Windermere Vacations from ￥183,752

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The Latest Windermere Vacation Packages

Price found within the past 48 hours. Click for updated prices.
WorldMark Reunion

WorldMark Reunion

4 out of 5
Reunion
per person
Sep 9 - Sep 14
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
9.4/10 Exceptional! (553 reviews)
This was a great resort we stayed in the condos and it was 3bd/3bth full kitchen waterpark access the whole time and neighborhood pools. It was amazing not far from Walmart or Publix and food everywhere

Reviewed on Aug 3, 2025

ette hotel

ette hotel

5 out of 5
per person
Sep 9 - Sep 14
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
9.8/10 Exceptional! (313 reviews)
Everything was great other than the pool closing at 8 pm. The lighting in the room was a bit dim and the magnifying lit mirror in bathroom was not usable. It was activated by motion, but the sensor does not face you. Other than that, it was really good

Reviewed on Aug 1, 2025

Conrad Orlando at Evermore

Conrad Orlando at Evermore

5 out of 5
per person
Oct 6 - Oct 10
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
9.4/10 Exceptional! (247 reviews)
Beautiful property!!

Reviewed on Aug 3, 2025

Evermore Orlando Resort

Evermore Orlando Resort

4 out of 5
per person
Oct 6 - Oct 10
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
9.4/10 Exceptional! (354 reviews)
The property was amazing , very comfortable and spacious , very modern as well ! The pools are amazing and the staff is very nice Our family will definitely be back !!!!

Reviewed on Aug 2, 2025

Caribe Royale Orlando

Caribe Royale Orlando

4.5 out of 5
per person
Sep 9 - Sep 14
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
9.2/10 Wonderful! (4,300 reviews)
4th time staying here. I love it!!!!

Reviewed on Aug 3, 2025

Find the Best Windermere Vacation Packages

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 ￥13,658 per night from Aug 14 to Aug 15
￥13,658
￥15,365 total
Aug 14 - Aug 15
includes taxes & fees
8.2/10 Very Good! (6,484 reviews)
"Everything was ok until we found out that I have to pay for parking 33 a day. Cleanness was 8 out of10"

Reviewed on Aug 2, 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

4 out of 5
9300 Jeff Fuqua Boulevard, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is ￥29,333 per night from Aug 4 to Aug 5
￥29,333
￥33,000 total
Aug 4 - Aug 5
includes taxes & fees
9.4/10 Exceptional! (3,454 reviews)
Cruising next day? Stay here.
"Our family flew in from CT. Perfect location if you are planning to catch a shuttle to the cruise port the next day. McCoys is a great and convenient place for a family dinner. Room was clean, spacious and surprisingly quiet, given that we are at an airport."

Reviewed on Aug 3, 2025

Hyatt Regency Orlando International Airport
Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is ￥12,853 per night from Aug 24 to Aug 25
￥12,853
￥14,461 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (2,749 reviews)
"We loved the grrill by the pool and the and our room was a dream come true overlooking the lake and watching the fireworks at night.we can't wait to book our next trip."

Reviewed on Aug 3, 2025

Marriott's Grande Vista
See all 52,409 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.

Discover the most popular places to visit in Windermere

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
Universal Studios Florida™

Universal Studios Florida

4.5/5(9,273 reviews)

Movie sets and thrill rides combine to create this internationally acclaimed theme park.

Universal Studios Florida
Universal Studios Orlando showing street scenes, a city and rides

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

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

￥3,774
per adult
90% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Aquatica Orlando

Aquatica Orlando

￥7,150
per traveler
82% of travellers recommend
Aquatica Orlando
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

￥9,807
per traveler
84% of travellers recommend
LEGOLAND® Florida Tickets
See all activities in Windermere

Frequently asked questions

How much does a Windermere vacation package cost?
You'll find cheap prices from ￥183,752 on Expedia for your Windermere getaway. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Windermere costs.
What are the cheapest months to go to Windermere?
Plan your trip for the off-peak season and you're likely to get cheap Windermere vacation packages. Bear in mind that public holidays and local events and festivals can have an impact on prices, so do some research before booking.
How many days is enough for Windermere?
Windermere vacations can be short or long, but to really sink your teeth into this destination, we reckon 3 days is a good ballpark. This will mean you can fit in top attractions like Windermere Country Club and Windermere Country Club and seek out some hidden gems. Don't forget to explore neighborhoods such as Florida Center and Lake Buena Vista North either. If you're smart with your time, you can even schedule a day trip or two from Windermere too.
Is it worth booking a vacation package to Windermere?
Windermere is a good vacation destination with attractions like Isleworth Golf and Country Club among the many things to keep you entertained. Whether you're traveling with the family or getting away with friends, a Windermere vacation promises a good time for everyone.
How to find the best Windermere package deals?
Use Expedia's handy filters to help you find some tempting Windermere package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Windermere package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Windermere vacation as a package?
You can enjoy significant savings on your Windermere getaway by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to see the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Windermere?
If you have your Windermere vacation dates confirmed, book as soon as you can to snap up some awesome deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Windermere?

  1. Choose your dates: What you want to do in Windermere and your preferred season will help you decide when to travel.
  2. Figure out your budget: Ensure you have enough money to cover everything from food and transportation to activities and airfares. Your accommodations will likely be the largest expense during your trip to Windermere.
  3. Decide your trip length: Think about how much time you'd like to spend exploring Windermere. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a tailored Windermere vacation package.

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