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 October 10, 2023.
1. Waterfront house with sunrise views (from USD 415)
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.
Top guest reviews
Amenities & Room:
great 3-season porch and deck off the kitchen with a beautiful view of the lake behindthe comfortable beds and the high quality linen is worth extra mentioninglarge rooms and plenty of space to host small dinners with friendsCleanliness:
very clean and spaciousthe house was very clean and well maintainedthe house was clean and comfortablethe house was lovely clean and well stocked with towels and kitchen needsthis was a great place to stay very clean & upgradedHost:
the host william was great and very responsivegreat experience very friendly host who was communicative and proactive in reaching outwilliam was a great host with great communicationthis location is incredible and the host is very accommodating and helpfulowner was very communicative and worked to ensure we had a pleasant stayRead more reviewsLocation:
good location and great fishing dockhouse was in a beautiful locationvery close to downtown winter garden which had great restaurants and shoppingvery quiet and peaceful yet close to shopping restaurants etcthe biggest asset of this house is the location
Superhost
2. Blue Heron Bungalow (from USD 86)
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.
Top guest reviews
Cleanliness:
very clean quiet nice and convenient locationeverything you need is there and the place is extremely clean and comfortableHost:
thank you lisa and mike for being great hoststhe accommodations were comfortable very clean and the hosts were amazingRead more reviewsLocation:
fantastic getaway spot walking distance to the charming town center of winter gardensthe location is perfect being so close to downtown and with access to the west orange trailwe would definitely recommend lisa's place to stay
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!
Top guest reviews
Amenities & Room:
bed is okay but the couch was not very comfortable for relaxing and watching a moviethere is a sleep number bed which my husband with back issues really appreciatedCleanliness:
becky provides a clean peaceful and accomodating houseit is very clean and had everything we neededit was very quite clean and a great locationnice cozy and clean casita within walking distance to downtownHost:
becky was a great hostbecky was very accommodating and has a great list of recommendations in the areabecky was responsive and took care of anything that needed to be donethe home is very clean and the host is greatRead more reviewsLocation:
the location is great for us near family and near amenitiesperfect location place has everything you need and it is really cute inside and outvery nice house just a short walk from downtown winter gardencute cozy airbnb close to the parks winter garden garden is amazing the farmers market is incrediblecute little place perfect for a weekend getaway
4. Renovated guest suite with high-speed WiFi (from USD 68)
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.
Top guest reviews
Amenities & Room:
comfortable place with many extra amenities such as coffee extra towels extra linen shampoo cosmetic removermodern kitchen we’ll stocked good tvthe beds were super comfortable and it had everything i could have neededbeds were very comfortable and bathroom well stocked with towels and kitchen had a lot of staples availablebeautiful new kitchen appliances perfect apartment for 3-4 person familyCleanliness:
place was clean and as advertisedvery clean on entryvery clean and super comfortablegreat stay beds were so clean and comfortableeverything was spotless in working order & comfortableHost:
orion was a great hostorion is a fantastic hostorion was a great host and answered any questions i had promptly and effectivelyorion was super helpfulhost is very communicative and helpfulRead more reviewsLocation:
great location close to so muchand a great distance from the major parksgreat place nicely decorated comfortable bed close to downtown winter gardensuch a clean and comfortable place very convenient to get to and close to everythinggreat and cozy place would recommend it
5. Historic cottage in Downtown Winter Garden (from USD 130)
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!
Top guest reviews
Amenities & Room:
great tv/ wifi servicebed mattresses were better than most places we've stayed atexcellent air conditioner at cooling the home - but was loudthe wifi was pretty good too ” check in and check out was seamlesscomfortable beds and amazing showerCleanliness:
exceptionally clean kitchen was well stockedthe place was very clean and looked exactly like the picturesthe house was very clean and had all the essentialsgreat clean place in outstanding locationclean comfortable and well updated along with a great locationHost:
jill was responsive when we had questions and a very inviting hostjill was very responsive and helpful instructions were clear and easy to followjill is the perfect host anticipated all our needs and provided just the right amount of communicationas always a perfect stay wonderful hosts and an excellent location thank you againRead more reviewsLocation:
cute place and great locationthe location is perfectgreat location for walking to winter garden's downtownlocation is wonderful to downtown and the bike trailthe location couldn’t be better
6. Mid-Century Hipster (from USD 159)
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.
