Holiday rentals in Windermere

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Top-rated holiday rentals in Windermere

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Top guest favourite

Home in Winter Garden

4.97 out of 5 average rating, 124 reviews

Experience Downtown Winter Garden, One Block from It All

This 1920's home has been fully updated to include new kitchen, bath, fixtures, appliances, and more. The home has 2 bedrooms with one having a king bed and the other a queen bed. Beds feature super comfy Tuft & Needle mattresses ! Kitchen covers all of your basic cooking needs, has stainless appliances, refrigerator with ice maker, and Keurig coffee maker. The dining table comfortably seats 4 and is perfect for a meal or to use as a work space. New full size washer and dryer in carport laundry room. Grab a bottle of wine from Tony's less than 1 block away and relax in the screened-in front porch. Depending on the season grab a Valencia orange off the citrus tree in the back yard. You can use the entire home! There are 2 spacious bedrooms, 1 bath, dining room, kitchen, and a full washer and dryer in the laundry room (located in the carport). Owners live less than a mile away and are available as needed. We can meet you if you need anything! Just a few short steps from the famous Farmer's Market, Crooked Can Brewing, the Plant Street Market, the West Orange Bike Trail, Garden Theater, countless restaurants, and all that Downtown Winter Garden has to offer. This historic home is the perfect escape from the bustle of the tourist district, less than 30 minutes to Disney World, 25 minutes to Universal Studios, 30 minutes to Sea World. You can easily walk the 1 block to Plant St where most of the amenities of Downtown Winter Garden are located. You'll be just 25 minutes from Universal Studios and I-Drive via the Turnpike and 25 minutes from Disney via hwy 429. Also if you are into biking you can rent them at Wheel Works or the West Orange trail head and hit the famous West Orange Trail. There is a 2 car covered carport on site. Across the street from an elementary school so during the school year, there is some traffic in the morning and afternoon. Please be mindful and a good neighbor!

Guest favourite

Home in Florida Center

4.95 out of 5 average rating, 125 reviews

Modern Universal Orlando

Modern Universal Orlando is a stylish and family-friendly home with 2 Bedrooms and 2 Bathrooms that is located right outside the gates of Universal Studios Florida. With 2 beds and a pull out couch there is plenty of room for a family of 6 to set up home base when visiting the parks. From door to door it is a 1 Mile/15 Minute scenic walk to the gates of Universal Studios. A full kitchen, fenced in backyard, and 2 patios give you all the comfort and functionality of home with central location!

Guest favourite

Flat in Windermere

4.97 out of 5 average rating, 39 reviews

Pool, Gym, Parking Access - Lakeside Haven Stay

Located in Windermere, our Waterfront Retreat combines suburban tranquility with proximity to Orlando's buzz. This quiet getaway offers serene lake views around the property, a private balcony, modern comforts in a cozy queen bedroom with a smart TV, and a kitchen equipped with a dishwasher for your culinary exploits. Enjoy added conveniences like in-unit laundry and exclusive access to a resort-style pool and gym. Perfect for those looking for a peaceful escape near the city's top attractions.

Top guest favourite

Guest suite in Orlando

4.97 out of 5 average rating, 291 reviews

Location, Location, Location near all attractions

This is a poolside in-law apartment with a full kitchen, bedroom, full bath & a living room located in a quiet, residential neighborhood in an upper scale part of town. It has a king size bed & will accommodate 2 adults comfortably. This in-law apartment is an addition that was built onto the back of our home. We live in the main house. The apartment is closed off from the our main house and has it's own main entrance so it is private. So, you will have the apartment all to yourselves.

