Winter Garden Vacations

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Winter Garden Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Banana Leaf Villa

Banana Leaf Villa

Orlovista
Save 100% on your flight
$200
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Orlando (MCO)
Stay at this hotel in Orlando. Enjoy free WiFi, free parking, and a garden. Popular attractions The Wizarding World of Harry Potter™ and Universal Studios Florida are located nearby.
Easy check-in staff was amazing everything about the experience of staying there was amazing. I definitely would recommend going there again.

Reviewed on Sep 20, 2026

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

Save 100% on your flight
$404
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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.
Excellent location, nice and clean rooms, 10.

Reviewed on Sep 22, 2026

The Delaney Hotel

The Delaney Hotel

South Orange
Save 100% on your flight
$419
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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.
First impressions were great. The suite was huge! The Tavern was awesome, and management resolved concerns promptly. Its a bonus to have access to a fridge and microwave. The coffee makers were nice for making mini coffees. The only suggestion I'd have is to adjust the doors to not slam so loudly! I'd stay here again!

Reviewed on Sep 23, 2026

Century Millenia

Century Millenia

Florida Center
Save 100% on your flight
$342
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Orlando (MCO)
Stay at this apartment in Orlando. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Orlando International Premium Outlets and Universal Orlando Resort are located nearby.
El lugar está bien solo tengo algunas recomendaciones,las camas se quejan mucho como q están para cambio,afuera en la propiedad la basura esta afuera de contenedor y se ve feo al visitante,pero es recomendable el lugar muy centrico.

Reviewed on Sep 21, 2026

The Eo Inn - Downtown

The Eo Inn - Downtown

South Eola
Save 100% on your flight
$352
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Orlando (MCO)
Stay at this hotel in Orlando. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Kia Center and Camping World Stadium are located nearby.
The age of the place is part of its charm. It defiantly needs some needs some TLC but the location and staff make up for all of that.

Reviewed on Sep 21, 2026

Hyatt House Orlando International Drive

Hyatt House Orlando International Drive

International Drive District
Save 100% on your flight
$311
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Orlando (MCO)
Book a stay at this business-friendly hotel in Orlando. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Popular attractions Orlando International Premium Outlets and Universal CityWalk are located nearby.
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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 54910 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 ...
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 ...
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 ...
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 ...
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

2111 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 2 bars/lounges. Our guests praise the breakfast and the pool ...
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 ...
Avanti International Resort

Avanti International Resort

8738 International Dr Orlando FL
17.96 km from city center
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the helpful ...
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 ...
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

9500 Turkey Lake Rd Orlando FL
18.65 km from city center
Book a stay at this spa hotel in Orlando. Enjoy free parking, 7 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
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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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