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 bathsWinter Haven, Florida, United StatesAccommodates: 12
Top guest reviews
Read more reviewsHost:
patrick was extremely responsive and helpful in his conversations about the place
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!
💎LakeFront💎ModernCottageTiny-Home☀🎢4milesLEGOLAND🎢Winter Haven, Florida, United StatesSuperhost
Accommodates: 3
Top guest reviews
Amenities & Room:
super cute tiny home beautiful view of the lake everything we needed huge tv and super comfortable mattressCleanliness:
a great clean and surprisingly spacious tiny housenice clean would stay there againeverything is clean and doesn’t feel crowdedthe loft bed is comfortable everything was *clean* (i have extremely high standards)the tiny house was perfect it was super cleanHost:
jin & pedro were great hosts they were super responsive if we had any questions or concernsvery clean great response time from hostsRead more reviewsLocation:
great place right on the lake and close to everythingcute little place to stayi enjoyed my stay and the peaceful quiet of the locationself check-in is very easy great location close to legoland many restaurants and grocery storesthis was a nice place to get away for a little while
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 HouseWinter Haven, Florida, United StatesAccommodates: 4
Top guest reviews
Amenities & Room:
the view from the pool was amazingthe furnishings finishes and beds are all designer and beautifully builtbeds are super comfythe beds and the bed sheets were amazingpool was great for the warm days we hadCleanliness:
the cabana was very clean and had everything you would needsuch a beautiful place nice and cleanvery clean space in a quiet neighborhood would definitely stay here againno hassle sparkling clean cozy and comfortable thank you bobbiethe cabana was very cute and cleanHost:
everything was great our host was friendly helpful and privatebobbie is a great hostand the host is amazing so accommodatingbobbie was a perfect host and was very responsivethank you so much for hosting us bobbieRead more reviewsLocation:
cute place in a fun neighborhoodthe location was perfect and beautiful and close to what we neededbeautiful location that is easy to get tothe location is great and very peacefulperfect little bungalow in a perfect location
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 bathsWinter Haven, Florida, United StatesAccommodates: 6
Top guest reviews
Amenities & Room:
incredible amenities cozy and comfortablethe tv sets were greatthe king bed was amazingly comfortableso comfortable my sister is buying the same mattress for her roomthe beds were super comfortable and my daughter loved her room with games and toysCleanliness:
everything was clean and spaciousgreat clean place to staythe place is very clean and niceeverything was amazing clean and quick respondan amazingly beautiful clean and great local place to stayHost:
jin and pedro very nice hostsjin as the host is very responsivevery responsive hostsgreat and quick communications with ownerjin and pedro are awesome hostsRead more reviewsLocation:
super close to legolandgreat location for legolandgreat location for anyone visiting legolandnice place that is close to legolandgreat place and close to all winter haven activities
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 NoCleaningFeesWinter Haven, Florida, United StatesAccommodates: 6
Top guest reviews
Amenities & Room:
pool area and view were beautifulthe pool was amazing and the view was breath takingquite spacious quiet with a lovely pool and beautiful view of the lakeplenty of space with a king size pool and beautiful lakefront viewthe three rooms with their own restrooms was a really nice featureCleanliness:
it is clean spacious and perfect for a family retreatexceptionally clean and well stocked with little things you may have forgottenrandy's home is clean and well describedthe house was extremely clean and stocked up with everything you could possibly need and moreHost:
randy was a great hostrandy is a great host who responds very quicklyexcellent host to deal with - very helpful and responsivehe replied very quickly with any questions and was very helpful with extending our staythe most down to earth easy going host we’ve ever had for airbnbRead more reviewsLocation:
the location is perfect very close to shops and restaurants while tucked away in a cozy neighborhoodit was a fun family place close to legolandit was an easy short trip to legoland and and the neighborhood is quiet and relaxingit was the perfect place to come back and relax after a day at legolandthe house is great close to legoland publix walmart and many restaurants
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 FlamingoWinter Haven, Florida, United StatesAccommodates: 6
Top guest reviews
Amenities & Room:
there is a real dining room table a nice roll-top desk and good wifiincredibly spacious clean and the kitchen had a lot of appliances and all of the necessary dishwarebeds are very good and there is seating for at least five in the living roomthree good sized bedrooms and two full bathrooms worked wonderfully for my group of travelerswished there was a tv remote for the tv but other than that pleasant placeCleanliness:
clean cozy quiet placesuper clean place in quiet neighborhoodthe house was very clean and nicely decoratedthe house had everything very clean organized and comfortablebeautiful stay clean and spacious for a wonderful price in a quiet and serene neighborhoodHost:
carol is a wonderful host and her home is quite cozya truly excellent hostcarol is very responsive to questionsexactly like the pictures and carol was a great hostfantastic place spacious house and very responsive hosts a must stayRead more reviewsLocation:
great location for legolandgreat place and close to many places in walking distancegreat place in terrific locationallowing for a enjoyable stay and conveniently close to legolandloved the walk-in shower
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 dwntwnWinter Haven, Florida, United StatesAccommodates: 7
Top guest reviews
Amenities & Room:
kitchen has good amenities for cooking mealsthe space was comfortable and great for families traveling with childrenthe open living/kitchen/play area made it so easy to keep an eye on the kids while making mealsCleanliness:
