Winter Garden Vacations

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Winter Garden Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

Save 100% on your flight
$344
per person
Sep 21 - Sep 25
found 21 hours ago
Roundtrip non-stop flight included
Atlantic City (ACY) to Orlando (MCO)
Stay at this hotel in Kissimmee. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.
My absolute only issue with all my stays here is that the ice machine in NEVER working. Otherwise, for the price, a VERY GREAT DEAL. Zero issues with bugs (bed bugs specifically are a deal breaker for me obviously) and this hotel always seems to be clean and well kept. Breakfast is solid, decent pool and great location, staff is always very nice. 9/10 if ice machine gets fixed, then I'll give 9.5/10 for the value and overall experience for the money :)

Reviewed on Aug 8, 2026

The Delaney Hotel

The Delaney Hotel

South Orange
$823
per person
Oct 26 - Nov 3
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the restaurant and the bar in our reviews. Popular attractions Kia Center and Florida Mall are located nearby.
We had a great stay at this hotel. The room was clean, comfortable, and well maintained, and the staff was friendly and welcoming. The location was also very convenient, making it easy to get around and enjoy the area. Overall, it was a very pleasant experience and a good value for the price. I would definitely recommend this hotel and would be happy to stay here again.

Reviewed on Aug 7, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Save 100% on your flight
$969
per person
Sep 21 - Sep 25
found 21 hours ago
Roundtrip non-stop flight included
Atlantic City (ACY) to Orlando (MCO)
Stay at this hotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.
Friendly and helpful staff.

Reviewed on Aug 6, 2026

Seasons Florida Resort

Seasons Florida Resort

$388
per person
Sep 21 - Sep 25
found 21 hours ago
Roundtrip non-stop flight included
Atlantic City (ACY) to Orlando (MCO)
Book a stay at this business-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.
The room was large and spotless. There was no plug for the bath tub. Price was great.

Reviewed on Aug 8, 2026

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

International Drive District
$480
per person
Sep 21 - Sep 25
found 21 hours ago
Roundtrip non-stop flight included
Atlantic City (ACY) to Orlando (MCO)
Stay at this hotel in Orlando. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Universal’s Volcano Bay and Universal’s Islands of Adventure are located nearby.
WorldQuest Orlando Resort

WorldQuest Orlando Resort

$556
per person
Sep 21 - Sep 25
found 21 hours ago
Roundtrip non-stop flight included
Atlantic City (ACY) to Orlando (MCO)
Book a stay at this family-friendly aparthotel in Orlando. Enjoy free WiFi, free parking, and a free theme park shuttle. Our guests praise the helpful staff in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.
We stayed here one night so it was fine for our party of four. Had booked a 2/2 but they changed us to 3/2. The unite was fully stocked and the AC worked well. However, it is a bit run down in the sense that you could tell there has been high traffic and visible wear and tear. Minor things but don't expect brand new. One note is the main bedroom was in the back of the unit, but the smaller bedrooms had big windows to the main hallway. This made me a bit uneasy as we were traveling with kids, but not huge deal since they were older. Definitely a deal for the space and kitchen (even pots and pans) and the location was central.

Reviewed on Aug 4, 2026

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Winter Garden Vacation Packages

Trying to plan a way to package your Winter Garden flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® Winter Garden vacation packages can help. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Winter Garden the best one yet. Our Travel Center is a one-stop shop where you can put together the best Winter Garden vacation package for you and your family. We have a huge choice of accommodations and flight, and local activities to pick from.

Winter Garden Hotels

You can choose from around 54263 hotels. Whether you want to stay in the heart of the city or pick a spot that is near all the Winter Garden hot spots, we have plenty of options available.

We have great deals on everything from all-inclusive resorts that satisfy all the vacation must-haves to affordable hotels which are great for those on wanting to save a little money. You can browse our vast catalog of possibilities and pick the hotel that is ideal for you. With AARP Travel Center's Winter Garden hotel packages, you not only get a great rate on your flight, but also a wonderful place to stay.

Things to do in Winter Garden

Winter Garden has around 40,356 people that call this city their home. If you needed a break from the hustle of a big city, then you are in the right spot. This city is known for always having something to see and do. But you may have your heart set on taking in the outdoor activities found around every corner.

Looking for more? Then Check out AARP Travel Center's "Things to Do" Page.

Save with a Winter Garden Vacation Package

With so much to see and do in Winter Garden, you'll be wanting to focus on your itinerary, not spending time to searching for the cheapest hotel. The AARP Travel Center Powered by Expedia® allows you to quickly book all you want, and save some cash. You can coordinate your whole holiday, including things to do in Winter Garden from only one site. So what are you waiting for? Bundle now and save!

Top Hotel Deals

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue Winter Garden FL
23.52 km from city center
Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

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

631 FLAGLER AVE Winter Garden FL
20.63 km from city center
Book a stay at this business-friendly hotel in Winter Garden. Enjoy free breakfast, free WiFi, and a free theme park shuttle. Our guests praise the breakfast ...
Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

341 Flagler Ave Winter Garden FL
20.57 km from city center
Book a stay at this business-friendly hotel in Winter Garden. Enjoy free breakfast, a free theme park shuttle, and a 24-hour fitness center. Our guests praise ...
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

17777 Bali Blvd Winter Garden FL
24.82 km from city center
Book a stay at this family-friendly hotel in Four Corners. Enjoy free WiFi, 2 outdoor pools, and free water park access. Our guests praise the pool and the helpful ...
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

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

13279 Hartzog Road Winter Garden FL
20.71 km from city center
Book a stay at this business-friendly hotel in Winter Garden. Enjoy free breakfast, free WiFi, and a free theme park shuttle. Our guests praise the breakfast ...
Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings

411 Flagler Ave Winter Garden FL
20.59 km from city center
Stay at this hotel in Winter Garden. Enjoy free breakfast, 2 bars/lounges, and a free theme park shuttle. Our guests praise the breakfast and the pool in our ...
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr Orlando FL
23.32 km from city center
Book a stay at this family-friendly aparthotel in Orlando. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL
15.87 km from city center
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

8442 Palm Parkway Orlando FL
21.66 km from city center
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and breakfast (surcharge). Our guests praise the breakfast and the pool ...
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

6550 Adventure Way Orlando FL
15.6 km from city center
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
Walt Disney World Swan

Walt Disney World Swan

1200 Epcot Resort Blvd Lake Buena Vista FL
22.4 km from city center
Book a stay at this beach resort in Lake Buena Vista. Enjoy free WiFi, a private beach, and 3 hot tubs. Our guests praise the pool and the helpful staff in our ...
Universal's Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites

7125 Universal Boulevard Orlando FL
16.85 km from city center
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 3 bars/lounges. Our guests praise the pool and the restaurant in ...
Walt Disney World Dolphin

Walt Disney World Dolphin

1500 Epcot Resort Blvd Lake Buena Vista FL
22.13 km from city center
Book a stay at this beach hotel in Lake Buena Vista. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant ...
Marriott's Grande Vista

Marriott's Grande Vista

5925 Avenida Vista Orlando FL
22.78 km from city center
Book a stay at this spa aparthotel in Orlando. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in ...
Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

6515 International Drive Orlando FL
16.4 km from city center
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, free parking, and private pools. Our guests praise the pool and the clean rooms in our ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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