Guest favourite

Home in Winter Garden

4.97 out of 5 average rating, 100 reviews

Waterfront EPIC views, Dock, wildlife Near Disney

Experience the stunning sunrise views over Lake Apopka from our newly refurbished, elegantly appointed 4-bedroom, 2.5-bath vacation home in Winter Garden, FL. This haven is close to Orlando's Universal Studios 20 min, Disney World 25 min) & shopping (Mall of Millenia, premium outlets 17 min) Modern amenities, spacious layout that promises relaxation and convenience making the perfect home for exploring all local attractions and enjoying Florida's natural beauty. Minutes from City Swimming Pool

Guest favourite

Apartment in Windermere

4.94 out of 5 average rating, 47 reviews

LuXury Apt with Lake View, Cable & fast WiFi

Enjoy a stylish experience at this centrally and conveniently located area. This home boasts of serenity and quite. Everything you need is in walking distance, grocery stores, banks, nail salons and restaurants. Close to the turnpike and major roads to connect you to all the attractions. Less than 20 mins drive to both Universal and Disney Theme parks, Sea World, Convention Center, Orlando Icon, Top Golf, Pointe Orlando, Main Event and downtown for entertainment, food and night life.

Top guest favourite

Cottage in Winter Garden

4.99 out of 5 average rating, 158 reviews

The Heart of Winter Garden: Walk to shops & dining

Stay in a completely renovated 1937 cottage that's located in the heart of historic downtown Winter Garden. It's walking distance from all of the shops, restaurants, and events (including the #1 rated farmers market in the nation every Saturday) that make Winter Garden one of the most desirable cities in Florida. Sit on the front porch and watch as people bike and jog on the famous West Orange Trail, or rent a bike from the corner and join them. The home is close to all major highways.

Top guest favourite

Tiny home in Spring Lake

4.97 out of 5 average rating, 772 reviews

The Little Treehouse 2 at Country Club of Orlando

With rustic urban charm, The Little Treehouse "2" is a perfect relaxation spot for your stay in the City Beautiful. This completely renovated 1926 carriage house downstairs unit is a 260 sq. ft. blend of cosmopolitan comfort and enchantment. Located 5 minutes from Downtown, Amway Arena, Camping World Stadium, 15 minutes to Universal Studios, 25 minutes to Disney and an hours drive to Florida's beautiful beaches! *Search "Little Tree House Orlando" in your browser for more info.

Top guest favourite

Treehouse in St. Cloud

4.96 out of 5 average rating, 998 reviews

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. Check out video tours on U-Tube. Type in Treehouse in the Cloud. There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; Country gem horses close to Theme parks [link] Which is 1,000 sq ft and sleeps six.

Top guest favourite

Guest house in Windermere

4.94 out of 5 average rating, 272 reviews

Paradise nook near Orlando's theme parks

A quick escape to an amazing stay. Immersed in green tropical vegetation, our unique tiny Guesthouse is where we usually host our visiting family and friends from out of town. It is also open to Airbnb guests who are visiting Greater Orlando! Perfect location to escape from the hustle and bustle of a big city, yet close to everything. Take advantage of its availability and join the great experience our guests are always talking about.

Guest favourite

Home in Orlando

4.96 out of 5 average rating, 238 reviews

The Lake House - Next to Universal Studios - NEW ♥️

Luxurious, modern and completely remodeled single-family home with lake access in the prestigious Doctor Phillips neighborhood. Centrally located hops away from all Orlando has to offer, 1.1 miles (3 minutes) from Universal Studios Theme Parks, 9.5 miles to Disney World and 5 miles to Seaworld Orlando. No other Airbnb offers this upscale living space with stunning outdoor area to kick back and enjoy after a long day at the parks.

Guest favourite

Home in Winter Garden

4.96 out of 5 average rating, 47 reviews

Cozy cottage in Winter Garden

This newly renovated, cute and cozy home is just what you're looking for your vacation in Orlando/Winter Garden area! It is in close proximity to Winter Garden Downtown with great restaurants, cafes and farmers market. Also the famous West Orange bike trail is just 4 minutes away. If you plan to visit Disney or Universal they're less than 30 minutes away. You'll have a great time at this comfortable place to stay.