10 Best Airbnb Vacation Rentals In Winter Haven, Florida - Updated 2021

airbnb winter haven fl

A peaceful and quiet city that is famous for its chain of lakes, Winter Haven is a great spot for vacationing with friends and family. That’s not all, this city is also close to the Legoland theme park and Disney World which makes it perfect for a family with kids as well. From taking wakeboarding lessons to browsing through antique shops or watching a movie in a classic theatre, there is a bunch of things to do here to keep yourself occupied. And to make your trip even more comfortable, we have listed down the best Airbnb vacation rentals in Winter Haven, Florida.

1. Cabana beside Lake Howard (from USD 85)

This cabana next to Lake Howard consists of one bedroom and offers two bunk beds that can accommodate four guests at a time. The house is complete with a walk-in shower and a toilet and offers basic amenities like heat, air conditioning, microwave, coffee maker, WiFi, and so on. They also have a pool that you can use but be careful with kids below 12 years as it can be dangerous for them. One of the best things about this property is the backyard that includes a dock so you can enjoy fishing here, too.

The Russell Lake House
Winter Haven, Florida, United States
84 reviews
Entire guesthouse 4 Beds 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
the view from the pool was amazing
the furnishings finishes and beds are all designer and beautifully built
beds are super comfy
the beds and the bed sheets were amazing
pool was great for the warm days we had
the cabana was very clean and had everything you would need
such a beautiful place nice and clean
very clean space in a quiet neighborhood would definitely stay here again
no hassle sparkling clean cozy and comfortable thank you bobbie
the cabana was very cute and clean
everything was great our host was friendly helpful and private
bobbie is a great host
and the host is amazing so accommodating
bobbie was a perfect host and was very responsive
thank you so much for hosting us bobbie
cute place in a fun neighborhood
the location was perfect and beautiful and close to what we needed
beautiful location that is easy to get to
the location is great and very peaceful
perfect little bungalow in a perfect location
Read more reviews

2. Duplex on lakefront property near Legoland (from USD 86)

A duplex built on a lakefront property, this vacation rental offers amazing hospitality and will provide you a comfortable stay. And this house is just 4 miles (6.4 kilometers) from Legoland theme park and other famous Orlando attractions so you can plan a day trip quite conveniently. As a result, this house is perfect for families, couples, and friend groups. They also offer full kitchen use so you can cook delicious meals while chilling on the dock. This kid-friendly Airbnb offers toys, a baby stroller, plastic utensils, and more, too, and provides free European-style breakfast during your stay here.

Winter Haven, Florida, United States
129 reviews
Entire house 3 Beds 3 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
incredible amenities cozy and comfortable
the tv sets were great
the king bed was amazingly comfortable
so comfortable my sister is buying the same mattress for her room
the beds were super comfortable and my daughter loved her room with games and toys
everything was clean and spacious
great clean place to stay
the place is very clean and nice
everything was amazing clean and quick respond
an amazingly beautiful clean and great local place to stay
jin and pedro very nice hosts
jin as the host is very responsive
very responsive hosts
great and quick communications with owner
jin and pedro are awesome hosts
super close to legoland
great location for legoland
great location for anyone visiting legoland
nice place that is close to legoland
great place and close to all winter haven activities
Read more reviews

3. Dual loft on Lake Mariana near Disney World (from USD 50)

This rustic tiny home is a dual loft that is joined by a bridge. This beautiful home is on Lake Mariana and quite close to popular attractions such as Legoland, Bok Tower Gardens, Disney World, and so on. There is a full-sized mattress in a loft and a twin bed in the other loft. This property is not suited for a family with young kids as there are no railings here. You also get access to two kayaks and canoe to enjoy in the lake. You can choose to fish on the dock or boat in the lake.

Disney/Legoland Lakeside TINYHOUSE!
Winter Haven, Florida, United States
280 reviews
Entire place 3 Beds 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
we loved the amenities: the lake wifi netflix
thank goodness the small space heater worked
the beds are on the floor in the loft & of average comfort
the bathroom was a good size and the water pressure and temperature proved to stay consistently comfortable
very clean and accommodating
very clean very nicely decorated
clean quiet and scenic area
the space was clean and comfortable
everything was clean and well supplied
she is very attentive and helpful
keypad access was convenient and the host was very helpful and quick to answer questions through text
such a fun place to stay anna is a great host and replied to every message really quick
the tiny home was great anna was easy to get in touch with and very responsive
she was very responsive and offered excellent suggestions for things to do and see while in the area
perfect distance to legoland and close attractions
i loved the location
this place is super cute
the location was perfect for my flight training at the airport across the street
we enjoyed the experience and greatly appreciated how close the tiny house was in location to legoland
Read more reviews

4. Antique 96-year-old home overlooking Little Lake Otis (from USD 148)

If you like old, historic homes then you should check out this 96-year-old custom home with a spacious swimming pool. This house has three bedrooms that can accommodate six guests and features tall ceilings with wooden floors throughout. One of the best things about this property is that the extra-large pool overlooks the Little Lake Otis so you are greeted with an amazing view all the time. You also get a free Living Water Boat Cruise on the chain of lakes on your stay here. Plus, this property is close to Downtown Winter Haven and Legoland so you can drive there anytime you want.

