20 Best Airbnb Vacation Rentals In Winter Haven, Florida

Rachita
Contributing Writer
Updated
| 9 min read

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. There are more than 50 lakes within the city, leading to its nickname the “City of the Chain of Lakes”. This city is also home to the Florida branch of Legoland theme park, and Disney World, which makes it perfect for families with kids. Other than that, you can take wakeboarding lessons, browse through antique shops, or watch a movie in a classic theatre - there’s a bunch of things to do here to keep yourself occupied. To make your trip even more comfortable, check out our list of the best Airbnb vacation rentals in Winter Haven, Florida.

Popular picks:

  • Gram Parsons Derry Down: Explore the historic Gram Parsons Derry Down and enjoy concerts, music festivals, and open mic nights. Here you may attend your favorite shows at no cost. Musicians of all levels are welcome to perform up to 3 songs here.

  • Winter Haven Food Tours: Winter Haven Food Tours offers a unique 2.5-hour food tour experience. Visitors can choose from five exciting tours, including options like the coffee, tea, and dessert tour or the Happy Hour Tour.

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 22, 2025.

Your options at a glance

Airbnb Vacation Rental
Best Feature
Price
Comfortable guesthouse with a smart TV Screened patio with comfy seating from USD 70
Spacious pet-friendly home Fenced backyard ideal for pets from USD 130
Lakefront retreat near Legoland Spectacular lake views from USD 70
The Russell Lake House Lakefront private pool from USD 59
Modern duplex best for families Three Smart TVs and a foosball table from USD 99
Historic home with a swimming pool Spacious pool patio with lake views from USD 534
Tastefully appointed abode with a backyard Screened patio with dining area from USD 81
Family-friendly cottage near Legoland Indoor games and piano from USD 90
Cosy lakehouse near Lake Otis Screened back porch with lake views from USD 1435
Well-located studio best for couples and solo travellers Picnic table and charcoal grill from USD 85
Charming pool house by the lake Shared saltwater pool from USD 63
Lakeside abode with hot tub and dock bar Private dock with bar from USD 307
Chic apartment in an antique building Located in a serene neighborhood from USD 91
Bungalow with contemporary commodities Located close to natural beauty from USD 95
Well-furnished condo with a shared hot tub One-minute away from Legoland from USD 108
Magical villa with swimming pool close to Legoland Fenced backyard with pool and outdoor dining from USD 125
Space for seven guests with a lake view Private dock access from USD 255

1. Comfortable guesthouse with a smart TV (from USD 355)

Highlights Couple Travel Budget Friendly Work Travel Good Location

This private guesthouse is the perfect romantic getaway for couples visiting Winter Haven, Florida. The home features cute and well-thought-out interiors which add to its charm. There is a sunroom where guests can enjoy their morning coffee or a drink at the end of the day. The kitchen is fully equipped and the rental has a grill if guests wish to have a barbecue.

The living room has a plush sofa and a smart TV with Hulu, Netflix, and Roku for entertainment. The air conditioning unit ensures maximum comfort.

Winter Haven, Florida, United States

3.37 km (2.1 mi) from LEGOLAND Florida Water Park
103 reviews   Airbnb superhost icon Superhost Wifi Available
Entire guest suite 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Host:
the host is very friendly
the host went above and beyond to make sure that my stay was comfortable
they are very friendly and accommodating and give you your privacy
very nice place to stay with great hosts
hosts were very responsive and helpful without any intrusion
Location:
good location close to everything needed
excellent and convenient location
nice location accurate descriptions good value
it was however in a great location for my needs i was here for work
the location was perfect since we were less than 1 mile from the chain of lakes park
Cleanliness:
and very clean love it
apartment was clean and comfortable
the place was clean and great
place was clean
the place was clean and comfortable
Amenities & Room:
nice tv and wifi
we didn’t use the pool or hot tub but the outdoor grill was very nice
all of the kitchen / bathroom essentials were there which was nice as well
bathroom is spacious and so elegant (lovely tilework & hooks/hangers are ample)
didn't want to leave it was that comfortable
Read more reviews

2. Spacious pet-friendly home (from USD 230)

Highlights Family Friendly Pet Friendly Work Travel Good Location

This spacious three-bedroom home is conveniently located near LEGOLAND® Florida making it the perfect vacation rental for families visiting Winter Haven. The heating and air conditioning ensure year-round comfort for guests.

The kitchen is well equipped, perfect for some culinary adventures on vacation. There is a television for entertainment and a dedicated workspace if guests need to get work done while on vacation. This is a pet-friendly rental, so guests can bring along their fur babies on vacation. Free parking spots are available on the property.

