Windermere Vacation Packages

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Your Windermere Vacation

An easy way to experience this unique city is with a tailor-made Windermere vacation package. Stay in the neighborhood of Ivanhoe Village, which is great for dining, bars and pubs and shopping or choose someplace else — our packages are all about you. Make your trip to Windermere even more enjoyable by including some sightseeing. Universal Studios Florida, Magic Kingdom® Park and Universal’s Islands of Adventure are some of the big attractions you'll want to explore. Browse Expedia's wide range of travel options and begin planning your ideal vacation to Windermere today.

Top Windermere Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
per person
Aug 26 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
7.8/10 Good! (1,649 reviews)
I liked everything about the property; however I did not get a balcony as it stated in my confirmation email and upon booking. I also did not like that the times available for the waterpark did not meet me needs at all, and it was closed as well as the pool whenever i wanted to go. I had a relative that stayed at the Westgate in Orlando, and their pool was open until 11pm and I enjoyed her balcony as I did not get one.

Reviewed on Jul. 22, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
per person
Sep 29 - Oct 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.2/10 Very Good! (5,097 reviews)
It has everything you’ll need for great family fun experience

Reviewed on Jul. 23, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
per person
Sep 27 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
8.6/10 Excellent! (1,006 reviews)
A very clean and fragrant hotel. Close to all the parks and restaurants. The girl who works at the cafe is very friendly. I highly recommend it.

Reviewed on Jul. 22, 2025

ette hotel

ette hotel

5 out of 5
per person
Aug 26 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
9.8/10 Exceptional! (313 reviews)
Love our honeymoon stay

Reviewed on Jul. 23, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
per person
Aug 26 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8/10 Very Good! (1,277 reviews)
Great place to spend time on property and parks.

Reviewed on Jul. 25, 2025

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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 CA $139 per night from Aug 14 to Aug 15
CA $139
CA $156 total
Aug 14 - Aug 15
includes taxes & fees
8.2/10 Very Good! (6,483 reviews)
"Its right next to the universal Studios. The location has many restaurants nearby."

Reviewed on Jul. 24, 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 CA $267 per night from Jul 30 to Jul 31
CA $267
CA $300 total
Jul 30 - Jul 31
includes taxes & fees
9.4/10 Exceptional! (3,406 reviews)
"Convenient stay for super late arrivals."

Reviewed on Jul. 24, 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 CA $119 per night from Aug 17 to Aug 18
CA $119
CA $134 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (2,680 reviews)
"The inability to order in room dining was disturbing"

Reviewed on Jul. 24, 2025

Marriott's Grande Vista
See all 52,659 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
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Discover the most popular places to visit in Windermere

Walt Disney World® Resort

Walt Disney World® Resort

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

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

Universal Studios Florida
Universal Studios Orlando which includes street scenes, a city and rides

Universal Orlando Resort

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

2014_AQ_KatasKookaburraCove_D4D_0772.jpg

Aquatica Orlando

CA $74
per traveller
82% of travellers recommend
Aquatica Orlando
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

CA $108
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
Indoor Karting

Andretti Indoor Karting & Games in Orlando

CA $42
per adult
80% of travellers recommend
Andretti Indoor Karting & Games in Orlando
See all activities in Windermere

Frequently asked questions

How much does a Windermere vacation package cost?
Offering great value package deals from CA $707 on Expedia, you'll be surprised at how little a vacation to Windermere costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Windermere?
The off-season is the best time to visit Windermere if you're hoping to keep costs down. Another tip for scoring cheap Windermere vacation packages? Try to avoid visiting during public holidays and any major festivals or events.
How many days is enough for Windermere?
We'd suggest booking a Windermere vacation for around 3 days. This gives you enough time to visit key attractions such as Magic Kingdom® Park and Orlando International Premium Outlets, as well as explore neighbourhoods like Florida Centre and Lake Buena Vista North. You could even make time for a day trip (or two) outside of Windermere.
Is it worth booking a vacation package to Windermere?
It's no wonder a Windermere vacation is on the to-do list of many travellers. Top attractions like Isleworth Golf and Country Club are just the beginning of things to keep you busy here.
How to find the best Windermere package deals?
Begin your search for a Windermere package deal by entering your travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Windermere package deal straight away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Windermere adventure off to a flying start.
Is it cheaper to book a Windermere vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component individually. And you'll still have the flexibility to create a personalized Windermere vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Windermere?
Secure fantastic discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Windermere getaway.
How to plan a trip to Windermere?

  1. Pick your dates: The things you plan to do in Windermere and your preferred season will help you decide when to travel.
  2. Budget wisely: In addition to the cost of your stay, you should consider other expenses too. These include transportation, food and flights. Also, put aside some extra funds for unexpected costs that could crop up during your trip to Windermere.
  3. Determine how many days away: Start by compiling a list of the sights and activities you want to get to in Windermere. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your accommodations and airfare: Once you've settled on your travel dates and duration, book the perfect Windermere vacation package for you.

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