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 11 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.
Universal's Cabana Bay Beach Resort
Florida Center
$799
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
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 our reviews. Popular attractions Universal’s Islands of Adventure and Universal’s Volcano Bay are located nearby.
Had a wonderful stay overall. Check in and check out was very easy, staff were really friendly and accommodating. Lots of activities to do in the resort, easy access to the parks via shuttle 2 min walk from the lobby or a boat taken from Sapphire Falls hotel across the road. Easy access to Volcano Bay waterpark (my favourite feature of the resort) with private security. Early park admission when you stay in this hotel - allows you to experience all the Universal rides that are usually long wait times during the day. Food court offers some good but limited food options for us so we preferred to eat out, complimentary gym was good with all the essential equipment. Starbucks onsite was really useful for quick service food and drinks. Lazy river and pools were good for lazy days. First room didn’t have the best view so asked reception who kindly swapped us to a better room with a view of the parks, Orlando area and Intl drive. Rooms were cleaned daily with fresh towels and soap. Would’ve preferred an anti-bac soap dispenser rather than soap bars but that’s personal preference. Bathroom was a little dated but pleasant. Beds were really comfortable and air-con was very good too. Overall I enjoyed my stay and would love to return again!
Reviewed on Aug 20, 2026
Club Wyndham Bonnet Creek
$917
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 resort in Orlando. Enjoy free WiFi, 4 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Epcot® and Disney's Hollywood Studios® are located nearby.
I loved our stay, my daughter and I got upgraded to a room with a balcony overlooking the fireworks which was such a beautiful experience. We will definitely be back. Thank you
Reviewed on Aug 18, 2026
Hyatt House Orlando International Drive
International Drive District
$459
per person
Oct 30 - Nov 3
found 11 hours ago
Roundtrip flight included
Dallas (DFW) 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.
The Eo Inn - Downtown
South Eola
$551
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
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
Wed, Dec 16 - Tue, Dec 29
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$199
Roundtrip
just found
Best neighborhoods in Orlando
Best points of interest in Orlando
- Lake Butler Vacations
- Isleworth Golf and Country Club Vacations
- Tibet Butler Preserve Vacations
- Walt Disney World® Resort Vacations
- Universal Studios Florida Vacations
- Universal Orlando Resort Vacations
- Disney SpringsTM Vacations
- Magic Kingdom® Park Vacations
- Disney's Animal Kingdom® Theme Park Vacations
More AARP Member Vacation Packages
- Las Vegas Vacations
- New York Vacations
- Orlando Vacations
- Los Angeles Vacations
- Miami Vacations
- San Francisco Vacations
- New Orleans Vacations
- Chicago Vacations
- Fort Lauderdale Vacations
- Boston Vacations
- Honolulu Vacations
- San Diego Vacations
- Washington Vacations
- Toronto Vacations
- Anaheim Vacations
- Atlanta Vacations
- Nashville Vacations
- Seattle Vacations
- Phoenix Vacations
- Myrtle Beach Vacations
- Vancouver Vacations
- Palm Springs Vacations
- Denver Vacations
- Tampa Vacations
- Niagara Falls Vacations
- San Antonio Vacations
- Atlantic City Vacations
- Philadelphia Vacations
- Austin Vacations
- Dallas Vacations