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

Holiday Homes in Winter Garden

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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, (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 AU$536
includes taxes & fees
7 Oct - 8 Oct
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 AU$732
includes taxes & fees
2 Oct - 3 Oct
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 AU$316
includes taxes & fees
6 Oct - 7 Oct
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 AU$911
includes taxes & fees
14 Oct - 15 Oct
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
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)
"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$149
includes taxes & fees
29 Sept - 30 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
9.8 out of 10, Exceptional, (8 reviews)
"Great place to stay. We plan on staying again."
United States
Nancee H.
The price is AU$192
includes taxes & fees
6 Oct - 7 Oct
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka

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 AU$194
includes taxes & fees
29 Sept - 30 Sept
Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.
A modern living room with a sofa, coffee table, TV, and decorative items.

9. 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 AU$590
includes taxes & fees
10 Oct - 11 Oct
Rose's Lakeview

10. 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, (35 reviews)
"Very nice neighborhood and great accommodations. "
United States
Kevin S.
The price is AU$200
includes taxes & fees
29 Sept - 30 Sept
Charming 2-bedroom apartment in house with AC, WiFi included
A modern hotel room with a wooden bed, a desk with chairs, a patterned wall, and a window with blinds.

11. 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 AU$245
includes taxes & fees
29 Sept - 30 Sept
Sunshine Escape Guesthouse ☀
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.

12. Entire guesthouse in Orlando, Florida

Entire guesthouse in Orlando, Florida
Tangelo Park
9.0 out of 10, Wonderful, (8 reviews)
"Great location close to Universal Epic and I drive, very nice and cozy, nicely remodeled, fantastic host. Will book again"
United States
TONY C.
The price is AU$184
includes taxes & fees
29 Sept - 30 Sept
Entire guesthouse in Orlando, Florida
A hot tub with a pool, surrounded by rocks and a wooden deck.

13. Pool + Heated spa Family friendly King suite Oasis

Pool + Heated spa Family friendly King suite Oasis
Minneola
10.0 out of 10, Exceptional, (35 reviews)
"We had a wonderful stay! The house was spotless, comfortable, and perfect for relaxing. The pool was the highlight"
United States
Jim G.
The price is AU$621
includes taxes & fees
8 Oct - 9 Oct
Pool + Heated spa Family friendly King suite Oasis
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)
"Family friendly great location to Parks "
United States
Joe R.
The price is AU$690
includes taxes & fees
19 Oct - 20 Oct
Mini golf course, 1 mile to Universal, Pool
A compact room with a bed, a small table with plates, a microwave, and a green wall with a neon sign.

15. CUTE and COZY studio w/ jacuzzi!

CUTE and COZY studio w/ jacuzzi!
Azalea Park
8.6 out of 10, Excellent, (10 reviews)
"Pet friendly, all you need for a quick trip to Orlando with a couple and their pet"
United States
Jackson K.
The price is AU$260
includes taxes & fees
29 Sept - 30 Sept
CUTE and COZY studio w/ jacuzzi!
A modern kitchen with dark cabinets, stainless steel appliances, a marble floor, and a bar area with stools.

16. The Grand Retreat at CG with pool

The Grand Retreat at CG with pool
4.0 star property
Champions Gate
The price is AU$613
includes taxes & fees
1 Oct - 2 Oct
The Grand Retreat at CG with pool
A spacious living room with a sofa, coffee table, and TV.

17. Mid-century Modern Villa w/ Pool Near Universal

Mid-century Modern Villa w/ Pool Near Universal
Orlando
9.8 out of 10, Exceptional, (36 reviews)
"Great location close to Universal! We really enjoyed the neighborhood which was great for walking our dog."
United States
Mike B.
The price is AU$769
includes taxes & fees
29 Sept - 30 Sept
Mid-century Modern Villa w/ Pool Near Universal
A hot tub with a waterfall feature, a covered seating area, and a bar with outdoor seating.

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

Private Luxury Pool / Swim up bar / Smart-home
College Park
9.8 out of 10, Exceptional, (86 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.
Private Luxury Pool / Swim up bar / Smart-home
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

19. Resort-Style Villa | Pool, Spa & Game Room!

Resort-Style Villa | Pool, Spa & Game Room!
4.0 star property
Kissimmee
8.0 out of 10, Very good, (1 review)
The price is AU$930
includes taxes & fees
12 Oct - 13 Oct
Resort-Style Villa | Pool, Spa & Game Room!
A modern bathroom with a double sink vanity, large mirrors, and a framed picture on the wall.

20. 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 AU$431
includes taxes & fees
29 Sept - 30 Sept
Relaxing Modern Home Sleeps 6/Pool/BBQ/Firepit
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Garden Hotel Reviews

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent
"Todo excelente buena atención todo muy limpio"
Andres 3-night trip
Posted less than an hour ago
Home2 Suites by Hilton Orlando at Flamingo Crossings

Find out more about Winter Garden

Winter Garden Holiday Homes information

Number of reviews
385
Accommodation
29090 Holiday Homes
Lowest Price
AU$149
Highest Price
AU$930