Windermere Vacations from $197

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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.

The Latest Windermere vacation packages

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

Westgate Vacation Villas Resort

4 out of 5
Price was $373, price is now $197 per person
$197
per person
Jan 29 - Feb 1
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (2,105 reviews)
.

Reviewed on Nov 14, 2026

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $607, price is now $304 per person
$304
per person
Jan 25 - Jan 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9/10 Wonderful! (4,064 reviews)

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was $1,159, price is now $596 per person
$596
per person
Jan 25 - Jan 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9.2/10 Wonderful! (1,002 reviews)

Oceanique Resort

Oceanique Resort

3.5 out of 5
Price was $1,925, price is now $1,070 per person
$1,070
per person
Feb 6 - Feb 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9.2/10 Wonderful! (462 reviews)
Beautiful view of the ocean, small resort style , quiet and peaceful. Large shopping center is a 10 minute speed walk.

Reviewed on Nov 6, 2026

Ocean Landings Resort and Racquet

Ocean Landings Resort and Racquet

2.5 out of 5
Price was $1,194, price is now $668 per person
$668
per person
Feb 6 - Feb 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
7.2/10 Good! (50 reviews)

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Stay near popular Windermere attractions

Tibet Butler Preserve

Explore 3.6 miles of trails through Florida's diverse ecosystems at this tranquil preserve near Orlando. The Vera Carter Environmental Center offers fascinating exhibits about local wildlife and habitats.
See properties

What to do in Windermere

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

$33
per traveler
86% of travellers recommend
LEGOLAND® Florida Tickets
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

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

$27
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Universal Orlando Resort Express Passes

Universal Orlando Resort Express Passes

$138
per traveler
80% of travellers recommend
Universal Orlando Resort Express Passes
See all activities in Windermere

Windermere Hotel Deals

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
$215 nightly
The price is $242 total per night from Nov 23 to Nov 24
$242 total
Nov 23 - Nov 24
Total with taxes and fees
Hyatt Regency Orlando International Airport
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
$111 nightly
The price is $125 total per night from Dec 15 to Dec 16
$125 total
Dec 15 - Dec 16
Total with taxes and fees
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
$96 nightly
The price is $108 total per night from Dec 10 to Dec 11
$108 total
Dec 10 - Dec 11
Total with taxes and fees
Marriott's Grande Vista
See all 56,015 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.

Find the Best Windermere Vacation Packages

Things to do near Windermere

Windermere, Florida, is a fantastic destination for families and outdoor enthusiasts alike, offering a variety of activities such as golfing, shopping, and enjoying resort amenities. Visitors can explore day trips and sightseeing tours to experience the area's natural beauty and attractions. With expert guides available, you can craft the perfect itinerary to make the most of your stay in this charming community.

Shopping

For a delightful shopping experience in Windermere, visit the Orlando International Premium Outlets, just 5 miles away, and explore a mix of entertainment and family-friendly vibes. Pointe Orlando and the Mall at Millenia, both 6 miles away, offer similar attractions. If you're up for a drive, consider other local options.

Recreation

Experience the energetic atmosphere at the Kia Center, just 10 miles away, perfect for sports enthusiasts. Enjoy a day of golfing at Shingle Creek Golf Course, 8 miles out, surrounded by nature. For family fun, visit Pirate's Cove Adventure Golf, 5 miles away, blending adventure and amusement.

Adventure

Experience the thrills at Universal’s Volcano Bay, a vibrant waterpark 4 miles from Windermere, offering exciting water attractions for the whole family. Enjoy stunning views from The Orlando Eye at ICON Park, located 5 miles away, or unleash your competitive spirit at Wonderworks, an arcade adventure zone 6 miles away.

Nightlife

Windermere's nightlife offers a relaxed charm with cozy bars and delightful dining. Visit the Windermere Wine & Beer Bar for a diverse selection of drinks. For a lively atmosphere, check out local restaurants featuring live music and outdoor seating, perfect for enjoying Florida's warm evenings.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Windermere

Windermere, Florida, is perfect for family-friendly outdoor vacations with plenty of entertainment options. Visitors can enjoy a variety of attractions, including theme parks, scenic lakes, and golf courses. Explore Lake Windermere for a relaxing day on the water, or take advantage of the area's cultural experiences and outdoor activities. This charming destination offers something for everyone, making it an ideal spot for a memorable getaway.