Winter Haven, Florida, United States

3.87 km (2.5 mi) from LEGOLAND Florida Water Park
184 reviews   Airbnb superhost icon Superhost Wifi Available
ENTIRE HOME 3 Beds 5 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 5

Top guest reviews
Host:
host was friendly and proactive
laura was a great host who responded almost immediately throughout any contact
what a lovely home and property and laura is a perfect host i loved the home's layout
the host was very easy to get in touch with
great stay they were very accommodating
Location:
the location of this property suited our needs perfectly
i would recommend this location whole heartedly
great place close to legoland and restaurants
we loved how close it was to legoland
definitely worth it it's a quiet neighborhood but still close to everything
Cleanliness:
very clean house and comfortable space
it was very clean and just as described
very clean and the beds were very comfortable
everything was clean and our family was very comfortable
laura’s house was clean and comfortable for our stay
Amenities & Room:
nice size closets hall & kitchen storage
it is decorated tastefully the washer and dryer kitchen and bath amenities were great
the main bedroom/second bedroom beds were very comfortable the twin for an adult was not
the spacious great room with open connection to a spacious kitchen) enables families to gather with no crowding
we could shower with ease and get the rest we needed
Read more reviews

3. Lakefront retreat near Legoland (from USD 154)

Highlights Waterfront Couple Travel Good Location Pet Friendly

Nestled along the tranquil waters of Lake Mariam, this three-bedroom house for rent in Winter Haven 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 up to spectacular views of the lake!

Winter Haven, Florida, United States

3.24 km (2.1 mi) from LEGOLAND Florida Water Park
220 reviews   Wifi Available
ENTIRE HOME 2 Beds 3 Guests 1 Bathroom

Accommodates: 3

Top guest reviews
Host:
jin & pedro were great hosts they were super responsive if we had any questions or concerns
very clean great response time from hosts
Location:
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
Cleanliness:
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
Amenities & Room:
super cute tiny home beautiful view of the lake everything we needed huge tv and super comfortable mattress
Read more reviews

4. The Russell Lake House (from USD 237)

Highlights Couple Travel Family Friendly Waterfront Private Pool Budget Friendly

This cheap Airbnb in Winter Haven 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, Wi-Fi, 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 which includes a dock so you can enjoy fishing here, too.

Winter Haven, Florida, United States

7.3 km (4.6 mi) from LEGOLAND Florida Water Park
278 reviews   Airbnb superhost icon Superhost Wifi Available
Entire guesthouse 4 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Host:
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
Location:
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
Cleanliness:
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
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
Read more reviews

5. Modern duplex best for families (from USD 251)

Highlights Waterfront Good Location Family Friendly Work Travel Pet Friendly

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 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

3.2 km (2.0 mi) from LEGOLAND Florida Water Park
326 reviews   Wifi Available
ENTIRE HOME 3 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Host:
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
Location:
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
Cleanliness:
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
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
Read more reviews

6. Historic home with a swimming pool (from USD 550)

Highlights Pet Friendly Work Travel Private Pool Family Friendly Waterfront Good Location

If you like old, historic homes then you should check out this 96-year-old custom home with a spacious swimming pool. This Airbnb near Legoland, Florida 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 during your stay here. Plus, this property is close to Downtown Winter Haven and Legoland so you can drive there anytime you want.

Winter Haven, Florida, United States

2.62 km (1.7 mi) from LEGOLAND Florida Water Park
188 reviews   Airbnb superhost icon Superhost Wifi Available
ENTIRE HOME 3 Beds 6 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 6

Top guest reviews
Host:
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
Location:
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
Cleanliness:
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
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
Read more reviews

7. Tastefully appointed abode with a backyard (from USD 783)

Highlights Family Friendly Work Travel Good Location

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 Wi-Fi, 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.

Winter Haven, Florida, United States

7.77 km (4.9 mi) from LEGOLAND Florida Water Park
127 reviews   Airbnb superhost icon Superhost Wifi Available
ENTIRE HOME 3 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Host:
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
Location:
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
Cleanliness:
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
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
Read more reviews

8. Family-friendly cottage near Legoland (from USD 292)

Highlights Good Location Family Friendly Work Travel Budget Friendly

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.

