Top 10 Airbnb Vacation Rentals In Winter Garden, Florida

Pavan Kumar
Pavan Kumar 
Contributing Writer
| 5 min read

Winter Garden, the former citrus town, is home to a diverse range of historical and natural wonders. Situated next to Lake Apopka and about a short drive from Orlando, this town is both the commercial and cultural capitol of West Orange County.

From the vibrant Garden Theatre to SOBO Art Gallery, this place has got it all. The best part about Winter Garden is that this charming town with unique farmers and street markets is just 12.3 miles (19.79 kilometres) away from Walt Disney World Resort in Orlando! So get ready for the time of your life, and do not forget to book one of these Airbnb vacation rentals in Winter Garden, Florida, to experience a flawless vacation experience.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on June 02, 2024.

1. Waterfront house with sunrise views (from USD 339)

If you are looking for an escape from the routine of your daily life, then this rental home is the perfect accommodation for you. Surrounded by nature, this waterfront house offers stunning sunrise views.

This vacation home features a fully equipped kitchen where you can craft culinary wonders. There are several outdoor patios and an outdoor fire pit where you can lounge and relax. From the glorious views of birds and wild animals flocking the nature reserve to entertainment on the multiple smart televisions, you can have it all at this Florida-style vacation home!

Moreover, you can also avail yourself of the complimentary parking space at this property.

Stayed at this property?
Winter Garden, Florida, United States
64 reviews   Superhost Wifi Available
ENTIRE HOME 5 Beds 8 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
great 3-season porch and deck off the kitchen with a beautiful view of the lake behind
the comfortable beds and the high quality linen is worth extra mentioning
large rooms and plenty of space to host small dinners with friends
very clean and spacious
the house was very clean and well maintained
the house was clean and comfortable
the house was lovely clean and well stocked with towels and kitchen needs
this was a great place to stay very clean & upgraded
the host william was great and very responsive
great experience very friendly host who was communicative and proactive in reaching out
william was a great host with great communication
this location is incredible and the host is very accommodating and helpful
owner was very communicative and worked to ensure we had a pleasant stay
good location and great fishing dock
house was in a beautiful location
very close to downtown winter garden which had great restaurants and shopping
very quiet and peaceful yet close to shopping restaurants etc
the biggest asset of this house is the location
Read more reviews

2. Blue Heron Bungalow (from USD 84)

Blue Heron Bungalow is a popular vacation rental due to its close proximity to Downtown Winter Garden and West Orange Trail. This studio apartment can comfortably accommodate up to four guests and features a private patio or balcony where you can feel the cool breeze and gaze at the glorious sky shades.

The kitchen is installed with all the essential amenities to ensure that you have a seamless cooking experience. If you are travelling in your own vehicle, then feel free to utilise the complimentary parking space available onsite.

Stayed at this property?
Winter Garden, Florida, United States
55 reviews   Superhost Wifi Available
Entire guesthouse 2 Beds 4 Guests 1 Bathroom

Accommodates: 4

Top guest reviews
very clean quiet nice and convenient location
everything you need is there and the place is extremely clean and comfortable
thank you lisa and mike for being great hosts
the accommodations were comfortable very clean and the hosts were amazing
fantastic getaway spot walking distance to the charming town center of winter gardens
the location is perfect being so close to downtown and with access to the west orange trail
we would definitely recommend lisa's place to stay
Read more reviews

3. Cosy house in a serene neighbourhood (from USD 99)

If you want to experience a serene hometown setting, this cosy vacation rental is the one for you. This property is perfect for couples and small families. Nestled in a small town setting, this rental provides you with a respite from city life and traffic.

Amenities such as a kitchen and washing machine are available so that you can cook scrumptious meals and prevent the gigantic piling up of your laundry. Free parking space is available on the premises and the best part is that this rental is pet-friendly, which means your pet buddy can also be a part of your vacation!

Stayed at this property?
Winter Garden, Florida, United States
170 reviews   Superhost Wifi Available
ENTIRE HOME 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
bed is okay but the couch was not very comfortable for relaxing and watching a movie
there is a sleep number bed which my husband with back issues really appreciated
becky provides a clean peaceful and accomodating house
it is very clean and had everything we needed
it was very quite clean and a great location
nice cozy and clean casita within walking distance to downtown
becky was a great host
becky was very accommodating and has a great list of recommendations in the area
becky was responsive and took care of anything that needed to be done
the home is very clean and the host is great
the location is great for us near family and near amenities
perfect location place has everything you need and it is really cute inside and out
very nice house just a short walk from downtown winter garden
cute cozy airbnb close to the parks winter garden garden is amazing the farmers market is incredible
cute little place perfect for a weekend getaway
Read more reviews

4. Renovated guest suite with high-speed WiFi (from USD 159)

This Airbnb vacation rental is just minutes away from shopping centres and Downtown Winter Garden. This renovated and remodelled property exudes a modern charm and timeless style. Wake up to the Floridan sun streaming through the large windows in the bedroom and living room.

