

Are pets allowed in vacation homes in Winter Garden?

If you are traveling with a dog in Winter Garden - 38% of vacation homes are pet-friendly.

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