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 Lakes Resort & Spa Universal Studios Area
Westgate Town Center Resort
The Shores Resort & Spa
Westgate Blue Tree Resort in Lake Buena Vista

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

Things to do near Windermere

Windermere, Florida, is perfect for families seeking outdoor entertainment and relaxation. Enjoy a variety of activities including golfing, exploring local shopping areas, and staying at resorts. Consider joining tour packages or private tours to immerse yourself in the local culture. Day trips and guided excursions are also available, ensuring a memorable experience for visitors. Windermere offers a delightful blend of leisure and adventure for all ages.

Shopping

If you're up for a drive, the Orlando International Premium Outlets, located 8.0km away, offers a variety of shops in a vibrant atmosphere. Pointe Orlando and the Mall at Millenia, both 9.7km away, provide excellent shopping options with entertainment and family-friendly vibes.

Recreation

The Kia Center, a vibrant sports facility 16.1km from Windermere, offers an energetic atmosphere for fitness enthusiasts. For golf lovers, Grand Cypress Golf Club, located 9.7km away, provides beautiful outdoor settings. Pirate's Cove Adventure Golf, just 8.0km away, promises fun-filled mini-golf for the whole family.

Adventure

At Universal’s Volcano Bay, 6.4km from Windermere, dive into thrilling water rides and relax in tropical surroundings. Experience The Orlando Eye at ICON Park, 8.0km away, for breathtaking views. For family fun, explore Wonderworks, 9.7km distant, with its interactive arcade adventures for all ages.

Nightlife

Windermere's nightlife offers a charming blend of cozy bars and vibrant entertainment. Visit the local wine bar for exquisite selections, then head to a nearby tavern for live music and delicious pub fare. Enjoy the warm atmosphere and friendly locals as you unwind after a day of exploration.

*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 an ideal destination for families seeking entertainment and outdoor activities. Visitors can explore popular attractions such as theme parks, picturesque lakes, and golf courses. Additionally, the area offers cultural experiences and opportunities to enjoy the stunning scenery of nearby Lake Windermere. With a focus on family-friendly activities and outdoor adventures, Windermere provides a delightful getaway for travellers looking to create lasting memories.

  • Walt Disney World® Resort: Located 9.7km from Windermere, this iconic theme park offers an enchanting experience for families. With its immersive attractions, beloved characters, and magical atmosphere, it’s a place where dreams come true and memories are made.
  • Orange County Convention Center: Also 9.7km away, this arts centre is a cultural hub featuring diverse events, exhibitions, and conventions. It’s the perfect venue to explore local and international art, showcasing the vibrant culture of the region.
  • Universal CityWalk: A mere 6.4km from Windermere, this lively outdoor precinct is ideal for families. Enjoy shopping, dining, and entertainment in a vibrant atmosphere, making it a great spot to unwind after a day of adventure.

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 during the off-peak season (typically August to September and November) for more affordable package holidays to Windermere.
  • 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.

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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 CA $178 per night from Mar 15 to Mar 16
CA $178
CA $200 total
Mar 15 - Mar 16
includes taxes & fees
9.2/10 Wonderful! (4,567 reviews)
Beautiful property, clean and well maintained rooms, very nice staff.

Reviewed on Feb 11, 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/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 $339 per night from Feb 22 to Feb 23
CA $339
CA $381 total
Feb 22 - Feb 23
includes taxes & fees
9.4/10 Exceptional! (3,990 reviews)
The room was amazing! Very clean, spacious and absolutely beautiful!

Reviewed on Feb 10, 2026

Hyatt Regency Orlando International Airport
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
Fully refundableReserve now, pay when you stay
The price is CA $229 per night from Feb 25 to Feb 26
CA $229
CA $333 total
Feb 25 - Feb 26
includes taxes & fees
8/10 Very Good! (9,004 reviews)
Everything ws perfect

Reviewed on Feb 12, 2026

The Grove Resort & Water Park Orlando
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.

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