Holiday rentals in Windermere

4.97 out of 5 average rating, 121 reviews

Home in Winter Garden

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!

4.97 out of 5 average rating, 38 reviews

Flat in Windermere

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.

4.98 out of 5 average rating, 40 reviews

Flat in Winter Garden

StylishAptWtrGrdnOppLake&Prk&Yrd

*Brand new one bedroom apartment near downtown Winter Garden, across from Lake Apopka and Newton Park *Private fenced yard with BBQ, picnic table, and hammock. *Short golf cart ride to shops and restaurants in downtown Winter Garden *Opposite Newton Park with its breathtaking sunset views and many amenities (playground, public pool, boat ramp) and wildlife *Nearby Tanner Hall is available for private events and functions *Less than 30 min to Orlando Airport, Universal, Disney, and major malls

Superhost

Home in Windermere

4.91 out of 5 average rating, 23 reviews

Water Front Haven

Skip the crowds and experience the true Florida lifestyle. Beautiful home on a safe, quiet street with access to 12 lakes in your back yard. Simple & clean decor. Outdoor dining on porch & dock. Close to attractions & beaches (45 min). Nestled among palm, oak & camphor trees. Feed the fish and turtles from your private dock. Rent a boat and explore lovely lakes. Enjoy nightly walks on sandy streets canopied by old oak trees. Walk to parks, coffee shops, cafes and swimming areas.

5 out of 5 average rating, 6 reviews

Flat in Winter Garden

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.

4.93 out of 5 average rating, 45 reviews

Apartment in Windermere

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.

4.99 out of 5 average rating, 154 reviews

Cottage in Winter Garden

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.

5 out of 5 average rating, 22 reviews

Flat in Ocoee

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.

4.96 out of 5 average rating, 980 reviews

Treehouse in St. Cloud

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.

Guest house 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.

4.95 out of 5 average rating, 42 reviews

Flat in Winter Garden

Pet-Friendly, King Bed, 15 Min to Parks, Amenities

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.

4.93 out of 5 average rating, 61 reviews

Flat in Windermere

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)

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Popular amenities for Windermere holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Windermere

4.97 out of 5 average rating, 261 reviews

Studio Guest House (Private Not Shared)

AmirRating, 5 stars2 weeks ago

It was great and it’s exactly as in pictures, close to everything universal studio and lake.

Private room in Windermere

4.91 out of 5 average rating, 78 reviews

Disney Neighbors!

LaraRating, 5 stars1 month 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!

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.

4.93 out of 5 average rating, 906 reviews

Lakefront near Universal (no other host fees)

MikaylaRating, 5 stars2 weeks ago

We decided to extend our stay for a day. Perfect location. View was nice .

Superhost

Private room in Windermere

4.88 out of 5 average rating, 24 reviews

Beautiful Windermere home with pool near parks

MaryRating, 5 stars4 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.

4.9 out of 5 average rating, 48 reviews

Private room in Ocoee

Centrally located Private Studio

LatoyaRating, 5 stars3 weeks ago

Very quiet place, very neat and description matches pictures.

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.