Windermere Vacations from ￥178,934

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The Latest Windermere Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Florida Center
per person
Aug 22 - Aug 27
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Orlando (MCO)
8.6/10 Excellent! (1,001 reviews)
The location was amazing!

Reviewed on Jun 15, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Orlando (MCO)
8/10 Very Good! (1,261 reviews)
Food pricey and low quality. After 6 pm most all the amenities closed. Not a hotel not a resort. Two days it is enough to stay.

Reviewed on Jun 18, 2025

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Orlando (MCO)
9/10 Wonderful! (1,001 reviews)
We rented a cottage for a week and enjoyed our time there. The cottage was clean orderly and delivered as indicated in description. Check in was easy and staff member at the desk was helpful. Pool area clean, lots of options for drinks and food items. Our cottage was about a 7-8 minute walk to the pool area. We had complimentary passes to nearby water park and enjoyed those days. Easy to get around the area

Reviewed on Jun 16, 2025

Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Orlando (MCO)
8.4/10 Very Good! (988 reviews)
Good and clean close to dining

Reviewed on Jun 15, 2025

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Orlando (MCO)
7.8/10 Good! (1,620 reviews)
Good: You could do something everyday on site. If you needed a replacement item for in the room they would bring it within the hour. There was ice cream on site and Starbucks! Plenty of pools to choose from. Wall Mart is within 3 min drive of where we were staying in P building. NOT Good: I choose there because of the water park but you have to pay $25 per person daily to go in!!!! The market on site did not have hardly any groceries, more gift shop.

Reviewed on Jun 17, 2025

Find the Best Windermere Vacation Packages

Windermere Hotel Deals

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 ￥15,003 per night from Jul 9 to Jul 10
￥15,003
￥16,878 total
Jul 9 - Jul 10
includes taxes & fees
8.8/10 Excellent! (2,522 reviews)
"Super evening"

Reviewed on Jun 17, 2025

Marriott's Grande Vista
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
4 out of 5
8800 Vistana Centre Dr, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is ￥16,936 per night from Jul 16 to Jul 17
￥16,936
￥19,053 total
Jul 16 - Jul 17
includes taxes & fees
9.2/10 Wonderful! (3,064 reviews)
"Good"

Reviewed on Jun 16, 2025

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Rosen Inn Lake Buena Vista
Rosen Inn Lake Buena Vista
3.5 out of 5
8442 Palm Parkway, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is ￥9,510 per night from Jun 22 to Jun 23
￥9,510
￥10,698 total
Jun 22 - Jun 23
includes taxes & fees
8.4/10 Very Good! (5,153 reviews)
"Small, quaint and proximity"

Reviewed on Jun 18, 2025

Rosen Inn Lake Buena Vista
See all 51,979 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.

Frequently asked questions

How much does a Windermere vacation package cost?
You'll find cheap prices from ￥178,934 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.

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

￥3,941
per adult
90% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

￥11,021
per traveler
84% of travellers recommend
LEGOLAND® Florida Tickets
2014_AQ_KatasKookaburraCove_D4D_0772.jpg

Aquatica Orlando

￥7,489
per traveler
82% of travellers recommend
Aquatica Orlando
See all activities in Windermere
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.