Windermere Vacations

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Find the Best Windermere Vacation Packages

Windermere Hotel Deals

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 ₩158,973 per night from Jul 28 to Jul 29
₩158,973
₩178,843 total
Jul 28 - Jul 29
includes taxes & fees
9.2/10 Wonderful! (3,113 reviews)
Family Trip
"We went for two nights during a Disney visit. The 2 bedroom unit was large, comfortable and updated. However, the water pressure in the showers was below lack luster and the water temperature was either burning hot or frigid."

Reviewed on Jun 25, 2025

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
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 ₩139,667 per night from Jul 22 to Jul 23
₩139,667
₩157,126 total
Jul 22 - Jul 23
includes taxes & fees
8.8/10 Excellent! (2,544 reviews)
"I had a fantastic stay!"

Reviewed on Jun 25, 2025

Marriott's Grande Vista
Rosen Inn at Pointe Orlando
Rosen Inn at Pointe Orlando
3 out of 5
9000 International Drive, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is ₩171,481 per night from Jul 11 to Jul 12
₩171,481
₩192,918 total
Jul 11 - Jul 12
includes taxes & fees
8.4/10 Very Good! (4,558 reviews)
"Friendly staff location was perfect for our trip."

Reviewed on Jun 26, 2025

Rosen Inn at Pointe Orlando
See all 52,028 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 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.