Windermere Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Windermere Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort
$421
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 Delaney Hotel
South Orange
$597
per person
Oct 30 - Nov 3
found 2 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Florida Hotel & Conference Center in the Florida Mall
$550
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 Universal Epic Universe are located nearby.
Riviere Apartments King Bed Suite & Pool & Gym & Pet Friendly & Near Epic Universe
International Drive District
$829
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Orlando (MCO)
Stay at this apartment in Orlando. Enjoy free parking, a fitness center, and an in-room coffeemaker. Popular attractions Orlando International Premium Outlets and Universal CityWalk are located nearby.
Riviere 2BR Apartment Pet Friendly Oasis Sleeps 6 Close to Epic Universe Pool & Gym
International Drive District
$1,058
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Orlando (MCO)
Stay at this apartment in Orlando. Enjoy free parking, a fitness center, and an in-room coffeemaker. Popular attractions Orlando International Premium Outlets and Universal CityWalk are located nearby.
Holiday Inn Express & Suites, International Drive by IHG
International Drive District
$535
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Orlando (MCO)
Book a stay at this business-friendly hotel in Orlando. Enjoy free breakfast, free WiFi, and a free theme park shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Universal’s Volcano Bay and The Orlando Eye are located nearby.
Very clean room, Extremely helpful staff and manager
Reviewed on Aug 20, 2026
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 53705 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
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 ...
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 ...
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 ...
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 ...
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 ...
Walt Disney World Swan
1200 Epcot Resort Blvd Lake Buena Vista FL
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
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 ...
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 ...
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 ...
Wyndham I-Drive Avanti Resort & Conference Center
6515 International Drive Orlando FL
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 ...
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 ...
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 ...
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 ...
Holiday Inn Resort Orlando Suites - Waterpark by IHG
18000 International Dr S. Orlando FL
Book a stay at this family-friendly hotel in Orlando. Enjoy 2 outdoor pools, 5 restaurants, and 2 hot tubs. Our guests praise the clean rooms and the family ...
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 ...
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, Sep 9 - Tue, Sep 15
ORD
O'Hare Intl.
MCO
Orlando Intl.
$108
Roundtrip
found 5 days ago
Tue, Oct 6 - Tue, Oct 13
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$172
Roundtrip
found 2 days ago
Tue, Sep 1 - Sun, Sep 27
SWF
Stewart Intl.
MCO
Orlando Intl.
$173
Roundtrip
found 6 days ago
Sat, Jan 16 - Sat, Jan 23
ORD
O'Hare Intl.
MCO
Orlando Intl.
$195
Roundtrip
found 6 days ago
Fri, Oct 2 - Wed, Oct 7
LGA
LaGuardia
MCO
Orlando Intl.
$199
Roundtrip
found 8 hours ago
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