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

Winter Garden Vacation Rentals

Q: What's the top vacation rental that Winter Garden has to offer?

Formosa Valley Resort by UNE Homes : You might like this vacation home rental near Winter Garden. It is equipped with an outdoor pool, air-conditioning, and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop.

Dates

November 2026

December 2026

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Our top choices for Winter Garden vacation rentals

An aerial view of a coastal property with a swimming pool, tennis courts, and a marina.

1. StylishAptWtrGrdnOppLake&Prk&Yrd

Winter Garden

Lindsey W.

SAR 704 total

includes taxes & fees

6 Dec - 7 Dec

2. FunTropicalTinyHomeGolfCartLake

Winter Garden

Emily R.

SAR 761 total

includes taxes & fees

12 Nov - 13 Nov

A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a refrigerator.

3. Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL

Winter Garden

Steve S.

SAR 1,445 total

includes taxes & fees

8 Dec - 9 Dec

A spacious lobby with a high ceiling, exposed brick walls, and modern lighting fixtures.

4. Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room

Winter Garden

isaac

SAR 1,490 total

includes taxes & fees

30 Nov - 1 Dec

A living room with a sectional sofa, a wooden coffee table, and a ceiling fan.

5. Fire Pit & Yard: Updated Winter Garden Home!

Winter Garden

SAR 1,874 total

includes taxes & fees

8 Nov - 9 Nov

6. Upstay: Stylish 3BR Condo w Pationear Disney

Winter Garden

Ismael

SAR 867 total

includes taxes & fees

30 Nov - 1 Dec

A modern interior with a curved sectional sofa, a round coffee table with a plant, and a brick wall.

7. Cozy 1-bedroom with AC in awesome Winter Garden

Winter Garden

"We enjoyed our stay and had a great experience. Gina communicated with us right away, so we knew how to check in or had any questions answered. The property is very cute and looks new and was spotless. The location of the property is great as well. Downtown Winter Garden is adorable with great restaurants and is an easy drive down Plant St. It also was very convenient to where we were visiting in Ocoee and Orlando.We had everything we needed, highly recommend this property, and would stay there...

Anonymous traveler

SAR 1,296 total

includes taxes & fees

17 Nov - 18 Nov

8. Upstay Stylish 3BR Condo w Patio Near Disney

Winter Garden

SAR 1,007 total

includes taxes & fees

30 Nov - 1 Dec

A bedroom with a bed, a bedside table with a lamp, and a wall decorated with woven baskets.

9. Fire Pit & Yard: Updated Winter Garden Home!

Winter Garden

Patrick O.

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

10. House with large deck, walking distance to Historic Downtown Winter Garden

Winter Garden

Thomas C.

11. Upstay: Stylish 3BR Condo w Patio—near Disney

Winter Garden

Discover the winding lazy river, perfect for a refreshing float on a sunny day.

12. Studio Near Disney World Resort with Pools + more

Kissimmee

Aerial View Of The Resort-Style Complex Featuring A Large Pool And Serene Surroundings

13. Winter Garden Family-friendly Condo w Resort Pool

Winter Garden

A spacious lobby with a large seating area, a flat-screen TV mounted on the wall, and large windows offering a view of the outdoors.

14. Family-Friendly 2BR Condo w Resort Pool & Sauna

Winter Garden

15. Upstay: 3BR Family Condo w Pool & Sauna

Winter Garden

A balcony with a view of a natural landscape, a chair, and a table.

16. Upstay Large Family Condo w Pool, Sauna

Winter Garden

SAR 938 total

includes taxes & fees

10 Nov - 11 Nov

Stunning Aerial View Of The Property Surrounded By Nature

17. Family Fun Condo Pool and Sauna near Disney

Winter Garden

John and Dawn R.

18. Upstay - Condo Near Disney w Pool Hot tub Sauna

Winter Garden

SAR 900 total

includes taxes & fees

18 Nov - 19 Nov

A balcony with a ceiling fan, a white cushioned chair, a small table, and a potted plant.

19. Upstay - Pet-Friendly Condo - Sauna, Pool

Winter Garden

KELLEE

20. Upstay Modern 2BR Condo Near Disney

Winter Garden

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Find vacation rentals that suit your style

Top Winter Garden Hotel Reviews

A hotel pool area with lounge chairs and umbrellas, surrounded by tall buildings and a sunset sky.

Drury Plaza Hotel Orlando - Disney Springs Area

Lake Buena Vista

10/10 Excellent

Amy Dawn

A large hotel with multiple floors, a central courtyard, and a reflective water feature.

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Bay Lake

10/10 Excellent

We had an excellent stay! The hotel is clean, modern, and very well-appointed, with comfortable rooms that made us feel right at home. Traveling with our toddler, we found everything to be exceptional—the accommodations were spacious and family-friendly. The free breakfast was a fantastic bonus, with a variety of options, including some vegan-friendly choices, which we really appreciated. The staff was welcoming and attentive, ensuring we had everything we needed for a great stay. We would...

Nicolette

Rosen Shingle Creek

Orlando

10/10 Excellent

Narciso

A spacious restaurant with high ceilings, hanging pendant lights, and a variety of seating arrangements.

Embassy Suites by Hilton Orlando Lake Buena Vista South

Kissimmee

10/10 Excellent

Chris

A stone wall, a brown sofa with orange and yellow cushions, a glass table with a fire feature, and a wooden door with decorative glass panels.

