Holiday houses in Windermere

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Top-rated holiday rentals in Windermere

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Guesthouse in Orlando

4.94 out of 5 average rating, 240 reviews

Modern Guest Studio (Private) Pool / Spa available

Private Guest Studio (Not Shared ) in a Perfect Orlando location, 5 minutes from I-Drive, Universal Studios, Disney World & Premium Shopping Outlets. Very Quiet lovely neighborhood with Biking distance to "Restaurant Row" where all your favorite restaurants are located. Pool & Spa available (Not Shared) All major highways at your finger tips / ride 15 min to Disney! This space has an industrial modern look with high ceilings, Stay and cook with all the amenities including a Washer and Dryer.

Guest favourite

Home in Winter Garden

4.91 out of 5 average rating, 116 reviews

Luxury Home Winter Garden Near Disney & Universals

Looking for luxury and convenience? Stay in our newly renovated home, just minutes from Disney and Universal. With a one-minute walk to local shops, bars, restaurants, and farmers market, you'll experience the best Winter Garden has to offer. Book now for a memorable stay! Golf Cart and Bike Rentals Available! Send DM NO PETS Strict No Parties or Gatherings Allowed Quiet Hours from 9pm-8am as this is a family friendly neighborhood No more than 8 guests Only 2 Cars allowed on the property.

Guest favourite

Home in Winter Garden

4.91 out of 5 average rating, 186 reviews

Cozy Winter Garden Home 20 MINUTES FROM DISNEY

Get the small home-town feeling and still be only 20 minutes from Disney. This little house is perfect for a couple or small family who wants to visit Orlando and all the attractions, but also get away from the traffic & stay in a desirable small town setting. Located a mile from downtown Winter Garden - home to the number 1 rated farmer's market by American Farmland Trust, & the 22-mile West Orange Trail that's home to runners, bicyclists and anyone else who wants to enjoy the sunshine.

Guest favourite

Cottage in Winter Garden

4.98 out of 5 average rating, 133 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.

Guest favourite

Tiny home in Spring Lake

4.98 out of 5 average rating, 694 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.

Guest favourite

Treehouse in Saint Cloud

4.96 out of 5 average rating, 887 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.

Superhost

Guest suite in Ocoee

4.82 out of 5 average rating, 144 reviews

Charming Studio with Garden (West of Orlando)

We are proud to present a No Smoking on Premises Airbnb. My studio apartment is just the perfect place to hangout. There is a nice fire pit on the back patio and logs to relax with friends and enjoy the warm weather. The black gravel parking space is for the use of the Studio guests. The main house guests park in the driveway. We have an onsight massage therapist that can come to your place as an upgrade. Text me for more details. Please NO SMOKING on premises.

Guest favourite

Guest suite in Orlando

4.98 out of 5 average rating, 260 reviews

Location, Location, Location near all attractions

This is a poolside in-law apartment with a full kitchen, bedroom, full bath and 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. It is completely 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.

Superhost

Guest suite in Winter Garden

4.82 out of 5 average rating, 321 reviews

Private In-Law Suite Near Disney/Universal/DT

This newly renovated, modern, and clean Mother-in-Law Suite is freshly designed with bright colors and all new furnishings. Everything is thoughtfully selected to create the perfect Airbnb stay. You'll have coffee, decaf, tea, 200mbps Wi-Fi, and high-end mattresses for the perfect night's sleep. You'll stay in the Orlando area, 20min from Disney/Universal/DT Orlando, and minutes from DT Winter Garden, shopping center, & famous 22mile West Orange Bike trail

Guest favourite

Home in Winter Garden

4.99 out of 5 average rating, 125 reviews

Downtown Winter Garden, Florida

Charming two bedroom, one bathroom home just three blocks from downtown Winter Garden Florida. Across the street from the West Orange Bike Trail and walking distance to restaurants, Splash pond, shopping and Farmers Market. The fenced in back yard is shaded by a 100 year old live oak tree. There is a “no pet policy” at the house. We do not accept guests under the age of 12. There are NO cameras on or around the property. I respect the privacy of my guests.

Guest favourite

Guest suite in Orlando

4.91 out of 5 average rating, 248 reviews

Lakeview Vacation Studio

Lake front one bedroom studio apartment with own entry. Walking distance from Universal Studios, and ten minutes drive to Disney and other attractions. Near to the Millenia Mall, Sand lake road and International Drive, with great restaurants. This neighborhood has everything to make your stay in Orlando fantastic. Minimum stay 2 nights. Need extra space? 3 bed and 3 bath house available to rent: airbnb.com/h/lakeview-vacation-house-2

Guest favourite

Guesthouse in Windermere

4.94 out of 5 average rating, 251 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.