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

Top guest favorite

A bright living area features a light gray sofa adorned with yellow and blue cushions, accompanied by a comfortable recliner. A decorative round ottoman sits in the center on a floral area rug. Natural light enters through two large windows, complemented by light-filtering curtains.

Home in Winter Garden

4.97 out of 5 average rating, 121 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 favorite

A scenic view is presented of a landscaped pool area surrounded by palm trees and a serene lake. In the background, vibrant greenery complements the elegant architecture of neighboring buildings, while a fountain adds a tranquil touch to the picturesque setting.

Apartment in Windermere

4.97 out of 5 average rating, 38 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 favorite

A grand castle features tall towers adorned with purple peaks and golden accents. A statue of Walt Disney stands in front of the castle alongside Mickey Mouse, surrounded by vibrant pink flowers and lampposts. The scene is set against a clear blue sky.

Apartment in Winter Garden

5 out of 5 average rating, 5 reviews

Winter Garden Charm, Near Disney

2 Bedroom | 2 Bath | Prime Winter Garden Location | Near Disney & Universal Nestled in the heart of charming Winter Garden, this beautifully designed 2-bedroom, 2-bath apartment offers the perfect blend of modern luxury and small-town charm — just 20 minutes from Walt Disney World and Orlando’s top attractions. Located on the iconic Plant Street, you’ll be steps away from historic downtown Winter Garden, home to popular restaurants, boutiques, coffee shops, and the famous West Orange Trail.

Guest favorite

A modern open-plan living and dining area features a round table with a bold centerpiece of flowers. Blue sofas provide comfortable seating, and large windows allow natural light to illuminate the room, revealing views of the outside area.

Condo in Windermere

4.93 out of 5 average rating, 45 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.

Guest favorite

A brick archway is adorned with a tiled roof and a prominent clock at its center, marking the entrance to Winter Garden. Bicyclists are seen stopping beneath the arch, surrounded by lush green trees that line the street. Shops and outdoor seating are visible in the background.

Home in Winter Garden

4.91 out of 5 average rating, 202 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.

Top guest favorite

The exterior of a charming white cottage is shown, featuring a welcoming porch with a wooden bench. Lush green plants are placed in terracotta pots on either side of the entrance, and a neatly maintained lawn is present. A fenced area and driveway are visible in the background.

Cottage in Winter Garden

4.99 out of 5 average rating, 153 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 favorite

An open kitchen area features modern wood cabinetry and stainless steel appliances. A central island with seating for four is highlighted by pendant lighting. Natural light is provided through large windows adorned with sheer and dark curtains, creating a bright yet cozy atmosphere.

Apartment in Ocoee

5 out of 5 average rating, 22 reviews

The Cozy Escape Close to Windermere & WinterGarden

This beautiful suite has a unique style of its own. A place to relax and unwind after a long day. This beautiful place has an open floor plan , that includes a full kitchen equipped with everything you will need for your stay including stainless steel appliances, a living room with combined dining. The bedroom is separated for privacy with beautiful privacy curtains. The bedroom is equipped with a queen size platform bed with side lamps with charging ports & walk in closet.

Top guest favorite

Treehouse in St. Cloud

4.96 out of 5 average rating, 979 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 favorite

The exterior features a wooden deck adorned with plants and greenery. A round table with four chairs is positioned in front of the guesthouse, which has a sandy pink hue. Large windows provide ample natural light, and an air conditioning unit is visible on the side.

Guesthouse in Windermere

4.94 out of 5 average rating, 269 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.

Top guest favorite

Apartment in Winter Garden

5 out of 5 average rating, 17 reviews

King Bed |Pets Welcome |Top Amenities, Near Parks

Welcome to our Modern 1-Bedroom, 1-Bathroom Apartment in Winter Garden, FL! This stylish and cozy apartment is the perfect home base for your Florida getaway, offering a relaxing atmosphere and convenient access to nearby theme parks, shopping, and dining. Enjoy resort-style amenities and a comfortable stay in the charming Winter Garden area. Please reach out for any potential multi-day discounts available.

Guest favorite

A glass of red wine is held in front of a sparkling pool. The water is clear and reflects the surrounding greenery, while patio furniture is visible in the background. A staircase leads into the pool area, offering easy access for relaxation.

Guest suite in Orlando

4.93 out of 5 average rating, 213 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!!!

Guest favorite

A smart lock is shown being activated by a smartphone. The lock is sleek and modern, featuring a black finish with illuminated numbers indicating its technological features. The background consists of vertical blinds, adding subtle texture to the image.

Apartment in Windermere

4.93 out of 5 average rating, 61 reviews

Luxury Family Resort Styled Apartment Near Disney

Centrally located in the desirable Windemere FL Minutes from Isleworth Golf and Country Club Not far from Golden Bear Club Close to Metrowest 12.5 miles from Downtown Orlando 20 minutes to Disney 20 minutes to Universal Studios 25 minutes to MCO International 40 minutes to Lego Land 15 Minutes to Winter Garden Mall (Target, Walmart, Publix, Restaurants)

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Hotels

Stylish accommodations and amenities

Popular amenities for Windermere vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Windermere

Top guest favorite

A screened-in porch features a large sectional sofa adorned with colorful accent pillows, surrounding a central coffee table. Soft lighting from string lights enhances the inviting atmosphere. The tiled floor is complemented by a geometric-patterned area rug, and potted plants add a touch of greenery to the space.

