Find Hotels with Bars in Winter Garden, FL

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Check availability on Winter Garden Hotels with Bars

Our top choices for Winter Garden hotels with a bar

Free daily buffet breakfast
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

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

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
2.5 star property
Bay Lake
9.4 out of 10, Exceptional, (4382)
"Great trip great place to stay"
United States
Tammy
The price is NT$3,646
NT$4,102 total
includes taxes & fees
Jan 7 - 2026/1/8
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Outdoor pool, a heated pool
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

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

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
Bay Lake
9.0 out of 10, Wonderful, (2244)
"breakfast was great, room was clean, excellent stay "
United States
Matt
The price is NT$3,583
NT$4,031 total
includes taxes & fees
Jan 19 - 2026/1/20
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Outdoor pool, open 9:00 AM to 10:00 PM, pool umbrellas, sun loungers
Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
Bay Lake
9.2 out of 10, Wonderful, (5139)
"Amazing Hotel, clean and staff very friendly!!"
United States
sheila
The price is NT$3,575
NT$4,022 total
includes taxes & fees
Jan 25 - 2026/1/26
Home2 Suites by Hilton Orlando at Flamingo Crossings
Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
3.0 star property
Bay Lake
9.6 out of 10, Exceptional, (1979)
"Great location, good, staff, and rooms "
Canada
Jobin
The price is NT$4,495
NT$5,057 total
includes taxes & fees
Jan 19 - 2026/1/20
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Exterior
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
4.0 star property
Winter Garden
8.8 out of 10, Excellent, (4075)
"Excellent Hotel, comfort room and area pool, recommend and select in other moment to visit Orlando. "
United States
Ramon Gilberto Ayala
The price is NT$3,340
NT$4,642 total
includes taxes & fees
Jan 12 - 2026/1/13
Hilton Vacation Club Aqua Sol Orlando West
Outdoor pool, a heated pool
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

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

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
Bay Lake
9.0 out of 10, Wonderful, (1660)
"The room and location were excellent. "
United States
Micah
The price is NT$3,583
NT$4,031 total
includes taxes & fees
Jan 7 - 2026/1/8
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers
Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
Bay Lake
9.4 out of 10, Exceptional, (2167)
"Very nice hotel, great amenities and friendly staff."
United States
Latasha
The price is NT$4,098
NT$4,611 total
includes taxes & fees
Jan 26 - 2026/1/27
Homewood Suites by Hilton Orlando at Flamingo Crossings
Aerial view
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
4.0 star property
Winter Garden
8.0 out of 10, Very Good, (8844)
"Excellent Resort! "
United States
Chelsea
The price is NT$5,312
NT$7,709 total
includes taxes & fees
Jan 5 - 2026/1/6
The Grove Resort & Water Park Orlando
Lobby
Orange County National Lodge

Orange County National Lodge

Orange County National Lodge
3.0 star property
Horizon West
7.4 out of 10, Good, (260)
"Rooms need significant updating "
United States
Cal
The price is NT$5,972
NT$6,719 total
includes taxes & fees
Jan 1 - 2026/1/2
Orange County National Lodge
Property amenity
Holiday Inn Express & Suites Clermont Se West Orlando by IHG

Holiday Inn Express & Suites Clermont Se West Orlando by IHG

Holiday Inn Express & Suites Clermont Se West Orlando by IHG
2.5 star property
Clermont
8.4 out of 10, Very Good, (1083)
"Friendly staff, clean property, appreciate transportation to WDW and light breakfast included. "
United States
Janet
The price is NT$3,458
NT$3,838 total
includes taxes & fees
Jan 27 - 2026/1/28
Holiday Inn Express & Suites Clermont Se West Orlando by IHG
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

Top Winter Garden Hotel Reviews

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

10/10 Excellent
"Great experience. Thank you."
RIANELLE 2-night trip
Posted 11 hours ago
Rosen Inn at Pointe Orlando

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 378 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. Home2 Suites by Hilton Orlando at Flamingo Crossings: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. Hilton Vacation Club Aqua Sol Orlando West: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Homewood Suites by Hilton Orlando at Flamingo Crossings: Hotel with restaurant. 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 in the area by visiting Kia Center and ESPN Wide World of Sports Complex, 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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