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.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
per person
Jun. 1 - Jun. 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8.8/10 Excellent! (2,698 reviews)
Mainly a building on a parking lot

Reviewed on Apr. 29, 2025

Meliá Orlando Celebration

Meliá Orlando Celebration

4 out of 5
Save 100% on your flight
per person
Jul. 15 - Jul. 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
8.6/10 Excellent! (1,567 reviews)
Our favorite place to stay in Central Florida, everything was perfect.

Reviewed on Apr. 24, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
per person
Jul. 15 - Jul. 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
7.8/10 Good! (1,199 reviews)
Tv didn’t work , water didn’t cut off

Reviewed on Apr. 28, 2025

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
Jun. 1 - Jun. 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8/10 Very Good! (4,595 reviews)
We stayed in a two bedroom condo it was very spacious and the kitchen was pretty well stocked for plates, cups etc. the property is quite large but they do have shuttle carts going by every few minutes. My only complaint is there is only one option for food on the property - the food at it was great, but it would be nice to have other options.

Reviewed on Apr. 29, 2025

Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Save 100% on your flight
per person
Jul. 10 - Jul. 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Orlando (MCO)
8.4/10 Very Good! (949 reviews)
Very clean and comfortable

Reviewed on Apr. 21, 2025

Ready to book your vacation to Windermere?

 

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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 $128 per night from May 6 to May 7
CA $128
CA $144 total
includes taxes & fees
May 6 - May 7
8.2/10 Very Good! (6,212 reviews)
"Walkable to Universal Studios. Great location for restaurants. Fast and easy check in via phone."

Reviewed on Apr. 29, 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 $261 per night from May 13 to May 14
CA $261
CA $294 total
includes taxes & fees
May 13 - May 14
9.2/10 Wonderful! (3,228 reviews)
"So convenient when flying in. Front desk service excellent!"

Reviewed on Apr. 28, 2025

Hyatt Regency Orlando International Airport
DoubleTree by Hilton Hotel Orlando at SeaWorld
DoubleTree by Hilton Hotel Orlando at SeaWorld
4 out of 5
10100 International Drive, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is CA $116 per night from May 27 to May 28
CA $116
CA $166 total
includes taxes & fees
May 27 - May 28
7.2/10 Good! (5,915 reviews)
"great property sven greater staff!"

Reviewed on Apr. 28, 2025

DoubleTree by Hilton Hotel Orlando at SeaWorld
See all 52,122 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

Family Vacations

Family Vacations

Frequently asked questions

How much does a Windermere vacation package cost?
Offering great value package deals from CA $603 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.

Discover the most popular places to visit in Windermere

Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(226 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(988 reviews)

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

Universal Studios Florida
Disney Springs™

Disney Springs™

4.5/5(1,107 reviews)

You can search for that perfect souvenir when you visit Disney Springs™, a favorite shopping spot in Lake Buena Vista. Experience the entertainment choices and acclaimed theater scene in this family-friendly area.

Disney Springs™

What to do in Windermere

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

CA $94
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
2014_AQ_KatasKookaburraCove_D4D_0772.jpg

Aquatica Orlando

CA $69
per traveller
82% of travellers recommend
Aquatica Orlando
Bamboo Dune Buggy Tour

Fort Meade: Bamboo Dune Buggy Tour

CA $97
per adult
100% of travellers recommend
Fort Meade: Bamboo Dune Buggy Tour
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.