Winter Garden Vacations

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Winter Garden Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort

Seasons Florida Resort

Save 100% on your flight
$322
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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.
Very clean, very QUIET AND PEACEFUL. closed to shopping. Staff were very nice

Reviewed on Sep 10, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Save 100% on your flight
$818
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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.
The Delaney Hotel

The Delaney Hotel

South Orange
Save 100% on your flight
$642
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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.
The hotel was very quaint, just make sure they dont give you a room facing the street. We heard sirens all night. The beds are super comfortable, and housekeeping is right on the job.

Reviewed on Sep 9, 2026

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

Save 100% on your flight
$586
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Orlando (MCO)
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Florida Mall and Orlando International Premium Outlets are located nearby.
Clean room. Helpful, knowledgeable and courteous staff. Starbucks was open. Many shops, stores and restaurants nearby. Great Asian takeout located in the Florida Mall. Ample parking.

Reviewed on Sep 5, 2026

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

$347
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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.
Excellent property to stay with many amenities, great rooms and comfortable beds and sofa, to relax and enjoy a great getaway . Also theater by the pool and you can relax at the cabans available. I have stayed here many times in the past and do go anywhere else. I Feel at my as my 2nd home here. The Front Desk Staff are all Excellent,great service, and helpfull all the time.

Reviewed on Sep 9, 2026

Crowne Plaza Orlando - Lake Buena Vista by IHG

Crowne Plaza Orlando - Lake Buena Vista by IHG

$460
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Orlando (MCO)
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Orlando Vineland Premium Outlets and Disney Springs™ are located nearby.
Overall, a great experience. We had an issue with our tub not draining, and the staff took care of it as soon as we reported it. The shuttle to Epcot and Hollywood Studios was very convenient. Would definitely stay here again!

Reviewed on Sep 9, 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 55378 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 ...
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 ...
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 ...
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

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

13295 Hartzog Road Winter Garden FL
20.8 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 ...
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard Orlando FL
31.24 km from city center
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the restaurant ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

12401 International Dr Orlando FL
22.46 km from city center
Book a stay at this family-friendly aparthotel in Orlando. Enjoy free WiFi, 5 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
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See all available properties in Winter Garden
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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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Breeze Airways
American Airlines
JetBlue Airways
Delta