Windermere holiday lettings

We found 34,227 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:21 Nov - 28 Nov
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Find out more about Windermere

Find out more about Windermere

Why visit Windermere

  • Family-friendly attractions: Windermere is perfect for families with a variety of activities, including theme parks and lakes.
  • Charming village atmosphere: Explore the quaint town of Windermere, filled with picturesque views and friendly locals.
  • Outdoor adventures: Enjoy a range of outdoor pursuits, from golfing to water sports in the beautiful surroundings.
  • Delightful holiday accommodations: Choose from a selection of cosy cottages, villas, and condos for a relaxing stay.
  • Serene retreats: Unwind in the idyllic settings that make Windermere a perfect escape for couples and families alike.

Popular types of accommodation in Windermere

Planning a getaway to Windermere? The adventure begins with selecting your perfect accommodation. Discover a fantastic range of houses, villas, and condos designed to suit every traveller's needs. From charming holiday cottages to spacious holiday lettings, Windermere offers an array of holiday homes that promise comfort and relaxation. Start your journey by exploring the ideal Windermere holiday cottages and make the most of your stay in this picturesque destination.

  • Houses: The top choice for visitors to Windermere, these homes offer ample space and privacy for families, friends, or couples seeking a home-away-from-home experience.
  • Villas: These luxurious, spacious properties are the second most sought-after option, perfect for those wanting a touch of elegance during their stay.
  • Condos: Ideal for smaller groups, these modern accommodations provide convenience and comfort, making them a popular third choice.
  • Apartments: A practical choice for shorter stays, apartments offer a cosy and self-sufficient environment for guests.
  • Cottages: Charming and quaint, cottages are a delightful option for those looking for a traditional and picturesque retreat.**

Top attractions near Windermere

Windermere is an ideal destination for families and those seeking outdoor entertainment. Visitors can enjoy a variety of attractions, including theme parks, beautiful lakes, and golf courses. The area's points of interest cater to travellers looking for family-friendly activities, cultural experiences, and outdoor adventures. Whether you're visiting with family or friends, Windermere offers a delightful blend of leisure and excitement for everyone.

  • Walt Disney World® Resort: Just 3.7km from Windermere, this iconic theme park offers a magical experience with enchanting attractions, thrilling rides, and beloved characters, perfect for families seeking joy and adventure.
  • Orange County Convention Center: Located 3.7km away, this vibrant arts centre hosts various cultural events and exhibitions, providing a delightful glimpse into the local arts scene and engaging activities.
  • Universal CityWalk: A mere 2.5km from Windermere, this lively tourist precinct features outdoor dining, shopping, and entertainment, making it an ideal spot for families to enjoy a fun-filled day.

Things to do recommended for couples

If you're seeking a romantic getaway in Windermere, consider a ride on The Orlando Eye for stunning views, indulge in a delightful meal at Pirate's Dinner Adventure, or experience the thrill of indoor skydiving at iFly Orlando. Each offers a unique vibe perfect for couples.

Things to do recommended for families

Families will have a thrilling time at Universal’s Volcano Bay, a fantastic waterpark only 2.5km from Windermere. For sports enthusiasts, the Kia Center offers excitement 6.2km away, while Wonderworks, an engaging arcade adventure zone, is just 3.7km from your base.

Things to do recommended for groups

Embark on a shopping spree at the Orlando International Premium Outlets, only 3.1km from Windermere. Enjoy a round of golf at Shingle Creek Golf Course, 5.0km away, or experience an entertaining evening at Sleuth's Mystery Dinner Show, located just 3.1km from your base.

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

If you're travelling with a group, with family, bringing your pets along, or seeking extended stays, it's important to prioritise your filters accordingly. Here are some helpful booking tips for using Vrbo.

  • Traveling to Windermere with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Windermere with young kids: Travelling with young children can indeed be quite demanding. It’s important to prioritise their comfort and safety, as well as seek out suitable amenities, like a private swimming pool. Additionally, it’s wise to think about your closeness to attractions that are suited for families.
  • Taking your pets with you to Windermere: For many, a family holiday wouldn’t feel complete without their four-legged companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and bedding, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Windermere: If you’re in search of holiday rentals that offer special rates for stays of a month or more, you’ve come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly accommodations. 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 near Windermere

Windermere, Florida, offers a charming escape for families and couples alike, with picturesque views and friendly locals. Explore the quaint Windermere town and indulge in the idyllic surroundings that make it a perfect getaway. Don’t miss the delightful cottages nearby, where you can unwind and soak in the beauty of Windermere village. With a blend of outdoor adventures and serene retreats, your holiday promises to be both entertaining and romantic.

  • Orlando: A vibrant metropolis located 6.2km away from Windermere, Orlando is renowned as a family-friendly destination bursting with entertainment options. Visitors can indulge in thrilling theme parks, discover a range of shopping areas, and immerse themselves in the arts at local centres. Don't miss the chance to explore iconic landmarks like world-famous theme parks and film studios, as well as relaxing days at nearby beaches. Orlando offers an exhilarating travel experience that caters to all ages.
  • Lake Buena Vista: Situated 4.3km from Windermere, Lake Buena Vista is a charming city that combines family fun with business-friendly amenities. This locale is home to luxurious resorts, expansive shopping areas, and vibrant shopping mall centres. The city is closely associated with major attractions like theme parks and film studios, ensuring a memorable visit. Whether you're here for leisure or business, Lake Buena Vista presents a balanced experience with plenty to see and do.
  • Bay Hill: Only 1.2km from Windermere, Bay Hill is a picturesque neighbourhood known for its outdoor activities and family-oriented atmosphere. Visitors can enjoy luxury resorts and pristine golf courses, making it a haven for golf enthusiasts. The area also features attractions such as theme parks, film studios, and event venues, providing diverse options for entertainment and leisure. Bay Hill is a perfect spot to unwind and engage in recreational pursuits while being close to the main attractions.

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. Peak season runs in April, July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

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

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a handy platform for you to plan new journeys, resume from where you last left off, or manage your travel arrangements. You can easily view properties you’ve saved or booked, neatly organised under Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-gb/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 rental 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. Vrbo 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 rental 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 Vrbo holiday rentals 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 rental. Type in your Windermere travel dates to view your available options on Vrbo. 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 rentals in Windermere?
Yes. There are. Pick from four stays that welcome pets in Windermere on Vrbo. Our furry best friends also deserve a getaway, so simply use our search function for pet-friendly holiday rentals 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 Vrbo. 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 rental amenities in Windermere?
Tennis, a firepit and a swimming pool top the list of most popular rental amenities in Windermere. Whether you're heading away by yourself, with your spouse or as a family, Vrbo will help you find a holiday home that fits your tastes with all the features you're looking for.
Are there large group holiday rentals 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 rentals 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 rentals with WiFi in Windermere?
You'll have a choice of two holiday rentals 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 Vrbo.
How can I find holiday rentals with air conditioning in Windermere?
Windermere has four holiday rentals where you can spend your days in air-conditioned comfort. To locate a stay on Vrbo 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 rental in Windermere?
The age limit can differ between properties on Vrbo, 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 rental 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 Vrbo. 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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