15 Best Airbnb Vacation Rentals In Winter Haven, Florida - Updated 2023


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 Airbnbs in Winter Haven, FL.

1. Cozy 1937 lakehouse near Lake Otis (from USD 684)

This gorgeous 1937 lakehouse boasts a cozy, bright interior for large groups, with 3 spacious bedrooms and 8 beds. The newly-renovated home features modern furnishings such as free wifi, a tv, and a fully equipped kitchen. Those here on business will love the dedicated office room that comes complete with a private bathroom.

This pet-friendly home also boasts a strategic location, just a 15-minute walk to downtown. It is just a few steps from Lake Otis, where guests can spend their afternoons enjoying watersports. Guests can also rent a jet-ski from the hosts, simply inform them beforehand, and it’ll be ready during your stay.

Free parking is also available on the premises for added convenience.

Get a $100 discount when you mention "Trip101" in a message to the host after booking! Click the link below to book now. Terms and conditions apply.

Home in Winter Haven · ★5.0 · 4 bedrooms · 8 beds · 3.5 baths
Winter Haven, Florida, United States
5 reviews  Wifi Available
ENTIRE HOME 8 Beds 12 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 12

Top guest reviews
patrick was extremely responsive and helpful in his conversations about the place
Read more reviews

2. Lakefront retreat near Legoland (from USD 100)

Nestled along the tranquil waters of Lake Mariam, this tiny home hosted by Jin is an ideal retreat if you fancy staying at a secluded place without being far from popular attractions in and around Winter Haven. The house boasts two lofted beds, a king and a twin, which can accommodate up to three people.

This space may be compact but it’s got all you’ll ever need to have a comfortable stay, from a full bathroom to a kitchenette. Free parking and Wi-Fi are also included. Not to mention, you’ll be waking to spectacular views of the lake!

Winter Haven, Florida, United States
157 reviews Superhost  Wifi Available
ENTIRE HOME 2 Beds 3 Guests 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
super cute tiny home beautiful view of the lake everything we needed huge tv and super comfortable mattress
a great clean and surprisingly spacious tiny house
nice clean would stay there again
everything is clean and doesn’t feel crowded
the loft bed is comfortable everything was *clean* (i have extremely high standards)
the tiny house was perfect it was super clean
jin & pedro were great hosts they were super responsive if we had any questions or concerns
very clean great response time from hosts
great place right on the lake and close to everything
cute little place to stay
i enjoyed my stay and the peaceful quiet of the location
self check-in is very easy great location close to legoland many restaurants and grocery stores
this was a nice place to get away for a little while
Read more reviews

3. The Russell Lake House (from USD 81)

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
187 reviews  Wifi Available
Entire guesthouse 4 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

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

4. Modern duplex best for families (from USD 257)

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 for rent in Winter Haven, FL, 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.

Home in Winter Haven · ★4.94 · 3 bedrooms · 3 beds · 2 baths
Winter Haven, Florida, United States
237 reviews Superhost  Wifi Available
ENTIRE HOME 3 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

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

5. Historic home with a swimming pool (from USD 220)

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.

Legoland Roaring 20s Lakehouse Pool NoCleaningFees
Winter Haven, Florida, United States
129 reviews Superhost  Wifi Available
ENTIRE HOME 3 Beds 6 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 6

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

6. Tastefully appointed abode with a backyard

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
98 reviews Superhost  Wifi Available
ENTIRE HOME 3 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

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

7. Family-friendly cottage near Legoland (from USD 147)

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 Winter Haven vacation rental, 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
176 reviews Superhost  Wifi Available
ENTIRE HOME 5 Beds 7 Guests 2 Bedrooms 1 Bathrooms

Accommodates: 7

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

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
130 reviews  Wifi Available
ENTIRE HOME 5 Beds 9 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 9

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. Well-located studio best for couples and solo travellers

Gladys’ studio apartment is a fine choice for solo travelers or couples wishing to stay near downtown Winter Haven and still have a homey getaway. This fully furnished and vintage-inspired studio is packed with all the luxurious essentials: a plush queen bed, a well-equipped kitchen with a Keurig and free coffee pods, a stylish bathroom with a full-sized shower, and free Wi-Fi and TV for entertainment.

This comfortable rental also offers guests access to a picnic table and grill in the yard which is shared with other guests on the property.

Soul Mate Vintage Studio
Winter Haven, Florida, United States
109 reviews  Wifi Available
ENTIRE RENTAL UNIT 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
and very responsive made the stay so honey and comfortable and easy to figure out
we had a fantastic time staying at this apartment as it exceeded our expectations
very amazing place and so clean and modern
great place to stay clean and comfortable
clean stylish cozy and was great for my husband and i
such a nice stay everything shown in the picture was there very clean
very clean and modern space i was very pleased 10/10 recommend
great host and space
beautiful stay host was responsive & answered any questions i had
gladys was a great host and her place was very welcoming
great host place was very nice and had beautiful touches
the host was always quick to respond to any request plus friendly and cozy environment
convenient location for traveling to the area's theme parks and attractions
perfect little hideaway on a quiet street yet close enough to shopping
it is an ideal place for a couple who want to have time to themselves
Read more reviews

10. Charming pool house by the lake (from USD 65)

The Pink Room is a private suite in a two-story Craftsman lakeside home. The room itself is equipped with two country-style double beds, a full bathroom, a TV, and a vanity. Free high-speed internet and parking are included throughout the stay. Guests will also have access to shared living spaces like the living and dining rooms, along with the spacious porch that boasts wonderful lake views. Of course, you can enjoy the outdoor saltwater pool to your heart’s content too.

