A child riding a bicycle on a wooden boardwalk with a body of water and trees in the background.

Search Holiday Homes in Winter Garden

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Winter Garden holiday homes

A bedroom with a bed, a bedside table with a lamp, and a wall decorated with woven baskets.

1. Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
Winter Garden
9.6 out of 10, Exceptional, (12 reviews)
"Amazing House! Would stay again anytime!"
United States
Patrick O.
The price is £382
includes taxes & fees
25 Oct - 26 Oct
Fire Pit & Yard: Updated Winter Garden Home!
Interior

2. FunTropicalTinyHomeGolfCartLake

FunTropicalTinyHomeGolfCartLake
Winter Garden
9.2 out of 10, Wonderful, (10 reviews)
"We had a great time! The host was spectacular. Our accommodations were very clean and comfortable! "
United States
Emily R.
The price is £175
includes taxes & fees
26 Oct - 27 Oct
FunTropicalTinyHomeGolfCartLake
A spacious living area with a dining table, chairs, a sofa, and a kitchen in the background.

3. House with large deck, walking distance to Historic Downtown Winter Garden

House with large deck, walking distance to Historic Downtown Winter Garden
Winter Garden
9.8 out of 10, Exceptional, (29 reviews)
"If you need a nice place to stay in downtown Winter Garden, please consider this place. It is the perfect size for a party of 4 and it is conveniently located to downtown restaurant’s. We stayed 8 nights and could not have been happier."
United States
Sam M.
The price is £244
includes taxes & fees
28 Oct - 29 Oct
House with large deck, walking distance to Historic Downtown Winter Garden
A wooden deck with a hot tub, a wooden dock extending into a body of water, and a view of the water and sky.

4. WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn

WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
Winter Garden
10.0 out of 10, Exceptional, (34 reviews)
"Great location and a comfortable stay. "
United States
Tim S.
The price is £600
includes taxes & fees
15 Nov - 16 Nov
WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
Aerial View Of The Resort-Style Complex Featuring A Large Pool And Serene Surroundings

5. Winter Garden Family-friendly Condo w Resort Pool

Winter Garden Family-friendly Condo w Resort Pool
Winter Garden
The price is £211
includes taxes & fees
26 Oct - 27 Oct
Winter Garden Family-friendly Condo w Resort Pool
A covered outdoor swimming pool with lounge chairs and a hot tub.

6. Private Spacious Room in Home, with Pool-The Oasis Room

Private Spacious Room in Home, with Pool-The Oasis Room
Clermont
9.4 out of 10, Exceptional, (40 reviews)
"Stayed for one night and looking forward to staying again. Communication was great and place as described"
United States
Juan m.
The price is £83
includes taxes & fees
23 Oct - 24 Oct
Private Spacious Room in Home, with Pool-The Oasis Room
Private kitchen

7. Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka

Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
Apopka
9.8 out of 10, Exceptional, (8 reviews)
"Great place to stay. We plan on staying again."
United States
Nancee H.
The price is £102
includes taxes & fees
25 Oct - 26 Oct
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
Terrace/patio

8. Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.

Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.
West Lakes District
10.0 out of 10, Exceptional, (4 reviews)
"Tammie is an amazing host! Super comfy and cute tiny home! Definitely booking again!"
United States
chelsea
The price is £119
includes taxes & fees
28 Oct - 29 Oct
Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.
A decorative stone fountain with a twisted base, surrounded by vibrant red flowers and tropical foliage, set against a backdrop of a pool and palm trees.

9. Maple Leaf Inn & Suites

Maple Leaf Inn & Suites
2.5 star property
Kissimmee
6.8 out of 10, (72 reviews)
"The room was clean and the staff was okay "
United States
Shaneka
The price is £50
includes taxes & fees
25 Oct - 26 Oct
Maple Leaf Inn & Suites
A modern hotel room with a wooden bed, a desk with chairs, a patterned wall, and a window with blinds.

10. Sunshine Escape Guesthouse ☀

Sunshine Escape Guesthouse ☀
Orlando
8.8 out of 10, Excellent, (20 reviews)
"The location worked perfect for our needs in a quiet and safe area. The host was very pleasant and we had a wonderful experience dealing with him and any concerns were met and promptly taken care of. We would definitely stay there again "
United States
Robin R.
The price is £130
includes taxes & fees
25 Oct - 26 Oct
Sunshine Escape Guesthouse ☀
Exterior

11. Charming 2-bedroom apartment in house with AC, WiFi included

Charming 2-bedroom apartment in house with AC, WiFi included
Apopka
9.8 out of 10, Exceptional, (38 reviews)
"Very nice neighborhood and great accommodations. "
United States
Kevin S.
The price is £106
includes taxes & fees
25 Oct - 26 Oct
Charming 2-bedroom apartment in house with AC, WiFi included
A modern dining area with a glass table and white chairs, a pendant light, and artwork on the walls.

