Windermere holiday homes

We found 35,404 holiday rentals — enter your dates for availability

Discover a selection of 14 homes and other holiday rentals in Windermere that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll have the best amenities for spending time at your home away from home, including Wi-Fi and parking. Whatever you're looking for, you're sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Windermere

Showing deals for:19 Dec - 26 Dec
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Why visit Windermere

  • Stunning Lakes: Explore the beautiful Lake Windermere, perfect for relaxing and enjoying nature.
  • Family-Friendly Activities: Enjoy nearby theme parks and outdoor adventures that cater to all ages.
  • Charming Downtown: Stroll through the picturesque town centre, filled with local culture and friendly locals.
  • Golfing Opportunities: Experience top-notch golf courses set in scenic landscapes, ideal for enthusiasts.
  • Romantic Escapes: Windermere offers a serene atmosphere, perfect for couples seeking a getaway.

Top attractions near Windermere

Windermere, Florida, is a fantastic destination for families and those seeking outdoor adventures. With attractions like theme parks, picturesque lakes, and golf courses, there's plenty to explore. Be sure to check out Lake Windermere and the charming town itself for a taste of local culture. Whether you're after thrilling entertainment or serene nature, Windermere has something for everyone to enjoy during your holiday.

  • Walt Disney World® Resort: A magical theme park, offering thrilling rides, enchanting attractions, and beloved characters, perfect for family fun just 9.7km from Windermere.
  • Orange County Convention Center: A vibrant arts centre featuring diverse cultural events and exhibitions, showcasing the rich artistic heritage of the region, also located 9.7km away.
  • Universal CityWalk: A lively tourist precinct with outdoor dining, shopping, and entertainment, providing a fantastic atmosphere for families, situated 6.4km from Windermere.

Things to do recommended for couples

Looking for a romantic getaway in Windermere? Enjoy a fun round at Pirate's Cove Adventure Golf or Disney's Fantasia Gardens Miniature Golf Course. For a touch of luxury, unwind at the Windermere Country Club. Perfect experiences for couples seeking adventure and relaxation.

Things to do recommended for families

Families visiting Windermere can splash around at Universal’s Volcano Bay, just 6.4km away, or have a blast at Disney's Typhoon Lagoon, 14.5km away. For more water fun, check out Disney's Blizzard Beach, located 16.1km from Windermere, all offering thrilling adventures and family-friendly vibes.

Things to do recommended for groups

In Windermere, groups can enjoy a round of golf at Disney's Osprey Ridge Golf Course, indulge in retail therapy at Orlando International Premium Outlets, or experience a fun-filled evening at Sleuth's Mystery Dinner Show for a touch of culture and entertainment.

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

What do I need to keep in mind when booking a vacation in Windermere

If you're planning a trip with a group, family, or even bringing your pets along, or if you're interested in longer stays, it's important to refine your search based on your key priorities. Here are some helpful booking tips for Vrbo to assist you.

  • Traveling to Windermere with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Windermere with young kids: Journeying with little ones can be quite a task. It's important to prioritise their comfort and safety, along with suitable facilities like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are fun for the whole family.
  • Taking your pets with you to Windermere: For many families, a holiday just isn’t the same without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Windermere: If you're in search of holiday rentals with discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you'll be able to easily discover and save on long-term rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Windermere

Windermere, a charming town in Central Florida's Orange County, offers a delightful blend of family-friendly activities and romantic experiences. Explore its picturesque downtown area, where you can enjoy scenic water views and the warmth of friendly locals. Just a stone's throw away, you'll find exciting excursions and entertainment options that make for an unforgettable holiday. Windermere is the ideal base for your adventures in this vibrant region, perfect for families and couples alike.

  • Orlando: Orlando is a bustling metropolis known for its vibrant family-friendly atmosphere and a plethora of entertainment options. Located right next to Windermere, it offers an exciting travel experience with access to world-famous theme parks, including Walt Disney World and Universal Studios. Visitors can explore shopping districts, indulge in fine dining, or immerse themselves in the local arts scene at various cultural centres. With stunning beaches and outdoor adventures nearby, Orlando is a fantastic destination for those seeking both relaxation and excitement.
  • Bay Hill: Just a couple of miles from Windermere, Bay Hill is a charming neighbourhood celebrated for its picturesque landscapes and outdoor activities. It’s best known for the prestigious Bay Hill Club & Lodge, a favourite among golf enthusiasts. Visitors can enjoy a leisurely day playing golf, relaxing at luxurious resorts, or exploring the nearby attractions, including iconic theme parks and film studios. With its family-friendly vibe and recreational opportunities, Bay Hill is perfect for those looking to unwind in a serene environment.
  • Lake Buena Vista: Located a short drive from Windermere, Lake Buena Vista is a lively city that caters to families and business travellers alike. This area is home to a number of resorts and shopping centres, making it an ideal spot for relaxation and retail therapy. Visitors can enjoy top-notch dining and entertainment options while being close to renowned theme parks and stadiums. With its unique blend of leisure and business amenities, Lake Buena Vista is a must-visit for anyone looking to experience the best of Florida.