Hidden Haven Roaring 20s Lakehouse with Pool
Winter Haven, Florida, United States
48 reviews
Entire house 3 Beds 3 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
pool area and view were beautiful
the pool was amazing and the view was breath taking
quite spacious quiet with a lovely pool and beautiful view of the lake
plenty of space with a king size pool and beautiful lakefront view
the three rooms with their own restrooms was a really nice feature
it is clean spacious and perfect for a family retreat
exceptionally clean and well stocked with little things you may have forgotten
randy's home is clean and well described
the house was extremely clean and stocked up with everything you could possibly need and more
randy was a great host
randy is a great host who responds very quickly
excellent host to deal with - very helpful and responsive
he replied very quickly with any questions and was very helpful with extending our stay
the most down to earth easy going host we’ve ever had for airbnb
the location is perfect very close to shops and restaurants while tucked away in a cozy neighborhood
it was a fun family place close to legoland
it was an easy short trip to legoland and and the neighborhood is quiet and relaxing
it was the perfect place to come back and relax after a day at legoland
the house is great close to legoland publix walmart and many restaurants
Read more reviews

5. Three-bedroom house close to Lake Cannon and Lake Mirror (from USD 80)

Another beautiful house that you can consider in Winter Haven is this recently painted and refurbished three-bedroom home. It is spacious and can easily accommodate six guests making it perfect for families, couples, and friends. There are several amazing great restaurants, shopping sites, and natural attractions nearby to keep you entertained. You also get access to the full kitchen along with basic amenities like WiFi, air conditioning, heat, oven, washing machine, etc. so you will be comfortable here. Plus, there is a patio and backyard to chill and relax during your stay here.

The Flamingo
Winter Haven, Florida, United States
56 reviews
Entire house 3 Beds 3 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
there is a real dining room table a nice roll-top desk and good wifi
incredibly spacious clean and the kitchen had a lot of appliances and all of the necessary dishware
beds are very good and there is seating for at least five in the living room
three good sized bedrooms and two full bathrooms worked wonderfully for my group of travelers
wished there was a tv remote for the tv but other than that pleasant place
clean cozy quiet place
super clean place in quiet neighborhood
the house was very clean and nicely decorated
the house had everything very clean organized and comfortable
beautiful stay clean and spacious for a wonderful price in a quiet and serene neighborhood
carol is a wonderful host and her home is quite cozy
a truly excellent host
carol is very responsive to questions
exactly like the pictures and carol was a great host
fantastic place spacious house and very responsive hosts a must stay
great location for legoland
great place and close to many places in walking distance
great place in terrific location
allowing for a enjoyable stay and conveniently close to legoland
loved the walk-in shower
Read more reviews

6. Bungalow with contemporary commodities (from USD 80)

This is a bungalow that is in the center of the town and has been recently remodeled with a new air-conditioning unit. This bungalow is a historic house with a refurbished 84-year-old wooden floor and several contemporary commodities. The house has three bedrooms and one bathroom and can accommodate four guests at a time. The neighborhood is also quite peaceful and is close to downtown, Lake Elbert, a hospital, and more. That’s not all–Lego Land is just 15 minutes away and Disney World is also just 33 miles (53.1 kilometres) away so you can easily plan a day trip from here.

Bungalow haven
Winter Haven, Florida, United States
15 reviews
Entire bungalow 2 Beds 3 Bedrooms 1 Bathroom
Top guest reviews
very clean quiet and comfortable
very clean house and nice place to stay
small home but very clean and perfect fit for what we needed
the house was very clean and owners were very kind
walter was an excellent host and we really enjoyed our stay
cute house in a very quiet neighborhood
park nearby too which was great
nice place for the price
this place was wonderful to stay at
Read more reviews

7. Cute cottage close to Legoland (from USD 121)

Are you planning a complete family vacation? If so, then this cottage with two bedrooms is perfect as it can accommodate seven guests easily. This home is located just 15 minutes away from Legoland and is close to shopping, dining, and entertainment shops in the city. At this home, you get access to not just a fully stocked kitchen but a washer, dryer, and foosball table, too. There are a lot of board games and bean toss games available here as well. Plus, you can request a high chair and a baby crib if you are travelling with a baby. They also provide you with propane and charcoal grills to enjoy a barbecue night in the backyard here.

