Windermere Vacations from $290

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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

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
per person
Jul 11 - Jul 16
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8/10 Very Good! (3,865 reviews)
Excellent exerience, me and my family had a fantastic time with the amazing service, morning food service, and the friendly staff. I will recommend this to everyone.

Reviewed on May 3, 2024

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Florida Center
per person
Jul 13 - Jul 19
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.4/10 Very Good! (1,009 reviews)
Hotel is very close to the Universal Studios and provides Bus transport, which is very convenient. Pool and Hot tub is great.

Reviewed on May 1, 2024

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
per person
Jul 13 - Jul 19
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
7.6/10 Good! (1,182 reviews)
Night shift front desk did a great job

Reviewed on May 3, 2024

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Florida Center
per person
Jun 7 - Jun 14
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
7/10 Good! (2,343 reviews)
Great customer service

Reviewed on May 2, 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
Jul 11 - Jul 16
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
7.8/10 Good! (3,698 reviews)
Need more food choices

Reviewed on May 3, 2024

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

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 $202 per night from May 7 to May 8
$202
$278 total
includes taxes & fees
May 7 - May 8
8.2/10 Very Good! (5,314 reviews)
"I loved our time at the resort!"

Reviewed on May 3, 2024

The Grove Resort & Water Park Orlando
Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
3.5 out of 5
14500 Continental Gateway, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is $80 per night from May 6 to May 7
$80
$138 total
includes taxes & fees
May 6 - May 7
6.4/10 (5,275 reviews)
"We have been coming to this resort for 3 years and the amount of improvements they have been doing is awesome. This last trip we kept finding new things they have added on or improved. Painting, new sitting areas, more loungers around the pools, tables and even their gardens have been improved. The ..."

Reviewed on May 1, 2024

Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
Universal's Endless Summer Resort - Dockside Inn and Suites
Universal's Endless Summer Resort - Dockside Inn and Suites
3 out of 5
7125 Universal Boulevard, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is $144 per night from May 5 to May 6
$144
$162 total
includes taxes & fees
May 5 - May 6
9/10 Wonderful! (5,017 reviews)
"Ok- shouldn’t chatge for parking- room sheets and blankets had stains/dirty"

Reviewed on May 3, 2024

Universal's Endless Summer Resort - Dockside Inn and Suites
See all 53,678 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

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Frequently asked questions

How much does a Windermere vacation package cost?
Maybe less than you imagined — from only $290, 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

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