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
$315
per person
Sep 17 - Sep 21
found 15 hours ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Lo recomiendo 100% nos gusta mucho ya nos hemos hospedado varias veces y siempre nos hemos ido con una buena impresión desde el estacionamiento limpio cuartos limpios se descansa muy bien bien silencioso y todo accesible desde restaurantes hasta comercios
Reviewed on Aug 12, 2026
Palazzo Lakeside Hotel
$341
per person
Oct 29 - Nov 2
found 22 hours ago
Roundtrip non-stop flight included
New York (JFK) 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.
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
International Drive District
$424
per person
Oct 29 - Nov 2
found 21 hours ago
Roundtrip non-stop flight included
New York (JFK) to Orlando (MCO)
Stay at this hotel in Orlando. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Universal’s Volcano Bay and Universal’s Islands of Adventure are located nearby.
We decided to celebrate my birthday here. The pool closed around 8pm and the hot tub was included in that. Our tv didn’t work because if their WiFi. Our electrical portals didn’t work. The toilet was broken. Breakfast was an orange and a mini donut hole. This was NOT the way I wanted to experience Orlando for my birthday. The bed was comfortable but the pillows were flat. If you have a chance to book elsewhere, DO IT! Only perk?!
Comfortable bed
View
No resort fee.
And maybe that’s how they get you.
I’d rather pay a resort fee if that meant getting my money’s worth.
Zero stars!
Never again
Reviewed on Aug 14, 2026
The Delaney Hotel
South Orange
$528
per person
Sep 17 - Sep 21
found 15 hours ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Great hotel and excellent location!
Reviewed on Aug 14, 2026
Florida Hotel & Conference Center in the Florida Mall
$603
per person
Oct 2 - Oct 6
found 3 hours 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.
My stay was great. The staff was great.
Reviewed on Aug 10, 2026
Wyndham Grand Orlando Resort Bonnet Creek
$440
per person
Sep 17 - Sep 21
found 15 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
Book a stay at this spa resort in Orlando. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the breakfast and the pool in our reviews. Popular attractions Epcot® 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 52935 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 ...
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 ...
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 ...
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.
Mon, Oct 5 - Thu, Oct 22
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$80
Roundtrip
found 3 days ago
Fri, Sep 11 - Mon, Sep 14
SWF
Stewart Intl.
MCO
Orlando Intl.
$134
Roundtrip
found 3 days ago
Wed, Sep 23 - Tue, Sep 29
LGA
LaGuardia
MCO
Orlando Intl.
$156
Roundtrip
found 14 hours ago
Wed, Oct 14 - Sat, Oct 17
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$181
Roundtrip
found 2 days ago
Wed, Oct 21 - Wed, Oct 28
ORD
O'Hare Intl.
MCO
Orlando Intl.
$195
Roundtrip
found 3 days ago
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