Best time to go to Windermere

If you're planning a trip to Windermere, it's a good idea to check both the weather and property rates. The warmest month is August.

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

Booking with Vrbo is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that suits your budget, make use of our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a handy space for you to plan new adventures, continue from where you last stopped, or manage your travel arrangements. You'll discover your saved or booked properties sorted into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Travel to charming Windermere

The beaches and other outdoor surroundings create an inviting atmosphere in Windermere. This romantic city is known for its restaurants, shopping and sporting events. Universal Studios Florida and Universal Orlando Resort are just a couple of the must-see attractions in the area. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Windermere

Are you hoping to find things to do in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Windermere a fun spot to go on holiday. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Universal Studios Florida (4.1 mi / 6.6 km)
  • Universal Orlando Resort (4.4 mi / 7 km)
  • Magic Kingdom® Park (6.1 mi / 9.8 km)
  • Walt Disney World® Resort (6.2 mi / 9.9 km)
  • Epcot® (8.6 mi / 13.8 km)
  • Disney's Animal Kingdom® Theme Park (10 mi / 16.1 km)

Exploring the natural features in Windermere

Whether you're an adventurous traveller or just want to take in the scenery, Windermere is a great place to get outside. These are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Lake Butler (2.3 mi / 3.6 km)
  • Tinker Field (8.5 mi / 13.6 km)
  • Lake Bryan (9.1 mi / 14.6 km)
  • Lake Eola Park (10.3 mi / 16.6 km)
  • Lake Eola (10.4 mi / 16.7 km)
  • Lake Louisa State Park (11.6 mi / 18.7 km)

Travelling to and around Windermere

Fly into Orlando International Airport (MCO), the closest airport, located 14.5 mi (23.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Kissimmee, FL (ISM-Kissimmee Gateway), which is 15.2 mi (24.4 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Windermere?
Based on our research, houses are the most sought-after type of property in Windermere. But of course, everyone's idea of an epic stay isn't the same. Bookabach has holiday homes of all shapes and sizes, and we'll help you discover the perfect fit for you.
How much does it cost to rent a holiday home in Windermere?
Season, length of stay and property type are some of the things that can influence the price of a holiday home. Simply add your dates of travel to find your perfect match. From homey country cottages to sprawling luxury villas, all Bookabach holiday homes offer amazing value.
How much does it cost to rent a beach house in Windermere?
When you travel and the size and style of the property will influence the cost of your beachside holiday home. Type in your Windermere travel dates to view your available options on Bookabach. Did someone just say "private pool"? Use our filters to choose the amenities and features you want in your holiday home.
Are there pet-friendly holiday homes in Windermere?
Yes. There are. Pick from four stays that welcome pets in Windermere on Bookabach. Our furry best friends also deserve a getaway, so simply use our search function for pet-friendly holiday homes to find a perfect pad where Fido can be near his favourite humans.
Can I rent a house with a pool in Windermere?
Tick the "pool" box in our handy filter tool and you can choose from two houses with private pools in Windermere on Bookabach. Lazy soak or races and ball games? Free time is up to you when your holiday home comes with its own pool.
What are popular home amenities in Windermere?
Tennis, a firepit and a swimming pool top the list of most popular home amenities in Windermere. Whether you're heading away by yourself, with your spouse or as a family, Bookabach will help you find a holiday home that fits your tastes with all the features you're looking for.
Are there large group holiday homes in Windermere?
Take your pick of three holiday properties in Windermere that can accommodate 10 or more guests. Whether you're organising a family trip or a celebration like an anniversary, there's enough room to get your loved ones together under the same roof.
Are there holiday homes in Windermere that welcome kids?
Bring the whole family together for a fun-packed adventure in Windermere at one of our four family-friendly holiday properties. Lots of these stays provide amenities that are just perfect for getaways with youngsters, like kitchens, multiple bedrooms and swimming pools. Simply check the "Properties good for families" filter and choose your favourite option.
What are the top attractions for families in Windermere?
Keeping the kids entertained during your Windermere holiday is a snap with these exciting family-friendly attractions:

  • Walt Disney World® Resort
  • Universal Studios Florida
  • Universal Orlando Resort

Are there holiday homes with WiFi in Windermere?
You'll have a choice of two holiday homes with WiFi in Windermere. If you want to disconnect from daily life on your holiday, but still need to be connected to the internet, these properties are just what you need. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in Windermere?
Windermere has four holiday homes where you can spend your days in air-conditioned comfort. To locate a stay on Bookabach that has this amenity, enter your desired travel dates and use the filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Windermere?
The age limit can differ between properties on Bookabach, so look at the rules of the holiday home in Windermere you're considering. But normally, it's 16, 18 or 21.
How long can I rent a holiday home in Windermere for?
It's really down to the Windermere property. To view all available options offering extended stays, simply enter your dates and guest number into Bookabach. You can look forward to having the property to yourself, as well as amenities such as a kitchen, air conditioning and a backyard where the little ones can play. Be on the lookout for long-term stays that offer weekly or monthly discounts.

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