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Check prices for these dates

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

Our top choices for Winter Garden vacation homes

Interior

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 ￥22,361
￥47,581 total
includes taxes & fees
Sep 13 - Sep 14
House with large deck, walking distance to Historic Downtown Winter Garden
2 bedrooms, WiFi, bed sheets

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 ￥25,627
￥80,474 total
includes taxes & fees
Sep 18 - Sep 19
Fire Pit & Yard: Updated Winter Garden Home!
Interior

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 ￥18,751
￥34,690 total
includes taxes & fees
Sep 7 - Sep 8
FunTropicalTinyHomeGolfCartLake
Pool

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 ￥43,284
￥80,260 total
includes taxes & fees
Sep 14 - Sep 15
WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
Exterior

5. Winter Garden Family-friendly Condo w Resort Pool

Winter Garden Family-friendly Condo w Resort Pool
Winter Garden
The price is ￥10,938
￥43,217 total
includes taxes & fees
Sep 7 - Sep 8
Winter Garden Family-friendly Condo w Resort Pool
Outdoor pool

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 ￥8,438
￥16,828 total
includes taxes & fees
Sep 7 - Sep 8
Private Spacious Room in Home, with Pool-The Oasis Room
Microwave, oven, stovetop, paper towels

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 ￥10,938
￥20,704 total
includes taxes & fees
Sep 7 - Sep 8
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
Smart TV

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 ￥22,501
￥65,433 total
includes taxes & fees
Sep 7 - Sep 8
Rose's Lakeview
Exterior

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 ￥14,063
￥21,584 total
includes taxes & fees
Sep 13 - Sep 14
Charming 2-bedroom apartment in house with AC, WiFi included
Desk, WiFi, bed sheets

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 ￥7,425
￥24,614 total
includes taxes & fees
Sep 7 - Sep 8
Studio in the heart of Orlando
Terrace/patio

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 ￥12,657
￥23,517 total
includes taxes & fees
Sep 29 - Sep 30
Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.
Interior

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 ￥25,783
￥66,998 total
includes taxes & fees
Sep 7 - Sep 8
PROMO NOW: The Secret Garden Games Getaway
Fridge, microwave, oven, stovetop

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 ￥18,126
￥46,000 total
includes taxes & fees
Sep 8 - Sep 9
Stylish & Cozy King Bed Retreat @ Baldwin Park
Pool

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.
The price is ￥31,096
￥57,163 total
includes taxes & fees
Sep 9 - Sep 10
Mini golf course, 1 mile to Universal, Pool
Microwave, oven, stovetop, dishwasher

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 ￥23,439
￥72,544 total
includes taxes & fees
Sep 8 - Sep 9
Lovely 2-bedroom house in Howey-in-the-Hills
Interior

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 ￥21,822
￥48,074 total
includes taxes & fees
Sep 9 - Sep 10
Relaxing Modern Home Sleeps 6/Pool/BBQ/Firepit
Outdoor pool

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 ￥9,219
￥10,464 total
includes taxes & fees
Sep 7 - Sep 8
Maple Leaf Inn & Suites
Exterior detail

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 ￥21,525
￥56,212 total
includes taxes & fees
Sep 7 - Sep 8
Lake House Pets allowed
Exterior

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 ￥13,360
￥70,561 total
includes taxes & fees
Sep 7 - Sep 8
Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool
Outdoor pool, a heated pool

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 ￥17,579
￥40,540 total
includes taxes & fees
Sep 7 - Sep 8
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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"First time staying here and we loved it! We came down to Orlando to celebrate our daughter and our only regret is not staying longer. Very clean, beautiful property, staff was great!"
Vanessa 2-night trip
Posted less than an hour ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Find out more about Winter Garden

Winter Garden Vacation Homes information

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