To make your stay extra special, continental breakfast and light snacks are served in the guest area!

The Pink Room * Pool * WiFi * Romantic Lakeside
Winter Haven, Florida, United States
123 reviews Superhost  Wifi Available
Private room in home 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
beautiful view of the lake room b comfortable surroundings
beautiful view by the lake breakfast amenities within minutes of everything you can think of and amazing hospitality
the breakfast nook is outstanding
the front patio and the breakfast were a highlight
stanton decorates the breakfast table so nice and provides everything you need to enjoy your meal
the house is huge sparkling clean and beautifully decorated
the rooms are big clean and well organized as well as the bathroom
the place is as advertised room was clean and the pool is perfect for adults and kids
the pink room was amazing - decorated with vintage items and everything was sparkling clean
it was quiet private clean and the best part was the continental breakfast
stan and barbara are very gracious hosts
our hosts were lovely their home is absolutely beautiful and comfortable
hosts are very warm and welcoming
a great house with wonderful hosts
nice place to stay at host were very accompanying and made us feel welcome
the location is great
great location close to cute downtown
highly recommend close to area attractions especially legoland
good location old house with antique decor very clean
we needed a place to shower and rest this was perfect
Read more reviews

11. Well-furnished condo with a shared hot tub

This modestly furnished condo in Winter Haven is fairly affordable for a group of five guests. Sam’s rental features two bedrooms, one with a queen bed and the other with a double and a bunk bed. The home boasts a fully equipped kitchen, a dining area with a view, and a simple living area with a comfy couch.

Guests of this condo are more than welcome to enjoy the community pool and hot tub. The lake and the community dock can be easily explored from the gated complex too!

Condo with Character (1 month minimum stay)
Winter Haven, Florida, United States
16 reviews  Wifi Available
Entire condo 3 Beds 5 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 5

Top guest reviews
Amenities & Room:
the condo has a great ac hot water and fast speed wifi
it was clean upon arrival and the flooring  was recently replaced
once we had cleaned up a bit we had a very enjoyable time during our stay
sam as a host was great at responding to questions or concerns
this was my first time staying in an airbnb property and i loved it the host sam was awesome
very responsive and helpful
i messaged a lot of hosts however sam was the most understanding and very kind
the condo is in a great location and very secure
Read more reviews

12. 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.

Waterfront Winter Haven Home with Dock & Hot Tub!
Winter Haven, Florida, United States
30 reviews  Wifi Available
ENTIRE HOME 6 Beds 12 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 12

Top guest reviews
Amenities & Room:
great master bathroom yard is beautiful and deck is amazing
Read more reviews

13. Chic apartment in an antique building (from USD 92)

This one-bedroom apartment welcomes four guests comfortably and offers a queen bed and a sofa bed for restful evenings. It is located on the second floor of an antique building that’s been carefully restored so it maintains that old aesthetic. The property is surrounded by lush greens and is a great place to spend some quiet time with the family.

Guests will find their stay here convenient as the rental is fitted with amenities like the full kitchen. Both air conditioning and heating are provided so you can stay cozy no matter the weather. If you’re a family with children, this apartment is highly recommended since it offers baby-friendly items like a travel crib, toys, a high-chair, and some children’s books.

Serenity Retreat, Confidently Clean!
Winter Haven, Florida, United States
115 reviews  Wifi Available
ENTIRE RENTAL UNIT 2 Beds 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
the pull out couch is comfortable and my 6'3 son fit with no issues
the description was accurate with several amenities and extras to make or stay extra comfortable
bathroom with claw foot tub was awesome bed was incredibly comfy
super clean and comfortable 10/10 would recommend
very clean and host responds quickly
loved our visit so clean and comfortable
this place was awesome everything was clean and beautiful
place is super clean
this host is amazing
glady was a great host
gladys is a great host
gladys was an amazing host response back very fast with any questions or issues
gladys was a perfect host and the apartment was immaculate and felt like home
the place is cute and cozy
apartment was immaculate bed is very comfortable great location
great place to stay at
a great place to stay
amazing place to stay definitely staying here again
Read more reviews

14. Bungalow with contemporary commodities

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
32 reviews Superhost  Wifi Available
Entire bungalow 2 Beds 4 Guests 3 Bedrooms 1 Bathroom

Accommodates: 4

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

15. Dual loft on Lake Mariana near Disney World

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

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.

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