Although this vacation home is a duplex, you will have your own private entrance. The kitchen comes equipped with all the basic appliances so that you don’t have to dine out. With 200 Mbps WiFi and televisions, you do not have to worry about entertainment! You can utilise the free on-street parking space while enjoying your stay here.

Stayed at this property?
Winter Garden, Florida, United States
272 reviews   Superhost Wifi Available
Entire guest suite 3 Beds 6 Guests 1 Bedroom 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
comfortable place with many extra amenities such as coffee extra towels extra linen shampoo cosmetic remover
modern kitchen we’ll stocked good tv
the beds were super comfortable and it had everything i could have needed
beds were very comfortable and bathroom well stocked with towels and kitchen had a lot of staples available
beautiful new kitchen appliances perfect apartment for 3-4 person family
place was clean and as advertised
very clean on entry
very clean and super comfortable
great stay beds were so clean and comfortable
everything was spotless in working order & comfortable
orion was a great host
orion is a fantastic host
orion was a great host and answered any questions i had promptly and effectively
orion was super helpful
host is very communicative and helpful
great location close to so much
and a great distance from the major parks
great place nicely decorated comfortable bed close to downtown winter garden
such a clean and comfortable place very convenient to get to and close to everything
great and cozy place would recommend it
Read more reviews

5. Historic cottage in Downtown Winter Garden (from USD 120)

Nestled in the heart of the historic Downtown Winter Garden, this Airbnb property dates back to 1937. Shops, restaurants and even the enchanting farmer’s market are within walkable distance range.

The 50-inch smart TV allows you to access the Netflix, Hulu and Disney+ accounts, ensuring an uninterrupted entertainment source. Moreover, are you worried about getting behind on work? With WiFi and a dedicated workspace being available, you can wrap up your office work before going out!

Stayed at this property?
Winter Garden, Florida, United States
114 reviews   Superhost Wifi Available
Entire cottage 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
great tv/ wifi service
bed mattresses were better than most places we've stayed at
excellent air conditioner at cooling the home - but was loud
the wifi was pretty good too ” check in and check out was seamless
comfortable beds and amazing shower
exceptionally clean kitchen was well stocked
the place was very clean and looked exactly like the pictures
the house was very clean and had all the essentials
great clean place in outstanding location
clean comfortable and well updated along with a great location
jill was responsive when we had questions and a very inviting host
jill was very responsive and helpful instructions were clear and easy to follow
jill is the perfect host anticipated all our needs and provided just the right amount of communication
as always a perfect stay wonderful hosts and an excellent location thank you again
cute place and great location
the location is perfect
great location for walking to winter garden's downtown
location is wonderful to downtown and the bike trail
the location couldn’t be better
Read more reviews

6. Mid-Century Hipster (from USD 196)

Mid-Century Hipster is located in the Downtown Winter Garden. This vacation rental is pet-friendly. All you have to do is pay an extra fee and get ready to scramble and run as your pets enjoy the quaint ambience!

The kitchen is stocked with an assortment of condiments, spices and utensils to help you cook wonders and have a hearty meal. A workspace is also available in case some emergency workplace task has to be completed.

This vacation rental also features a 65-inch smart television, which will take care of all your entertainment needs. Lastly, feel free to use the complimentary parking space available on-site.

Stayed at this property?
Winter Garden, Florida, United States
60 reviews   Superhost Wifi Available
ENTIRE HOME 3 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
i liked that each room had an a/c unit
plus the minisplits in each room are great
the beds were comfortable
place is clean and well kept
house was very clean and beds are comfortable
home was clean well stocked and cozy
the house was extremely clean
mary anne's place was very clean and comfortable with modern touches
the hosts we’re awesome
host is very nice and thoughtful
the host was quick to respond at every opportunity
she was very responsive and made sure that everything was taken care of
host is very easy to communicate with and readily available to answer questions or address concerns
great location walking distance to downtown winter garden
the location is perfect for walking to downtown winter garden
great location and value very spacious
we enjoyed the saturday farmer's market as well as the cute shops
great place a stones throw from downtown winter garden and shopping at winter garden village
Read more reviews

7. Luxury house with spacious backyard (from USD 54)

Featuring an eclectic blend of luxury and comfort, this Airbnb rental is an excellent stay option. Craft unforgettable memories as you unwind in the backyard, which is a beautiful oasis. Moreover, the yard is dotted with fruit-bearing trees.

The living room is fitted with large windows to let the sunlight filter into this luxury home. Although this property is nestled in a quiet neighbourhood, restaurants and shopping centres are just minutes away! Savour the complimentary tea, snacks and WiFi services as you enjoy your stay in this modern home. Lastly, do not forget this property only allows a maximum capacity of eight guests.

