Holiday Homes in Winter Garden

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Check prices for these dates

Our top choices for Winter Garden holiday homes

1. FunTropicalTinyHomeGolfCartLake

FunTropicalTinyHomeGolfCartLake
Winter Garden
9.4 out of 10, Exceptional, (11 reviews)
"We had a great time! The host was spectacular. Our accommodations were very clean and comfortable! "
United States
Emily R.
The price is AU$302
includes taxes & fees
16 Nov - 17 Nov
FunTropicalTinyHomeGolfCartLake

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 AU$695
includes taxes & fees
15 Nov - 16 Nov
Fire Pit & Yard: Updated Winter Garden Home!

3. Winter Garden Family-friendly Condo w Resort Pool

Winter Garden Family-friendly Condo w Resort Pool
Winter Garden
The price is AU$386
includes taxes & fees
17 Nov - 18 Nov
Winter Garden Family-friendly Condo w Resort Pool

4. 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, (41 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 AU$148
includes taxes & fees
15 Nov - 16 Nov
Private Spacious Room in Home, with Pool-The Oasis Room

5. Maple Leaf Inn & Suites

Maple Leaf Inn & Suites
2.5 star property
Kissimmee
7.0 out of 10, Good, (73 reviews)
"Yes recomende"
United States
Alex
The price is AU$99
includes taxes & fees
15 Nov - 16 Nov
Maple Leaf Inn & Suites

6. 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, (5 reviews)
"Tammie is an amazing host! Super comfy and cute tiny home! Definitely booking again!"
United States
chelsea
The price is AU$218
includes taxes & fees
18 Nov - 19 Nov
Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.

7. 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 AU$309
includes taxes & fees
26 Nov - 27 Nov
Midway between Disney and the Gulf beaches

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

Charming 2-bedroom apartment in house with AC, WiFi included
Apopka
9.6 out of 10, Exceptional, (40 reviews)
"Very nice neighborhood and great accommodations. "
United States
Kevin S.
The price is AU$193
includes taxes & fees
17 Nov - 18 Nov
Charming 2-bedroom apartment in house with AC, WiFi included

9. Sunshine Escape Guesthouse ☀

Sunshine Escape Guesthouse ☀
Orlando
8.6 out of 10, Excellent, (21 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 AU$241
includes taxes & fees
17 Nov - 18 Nov
Sunshine Escape Guesthouse ☀

10. 7BR Near Disney with Private Pool, Games and 4 King Suites

7BR Near Disney with Private Pool, Games and 4 King Suites
3.0 star property
Kissimmee
The price is AU$873
includes taxes & fees
15 Nov - 16 Nov
7BR Near Disney with Private Pool, Games and 4 King Suites

11. 3BR townhouse at Fiesta Key in kissimmee

3BR townhouse at Fiesta Key in kissimmee
Kissimmee
The price is AU$509
includes taxes & fees
29 Nov - 30 Nov
3BR townhouse at Fiesta Key in kissimmee

12. 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 AU$222
includes taxes & fees
30 Nov - 1 Dec
Studio in the heart of Orlando

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, (4 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 AU$184
includes taxes & fees
14 Dec - 15 Dec
Cozy private Room Close to Theme Parks and Airport

14. Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!

Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!
Azalea Park
9.8 out of 10, Exceptional, (26 reviews)
"Quiet neighborhood, good location."
United States
River
The price is AU$391
includes taxes & fees
15 Nov - 16 Nov
Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!

15. Chic Orlando Family Getaway w/ Fenced Yard!

Chic Orlando Family Getaway w/ Fenced Yard!
Rosemont
9.4 out of 10, Exceptional, (30 reviews)
"This is a great location for those traveling with families. It was close enough to the main Orlando attractions and great room for 7 people. Very clean and host is amazing at communicating."
United States
Kassandra H.
The price is AU$705
includes taxes & fees
22 Nov - 23 Nov
Chic Orlando Family Getaway w/ Fenced Yard!

16. 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)
"Everything about the house was great. Great house for the price!"
United States
Charles T.
The price is AU$344
includes taxes & fees
17 Nov - 18 Nov
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

17. Tiny tropical Orlando Univesal-Disney

Tiny tropical Orlando Univesal-Disney
Orlando
6.8 out of 10, (40 reviews)
"Great stay!"
United States
Allison C.
The price is AU$297
includes taxes & fees
16 Nov - 17 Nov
Tiny tropical Orlando Univesal-Disney

18. 10 mins to parks in Orlando,Kissimmee, with gated community and pool

10 mins to parks in Orlando,Kissimmee, with gated community and pool
Cumbrian Lakes
9.6 out of 10, Exceptional, (124 reviews)
"Great house, easy to get t o all the parks . Would definitely stay there again "
United States
Corey C.
The price is AU$634
includes taxes & fees
15 Nov - 16 Nov
10 mins to parks in Orlando,Kissimmee, with gated community and pool

19. Near Disney, Universal & SeaWorld - Pool Home

Near Disney, Universal & SeaWorld - Pool Home
Orlando
9.8 out of 10, Exceptional, (17 reviews)
"Check in was easy and house was nice would definitely stay again"
United States
bonny
The price is AU$471
includes taxes & fees
7 Dec - 8 Dec
Near Disney, Universal & SeaWorld - Pool Home

20. Private Pool & Fire Pit Near Springs | Love Shack

Private Pool & Fire Pit Near Springs | Love Shack
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 AU$495
includes taxes & fees
15 Nov - 16 Nov
Private Pool & Fire Pit Near Springs | Love Shack
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.

Learn more about Winter Garden

Stroll the charming brick-lined streets of historic city centre where the Plant Street Market buzzes with local food vendors and craft beer. Pedal along the West Orange Trail that cuts through town, stopping at the Heritage Museum or to catch a show at the Garden Theatre.

A brick building with a clock tower and a sign that reads "Winter Garden."