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

Search Town Houses in Winter Garden

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November 2026

December 2026

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No exact matches found, but these alternatives could be just right

Recommended hotels in Winter Garden

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

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

Bay Lake

kenyetta

AED 327 total

includes taxes & fees

8 Dec - 9 Dec

A swimming pool with lounge chairs and a view of a building in the background.

2. Home2 Suites By Hilton Winter Garden

Winter Garden

Enrique

AED 453 total

includes taxes & fees

29 Nov - 30 Nov

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

3. Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Bay Lake

Michael

AED 446 total

includes taxes & fees

8 Dec - 9 Dec

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

4. Home2 Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

Melissa

AED 403 total

includes taxes & fees

29 Nov - 30 Nov

A pool area with lounge chairs, a fire pit, and palm trees.

5. SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

Bay Lake

James

AED 324 total

includes taxes & fees

29 Nov - 30 Nov

6. TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

Bay Lake

Ramon

AED 393 total

includes taxes & fees

29 Nov - 30 Nov

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

7. Homewood Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

Timothy

AED 505 total

includes taxes & fees

29 Nov - 30 Nov

A resort with multiple swimming pools, lounge areas, and a view of the sea.

8. The Grove Resort & Water Park Orlando

Winter Garden

Jessica

AED 883 total

includes taxes & fees

10 Dec - 11 Dec

A resort with multiple buildings, a central swimming pool, and a waterway.

9. Hilton Vacation Club Aqua Sol Orlando West

Winter Garden

Travis

AED 510 total

includes taxes & fees

17 Nov - 18 Nov

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

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

Winter Garden

isaac

AED 1,524 total

includes taxes & fees

1 Dec - 2 Dec

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

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

Winter Garden

Steve S.

AED 1,229 total

includes taxes & fees

12 Nov - 13 Nov

12. FunTropicalTinyHomeGolfCartLake

Winter Garden

Emily R.

AED 729 total

includes taxes & fees

12 Nov - 13 Nov

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

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

Winter Garden

AED 1,833 total

includes taxes & fees

12 Nov - 13 Nov

14. StylishAptWtrGrdnOppLake&Prk&Yrd

Winter Garden

Lindsey W.

A spacious living area with a modern sofa set, a coffee table, and a decorative vase.

15. The Garden Luxe Retreat

Winter Garden

Corey K.

AED 1,239 total

includes taxes & fees

29 Nov - 30 Nov

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

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

Winter Garden

Patrick O.

AED 1,758 total

includes taxes & fees

12 Nov - 13 Nov

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

17. 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

AED 1,325 total

includes taxes & fees

17 Nov - 18 Nov

18. Upstay Tropical Style Family Condo w Pool

Winter Garden

AED 1,070 total

includes taxes & fees

29 Nov - 30 Nov

19. Upstay: Stylish 3BR Condo w Pationear Disney

Winter Garden

Ismael

AED 849 total

includes taxes & fees

29 Nov - 30 Nov

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.

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

Winter Garden

AED 872 total

includes taxes & fees

12 Nov - 13 Nov

View all properties

Learn more about Winter Garden

Stroll the charming brick-lined streets of historic downtown 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.

See all hotels in Winter Garden

Top reviews in Winter Garden

Home2 Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

10/10 Excellent

Joel

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

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

Bay Lake

10/10 Excellent

Bharat

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

Rosen Shingle Creek

Orlando

10/10 Excellent

Narciso

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

Bay Lake

10/10 Excellent

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

Bay Lake

10/10 Excellent

Zavier

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 with a waterfall feature, surrounded by palm trees and a multi-story building with colorful windows.

Universal's Cabana Bay Beach Resort

Florida Center

10/10 Excellent

When I booked, I honestly wasn’t sure what to expect, but Cabana Bay exceeded our expectations. Friendly staff, a charming theme, great communal areas and lovely rooms. We ended up with a volcano view room in the Beachside building and it was a 10/10. We had an awesome view of Volcano Bay which we ended up deciding to do on our last day (also recommend!). We explored the pools, enjoyed s’mores by the fire pits, played in the arcade, enjoyed early park access and transportation to the parks, ate...

Amanda

A pool area with people swimming and relaxing.

Universal's Endless Summer Resort - Dockside Inn and Suites

Florida Center

10/10 Excellent

cynthia

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 hotel room with a bed, a sofa, a desk, a TV, and a painting on the wall.

Wingate by Wyndham - Orlando International Airport

Airport North

10/10 Excellent

Mary

An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.

Caribe Royale Orlando, WorldHotels Elite

Orlando

10/10 Excellent

While this resort is beautiful and clean we had a few issues. First, it would have been wonderful to know that they will rent out many of the common areas (pool), restaurants and bars for private events. There was an event just about every night we during our 7 day stay. Some nights we were not able to use the bridge to cross to our villa so we (3 adults, 3 small children) had to walk around extra 4 buildings, other nights we were not able to use the main pool, sports bar or pool side bar. This...

Shannon