The Delaney Hotel

South Orange

10/10 Excellent

Chelsea

An outdoor patio area with a fire pit, yellow and blue seating, and a covered section with a pergola.

Home2 Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

10/10 Excellent

Joel

A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Bay Lake

10/10 Excellent

Bharat

A swimming pool with a slide and a small waterfall feature, surrounded by lounge chairs and umbrellas.

Homewood Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

10/10 Excellent

The property was amazing it is 10 mins away from Disney parks and 5 mins away from the Disney entrance gates. There is a target, 5-below, lime fresh Mexican grill, and a Starbucks at walking distance. The pool is very large and amazing for kids. The hotel rooms are very large with pull couches, comfortable beds, and a fully stocked kitchen perfect cooking. The hotel staff is on another level they offer top-tier service at all hours. The free breakfast is great. Parking is 20 dollars per day and...

Jada

An outdoor seating area with green chairs and umbrellas, a fire pit, and a building with large windows in the background.

Hampton Inn & Suites Orlando Airport @ Gateway Village

Airport North

10/10 Excellent

Christine

Holiday Inn Orlando - I-Drive North by IHG

International Drive District

10/10 Excellent

Blanca

A spacious lobby with a grand chandelier, modern seating, and a view of the outdoor area.

Kompose Boutique Resort at Theme Parks

Kissimmee

10/10 Excellent

Patrik

A hotel pool area with lounge chairs and umbrellas, surrounded by palm trees and modern buildings.

Universal's Endless Summer Resort - Surfside Inn and Suites

International Drive District

10/10 Excellent

The beginning of a great stay started with Carmen at the front desk. We felt welcomed, informed and appreciated. I read reviews about the hot water, but we had no problem; the shower was great with adequate hot water. The rooms were clean and cleaned daily. The mattresses isn’t plush but I slept well. The shuttle to City Walk and Universal Studios theme parks and early entry into parks was a plus. The restaurant and Starbucks on property were convenient. The property is in a great location and...

Tanya

A modern building with a distinctive facade featuring circular windows and a reflective water feature in front.

Universal's Stella Nova Resort

Orlando

10/10 Excellent

A large pool with lounge chairs and palm trees, surrounded by a modern building with a patterned facade.

Universal's Terra Luna Resort

Orlando

10/10 Excellent

Kim

A spacious lobby with a reception desk, seating area with sofas and armchairs, and a bar area.

Hyatt House Orlando International Drive

International Drive District

10/10 Excellent

jordan

A hotel room with a bed, a desk, a chair, a sofa, and a TV.

Pestana Orlando Suites - Lake Buena Vista

Orlando

10/10 Excellent

Christopher

Frequently Asked Questions

Can I find a vacation rental in Winter Garden?

Yes, we offer vacation rentals in Winter Garden close to Surfari Water Park, or you can go with a more remote option if you'd like a relaxing place to stay. Tourists who visit Winter Garden speak highly of the fun-filled theme parks and array of shops. While you're here, grab a bite or have a drink at the top-notch restaurants.

What's the top vacation rental that Winter Garden has to offer?

Formosa Valley Resort by UNE Homes: You might like this vacation home rental near Winter Garden. It is equipped with an outdoor pool, air-conditioning, and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop.

How many vacation rentals are there in Winter Garden?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Winter Garden stay.

What can I see and do in Winter Garden?

Family-friendly attractions include Surfari Water Park and Central Florida Railroad Museum, whereas Lake Louisa State Park and West Orange Trail are a couple of great spots to enjoy the outdoors. Universal Studios Florida and Universal Orlando Resort are other popular places to visit in the area.

What are vacation rentals like in Winter Garden?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Winter Garden. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for family trips.

Winter Garden Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winter Garden vacation rentals

1. StylishAptWtrGrdnOppLake&Prk&Yrd

2. FunTropicalTinyHomeGolfCartLake

3. Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL

4. Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room

5. Fire Pit & Yard: Updated Winter Garden Home!

6. Upstay: Stylish 3BR Condo w Pationear Disney

7. Cozy 1-bedroom with AC in awesome Winter Garden

8. Upstay Stylish 3BR Condo w Patio Near Disney

9. Fire Pit & Yard: Updated Winter Garden Home!

10. House with large deck, walking distance to Historic Downtown Winter Garden

11. Upstay: Stylish 3BR Condo w Patio—near Disney

12. Studio Near Disney World Resort with Pools + more

13. Winter Garden Family-friendly Condo w Resort Pool

14. Family-Friendly 2BR Condo w Resort Pool & Sauna

15. Upstay: 3BR Family Condo w Pool & Sauna

16. Upstay Large Family Condo w Pool, Sauna

17. Family Fun Condo Pool and Sauna near Disney

18. Upstay - Condo Near Disney w Pool Hot tub Sauna

19. Upstay - Pet-Friendly Condo - Sauna, Pool

20. Upstay Modern 2BR Condo Near Disney

Find vacation rentals that suit your style

Top Winter Garden Hotel Reviews

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent

Frequently Asked Questions

Can I find a vacation rental in Winter Garden?

What's the top vacation rental that Winter Garden has to offer?

How many vacation rentals are there in Winter Garden?

What can I see and do in Winter Garden?

What are vacation rentals like in Winter Garden?