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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

Interior

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

2. 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!
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
Aerial View Of The Resort-Style Complex Featuring A Large Pool And Serene Surroundings

4. Winter Garden Family-friendly Condo w Resort Pool

Winter Garden Family-friendly Condo w Resort Pool
Winter Garden
The price is £212
includes taxes & fees
26 Oct - 27 Oct
Winter Garden Family-friendly Condo w Resort Pool
A wooden deck with a hot tub, a wooden dock extending into a body of water, and a view of the water and sky.

5. 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
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
1 Nov - 2 Nov
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 modern hotel room with a wooden bed, a desk with chairs, a patterned wall, and a window with blinds.

9. 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 ☀
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.

10. 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
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 kitchen with dark cabinets, stainless steel appliances, a marble floor, and a bar area with stools.

12. The Grand Retreat at CG with pool

The Grand Retreat at CG with pool
4.0 star property
Champions Gate
The price is £305
includes taxes & fees
9 Nov - 10 Nov
The Grand Retreat at CG with pool
A compact room with a bed, a small table with plates, a microwave, and a green wall with a neon sign.

13. 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 £137
includes taxes & fees
27 Oct - 28 Oct
CUTE and COZY studio w/ jacuzzi!
A modern dining area with a glass table and white chairs, a pendant light, and artwork on the walls.

14. 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 modern kitchen with a central island, bar stools, and a ceiling fan.

15. 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 £281
includes taxes & fees
4 Nov - 5 Nov
Mid Century Gem Near Theme Parks
A modern kitchen with white cabinetry, stainless steel appliances, and pendant lighting.

16. 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 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 guesthouse in Orlando, Florida

Entire guesthouse 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
27 Oct - 28 Oct
Entire guesthouse in Orlando, Florida
A kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

18. Midway between Disney and the Gulf beaches

Midway between Disney and the Gulf beaches
Polk City
9.8 out of 10, Exceptional, (85 reviews)
"Property was close to everything we wanted tod do, easy access, clean and the host was great. "
United States
Herb
The price is £164
includes taxes & fees
23 Oct - 24 Oct
Midway between Disney and the Gulf beaches
A modern kitchen with a central island, white cabinets, a stainless steel refrigerator, and a black and white geometric backsplash.

19. Renovated Peaceful Luxury Walk to Mall Park Publix

Renovated Peaceful Luxury Walk to Mall Park Publix
Altamonte Springs
9.0 out of 10, Wonderful, (23 reviews)
"Host responded quickly to our texts.Location was excellent for our needs."
United States
Angie Y.
The price is £144
includes taxes & fees
23 Oct - 24 Oct
Renovated Peaceful Luxury Walk to Mall Park Publix
A bedroom with a bed, a mirror, a wardrobe, and a floral artwork on the wall.

20. Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Casselberry
9.8 out of 10, Exceptional, (58 reviews)
"This home was just what we needed, it was clean and comfortable. Great communication with the owner. Nice, safe neighborhood."
United States
Angie P.
The price is £194
includes taxes & fees
26 Oct - 27 Oct
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
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

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent
"Best hotel & staff - we will be back"
Susan 3-night trip
Posted 2 hours ago
Home2 Suites by Hilton Orlando at Flamingo Crossings

Find out more about Winter Garden

Winter Garden Holiday Homes information

Number of reviews
377
Accommodation
29064 Holiday Homes
Lowest Price
£50
Highest Price
£600