12. Cozy Apt w/ Pool, Hot Tub, Golf, Near Downtown!

Cozy Apt w/ Pool, Hot Tub, Golf, Near Downtown!
Ventura
8.6 out of 10, Excellent, (9 reviews)
"For the cost and location and for what we were doing, this property worked out well for us. We mainly slept showered and had breakfast in the morning and was gone for most of the day."
United States
Richard M.
The price is £155
includes taxes & fees
31 Oct - 1 Nov
Cozy Apt w/ Pool, Hot Tub, Golf, Near Downtown!
A suburban house with a garage, a driveway, and well-maintained landscaping.

13. Cozy private Room Close to Theme Parks and Airport

Cozy private Room Close to Theme Parks and Airport
Southchase
10.0 out of 10, Exceptional, (3 reviews)
"Amazing property with an even more amazing host ! The whole process went smoothly from booking the stay to communication with host to check in and check out. I appreciated being allowed to decorate the room for a special occasion which was very important to me. This is my go to place for my future stays in the area."
United States
Anthony S.
The price is £88
includes taxes & fees
11 Nov - 12 Nov
Cozy private Room Close to Theme Parks and Airport
A compact room with a bed, a small table with plates, a microwave, and a green wall with a neon sign.

14. CUTE and COZY studio w/ jacuzzi!

CUTE and COZY studio w/ jacuzzi!
Azalea Park
8.6 out of 10, Excellent, (10 reviews)
"This cute lil place is perfect for a few nights for one person or a couple. It’s quiet, private and safe, and appointed with everything you need. The bed is comfy and the coffee was great. "
United States
Lindsay W.
The price is £136
includes taxes & fees
26 Oct - 27 Oct
CUTE and COZY studio w/ jacuzzi!
A modern kitchen with white cabinetry, stainless steel appliances, and pendant lighting.

15. My hide away by the lake.

My hide away by the lake.
Mount Dora
8.8 out of 10, Excellent, (6 reviews)
"Nice property in a quiet neighborhood "
United States
Scott G.
The price is £390
includes taxes & fees
25 Oct - 26 Oct
My hide away by the lake.
A modern kitchen with a central island, bar stools, and a ceiling fan.

16. Mid Century Gem Near Theme Parks

Mid Century Gem Near Theme Parks
Ocoee
9.8 out of 10, Exceptional, (18 reviews)
"The place was just what we needed. Mary Anne was fantastic."
United States
Rick S.
The price is £284
includes taxes & fees
29 Oct - 30 Oct
Mid Century Gem Near Theme Parks
A compact kitchen with white cabinets, a microwave, and a stove. There is a dining area with a black table, white plates, and a vase of flowers.

17. Entire Guest House in Orlando, Florida

Entire Guest House in Orlando, Florida
Tangelo Park
9.4 out of 10, Exceptional, (11 reviews)
"Property was small a true guest house but definitely priced appropriately"
United States
James V.
The price is £110
includes taxes & fees
26 Oct - 27 Oct
Entire Guest House in Orlando, Florida
A hot tub with a pool, surrounded by rocks and a wooden deck.

18. Pool + Heated spa Family friendly King suite Oasis

Pool + Heated spa Family friendly King suite Oasis
Minneola
10.0 out of 10, Exceptional, (36 reviews)
"Great place to stay and convenient location! loved the pool oasis!"
United States
michelle e.
The price is £341
includes taxes & fees
2 Nov - 3 Nov
Pool + Heated spa Family friendly King suite Oasis
A two-story house with a garage, a large arched window, and a palm tree in the front yard.

19. Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool

Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool
Orlando
8.6 out of 10, Excellent, (116 reviews)
"Great communication from host and beautiful house."
United States
Gerimiah R.
The price is £343
includes taxes & fees
23 Oct - 24 Oct
Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool
A bedroom with a bed, a ceiling fan, a window with blinds, a door, and a TV mounted on the wall.

20. Cozy home stay

Cozy home stay
Tangelo Park
The price is £191
includes taxes & fees
29 Oct - 30 Oct
Cozy home stay
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winter Garden Hotel Reviews

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

8/10 Good
"The bathroom was undersized, had to reach over the toilet to turn on shower. Came in the afternoon, couldn't buy a container of yogurt, had to go to walgreens , down the street. Hot tub area and pool had run out of towels. It was the small things. It almost seemed like a lack of staff."
Maryanne 4-night trip
Posted less than an hour ago
DoubleTree by Hilton at the Entrance to Universal Orlando

Find out more about Winter Garden

Winter Garden Holiday Homes information

Number of reviews
366
Accommodation
29064 Holiday Homes
Lowest Price
£50
Highest Price
£600