Private room in Ocoee

4.92 out of 5 average rating, 62 reviews

Simple & Clean 2

CaitlinRating, 5 stars3 weeks ago

Have been to quite a few Airbnb’s in the area, this is definitely the best deal available. Safe neighborhood, clean house, and all the amenities you could need to be comfortable. Everything is labeled, easy to find, and host is very responsive as well. Highly recommend.

Top guest favorite

A gathering area features wooden benches set on a deck surrounded by lush greenery and palm trees. Soft lighting hangs above, creating a serene outdoor atmosphere. The backdrop showcases a vibrant sunset over the lake, enhancing the tranquil setting.

Private room in Orlando

5 out of 5 average rating, 26 reviews

Sand Lake Suite

PeggyRating, 5 stars1 week ago

I can't say enough great things about this little trip. Host we've above and beyond, always responding to any questions and being flexible with check out since flight was a little later. Super easy to find and navigate gate entry, loved the pier to the lake, so serene to read and watch sun set. Didn't check out pool bc it rained last night but it was open one day and it was gorgeous. Absolutely will be returning next year when going back to conference!! The added touches in bathroom and laundry made it A+ service. Exactly what I needed as a solo traveler. thanks Carol

Guest favorite

A modern en suite bathroom features a clean design with a granite countertop and a large mirror above the sink. The bathtub is accompanied by a shower, and a small plant adds a touch of greenery. The space is well-lit and neutral in color.

Private room in Kissimmee

5 out of 5 average rating, 6 reviews

Private King Bedroom Near Disney

KaiRating, 5 stars1 month ago

This was a great experience, very comfortable room and the entire process was smooth. I’d highly recommend it.

Guest favorite

A neatly arranged bed displays a white towel embroidered with the word 'Welcome'. The towel is placed centrally atop a textured bedspread, flanked by two dark blue knitted throws that provide a warm contrast.

Private room in Windermere

4.91 out of 5 average rating, 78 reviews

Disney Neighbors!

LaraRating, 5 stars4 weeks ago

Great location, as I attended a Safety Conference held at Disney Contemporary Resort. (20 min drive) Great communication, clean bedroom and bathroom, fast wifi, good parking options and cool/comfortable house temperature. Would absolutely stay here again!

Guest favorite

A shaded outdoor seating area features a large umbrella, providing cover over a mixture of cushioned chairs and a small table. The space is set on a wooden deck, surrounded by a grassy yard and wooden fencing, creating a relaxed environment.

Private room in Orlando

4.89 out of 5 average rating, 37 reviews

Private Room 2 | Tiny Cottage | 15 min Universal

HannahRating, 5 stars3 months ago

The place was great, just as advertised and in a quiet area. Would recommend having a vehicle if you’re staying here (or anywhere in Orlando really); I took the bus a couple times and it wasn’t too far to walk to the bus stop, but the bus ride is fairly long (though still doable). I had no issues getting in and using the amenities, and my neighbour in the other room was quiet and respectful - good since we share the common space.

Superhost

A sparkling pool is surrounded by a screened enclosure, featuring a gentle waterfall on one side. Paved with clean stone tiles, the pool area is accented by lush greenery and potted plants, providing a serene outdoor space for relaxation.

Private room in Windermere

4.88 out of 5 average rating, 24 reviews

Beautiful Windermere home with pool near parks

MaryRating, 5 stars3 months ago

We had a great stay at this AirBnB. Marjorie was a warm and friendly host and made sure we were comfortable. Her home has lots of space, a huge yard and a designated bathroom. I would love to return some day.

A lively event space is filled with attendees gathered around a large T-Rex skeleton. Colorful lighting illuminates the area, highlighting various seating arrangements and decorative elements. Tall hanging chandeliers create a vibrant atmosphere as guests engage in conversation and festivities.

Hotel room in Kissimmee

4.78 out of 5 average rating, 926 reviews

Your Orlando Escape | Infinity Pool. Gym. 1BR

MarcoRating, 5 stars2 weeks ago

Really great spot with lots of things to do near by.

Guest favorite

A bathroom area features a light-colored vanity with a round sink and a large mirror above it. A shower with a striped curtain is visible along with a toilet. Neutral tile flooring complements the space.

Private room in Windermere

4.92 out of 5 average rating, 63 reviews

15 mins away from Disney in a quiet neighborhood

RyanRating, 5 stars1 month ago

Farhan was a terrific host. Farhan's unit was as described, clean, and overall a very nice stay. Definitely best for one or two travelling people that just need a night or two stay while in town for an event.

Show all

Vacation rentals in Windermere

Top-rated vacation rentals in Windermere

Vacation rentals for every style

Popular amenities for Windermere vacation rentals

Other great vacation rentals in Windermere

Destinations to explore