Stayed at this property?
Winter Garden, Florida, United States
93 reviews   Superhost Wifi Available
ENTIRE HOME 5 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
it was clean and comfortable
the house was cleaned and nice
it was a clean environment that was great for my family
very relaxing stay clean comfortable & convenient
very nice and clean highly recommended
thank you fatima for being a great host
the host is also very kind and accommodating
the host was awesome and very responsive and dependable
fatima was a great host
the host was very friendly and made me feel welcome throughout my stay
beautiful house in an amazing location close to tons of restaurants and only 20 minutes to universal
this location was perfect for what we wanted
the location in a peaceful neighborhood was perfect providing a tranquil getaway
i was very thankful to find this house so close to downtown
we enjoyed drinks at the local bar less than 5 minutes from the location
Read more reviews

8. Peaceful ranch with oak tree views (from USD 129)

If you have ever wanted a ranch experience with horses and pigs, look no further! Get ready to experience your vacation in the cowboy style. Located only a block from the legendary West Orange Trail, this ranch is close to various shops, a brewery and a theatre! The property is surrounded by oak trees and it also has dogs.

You can also rent a bike on-site or experience grooming a trained miniature therapy horse. You’ll get to know what it takes to handle a horse for a price of 45 USD per person.

Stayed at this property?
Winter Garden, Florida, United States
47 reviews   Superhost Wifi Available
Farm stay 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
clean and comfortable accommodation
accomodation: the room was very comfortable and all the house is clean
it's right on the west orange trail and very clean and cozy
host was great lovely home and property
she was a very responsive and accommodating host
host: susan was very welcoming and helpfull
a tranquil stay with a friendly and interesting host
there's a cat a couple of friendly dogs and 6 horses nice home friendly host
perfect location and house for a relaxing stay
we went to ride the west orange trail and enjoy downtown winter gardens perfect location for both
it is wonderfully located in central florida and susan is a most wonderful host
susan was a great host her place is super cute and convenient for downtown winter garden
we had a wonderful time in susan's place
Read more reviews

9. A charming one-bedroom guest suite (from USD 106)

Located right on West Orange Trail, this vacation rental is a hotspot! Open the doors and explore the bike trails or take a short walk and drop by the downtown coffee and retail shops. Experience the tranquillity of this chic house and take advantage of complimentary services such as parking premises. This property also features Amenities such as a washing machine, hair dryer and toiletries.

This Airbnb rental is only a short drive away from both Walt Disney World Resort and Universal Studios Florida Theme Park. If you are here on Saturday morning, then visiting the Winter Garden Farmers Market is a must!

Stayed at this property?
Winter Garden, Florida, United States
39 reviews   Wifi Available
Entire guest suite 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
comfortable couch and small table to sit and eat
clean bathroom with plenty of towels and great shower
it was clean and simple and had everything we needed
jason was responsive helpful and welcomed me with a clean place
the airbnb was clean well stocked and the location could not be beat
kitchen had everything we needed to cook and clean
jason is a wonderful host
jason was helpful and easy to communicate with throughout our stay
we greatly appreciated the waters and snacks upon arrival jason was very responsive and provided clear instructions
jason was responsive to any needs i had the entire stay
great location for enjoying the greatness of winter park
great place to stay and short distance from orlando studios
it’s so close to many great restaurants and local attractions
perfect location and just what you need for day to day
we couldn’t have asked for a more perfect location
Read more reviews

10. A cosy villa with garden view

Whether you are here on a vacation or are simply staying here during your relocation, this vacation rental will not disappoint you. This property is a short drive away from the lively downtown, where you can indulge in various community events or feel the adrenaline rush while kayaking and hiking.

After a busy day, you can retire to the backyard and sit by the fire pit while grilling your dinner with your family. A dedicated workspace with high-speed WiFi is also available to ensure that you can work efficiently without any hassles. Lastly, do not forget to talk to your host in case you are organising a party or event at the property!

Stayed at this property?
Winter Garden, Florida, United States
74 reviews   Superhost Wifi Available
ENTIRE HOME 5 Beds 7 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 7

Top guest reviews
Amenities & Room:
the property was exactly as described and had all of the amenities we needed especially good wifi
it was very clean and smelled great
such a clean and amazing place
everything is very clean and in order and also quiet
great place very clean and plenty of room
it was absolutely spotless comfortable and better than described
shawn & jenny were great hosts
shawn jenny was a great host
shawn & jenny were very responsive and accommodating
host very responsive and available
awesome host they provided me with everything i needed and were very polite and courteous
location is close to disney and winter garden’s beautiful downtown
this place was in a perfect location and exactly as advertised
if you’re coming to winter garden this little place is very well situated
for us the location was great and accommodated our kids better than a hotel
great host great location great place
Read more reviews

Experience a serene getaway in Winter Garden

From sizzling up your romance to having an adventurous time with your family, Winter Garden offers it all! Enjoy the live performances and stroll the Saturday markets to experience once-in-a-lifetime moments. Even if you are here to visit the myriads of theme parks in Orlando, staying in Winter Garden will definitely elevate your vacation experience.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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A person who seeks adventure in all his travel journeys. From cliff-jumping in offbeat locations to a deep dive into the spiritual realms, he has done it all. His interest in travel writing...Read more

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