Vacation rentals in Windermere

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Windermere

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Guesthouse in Clermont

4.98 out of 5 average rating, 101 reviews

Downtown Apartment - Walk to Lake, Shops & Dining

This stylish apartment, in Downtown Clermont is @ the center of the coast-to-coast bike trail. Enjoy the quaint lake town experience to the fullest without having to drive anywhere. Lakefront, breweries, retail, dining- all within a 3 min walk! Best features indoors include comfy beds, a double shower, smart TV, & cozy aesthetics. The space is well stocked w/ all the essentials. Small appliances for cooking include an air fryer, crockpot & skillet. Garage storage available 4 recreational gear.

May 11 – 18

$221 CAD per night

Guest favourite

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.

Jan. 28 – Feb. 4

$194 CAD per night

Guest favourite

Home in Winter Garden

4.92 out of 5 average rating, 166 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.

Apr. 7 – 14

$198 CAD per night

Guest favourite

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.

Jul. 19 – 26

$304 CAD per night

Guest favourite

Tiny homes in Orlando

4.98 out of 5 average rating, 636 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.

Dec. 3 – 10

$204 CAD per night

Guest favourite

Guest suite in Orlando

4.99 out of 5 average rating, 243 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.

Oct. 4 – 11

$240 CAD per night

Guest favourite

Treehouse in Saint Cloud

4.97 out of 5 average rating, 789 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. 25 – Apr. 1

$263 CAD per night

Guest favourite

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.

Jun. 13 – 20

$214 CAD per night

Guest favourite

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.

Aug. 2 – 9

$248 CAD per night

Guest favourite

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.

May 23 – 30

$385 CAD per night

Guest favourite

Home in Apopka

4.96 out of 5 average rating, 189 reviews

Farm feel in the city

Cozy, beautifully renovated 2 bedroom cottage on 2.5 acres. Farm setting with horses usually on the property. Only 2 miles from shopping, dining, and downtown Apopka. For nature lovers we are 2 miles from the Wekiva State Park and 40 minutes from Disney and major attractions. High speed internet available.

Sep. 27 – Oct. 4

$173 CAD per night

Guest favourite

Apartment in Winter Garden

4.88 out of 5 average rating, 111 reviews

Stay A While

Welcome to our secluded away from home. Minutes away to supermarkets, shopping stores, and 25 minutes away from theme parks and nightlife. Approximately 40-minute drive to the Orlando International Airport. We have a dedicated parking area for guests who are traveling with moving trucks, boats, and rv's.

Aug. 14 – 21

$157 CAD per night