Vacation rentals 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!

Superhost

Guest suite in Winter Garden

4.83 out of 5 average rating, 348 reviews

Designer Guest Suite Near Disney/Universal/DT

This newly renovated, modern, and clean apartment has been freshly designed with wonderful & 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 with thick memory foam toppers 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

4.88 out of 5 average rating, 560 reviews

Bungalow in Maitland

Maitland-Orlando Area, FL. Pool House Bungalow

Large open space adjacent to a beautiful pool, waterfall, and fantastic lake view. 27 miles to Disney World, close to Park Avenue, local hospitals, Universities, and less than an hour to local beaches. Only 18 miles to MCO-Orlando International Airport. Great shopping within 3 miles. Location is secluded with large trees, lakeside, and adjacent to the commuter train track. The train runs by on regular basis. Please note in the pictures the pool creates the ambiance to make your stay complete.

4.91 out of 5 average rating, 203 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.

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.

4.82 out of 5 average rating, 159 reviews

Guest suite in Ocoee

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 in front 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.

4.97 out of 5 average rating, 124 reviews

Guesthouse in Clermont

Coastal Cottage in Clermont

Welcome to our newly renovated coastal cottage! Located in the heart of Clermont, only 1 mile from downtown, the south lake trail, & only minutes from all of the best restaurants, shopping, & coffee shops in Clermont! This is the perfect location for triathletes in training or families visiting Disney World (or any of the theme parks) – Orlando’s best attractions are less than 30 miles away! This sweet & sunny lakeside studio has everything you’ll need for a comfortable visit!

4.97 out of 5 average rating, 762 reviews

Tiny home in Spring Lake

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.

4.98 out of 5 average rating, 124 reviews

Home in Minneola

Cozy Studio Near Disney/Universal/Training center

This cozy stylish studio, detached guest house is perfect for short-term or extended stay in the beautiful city of Minneola. Sleeps 2, can accommodate up to 4. Features a large backyard and a fire pit. Close to Downtown Clermont, National Training Center, and 35 minutes to Disney World and other major attractions. This tranquil space features a queen bed with 3" memory foam mattress topper and a spacious living space that has a Multi-Functional Sofa that converts into a Bed.

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.

4.94 out of 5 average rating, 269 reviews

Guesthouse in Windermere

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.

4.98 out of 5 average rating, 201 reviews

Guest suite in Montverde

Green Mountain Getaway (No indoor Smoking or Pets)

(Non Smoker & No Pets) A secluded lot surrounded by FL’s beautiful tropical landscape. Golfer? We are 3 min. from the beautiful Bella Collina's luxury 18 hole golf course, a Nick Faldo design. Also 8 min. from Sanctuary Ridge Golf Club, a more affordable option. Biker? “Killarney Station", is an affordable place to rent bikes or bring your own to ride the beautiful 26 mile trail. 28 minutes to all the attractions!

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Other great vacation rentals in Winter Garden

Superhost

Guesthouse in Winter Garden

4.9 out of 5 average rating, 10 reviews

Cozy 1 bedroom with private access

WilliamRating, 5 stars1 month ago

Everything was as stated, very clean,downtown was in walking distance

Guesthouse in Winter Garden

4.92 out of 5 average rating, 90 reviews

Blue Heron Bungalow

KathleenRating, 5 stars3 weeks ago

We loved every aspect of our stay in the bungalow! The location is perfect - we walked to the local coffee shop and restaurants. The bungalow was immaculate and cozy, and almost every possible need was met! The neighborhood was quiet and peaceful and lined with beautiful live oaks, which made our walks to Plant street (the main drag) even more picturesque. We will absolutely stay here again. Thanks for a great stay!

Guest suite in Winter Garden

5 out of 5 average rating, 23 reviews

Winter Garden guest suite

JudyRating, 5 stars1 month ago

Each time I stay, the suite has been spotless - cleanness Airbnb I have stayed in the 15 years since I started. Switched are labeled, along with drawers; clear instructions on suite. I always feel safe and secure when staying there. Mary and Larry are both helpful and friendly.

4.98 out of 5 average rating, 41 reviews

Winter Garden Cottage w\fence

StephenRating, 5 stars1 month ago

This is a great 3 Bed Room house minutes from Downtown WG, Major shopping areas close by. Disney and other major attractions are also close by. John and Lynn are very responsive and very reachable with any questions you may have. 5 Stars all around for this Airbnb.

Apartment in Winter Garden

5 out of 5 average rating, 6 reviews

Winter Garden Charm, Near Disney

ShannaRating, 5 stars2 weeks ago

I had a great stay at Sebastian’s place. The apartment is well equipped and the complex has an amazing gym and a lovely pool. Location wise, there’s a Publix within a short drive as well as a nice little Downtown area that’s great for a stroll. What I appreciated most—and the main reason I chose this place—was that it made me feel like a local rather than a tourist, so it really fit the bill.

4.91 out of 5 average rating, 35 reviews

1921 Winter Garden home 22 min from Magic Kingdom

DuWayneRating, 5 stars4 weeks ago

The house was very clean. The bed was very comfortable. The host was very accommodating and responded quickly. There were so many amenities that we didn’t need a thing. Great place to stay! Thank you Gerald for a wonderful stay.

Apartment in Winter Garden

4.98 out of 5 average rating, 40 reviews

StylishAptWtrGrdnOppLake&Prk&Yrd

DevriRating, 5 stars1 month ago

William’s place was a great base for exploration of the Lake Apopka area. The apartment was very clean, well air-conditioned (in an Orlando-area early heat wave), the bed was comfortable, and close to the restaurants of Winter Garden. Sunset over the lake was steps away, and all-in-all, a beautiful, restful place. While we didn’t take advantage of golf-cart rental, William offers that too and that would have been a fun way to get around the area. I recommend William’s place to others and will look for his availability again in our next birding adventure to Orlando!