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

Holiday Homes in Winter Garden

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Winter Garden holiday homes

A spacious living area with a dining table, chairs, a sofa, and a kitchen in the background.

1. 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, (28 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 NZ$519
includes taxes & fees
12 Sept - 13 Sept
House with large deck, walking distance to Historic Downtown Winter Garden
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 NZ$862
includes taxes & fees
18 Sept - 19 Sept
Fire Pit & Yard: Updated Winter Garden Home!

3. 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 NZ$376
includes taxes & fees
7 Sept - 8 Sept
FunTropicalTinyHomeGolfCartLake
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 NZ$861
includes taxes & fees
14 Sept - 15 Sept
WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn

5. Winter Garden Family-friendly Condo w Resort Pool

Winter Garden Family-friendly Condo w Resort Pool
Winter Garden
The price is NZ$472
includes taxes & fees
7 Sept - 8 Sept
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
9.6 out of 10, Exceptional, (37 reviews)
"I enjoyed my stay very much. If I am ever in the area again, I would definitely stay here again. Very nice place."
United States
Matthew H.
The price is NZ$183
includes taxes & fees
7 Sept - 8 Sept
Private Spacious Room in Home, with Pool-The Oasis Room

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
10.0 out of 10, Exceptional, (6 reviews)
"Great place to stay. We plan on staying again."
United States
Nancee H.
The price is NZ$225
includes taxes & fees
7 Sept - 8 Sept
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
A modern living room with a sofa, coffee table, TV, and decorative items.

8. Rose's Lakeview

Rose's Lakeview
Orlando
9.0 out of 10, Wonderful, (22 reviews)
"Comfortable, clean stay - good location for our event. "
United States
Kari B.
The price is NZ$714
includes taxes & fees
6 Sept - 7 Sept
Rose's Lakeview

9. 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, (34 reviews)
"Very nice neighborhood and great accommodations. "
United States
Kevin S.
The price is NZ$235
includes taxes & fees
13 Sept - 14 Sept
Charming 2-bedroom apartment in house with AC, WiFi included
A bed with white bedding and two blue pillows with a coral reef design, a tall green plant beside the bed, and a window with grey curtains in the background.

10. Studio in the heart of Orlando

Studio in the heart of Orlando
Azalea Park
9.4 out of 10, Exceptional, (6 reviews)
"Can’t complain. Would re book for sure."
United States
Matthew
The price is NZ$268
includes taxes & fees
7 Sept - 8 Sept
Studio in the heart of Orlando

11. 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 NZ$256
includes taxes & fees
29 Sept - 30 Sept
Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.
A compact kitchen with a built-in refrigerator, a white door with glass panels, and a potted plant.

12. PROMO NOW: The Secret Garden Games Getaway

PROMO NOW: The Secret Garden Games Getaway
Orlando
9.6 out of 10, Exceptional, (11 reviews)
"Perfect spot for our family in for a reunion. Large home, nice remodel with upgrades, large well equipped kitchen. Little traffic on the road but easy to get out and over to our venue. We already recommended it to other family who are in town often"
United States
karen j.
The price is NZ$731
includes taxes & fees
6 Sept - 7 Sept
PROMO NOW: The Secret Garden Games Getaway
A modern kitchen with wooden cabinets, a black countertop, a stainless steel refrigerator, a microwave, and a coffee maker.

13. Stylish & Cozy King Bed Retreat @ Baldwin Park

Stylish & Cozy King Bed Retreat @ Baldwin Park
Orlando
10.0 out of 10, Exceptional, (16 reviews)
"The house was beautiful and the host was very responsive! "
United States
Dawn H.
The price is NZ$506
includes taxes & fees
8 Sept - 9 Sept
Stylish & Cozy King Bed Retreat @ Baldwin Park
A covered swimming pool with a view of the surrounding garden and trees.

14. Mini golf course, 1 mile to Universal, Pool

Mini golf course, 1 mile to Universal, Pool
Orlando
10.0 out of 10, Exceptional, (35 reviews)
"Great place, had everything we needed and more. Clean and comfortable was a great place to stay for our visit to Universal. "
United States
Marc B.
Mini golf course, 1 mile to Universal, Pool
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and bar stools.

15. Lovely 2-bedroom house in Howey-in-the-Hills

Lovely 2-bedroom house in Howey-in-the-Hills
HOWEY-IN-THE-HILLS
9.4 out of 10, Exceptional, (3 reviews)
"The interior of this property was super clean and looked exactly like the pictures online. You can tell the owner has made a big effort to stock the house with thoughtful and useful items a traveler might need or want. The kitchen was extremely well stocked also! The house was in a residential and rural area, don’t let the exterior fool you, it’s very modern and updated inside."
United States
Lisa M.
The price is NZ$791
includes taxes & fees
7 Sept - 8 Sept
Lovely 2-bedroom house in Howey-in-the-Hills
A modern bathroom with a double sink vanity, large mirrors, and a framed picture on the wall.

16. Relaxing Modern Home Sleeps 6/Pool/BBQ/Firepit

Relaxing Modern Home Sleeps 6/Pool/BBQ/Firepit
Sorrento
10.0 out of 10, Exceptional, (6 reviews)
"The place was very clean and organized pool was perfect for our family we really enjoyed our stay."
United States
Johana
The price is NZ$513
includes taxes & fees
7 Sept - 8 Sept
Relaxing Modern Home Sleeps 6/Pool/BBQ/Firepit
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.

17. Maple Leaf Inn & Suites

Maple Leaf Inn & Suites
2.5 star property
Kissimmee
6.8 out of 10, (71 reviews)
"The room was clean and the staff was okay "
United States
Shaneka
The price is NZ$114
includes taxes & fees
6 Sept - 7 Sept
Maple Leaf Inn & Suites
A greenhouse with a sign reading "L'ORANGERIE," surrounded by bamboo plants and stone walls.

18. Lake House Pets allowed

Lake House Pets allowed
Lake Weldona
9.8 out of 10, Exceptional, (62 reviews)
"Very convenient to downtown! The Host, Jerome was very accommodating! "
United States
Jason M.
The price is NZ$603
includes taxes & fees
6 Sept - 7 Sept
Lake House Pets allowed
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, (114 reviews)
"Great communication from host and beautiful house."
United States
Gerimiah R.
The price is NZ$775
includes taxes & fees
12 Sept - 13 Sept
Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool
A two-story house with a swimming pool, outdoor seating, and a covered patio area.

20. Large, beautiful, very comfortable one bedroom on small lake

Large, beautiful, very comfortable one bedroom on small lake
Lake Weldona
9.8 out of 10, Exceptional, (69 reviews)
"Love the location. "
United States
Jolyn W.
The price is NZ$446
includes taxes & fees
7 Sept - 8 Sept
Large, beautiful, very comfortable one bedroom on small lake
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

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

10/10 Excellent
"Clean room, breakfast was great, staff was amazing and helpful! My son loved the pools!!!"
claudia 4-night trip
Posted less than an hour ago
Kompose Boutique Resort at Theme Parks

Find out more about Winter Garden

Winter Garden Holiday Homes information

Number of reviews
425
Accommodation
29059 Holiday Homes
Lowest Price
NZ$114
Highest Price
NZ$862

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