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A lakeside community with houses and boats.

Windermere Vacation Rentals

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    Check prices for these dates, December 13 – 14, 2026

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    Our top choices for Windermere vacation rentals

    1. Rustic Hideaway - Great Location + Pet Friendly!

    Interior

    2. Shore Steps Cottage - Walking Distance To The Town Of Windermere

    A serene landscape with a pond, trees with Spanish moss, and a palm tree.

    3. The Farm House - Great Location + Pet Friendly!

    A modern kitchen with stainless steel appliances, a granite island, and a built-in oven.

    4. The Point Hotel & Suites Orlando

    A swimming pool with lounge chairs and palm trees.

    5. Marriott's Grande Vista

    A resort pool area with palm trees, lounge chairs, and umbrellas.

    6. The View Hotel Orlando, Trademark Collection by Wyndham

    A hotel room with a large bed, bedside lamps, a view of the city, a window with curtains, and a desk with a chair.

    7. Villatel Resort Orlando, Apartments by Marriott Bonvoy

    A resort with a central swimming pool, multiple lounge areas, and a view of the surrounding buildings.

    8. Vacation Village Orlando, Celebration

    A large hotel complex with multiple high-rise buildings, a central swimming pool, and surrounding greenery.

    9. Floridays Resort Orlando

    Children's play area - outdoor

    10. The Cabins at Disney's Fort Wilderness Resort

    A water slide structure with a person at the bottom of the slide, water splashing around.

    11. Suites by The Wellborn

    A sign with 'The Wellborn' written on it, surrounded by lush greenery and a building in the background.

    12. WorldQuest Orlando Resort

    Exterior

    13. Marriott's Royal Palms

    A resort with a central swimming pool, lounge areas, and a landscaped garden.

    14. Mini golf course, 1 mile to Universal, Pool

    A covered swimming pool with a view of the surrounding garden and trees.

    15. Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

    A resort pool with a central water feature, surrounded by palm trees and lounge chairs.

    16. Blue Tree Resort at Lake Buena Vista

    An aerial view of a resort with multiple swimming pools, lounge areas, and palm trees.

    17. staySky Suites - I Drive Orlando

    A swimming pool with lounge chairs and palm trees.

    18. Holiday Inn Club Vacations Orlando Breeze Resort by IHG

    A swimming pool with lounge chairs and umbrellas, a covered seating area, and a building with a balcony in the background.

    19. Mid-century Modern Villa w/ Pool Near Universal

    A spacious living room with a sofa, coffee table, and TV.

    20. Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

    An aerial view of a resort with multiple swimming pools, a large central pool, and surrounding greenery.

    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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    Top Windermere Hotel Reviews

    Holiday Inn Express & Suites, International Drive by IHG

    A Holiday Inn Express & Suites hotel with a prominent sign, multiple balconies, and a well-lit entrance.

    Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

    A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.

    Holiday Inn Orlando International Dr-ICON by IHG

    A Holiday Inn hotel with a modern design, featuring a registration area and a well-lit entrance.

    Rosen Shingle Creek

    Outdoor banquet area

    DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

    A modern hotel lobby with a reception desk, seating area, and a large chandelier.

    Wingate by Wyndham Convention Ctr Closest Universal Orlando

    A spacious lobby with a reception desk, leather sofas, and a large star-patterned floor design.

    Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

    A large hotel with multiple floors, a central courtyard, and a reflective water feature.

    Kompose Boutique Resort at Theme Parks

    A spacious lobby with a grand chandelier, modern seating, and a view of the outdoor area.

    Home2 Suites by Hilton Orlando at Flamingo Crossings

    An outdoor patio area with a fire pit, yellow and blue seating, and a covered section with a pergola.

    Pestana Orlando Suites - Lake Buena Vista

    A hotel room with a bed, a desk, a chair, a sofa, and a TV.

    Hyatt House Orlando International Drive

    A modern bathroom with a large mirror, a sink, and a shower area.

    Universal's Endless Summer Resort - Surfside Inn and Suites

    A hotel pool area with lounge chairs and umbrellas, surrounded by palm trees and modern buildings.

    Rosen Inn International

    A hotel with a modern design, featuring a prominent logo on the facade and a well-lit entrance.

    Universal's Endless Summer Resort - Dockside Inn and Suites

    A pool area with people swimming and relaxing.

    Drury Plaza Hotel Orlando - Disney Springs Area

    A hotel pool area with lounge chairs and umbrellas, surrounded by tall buildings and a sunset sky.

    SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista

    A modern indoor patio with a fire pit table, seating, a bar area, and large windows.

    Candlewood Suites Orlando - Lake Buena Vista by IHG

    A multi-story hotel with a modern facade, featuring a prominent logo at the top.

    City Express by Marriott Orlando International Drive

    A hotel room with a sofa, two beds, a table, and a view of buildings.

    Find out more about Windermere

    Everything you need to know about Windermere vacation rentals

    Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windermere vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

    There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windermere vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

    Windermere vacation rentals: An excellent choice for every season

    Whenever you want to travel, a warm welcome awaits you in Windermere. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windermere in high season.

    Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $75 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

    How to find incredible deals on Windermere rentals

    At Expedia, we put the best Windermere vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

    To find some top Windermere rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windermere vacation.

    If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windermere. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

    Frequently Asked Questions

    Can I find vacation rentals in Windermere?

    Yes, we offer vacation rentals where you'll be only 4.1 mi (6.6 km) from Universal Studios Florida, offering you a secluded option if you'd like a quiet spot to stay. Windermere is known for its restaurants and shopping. Make sure you have time to check out the beaches and sporting events during your trip.

    What's the top vacation rental that Windermere has to offer?

    Formosa Valley Resort by UNE Homes: You might want to consider this Windermere vacation home rental for your stay. It is equipped with an outdoor pool, air-conditioning, and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop.

    How many vacation rentals are there in Windermere?

    Expedia has 3 vacation rentals for your stay in Windermere.

    What’s there to see and do in Windermere?

    Lake Butler and Tibet Butler Preserve are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find popular places like Universal Studios Florida and Universal Orlando Resort.

    What’s a vacation rental in Windermere like?

    Vacation rentals are private properties you can book for several days or longer in Windermere. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for a family getaway.

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