Windermere Holidays

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Top Flight + Hotel Deals in Windermere

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel
Seasons Florida Resort
Evermore Orlando Resort
Embassy Suites by Hilton Orlando International Dr Conv Ctr
CoCo Key Hotel and Water Resort 

Things to do near Windermere

Windermere, Florida, offers a delightful array of family-friendly activities and outdoor adventures. Visitors can enjoy the scenic beauty while indulging in shopping, golfing, and exploring local resorts. With numerous family attractions and sightseeing opportunities, Windermere is perfect for those seeking both relaxation and entertainment. Don't miss out on the chance to experience the charm of this picturesque town during your holiday.

Shopping

For a delightful shopping experience in Windermere, visit the Orlando International Premium Outlets, just 8.0km away, and the Mall at Millenia, located 9.7km away. Both offer a vibrant atmosphere with a mix of shopping, entertainment, and family-friendly options. If you're up for a drive, check out Shoppers World Shopping Center, also 8.0km away.

Recreation

Experience the Kia Center for an energetic atmosphere filled with sports activities, located a mere 16.1km from Windermere. Enjoy the stunning landscapes at Grand Cypress Golf Club, just 9.7km away, perfect for a relaxing day on the green. For family fun, Congo River Golf offers adventurous mini-golf, only 8.0km away.

Adventure

Experience the thrills at Universal’s Volcano Bay, a vibrant waterpark 6.4km from Windermere, featuring exhilarating slides and wave pools for all ages. For a unique adventure, try iFly Orlando, located 8.0km away, where you can experience the sensation of indoor skydiving amidst exciting sports vibes.

Head to Carter Family Bowl, an arcade and adventure zone 8.0km from Windermere, where families can enjoy a variety of games and activities in a lively atmosphere, perfect for creating unforgettable memories together.

Nightlife

Windermere offers a charming nightlife with a relaxed atmosphere. Enjoy a cocktail at the elegant Windermere Wine & Cider Bar or savour a delightful meal at the nearby The Osprey Tavern. For a local pub experience, visit the historic The Olde Towne Tavern, perfect for unwinding 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 perfect for families seeking outdoor entertainment and cultural experiences. Visitors can explore attractions like theme parks, the beautiful lakes, and golf courses, offering a range of activities for all ages. Notable highlights include the scenic Lake Windermere, which provides a lovely backdrop for holidays, making it an ideal spot for both relaxation and adventure.

  • Walt Disney World® Resort: Just 9.7km away, this iconic theme park offers a magical experience for families and thrill-seekers alike. Immerse yourself in enchanting attractions, captivating shows, and beloved Disney characters, all within a vibrant atmosphere filled with joy and excitement.
  • Orange County Convention Center: Also 9.7km away, this cultural hub hosts a variety of events and exhibitions, showcasing the arts in all forms. Explore captivating displays, engage with local artists, and enjoy the diverse cultural vibes that make this venue a must-visit.
  • Arnold Palmer's Bay Hill Golf Club: Located 4.8km from Windermere, this prestigious golf course offers a family-friendly environment with opportunities for excursions and adventure. Enjoy the warm hospitality of friendly staff while playing on a beautifully manicured course.

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

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • 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.

Top hotels in Windermere

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 €125 per night from 22 Mar to 23 Mar
€125
22 Mar - 23 Mar
includes taxes & fees
9.2/10 Wonderful! (4,641 reviews)
This was great place to stay,close to everything! bed was comfortable. The super pool was amazing.

Reviewed on 18 Feb 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
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 €204 per night from 22 Feb to 23 Feb
€204
22 Feb - 23 Feb
includes taxes & fees
8/10 Very Good! (9,062 reviews)
Wonderful resort

Reviewed on 18 Feb 2026

The Grove Resort & Water Park Orlando
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 refundable
The price is €124 per night from 25 Feb to 26 Feb
€124
25 Feb - 26 Feb
includes taxes & fees
8.4/10 Very Good! (6,893 reviews)
Room has a mold smell and smoke smell

Reviewed on 19 Feb 2026

DoubleTree by Hilton at the Entrance to Universal 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.

Popular places to visit

What to do in Windermere

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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.