Windermere Vacations
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Windermere Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Clarion Inn Orlando International Drive - ICON Park
International Drive District
$409
per person
Dec 15 - Dec 23
found 19 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Orlando (MCO)
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, free parking, and a free theme park shuttle. Our guests praise the clean rooms in our reviews. Popular attractions Universal’s Volcano Bay and Orange County Convention Center are located nearby.
Unfortunately, my stay was very disappointing. The shower did not have a curtain, which caused water to spill out and flood the bathroom floor. The shower also made a very loud squeaking noise whenever it was turned on.
The bed made loud noises whenever I moved, which made it difficult to sleep. There was also a bad odor throughout the room. On top of that, the refrigerator was not working properly, and when I woke up, all of my drinks were warm.
Overall, the room did not feel properly maintained or comfortable. I expected much better for the price and would not stay here again unless these issues are addressed.
Reviewed on Oct 4, 2026
Legacy Vacation Resorts - Kissimmee/Orlando
$477
per person
Dec 17 - Dec 23
found 19 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Orlando (MCO)
Book a stay at this family-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and 4 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.
La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks
International Drive District
$542
per person
Dec 17 - Dec 23
found 19 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Orlando (MCO)
Book a stay at this business-friendly 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 Orange County Convention Center and Orlando Vineland Premium Outlets are located nearby.
Good
Reviewed on Oct 5, 2026
Lifetime of Vacations Resort
$478
per person
Dec 17 - Dec 23
found 19 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Orlando (MCO)
Stay at this condo in Kissimmee. Enjoy free WiFi, a fitness center, and a business center. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.
I had a very pleasant and relaxing seven-night stay at this resort. The unit was spacious, comfortable, and very well equipped, with a separate living room, a full kitchen stocked with dishes and appliances, and a very comfortable king-size bed. One of my favorite features was the beautiful lake view from the sliding glass door. The space was so peaceful and cozy that I actually spent much of my time just enjoying the unit itself rather than going out. That said, there are a few areas for improvement. First, the air conditioning system seemed to blow a fine black dust that accumulated on the living room table, so the filters or system may need maintenance. Second, there was no housekeeping service during my entire stay unless requested. For a seven-night visit, at least one basic cleaning would have been very helpful. I also appreciated having washers and dryers available in the buildings. The machines worked well and cleaned my clothes nicely. However, they are coin operated, which is inconvenient these days. I tried to get coins at the front desk, but they didn’t have any, and finding coins at nearby stores was surprisingly difficult. If the resort plans to keep coin-operated machines, having a change machine at the front desk would be extremely helpful. Even better, adding a card or digital payment option in the future. Overall, I really enjoyed my stay. With a few improvements in maintenance, housekeeping, and laundry convenience, the guest experience could be even better
Reviewed on Sep 10, 2026
Destiny Palms Hotel Maingate West
$482
per person
Dec 17 - Dec 23
found 19 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Orlando (MCO)
Stay at this hotel in Kissimmee. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.
Delta Hotels by Marriott Orlando Lake Buena Vista
$533
per person
Dec 17 - Dec 23
found 19 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 pool and the helpful staff in our reviews. Popular attractions Orlando Vineland Premium Outlets and Disney Springs™ are located nearby.
Windermere Vacation Packages
Looking for ways save some money and some time on your upcoming trip to Windermere? Don't worry, as AARP Travel Center Powered by Expedia® is here to help. We're here to book everything you'll need to make your Windermere trip one to remember. Our Travel Center is a one-stop shop where you can put together the best Windermere vacation package for you and your family. We have a huge list of accommodations and flight, as well as local things to do to select from.
Windermere Hotels
With 53762 hotels and resorts in Windermere to choose from, you will find one that is perfect for you.
From Windermere hotels with swimming pools and on-site restaurants, to boutique accommodations that add all the extra amenities, you'll find a hotel here that will make your trip one to remember. With AARP Travel Center's Windermere hotel packages, you not only get a great rate on your flight, but also a great place to stay.
Things to do in Windermere
Windermere is the ideal place when you need to a break from it all. With only around 3,249 people in the city, this hidden-gem is good for a quite vacation. This city is known for always having something to see and do. A lot of visitors enjoy the chance to experience the great outdoors.
Looking for more? Then Check out AARP Travel Center's "Things to Do" Page.
Package Your Windermere Vacation and Save
With so much going on in Windermere, you'll be wanting to plan your itinerary, not devoting time to searching for the cheapest hotel. The AARP Travel Center Powered by Expedia® allows you to easily get all you want, and save some cash. You can coordinate your entire vacation, including things to do in Windermere from only one place. So what are you waiting for? Book now and save!
Top Hotel Deals
Hyatt Regency Orlando International Airport
9300 Jeff Fuqua Boulevard Orlando FL
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
8800 Vistana Centre Dr Orlando FL
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
5925 Avenida Vista Orlando FL
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 ...
DoubleTree by Hilton at the Entrance to Universal Orlando
5780 Major Blvd Orlando FL
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 ...
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue Winter Garden FL
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 ...
Rosen Inn Lake Buena Vista
8442 Palm Parkway Orlando FL
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
6550 Adventure Way Orlando FL
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 ...
Westgate Lakes Resort & Spa Universal Studios Area
9500 Turkey Lake Rd Orlando FL
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 ...
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
12401 International Dr Orlando FL
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 ...
Walt Disney World Dolphin
1500 Epcot Resort Blvd Lake Buena Vista FL
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 Orlando Theme Park Resort
10100 International Drive Orlando FL
Book a stay at this family-friendly resort in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our ...
Universal's Endless Summer Resort - Dockside Inn and Suites
7125 Universal Boulevard Orlando FL
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 ...
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
631 FLAGLER AVE Winter Garden FL
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 ...
Kompose Boutique Resort at Theme Parks
7491 W Irlo Bronson Memorial Hwy Kissimmee FL
Stay at this resort in Kissimmee. Enjoy free breakfast, free WiFi, and 2 hot tubs. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World ...
Drury Plaza Hotel Orlando - Disney Springs Area
2000 Hotel Plaza Boulevard Lake Buena Vista FL
Book a stay at this business-friendly hotel in Lake Buena Vista. Enjoy free breakfast, free WiFi, and 3 restaurants. Our guests praise the breakfast and the ...
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.
Wed, Nov 11 - Tue, Nov 24
MSP
Minneapolis - St. Paul Intl.
MCO
Orlando Intl.
$106
Roundtrip
found 5 days ago
Sat, Oct 31 - Tue, Nov 17
BOS
Logan Intl.
MCO
Orlando Intl.
$159
Roundtrip
found 3 hours ago
Wed, Nov 11 - Sat, Nov 14
BOS
Logan Intl.
MCO
Orlando Intl.
$159
Roundtrip
found 3 hours ago
Sat, Oct 24 - Sun, Nov 1
SWF
Stewart Intl.
MCO
Orlando Intl.
$165
Roundtrip
found 14 hours ago
Wed, Oct 28 - Tue, Nov 10
BOS
Logan Intl.
MCO
Orlando Intl.
$179
Roundtrip
found 3 hours ago
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