Winter Haven, Florida, United States

4.13 km (2.6 mi) from LEGOLAND Florida Water Park
211 reviews   Airbnb superhost icon Superhost Wifi Available
Entire cottage 5 Beds 8 Guests 2 Bedrooms 1 Bathrooms

Accommodates: 8

Top guest reviews
Host:
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
Location:
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
Cleanliness:
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
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
Read more reviews

9. Cosy lakehouse near Lake Otis (from USD 1541)

Highlights Pet Friendly Family Friendly Waterfront Work Travel View

This gorgeous 1937 lakehouse boasts a cosy, bright interior for large groups, with 3 spacious bedrooms and 8 beds. The newly renovated pet-friendly Airbnb in Winter Haven, FL features modern furnishings such as free Wi-Fi, 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.

Winter Haven, Florida, United States

3.39 km (2.2 mi) from LEGOLAND Florida Water Park
24 reviews   Airbnb superhost icon Superhost Wifi Available
ENTIRE HOME 8 Beds 12 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 12

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

10. Well-located studio best for couples and solo travellers (from USD 98)

Highlights Couple Travel Budget Friendly Work Travel Good Location

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.

Winter Haven, Florida, United States

7.37 km (4.6 mi) from LEGOLAND Florida Water Park
165 reviews   Airbnb superhost icon Superhost Wifi Available
ENTIRE RENTAL UNIT 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Host:
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
Location:
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
Cleanliness:
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
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
Read more reviews

11. Charming pool house by the lake (from USD 66)

Highlights Budget Friendly Family Friendly Couple Travel Work Travel Waterfront

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!

Winter Haven, Florida, United States

3.88 km (2.5 mi) from LEGOLAND Florida Water Park
145 reviews   Wifi Available
PRIVATE ROOM IN HOME 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Host:
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
Location:
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
Cleanliness:
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
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
Read more reviews

12. Lakeside abode with hot tub and dock bar (from USD 1564)

Highlights Waterfront Family Friendly Work Travel Good Location Luxury

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, Florida, United States

2.82 km (1.8 mi) from LEGOLAND Florida Water Park
65 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 94)

Highlights Couple Travel Budget Friendly Good Location Work Travel Good Neighborhood

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.

Winter Haven, Florida, United States

7.51 km (4.7 mi) from LEGOLAND Florida Water Park
156 reviews   Airbnb superhost icon Superhost Wifi Available
ENTIRE RENTAL UNIT 2 Beds 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Host:
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
Location:
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
Cleanliness:
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
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
Read more reviews

14. Bungalow with contemporary commodities (from USD 465)

Highlights Budget Friendly Family Friendly Good Location Work Travel

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.

Winter Haven, Florida, United States

4.44 km (2.8 mi) from LEGOLAND Florida Water Park
53 reviews   Airbnb superhost icon Superhost Wifi Available
Entire bungalow 2 Beds 4 Guests 3 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Host:
walter was an excellent host and we really enjoyed our stay
Location:
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
Cleanliness:
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
Read more reviews

15. Well-furnished condo with a shared hot tub (from USD 1228)

Highlights Family Friendly Budget Friendly Long Term Stay Waterfront Work Travel Good Location

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!

Winter Haven, Florida, United States

2.92 km (1.9 mi) from LEGOLAND Florida Water Park
16 reviews   Wifi Available
ENTIRE CONDO 3 Beds 5 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 5

Top guest reviews
Host:
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
Location:
the condo is in a great location and very secure
Cleanliness:
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
Amenities & Room:
the condo has a great ac hot water and fast speed wifi
Read more reviews

16. Magical villa with swimming pool close to Legoland (from USD 428)

Highlights Private Pool Work Travel Pet Friendly Family Friendly Good Location

A Floridian adventure awaits those who choose this stunning 1950s home in Winter Haven. The property offers accommodation for up to six guests across three bedrooms, a kitchen, living room, and all essential modern conveniences. However, it is the outside of the property that really shines: you’ll be able to enjoy a stunning pool and pool deck, which should provide plenty of opportunity to lounge and enjoy the sunshine. If you wish to explore the surrounding area, then you’re in luck: Legoland is just 2.5 miles (4 km) away by car and downtown Winter Haven - and its restaurants and shopping opportunities - are just a 3.5 mile (5.6 km) drive away.

