Windermere vacation rentals

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Top-rated vacation rentals in Windermere

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

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Guest favorite

Guesthouse in Orlando

4.94 out of 5 average rating, 212 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.

Oct 8 – 15

ﺩ.ﺇ399 per night

Guest favorite

Home in Winter Garden

4.92 out of 5 average rating, 165 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.

Aug 7 – 14

ﺩ.ﺇ397 per night

Guest favorite

Cottage in Winter Garden

4.99 out of 5 average rating, 106 reviews

Come Stay In The Heart Of Winter Garden

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.

Sep 22 – 29

ﺩ.ﺇ632 per night

Guest favorite

Tiny home in Orlando

4.98 out of 5 average rating, 634 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.

Aug 25 – Sep 1

ﺩ.ﺇ467 per night

Guest favorite

Guest suite in Orlando

4.99 out of 5 average rating, 242 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.

Jan 4 – 11

ﺩ.ﺇ539 per night

Superhost

Guest suite in Winter Garden

4.82 out of 5 average rating, 286 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

Sep 29 – Oct 6

ﺩ.ﺇ322 per night

Guest favorite

Treehouse in Saint Cloud

4.97 out of 5 average rating, 788 reviews

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. For a video tour type the following link into your browser: https://tinyurl.com/a72vevp5 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; meemaws-country -cottage which sleeps six.

Mar 17 – 24

ﺩ.ﺇ616 per night

Guest favorite

Guesthouse in Windermere

4.94 out of 5 average rating, 239 reviews

Small Guesthouse 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.

Oct 14 – 21

ﺩ.ﺇ496 per night

Guest favorite

Home in Ocoee

4.9 out of 5 average rating, 121 reviews

Lakeview Sunsets with Loft Escape West of Orlando

We are proud to announce No Smoking on premises property. This Duplex A Lake house overlooks Starke Lake in Central Florida. Great fishing, magnificent sunsets and Disney fireworks every night . Close to Disney 19 miles & 12 miles to Universal & 14 miles to Downtown Orlando. Other activities include air boating, Cape Cape Canaveral and centrally located just 1 hour from ocean or gulf. Please NO SMOKING on premises.

Mar 26 – Apr 2

ﺩ.ﺇ536 per night

Guest favorite

Guest suite in Orlando

4.96 out of 5 average rating, 166 reviews

Flor de María beautiful and relaxing GUEST ROOM ☘️☘️

Nice and relaxed Guest room with King side bed!! Our beautiful studio is attached to our house. With entrance and bathroom private. Parking included. You can enjoy areas like pool, grill and fireplace (These areas are shared) Our Space is only for 2 adults. Sorry!!! We not accepting kid’s, baby’s or pest. We are sure!!! You will love our place!!! We offer faster WiFi and Nexflix!!!

Aug 18 – 25

ﺩ.ﺇ323 per night

Guest favorite

Home in Orlando

4.94 out of 5 average rating, 229 reviews

New studio in a newly renovated House

A new in-law suites studio in the heart of Dr Phillips with your own private entrance and parking. An excellent place to rest after a full day in parks or working, quiet neighborhood and safe for Kids Only 10min from Universal Studios, 25 min from Disney Springs, 15 min from Outlets and international Drive. We offer Netflix, Disney+ and Prime Video

Sep 30 – Oct 7

ﺩ.ﺇ298 per night

Guest favorite

Apartment in Windermere

4.99 out of 5 average rating, 104 reviews

Relaxing 2BR Lakeview Retreat Close to Attractions

Relaxing getaway with gorgeous lake views in historic Windermere just minutes from Disney, Universal, and all Orlando-area attractions. Skip the tourist traps and retreat to this charming, newly renovated apartment in quiet, old Florida. Perfect for families visiting the parks or anyone seeking a quiet getaway.

Sep 19 – 26

ﺩ.ﺇ882 per night