The Best Hotels with Bars in Winter Garden, FL from NT$2,666 in 2026

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Our top choices for Winter Garden hotels with a bar

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

A swimming pool with clear blue water, surrounded by lounge chairs and yellow umbrellas.

A hotel room with a large window overlooking a swimming pool and a landscaped area with trees and a building in the background.

A Marriott Fairfield hotel sign with a landscaped garden in front.

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

Bay Lake

Juana

NT$2,453

NT$2,760 total

includes taxes & fees

Nov 4 - Nov 5

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

A restaurant with outdoor seating, a bar, and a fire feature.

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

A bar area with a long counter, multiple chairs, and a variety of bottles.

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

Bay Lake

Maria

NT$2,549

NT$2,867 total

includes taxes & fees

Oct 27 - Oct 28

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

A hotel pool area with lounge chairs, a fire pit, and a large pool.

A covered outdoor seating area with tables and chairs, a ceiling fan, and a view of a pool and buildings in the background.

A modern lobby with a large fireplace, comfortable seating, and a well-lit ceiling.

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

Bay Lake

Michael

NT$3,154

NT$3,548 total

includes taxes & fees

Nov 17 - Nov 18

A lounge area with a fire feature, wicker furniture, and a bar in the background.

A hotel room with two beds, a desk, a chair, a small table, and a window with curtains.

A restaurant with outdoor seating, a fire feature, and a bar area.

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

Bay Lake

Jennifer

NT$2,821

NT$3,174 total

includes taxes & fees

Nov 4 - Nov 5

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

A restaurant with a bar area, seating, and a view of greenery outside.

A modern hotel room with a dining area, a living space with a sofa and coffee table, and a kitchenette.

A hotel pool area with multiple lounge chairs and umbrellas, a water slide, and palm trees.

5. Home2 Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

Saniya

NT$3,176

NT$3,573 total

includes taxes & fees

Nov 2 - Nov 3

A multi-story hotel with a central courtyard, featuring a prominent entrance with a stone archway and a sign that reads 'Homewood Suites by Hilton'.

A bar area with a stone wall, a flat-screen TV, and a beer tap.

An outdoor patio with a barbecue grill, dining area, and umbrella.

A hotel lobby with a long bench seating area, round tables, and modern pendant lighting.

6. Homewood Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

Suzanne M.

NT$4,110

NT$4,624 total

includes taxes & fees

Nov 23 - Nov 24

A resort with multiple swimming pools, palm trees, and a large building in the background.

A resort with multiple swimming pools surrounded by lush greenery and a large hotel building.

A modern lobby with a reception desk, seating area, and a bar.

A waterfront property with a dock, a gazebo, and a row of modern buildings in the background.

7. The Grove Resort & Water Park Orlando

Winter Garden

Jessica

NT$5,826

NT$8,349 total

includes taxes & fees

Oct 24 - Oct 25

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

A modern living room with a teal accent wall, a sofa, ottomans, a dining area with white chairs, and a balcony with a view.

A modern living room with a sofa, ottoman, and a TV on a stand.

A spacious lobby with a reception desk, wooden flooring, and modern chandeliers.

8. Hilton Vacation Club Aqua Sol Orlando West

Winter Garden

Kevin

NT$3,069

NT$4,369 total

includes taxes & fees

Oct 30 - Oct 31

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Top Winter Garden Hotel Reviews

Universal's Cabana Bay Beach Resort

8/10 Good

"We really enjoyed the lazy river, just with you provided free tubes instead of needing to buy one on site"

The Grove Resort & Water Park Orlando

10/10 Excellent

"Clean room everything we would need for our stay. Upgraded room. Very spacious with big beds and good size bathrooms"

Marriott's Grande Vista

10/10 Excellent

"I enjoyed my stay. I was here for a conference and I stayed 6 nights. The room was spacious, clean, and quiet. I had a view of the golf course that was perfect! Oh...the bed was one of the most comfortable beds ever!"

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

10/10 Excellent

"Convenient to the parks. Room was great and spacious with the bunk beds! ( So glad I got that!) Property was wonderful and loved the playground for the kids. Weather was a little chilly for swimming and since driving all day the playground allowed them to get out their wiggles! Breakfast was amazing! Will definitely stay here again"

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent

"Traveled as a family of 4. The breakfast was great. The evening snacks and beverages were super convenient especially after a long day at the parks. Free shuttle to Disney parks was great! Just know it's 1st come so arrive early. There aren't any stores nearby for minor things so you would have to drive or Uber to someplace if you forgot something from home. Disney springs is about a 15 min walk from property. Overall it was a great place to stay. This will be a place to stay for future visits to Orlando. It was convenient between both Universal and Disney parks. About equal distance to both."

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent

"Everything was great. Loved how the bedroom had its own door unlike a standard hotel. Pools were really nice, check in was extremely smooth. Only minor annoyance was we got called at least once a day about a “departure gift”. Once at 9 am when we were trying to get some sleep. After the 3rd time it got a bit annoying. No complaints about amenities"

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent

"Good breakfast"

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent

"Amazing place to stay at. The villas were clean and beautiful. Lots of of room and space. There was a back deck, which was a nice hangout spot. The pool and waterpark were great. The kids enjoyed it very friendly staff and great location not far from Disney World. Our stay definitely felt like we were “ welcomed home.” would stay again!!!"

Frequently asked questions

Searching for hotels with bars in Winter Garden?

If you prefer a place to stay where you can enjoy an evening cocktail after sightseeing, Winter Garden features 371 properties, including 10 accommodations with an onsite bar. While you're in the area, you can check out Universal Studios Florida and Universal Orlando Resort.

What are the best hotels with bars in Winter Garden?

Here's a few of the top Winter Garden accommodations with bars: The Grove Resort & Water Park Orlando: Resort with 3 restaurants. Enjoy the 3 poolside bars, free WiFi, and 6 outdoor pools. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. Home2 Suites by Hilton Orlando at Flamingo Crossings: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. Homewood Suites by Hilton Orlando at Flamingo Crossings: Hotel with restaurant. Enjoy the 2 bars, free breakfast, and free WiFi. Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance: Enjoy the 2 bars, free breakfast, and free WiFi.

How many hotels with onsite bars can I expect to find in Winter Garden?

Expedia has 10 hotels with a bar in Winter Garden.

What is there to do in Winter Garden?

Absorb the local culture by visiting ESPN Wide World of Sports Complex, Camping World Stadium, and Kia Center, then unwind with a refreshing drink. Other places to see include Orange County National Golf Club and Lake Louisa State Park. Winter Garden is recognized for its fun-filled theme parks, array of shops, and top-notch restaurants.

When is the best time to visit Winter Garden?

Visiting local bars in Winter Garden is more fun in good weather. These rainfall averages and temperatures can help you choose the best time for bar hopping. The hottest months are usually August and July with an average temp of 82°F, while the coldest months are January and February with an average of 64°F. The rainiest months in Winter Garden are August, July, September, and June, with each month seeing an average of 9 inches of rainfall.

How can I get to Winter Garden and around the area?

You might want to make the most of these transportation choices in and around Winter Garden: Fly into Orlando Intl. Airport (MCO), which is located 19.3 mi (31 km) from the city center. Otherwise, look for flights into Kissimmee, FL (ISM-Kissimmee Gateway), which is 20.8 mi (33.5 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

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Check availability on Winter Garden Hotels with Bars

Our top choices for Winter Garden hotels with a bar

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

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

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

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

5. Home2 Suites by Hilton Orlando at Flamingo Crossings