Winter Haven, Florida, United States

1.61 km (1.0 mi) from LEGOLAND Florida Water Park
324 reviews   Airbnb superhost icon Superhost Wifi Available
ENTIRE HOME 4 Beds 6 Guests 3 Bedrooms 1 Bathrooms

Accommodates: 6

Top guest reviews
Host:
owners are very responsive
our hosts were wonderful to work with
chad and catherine’s have a such a beautiful home and were very helpful throughout our trip
fabulous hosts couldn’t ask for better
responsive accessible even swing by half way through our stay make sure the pool was clean
Location:
great location as well
the location is very close to everything you need and the neighborhood is very safe and quiet
the location is perfect for a visit to legoland
location is close to everything would definitely stay again thanks so much
it was a great value and super close to legoland
Cleanliness:
very clean and comfy beds
sparkling clean warm & inviting
the house was very clean and inviting
we enjoyed the pool everyday and was also very clean
it was sparkling clean and insanely accommodating
Amenities & Room:
the pool was well kept and the amenities were even better than expected
the pool and the grill were great to have
awesome they had a high-chair and bunk beds for kids
my family loved the back patio and pool area
pool and patio relaxing
Read more reviews

17. Space for seven guests with a lake view (from USD 238)

Highlights View Waterfront Good Location Family Friendly

Located just four miles (6.4 km) from Legoland and within an hour’s drive of SeaWorld, Disney/Universal, the airport, and downtown Orlando, this beautiful unit in a duplex in Winter Haven is the ideal choice for those looking to explore central Florida in detail. The property itself is suitable for up to seven guests who can share the three bedrooms, two bathrooms, a kitchen, living room, dining room, and a private side porch. Furthermore, when you’re not exploring the wonderful tourist attractions nearby, you can relax and enjoy the stunning views of Lake Mariam.

Winter Haven, Florida, United States

3.2 km (2.0 mi) from LEGOLAND Florida Water Park
403 reviews   Wifi Available
ENTIRE HOME 3 Beds 7 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 7

Top guest reviews
Host:
the hosts were very kind
jin and pedro were great hosts
jin and pedro were wonderful hosts
the kind of place you feel like home away from home
the host was able to respond quickly to make sure everything was fine
Location:
great location close to legoland
perfect location for visiting legoland
family friendly so close to legoland
very nice house close to legoland
such a wonderful house and very close to legoland
Cleanliness:
house was clean and the beds were comfortable
very quiet and very clean place to stay
beautiful home everything was clean and tidy great accommodations
the place was clean and had adequate towels and anything else that you may need
the place was immaculate clean and beautiful
Amenities & Room:
plenty of sleeping options lots of kitchen amenities nice touches throughout
it’s very nicely designed full of comfortable furniture and has a lot of nice amenities from the hosts
it’s a place with lots of space very comfortable with a full kitchen washer and dryer dishwasher etc
the house includes additional amenities and extra touches that made our stay more comfortable
the beds are really comfortable there were great extra touches like coffee bottled water and snacks
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18. Dual loft on Lake Mariana near Disney World (from USD 50)

Highlights Budget Friendly Couple Travel Waterfront Good Location

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.

Winter Haven, Florida, United States

10.42 km (6.5 mi) from LEGOLAND Florida Water Park
280 reviews  
Entire place 3 Beds 1 Bedroom 1 Bathroom
Top guest reviews
Host:
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
Location:
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
Cleanliness:
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
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
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19. Studio with outdoor shower overlooking a lake (from USD 38)

Highlights View Waterfront Couple Travel Budget Friendly

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.

Winter Haven, Florida, United States

3.3 km (2.1 mi) from LEGOLAND Florida Water Park
45 reviews  
Entire guesthouse 1 Bed 0 Bedrooms 1 Bathroom
Top guest reviews
Host:
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
Location:
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
Cleanliness:
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
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
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20. Modern home with a spacious backyard (from USD 119)

Highlights Family Friendly Good Location

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.

Winter Haven, Florida, United States

3.19 km (2.0 mi) from LEGOLAND Florida Water Park
136 reviews   Wifi Available
ENTIRE HOME 5 Beds 9 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 9

Top guest reviews
Host:
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
Location:
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
Cleanliness:
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
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)
Read more reviews

Enjoy a lakeside vacation in Winter Haven

Since Winter Haven is home to lots of lakes, there are a lot of recreational activities to do here and natural attractions to explore. 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 book from the above list of Airbnb vacation rentals for an awesome time. For those seeking alternatives, explore the inviting hotels in Winter Haven to enhance your stay.

Frequently asked questions about Airbnb vacation rentals in Winter Haven, Florida

Which Airbnb vacation rentals in Winter Haven are ideal for long-term stays?

Which Airbnb vacation rentals in Winter Haven have parking?

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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1 Comments
Ben .about 4 years ago

We would love out Farm House to be featured here! airbnb.com/h/dehaven-family-farm

0 . Reply
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