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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Winter Garden vacation 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 ￥19,452
￥35,531 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥24,158
￥78,239 total
includes taxes & fees
Nov 3 - Nov 4
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)
"Super 2 bed 2 bath property walking distance to Winter Garden downtown area."
United States
Ron C.
The price is ￥32,459
￥60,377 total
includes taxes & fees
Nov 8 - Nov 9
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
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 ￥79,690
￥126,346 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥8,471
￥16,893 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥10,981
￥20,785 total
includes taxes & fees
Nov 1 - Nov 2
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
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.

8. 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 ￥9,255
￥10,505 total
includes taxes & fees
Oct 28 - Oct 29
Maple Leaf Inn & Suites
Terrace/patio

9. 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 ￥13,177
￥24,139 total
includes taxes & fees
Oct 28 - Oct 29
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.

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 ￥9,177
￥26,698 total
includes taxes & fees
Nov 1 - Nov 2
Sunshine Escape Guesthouse ☀
A modern dining area with a glass table and white chairs, a pendant light, and artwork on the walls.

11. 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.
Cozy Apt w/ Pool, Hot Tub, Golf, Near Downtown!
Exterior

12. 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 ￥14,118
￥21,668 total
includes taxes & fees
Oct 28 - Oct 29
Charming 2-bedroom apartment in house with AC, WiFi included
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 ￥9,917
￥28,114 total
includes taxes & fees
Oct 28 - Oct 29
CUTE and COZY studio w/ jacuzzi!
A modern kitchen with a central island, bar stools, and a ceiling fan.

14. 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 ￥24,707
￥58,464 total
includes taxes & fees
Nov 1 - Nov 2
Mid Century Gem Near Theme Parks
A hot tub with a pool, surrounded by rocks and a wooden deck.

15. 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)
"We had an enjoyable stay."
United States
Rebecca C.
The price is ￥32,331
￥69,536 total
includes taxes & fees
Nov 4 - Nov 5
Pool + Heated spa Family friendly King suite Oasis
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.

16. 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 ￥13,334
￥22,550 total
includes taxes & fees
Oct 28 - Oct 29
Entire Guest House in Orlando, Florida
A bedroom with a bed, a mirror, a wardrobe, and a floral artwork on the wall.

17. 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 ￥20,472
￥39,307 total
includes taxes & fees
Nov 2 - Nov 3
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
A modern living room with a sofa, coffee table, TV, and decorative items.

18. 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 ￥22,589
￥64,277 total
includes taxes & fees
Oct 28 - Oct 29
Rose's Lakeview
A swimming pool with a water slide, surrounded by palm trees and a sunset.

19. The Grand Retreat at CG with pool

The Grand Retreat at CG with pool
4.0 star property
Champions Gate
The price is ￥25,967
￥72,782 total
includes taxes & fees
Oct 28 - Oct 29
The Grand Retreat at CG with pool
A hot tub with a waterfall feature, a covered seating area, and a bar with outdoor seating.

20. Private Luxury Pool / Swim up bar / Smart-home

Private Luxury Pool / Swim up bar / Smart-home
College Park
9.8 out of 10, Exceptional, (87 reviews)
"Best VRBO thus far, the host were great and the smart house offered much more than expected, I’d recommend this house to any family! I’d definitely stay again!"
United States
Dennis P.
The price is ￥29,648
￥65,050 total
includes taxes & fees
Oct 28 - Oct 29
Private Luxury Pool / Swim up bar / Smart-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
"room was clean, great pool, staff is friendly and close to Disney World. I would stay here again."
Noe 1-night trip
Posted 2 hours ago
Home2 Suites by Hilton Orlando at Flamingo Crossings

Find out more about Winter Garden

Winter Garden Vacation Homes information

Number of reviews
404
Accommodation
29311 Vacation Homes
Lowest Price
￥10,505
Highest Price
￥126,346