  • Walt Disney World® Resort: Experience the magic at one of the world's most famous theme parks. With thrilling rides, enchanting parades, and beloved characters, it's a perfect destination for family fun just 6 miles from Windermere.
  • Orange County Convention Center: Immerse yourself in culture at this vibrant arts center, located 6 miles away. Hosting various events and exhibitions, it’s a hub for creativity and entertainment in the region.
  • Universal CityWalk: Enjoy a lively atmosphere at this outdoor tourist precinct, only 4 miles from Windermere. With dining, shopping, and entertainment options, it’s an ideal spot for family outings and relaxation.

Best time to go to Windermere

The best time to visit Windermere can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Windermere falls in August, when visitor numbers are average and weather is mostly sunny with moderate rain. The coolest average temperature in Windermere falls in January, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January60.3°F (15.7°C)Light RainMostly SunnyAverageAverage
February64.2°F (17.9°C)No RainMostly SunnyAverageAverage
March67.5°F (19.7°C)Light RainMostly SunnyAverageSlightly High
April72.5°F (22.5°C)Light RainMostly SunnySlightly HighSlightly High
May77.0°F (25.0°C)Light RainMostly SunnyAverageAverage
June80.8°F (27.1°C)Light RainMostly SunnyAverageAverage
July82.2°F (27.9°C)Moderate RainMostly SunnySlightly HighAverage
August82.4°F (28.0°C)Moderate RainMostly SunnyAverageSlightly Low
September80.2°F (26.8°C)Light RainMostly SunnySlightly HighSlightly Low
October75.0°F (23.9°C)Light RainMostly SunnySlightly LowAverage
November68.2°F (20.1°C)No RainMostly SunnySlightly LowSlightly Low
December64.0°F (17.8°C)No RainMostly SunnySlightly LowSlightly High

Tips to save on your trip to Windermere

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Windermere.
  • Consider traveling to Windermere during the low season (August to September and November) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Windermere Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Orlando Intl. Airport (MCO)
Population
3,200
Max Temp Winter
70ºF
Max Temp Summer
90ºF
Top Sights
Walt Disney World® Resort, Universal Orlando Resort and Magic Kingdom® Park

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Frequently asked questions

What is the best time to go to Windermere?
The best time to go for a Windermere vacation package is during December and March, which are the peak months for traveler demand. These periods often coincide with popular events and pleasant weather for exploring the area's attractions.

For those seeking a quieter experience or potentially lower prices, consider visiting in January, May, or August. These months typically see fewer crowds, offering a more relaxed atmosphere for your Windermere vacation.
How can I save money on a Windermere vacation package?
When you bundle, you can save up to 30%*. To save money on a Windermere package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What are the top things to do in Windermere?
A Windermere vacation centers around world-famous theme parks and entertainment options, making it ideal for families and fun-seekers:

Browse and book things to do in Windermere on Expedia.
Do you need to rent a car in Windermere, or is public transport enough?
For a Windermere vacation package, renting a car is generally recommended for the most flexibility, especially when exploring the area's many family-friendly attractions and entertainment options. While Windermere has a road network designed to manage traffic flow, including roundabouts, the major theme parks and other points of interest are spread out.

A rental car or reliance on local taxis and ride-share apps is the most practical ways to get around. This allows travelers booking Windermere vacation packages with flights to easily reach destinations like Walt Disney World® Resort and Universal Studios Florida from Orlando International Airport (MCO) and navigate between them at their own pace.
Are there vacation package hotels in Windermere within walking distance of restaurants and shops?
A Windermere vacation package can include hotels that place you within walking distance of extensive dining and shopping options, particularly those near the major theme park resorts.

Club Wyndham Bonnet Creek, a 3.5-star property rated 8.8 out of 10, is about a 5-minute walk from Walt Disney World® Resort, which offers numerous dining and retail experiences. For those visiting Universal Studios Florida, Universal's Loews Portofino Bay Hotel, a 4-star hotel rated 8.9 out of 10, and Universal's Hard Rock Hotel, a 4-star hotel rated 8.8 out of 10, are both about a 10-minute walk from the park's entertainment and dining areas.

Actual walking routes may differ from straight-line distances, so it's always a good idea to check the map for your selected hotel.
Can I change or cancel my Windermere vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Windermere vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Windermere vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Windermere vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Windermere?
To find last-minute vacation packages to Windermere, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Windermere vacation packages?
Free cancellation on a Windermere vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Windermere vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Windermere getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Windermere vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

Explore a world of travel with Expedia

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