Sweet Cottage- 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven, Florida, United States
78 reviews
Entire house 5 Beds 2 Bedrooms 1 Bathrooms
Top guest reviews
Amenities & Room:
kitchen has good amenities for cooking meals
the space was comfortable and great for families traveling with children
the open living/kitchen/play area made it so easy to keep an eye on the kids while making meals
everything was clean and organized
the house is very clean and kid friendly
the home is very clean and orderly
great house - clean and has everything you could need for your visit
the home is clean and comfortable
great place to stay layal and ray were great hosts and i would recommend a stay there anytime
hosts have lots of games for children to stay entertained
great place for everything kind of person family couples and humans with humanity in them lol
nice little place close to community college
the location and value are unbeatable
very close to legoland amazing place to unwind
a perfect quiet little get away place in central florida
Read more reviews

8. Modern home with a spacious backyard (from USD 114)

This modern home is perfect for large families or groups of friends as it can accommodate nine guests in the three bedrooms. One of the best things about this property is that they have a 24/7 security monitor so you can sleep soundly without worry. More importantly, this house is just 10 minutes away from stores and restaurants and is close to Legoland and Disney World, too. The house has a spacious fenced backyard where you can enjoy outdoor games such as volleyball, football, soccer, etc. You will be provided with all the outdoor gaming equipment as well.

LEGOLAND 10 Minutes away! Disney 45 minutes away!
Winter Haven, Florida, United States
56 reviews
Entire house 5 Beds 3 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
the coffee was fantastic and the smart tv's made life easy
enjoyed most of the stay love the living room a lot of space comfortable and nice furniture
the house was nice with a huge family room and a separate living room
the house was clean well located with alarm 2 led smart tv's with roku
my boys loved the bunk beds (and i loved having a full kitchen)
clean and well furnished
very clean and stylish place
house was clean and very nice inside
the place was super clean with an ample amount of towels and wash-clothes
this home was very clean and cozy
the host was a delight
the host was more than helpful and the home is beautiful
hector was a wonderful host
hector was a fantastic host
the home is also child friendly for families with small children
in a great location
great location as well
it is close to literally everything you can think of from shops amusement parks restaurants etc
very relaxing place to stay after extremely busy days at legoland
Read more reviews

9. Lakeside abode with hot tub and dock bar

Do you love relaxing in a hot tub? Then, this lakeside home is a dream come true for you. This 4-bedroom, 3-bath vacation rental can accommodate 12 people making it perfect for big families, couples, and large friends’ groups. With luxury amenities such as a 26-foot (7.9 metres) dock, hot tub, gazebo bar, swimming pool, etc., you will have the time of your life here. That’s not all–this house is located amidst the chain of lakes, close to many good restaurants, and near Legoland, too. You can use the boats at the property to travel around and make the most of your trip here.

Winter Haven Home with Dock & Hot Tub!
Winter Haven, Florida, United States
9 reviews
Entire house 6 Beds 4 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
great master bathroom yard is beautiful and deck is amazing
Read more reviews

10. Studio with outdoor shower overlooking a lake

This compact studio in Winter Haven can accommodate three guests and is perfect for small families, couples, and friends. With an outdoor and indoor shower with hot water, you will enjoy a relaxing bath here with Lake Lulu as your view. If you are nature enthusiasts then you would love spending time here among the beautiful birds, butterflies, and different trees and plants. There is a full-sized bed and a twin-size mattress here which are quite comfortable for sleeping. You also have a peaceful backyard where you can relax and chill when you don’t feel like going out.

LEGO my bungalow
Winter Haven, Florida, United States
45 reviews
Entire guesthouse 1 Bed 0 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
great small space with a twin bed kitchenette bathroom and private patio
outdoor shower was interesting but everything else was absolutely great experience also a very friendly cat on premises
the bungalow was spotlessly clean
the bungalow is very very clean and comfortable
private quiet very clean and at a great price
clean quiet and homey i couldn’t have asked for much more
very clean just the right amount of space for 1 person
me and my girlfriend loved it the owner replied fast and helped any way she could
the hosts are wonderful and johnnie-on-the-spot with any questions
mary is a wonderful host and her bungalow is exactly as it is presented online
great little spot nice touches and very cozy mary was an excellent host to me
great hosts great place unfortunate incident
it’s in a wonderful location for legoland visitors
the bungalow is just perfect a great location in the heart of winter haven
mary’s place is super cute and comfortable
outstanding place will come back and stay more times
the location is close to everything and the space is clean and private
Read more reviews

Enjoy a lakeside vacation in Winter Haven

Since Winter Haven is home to dozens of lakes, there are a lot of recreational activities to do here and natural attractions to explore. You can choose to spend a relaxing time by the lake, hike through the nearby reserves, or enjoy a trip to Legoland theme park. A trip to Winter Haven is sure to be fun and you can make it more memorable by choosing a nice and comfortable stay. So, do check out the above Airbnb vacation rentals in Winter Haven for an awesome time.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

Get Trip101 in your inbox

Unsubscribe in one click. See our privacy policy for more information on how we use your data

 Want to contribute as a Local Expert?
Explore Lakeland - Winter Haven
Good things are meant to be shared!