Windermere Vacations from $329

Book a Hotel + Flight or Car together to unlock savings

Choose one or more items to build your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to $580 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Windermere Vacation

Reserve a Windermere vacation package and get set to experience the best of this city. Consider staying in the neighborhood of Downtown Orlando, which is great for shopping, nightlife and dining. If a sightseeing tour is on the cards during your trip to Windermere, look around major attractions like Universal Studios Florida, Magic Kingdom® Park and Universal’s Islands of Adventure. Check out Expedia's wide range of travel options and start planning your ultimate vacation to Windermere now.

The Latest Windermere Vacation Packages

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Florida Center
per person
Jun 5 - Jun 11
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.4/10 Very Good! (1,009 reviews)
This property is very close to Universal parks. It's very clean, quiet and family oriented. My apartment was very spacious. I would recommend it.

Reviewed on Apr 22, 2024

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Save 100% on your flight
per person
May 24 - May 27
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8/10 Very Good! (3,850 reviews)
Overall was quite clean. Check in was very slow with staff having a difficult time communicating clearly. Noice in the hallway was quite loud with very little insulation in the door or between rooms. The breakfest and staff working in that area were very good

Reviewed on Apr 22, 2024

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
per person
May 23 - May 27
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
7.6/10 Good! (3,717 reviews)
Great property! The layout is nice when traveling with family. Only downside to the stay was they really push the timeshare! They have multiple people calling or putting notes on your door. They want 60-90 minutes but it’s really takes almost 3 hours for it! They get really annoyed when you say no to it

Reviewed on Apr 23, 2024

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 23
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
7.4/10 Good! (1,043 reviews)
The accommodation were excellent, as well as staff. The water park was a great way to spend a relaxing day, reasonable price.

Reviewed on Apr 22, 2024

Grand Beach Resort

Grand Beach Resort

3 out of 5
Save 100% on your flight
per person
May 24 - May 31
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9.4/10 Exceptional! (1,908 reviews)
Well maintained, staff super friendly, room was clean and went above my expexctations.would definatley use Grand Beach again if traveling to the area.

Reviewed on Apr 20, 2024

Prices and availability subject to change. Additional terms may apply.

Windermere Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Orlando Intl. Airport (MCO)
Population
3,200
Max Temp Winter
70ºF
Max Temp Summer
90ºF
Top Sights
Walt Disney World® Resort, Universal Orlando Resort and Magic Kingdom® Park

Windermere Hotel Deals

DoubleTree by Hilton at the Entrance to Universal Orlando
DoubleTree by Hilton at the Entrance to Universal Orlando
4 out of 5
5780 Major Blvd, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is $93 per night from May 20 to May 21
$93
$105 total
includes taxes & fees
May 20 - May 21
8.2/10 Very Good! (6,478 reviews)
"Walking distance to Universal Studios and close to premium outlets was great. Hotel had all the basic amenities plus good size pool, Starbucks, restaurants and ice cream shop on premise. My only complaint is that there was literally only one hook in the washroom for a room that sleeps four. A towel ..."

Reviewed on Apr 21, 2024

DoubleTree by Hilton at the Entrance to Universal Orlando
The Grove Resort & Water Park Orlando
The Grove Resort & Water Park Orlando
4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
Fully refundableReserve now, pay when you stay
The price is $197 per night from May 13 to May 14
$197
$272 total
includes taxes & fees
May 13 - May 14
8.2/10 Very Good! (5,248 reviews)
"Nice"

Reviewed on Apr 21, 2024

The Grove Resort & Water Park Orlando
Hyatt Regency Orlando International Airport
Hyatt Regency Orlando International Airport
4 out of 5
9300 Jeff Fuqua Boulevard, Orlando, FL
The price is $199 per night from Apr 24 to Apr 25
$199
$224 total
includes taxes & fees
Apr 24 - Apr 25
9.4/10 Exceptional! (4,717 reviews)
Great place to stay
"Excellent place to stay. Clean and enjoyable."

Reviewed on Apr 19, 2024

Hyatt Regency Orlando International Airport
See all 53,044 properties in Windermere
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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Windermere vacation package cost?
Maybe less than you imagined — from only $329, as a matter of fact! By bundling flights, hotels and car rentals into a custom-made package, your getaway to Windermere is just a few clicks away.
How do I get a cheap travel package to Windermere?
Bundle your flights and hotels with Expedia to save big on your next big adventure. With over 550 partner airlines and 1,000,000 hotel options across the world, your Windermere vacation package can be tailored exactly to suit your travel style. With all that extra cash, why not include one or two exciting tours and experiences? It’s an easy way to unlock even more bargains. Your dream vacation in Windermere is much closer than you thought!
Where should I stay in Windermere?
Stay close to the action. Many visitors book hotels around popular sights, like Arnold Palmers Bay Hill Golf Club, Isleworth Golf and Country Club and Windermere Country Club.
What are the top hotels in Windermere?
Captains Lake House is one of Windermere’s best hotels. Book a room here and you can sleep soundly knowing you’re in good hands.
How far in advance should I book my Windermere vacation?
To score rock-bottom prices, book ASAP. Air carriers usually advertise flight tickets, along with some of the lowest fares, around a year prior to departure. Hotels, car rental and experiences should also be booked well in advance so you can have the pick of the bunch. If you were hoping for a last-minute getaway in Windermere, there are always lots of great deals to be had on Expedia. Book something in today!
What does an Expedia Windermere travel package include?
It depends on what kind of getaway you want to have. Windermere travel deals can include flights, car rentals and hotels. You can mix and match to create the bundle that works for you! You can also add on experiences and activities after you’ve booked to land even bigger discounts.
What should I know before booking a Windermere travel package?
You can save big by bundling your hotels, flights and rental cars. Once you’ve made your booking, you can add on tours and activities. Your next awesome vacation is only a couple of clicks away.
Can I choose my airline with a Windermere Expedia vacation package?
You can. We have more than 550 airline partners all over the world, so pick the carrier that best fits your travel preferences.
If I'm not able to travel, can I cancel my Windermere vacation package?
It is possible to cancel your Windermere booking if your travel plans have changed. Whether you’ll incur a penalty or not depends on your hotel, airline or car rental company. You may be able to change or cancel your booking for free if you booked in the last 24 hours. Head to our Customer Service Portal to find out more.

Discover the most popular places to visit in Windermere

Image for Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(2,427 reviews)

Walt Disney World® Resort is part of Orlando. It makes up part of bustling metropolis that is home to 240,000 inhabitants. Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando’s city center. If you are flying in, Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando International Airport.

Walt Disney World® Resort
Image for Universal Studios Florida

Universal Studios Florida

4.5/5(9,273 reviews)

Thrill rides based on your favorite movies create this internationally acclaimed theme park.

Universal Studios Florida
Image for Universal Orlando Resort

Universal Orlando Resort

4.5/5(4,155 reviews)

Make your Florida vacation one to remember with a stay at this hotel and theme park complex.

Universal Orlando Resort

What to do in Windermere

Image for Aquatica Orlando

Aquatica Orlando

$48
Per adult
82% of travellers recommend
Aquatica Orlando
Image for Orlando: Museum of Illusions Admission Ticket

Orlando: Museum of Illusions Admission Ticket

$31
Per adult
84% of travellers recommend
Orlando: Museum of Illusions Admission Ticket
See all activities in Windermere

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.