Top guest reviews
Amenities & Room:
i liked that each room had an a/c unitplus the minisplits in each room are greatthe beds were comfortableCleanliness:
place is clean and well kepthouse was very clean and beds are comfortablehome was clean well stocked and cozythe house was extremely cleanmary anne's place was very clean and comfortable with modern touchesHost:
the hosts we’re awesomehost is very nice and thoughtfulthe host was quick to respond at every opportunityshe was very responsive and made sure that everything was taken care ofhost is very easy to communicate with and readily available to answer questions or address concernsRead more reviewsLocation:
great location walking distance to downtown winter gardenthe location is perfect for walking to downtown winter gardengreat location and value very spaciouswe enjoyed the saturday farmer's market as well as the cute shopsgreat place a stones throw from downtown winter garden and shopping at winter garden village
7. Luxury house with spacious backyard (from USD 113)
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.
Top guest reviews
Cleanliness:
it was clean and comfortablethe house was cleaned and niceit was a clean environment that was great for my familyvery relaxing stay clean comfortable & convenientvery nice and clean highly recommendedHost:
thank you fatima for being a great hostthe host is also very kind and accommodatingthe host was awesome and very responsive and dependablefatima was a great hostthe host was very friendly and made me feel welcome throughout my stayRead more reviewsLocation:
beautiful house in an amazing location close to tons of restaurants and only 20 minutes to universalthis location was perfect for what we wantedthe location in a peaceful neighborhood was perfect providing a tranquil getawayi was very thankful to find this house so close to downtownwe enjoyed drinks at the local bar less than 5 minutes from the location
8. Peaceful ranch with oak tree views (from USD 119)
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.
Top guest reviews
Cleanliness:
clean and comfortable accommodationaccomodation: the room was very comfortable and all the house is cleanit's right on the west orange trail and very clean and cozyHost:
host was great lovely home and propertyshe was a very responsive and accommodating hosthost: susan was very welcoming and helpfulla tranquil stay with a friendly and interesting hostthere's a cat a couple of friendly dogs and 6 horses nice home friendly hostRead more reviewsLocation:
perfect location and house for a relaxing staywe went to ride the west orange trail and enjoy downtown winter gardens perfect location for bothit is wonderfully located in central florida and susan is a most wonderful hostsusan was a great host her place is super cute and convenient for downtown winter gardenwe had a wonderful time in susan's place
9. A charming one-bedroom guest suite (from USD 137)
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!
Top guest reviews
Amenities & Room:
comfortable couch and small table to sit and eatCleanliness:
clean bathroom with plenty of towels and great showerit was clean and simple and had everything we neededjason was responsive helpful and welcomed me with a clean placethe airbnb was clean well stocked and the location could not be beatkitchen had everything we needed to cook and cleanHost:
jason is a wonderful hostjason was helpful and easy to communicate with throughout our staywe greatly appreciated the waters and snacks upon arrival jason was very responsive and provided clear instructionsjason was responsive to any needs i had the entire stayRead more reviewsLocation:
great location for enjoying the greatness of winter parkgreat place to stay and short distance from orlando studiosit’s so close to many great restaurants and local attractionsperfect location and just what you need for day to daywe couldn’t have asked for a more perfect location
10. A cosy villa with garden view (from USD 115)
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!
Top guest reviews
Amenities & Room:
the property was exactly as described and had all of the amenities we needed especially good wifiCleanliness:
it was very clean and smelled greatsuch a clean and amazing placeeverything is very clean and in order and also quietgreat place very clean and plenty of roomit was absolutely spotless comfortable and better than describedHost:
shawn & jenny were great hostsshawn jenny was a great hostshawn & jenny were very responsive and accommodatinghost very responsive and availableawesome host they provided me with everything i needed and were very polite and courteousRead more reviewsLocation:
location is close to disney and winter garden’s beautiful downtownthis place was in a perfect location and exactly as advertisedif you’re coming to winter garden this little place is very well situatedfor us the location was great and accommodated our kids better than a hotelgreat host great location great place
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.
History
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