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.
Holiday Inn Express Orlando – South Park by IHG
Save 100% on your flight
Price was $849, price is now $641 per person
$641
per person
Aug 27 - Sep 4
found 16 hours ago
Roundtrip flight included
New York (JFK) 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 Universal Epic Universe and Aquatica are located nearby.
The staff are amazing that we’re at the front desk when we tried to go to bed. Finally, our bed actually had somebody else’s funk on it and the front desk was able to get us a new bedding and did everything they could to make it right.
Reviewed on Jul 4, 2026
The Delaney Hotel
South Orange
Save 100% on your flight
Price was $1,339, price is now $848 per person
$848
per person
Aug 27 - Sep 4
found 16 hours ago
Roundtrip flight included
New York (JFK) 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 Camping World Stadium are located nearby.
Beautifully updated property. Great south downtown location away from the main tourists haunts. I would have loved to given an all five-star review, but there were minor and major deficiencies. I will start with the minor issues: hair present in the room and bathroom and minor mold present in bathroom. The king suite was extremely spacious and modernly adorned. A true five-star room. The major: both emergency exit stairwells were partially blocked with furniture, supplies, and junk at the ground floor level. This is not just a guest safety issue, but also a major fire code violation. This is the reason behind the 3-star rating. Pro tip: book with Expedia and you can save on the parking fee.
Reviewed on Jul 5, 2026
Florida Hotel & Conference Center in the Florida Mall
Save 100% on your flight
Price was $1,437, price is now $923 per person
$923
per person
Aug 27 - Sep 4
found 16 hours ago
Roundtrip flight included
New York (JFK) 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.
Thank you for all
Reviewed on Jun 30, 2026
AC Hotel by Marriott Orlando Downtown
Downtown Orlando
Save 100% on your flight
Price was $1,119, price is now $783 per person
$783
per person
Aug 27 - Sep 4
found 16 hours ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
Stay at this hotel in Orlando. Enjoy breakfast (surcharge), a fitness center, and valet parking (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Kia Center and Orlando International Premium Outlets are located nearby.
Great hotel loved the view.
Reviewed on Jul 4, 2026
NEW Listing Discount! • Near Manatees & Springs
Save 100% on your flight
Price was $1,023, price is now $772 per person
$772
per person
Sep 4 - Sep 11
found 12 hours ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Stay at this vacation home in Crystal River. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Three Sisters Springs and Homosassa Springs Wildlife State Park are located nearby.
The place was adorable! We loved the extra items like sunscreen, snacks and drinks that were waiting for us.
Reviewed on Jun 11, 2026
Crystal River Lullaby B&B
Save 100% on your flight
Price was $1,202, price is now $910 per person
$910
per person
Sep 4 - Sep 11
found 12 hours ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Book a stay at this family-friendly B&B in Crystal River. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Fort Island Gulf Beach and Three Sisters Springs are located nearby.
The food was unique and delicious!
Reviewed on Jun 28, 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 52222 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
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
14.47 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 ...
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue Winter Garden FL
18.7 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 ...
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
6.89 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 ...
Kompose Boutique Resort at Theme Parks
7491 W Irlo Bronson Memorial Hwy Kissimmee FL
18.63 km from city center
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 ...
Avanti International Resort
8738 International Dr Orlando FL
8.82 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 ...
Rosen Inn Lake Buena Vista
8442 Palm Parkway Orlando FL
12.64 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
1500 Epcot Resort Blvd Lake Buena Vista FL
14.48 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 ...
Hyatt Regency Orlando International Airport
9300 Jeff Fuqua Boulevard Orlando FL
23.56 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 ...
DoubleTree by Hilton at the Entrance to Universal Orlando
5780 Major Blvd Orlando FL
7.83 km from city center
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 ...
Walt Disney World Swan
1200 Epcot Resort Blvd Lake Buena Vista FL
14.68 km from city center
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 ...
Holiday Inn & Suites Orlando SW - Celebration Area by IHG
5711 W Irlo Bronson Memorial Hwy Kissimmee FL
18.07 km from city center
Book a stay at this family-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
14200 Bonnet Creek Resort Lane Orlando FL
15.75 km from city center
Book a stay at this luxury resort in Orlando. Enjoy 2 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff in our reviews. ...
Holiday Inn Resort Orlando Suites - Waterpark by IHG
18000 International Dr S. Orlando FL
15.61 km from city center
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 ...
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 - Fri, Oct 16
TTN
Mercer
MCO
Orlando Intl.
$86 Roundtrip, found 6 hours ago
$86
Roundtrip
found 6 hours ago
Sat, Oct 24 - Sat, Oct 31
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$112 Roundtrip, found 6 hours ago
$112
Roundtrip
found 6 hours ago
Wed, Oct 28 - Sat, Oct 31
LGA
LaGuardia
MCO
Orlando Intl.
$177 Roundtrip, found 3 hours ago
$177
Roundtrip
found 3 hours ago
Tue, Oct 13 - Tue, Nov 3
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$177 Roundtrip, found 3 hours ago
$177
Roundtrip
found 3 hours ago
Tue, Sep 22 - Wed, Oct 14
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$177 Roundtrip, found 3 hours ago
$177
Roundtrip
found 3 hours ago