everything was clean and organizedthe house is very clean and kid friendlythe home is very clean and orderlygreat house - clean and has everything you could need for your visitthe home is clean and comfortableHost:
great place to stay layal and ray were great hosts and i would recommend a stay there anytimehosts have lots of games for children to stay entertainedgreat place for everything kind of person family couples and humans with humanity in them lolRead more reviewsLocation:
nice little place close to community collegethe location and value are unbeatablevery close to legoland amazing place to unwinda perfect quiet little get away place in central florida
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 StatesAccommodates: 9
Top guest reviews
Amenities & Room:
the coffee was fantastic and the smart tv's made life easyenjoyed most of the stay love the living room a lot of space comfortable and nice furniturethe house was nice with a huge family room and a separate living roomthe house was clean well located with alarm 2 led smart tv's with rokumy boys loved the bunk beds (and i loved having a full kitchen)Cleanliness:
clean and well furnishedvery clean and stylish placehouse was clean and very nice insidethe place was super clean with an ample amount of towels and wash-clothesthis home was very clean and cozyHost:
the host was a delightthe host was more than helpful and the home is beautifulhector was a wonderful hosthector was a fantastic hostthe home is also child friendly for families with small childrenRead more reviewsLocation:
in a great locationgreat location as wellit is close to literally everything you can think of from shops amusement parks restaurants etcvery relaxing place to stay after extremely busy days at legoland
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 StudioWinter Haven, Florida, United StatesAccommodates: 2
Top guest reviews
Amenities & Room:
and very responsive made the stay so honey and comfortable and easy to figure outwe had a fantastic time staying at this apartment as it exceeded our expectationsCleanliness:
very amazing place and so clean and moderngreat place to stay clean and comfortableclean stylish cozy and was great for my husband and isuch a nice stay everything shown in the picture was there very cleanvery clean and modern space i was very pleased 10/10 recommendHost:
great host and spacebeautiful stay host was responsive & answered any questions i hadgladys was a great host and her place was very welcominggreat host place was very nice and had beautiful touchesthe host was always quick to respond to any request plus friendly and cozy environmentRead more reviewsLocation:
convenient location for traveling to the area's theme parks and attractionsperfect little hideaway on a quiet street yet close enough to shoppingit is an ideal place for a couple who want to have time to themselves
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 LakesideWinter Haven, Florida, United StatesAccommodates: 4
Top guest reviews
Amenities & Room:
beautiful view of the lake room b comfortable surroundingsbeautiful view by the lake breakfast amenities within minutes of everything you can think of and amazing hospitalitythe breakfast nook is outstandingthe front patio and the breakfast were a highlightstanton decorates the breakfast table so nice and provides everything you need to enjoy your mealCleanliness:
the house is huge sparkling clean and beautifully decoratedthe rooms are big clean and well organized as well as the bathroomthe place is as advertised room was clean and the pool is perfect for adults and kidsthe pink room was amazing - decorated with vintage items and everything was sparkling cleanit was quiet private clean and the best part was the continental breakfastHost:
stan and barbara are very gracious hostsour hosts were lovely their home is absolutely beautiful and comfortablehosts are very warm and welcominga great house with wonderful hostsnice place to stay at host were very accompanying and made us feel welcomeRead more reviewsLocation:
the location is greatgreat location close to cute downtownhighly recommend close to area attractions especially legolandgood location old house with antique decor very cleanwe needed a place to shower and rest this was perfect
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 StatesAccommodates: 5
Top guest reviews
Amenities & Room:
the condo has a great ac hot water and fast speed wifiCleanliness:
it was clean upon arrival and the flooring was recently replacedonce we had cleaned up a bit we had a very enjoyable time during our stayHost:
sam as a host was great at responding to questions or concernsthis was my first time staying in an airbnb property and i loved it the host sam was awesomevery responsive and helpfuli messaged a lot of hosts however sam was the most understanding and very kindRead more reviewsLocation:
the condo is in a great location and very secure
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 StatesAccommodates: 12
Top guest reviews
Read more reviewsAmenities & Room:
great master bathroom yard is beautiful and deck is amazing
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 StatesAccommodates: 3
Top guest reviews
Amenities & Room:
the pull out couch is comfortable and my 6'3 son fit with no issuesthe description was accurate with several amenities and extras to make or stay extra comfortablebathroom with claw foot tub was awesome bed was incredibly comfyCleanliness:
super clean and comfortable 10/10 would recommendvery clean and host responds quicklyloved our visit so clean and comfortablethis place was awesome everything was clean and beautifulplace is super cleanHost:
this host is amazingglady was a great hostgladys is a great hostgladys was an amazing host response back very fast with any questions or issuesgladys was a perfect host and the apartment was immaculate and felt like homeRead more reviewsLocation:
the place is cute and cozyapartment was immaculate bed is very comfortable great locationgreat place to stay ata great place to stayamazing place to stay definitely staying here again
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 HavenWinter Haven, Florida, United StatesAccommodates: 4
Top guest reviews
Cleanliness:
very clean quiet and comfortablevery clean house and nice place to staysmall home but very clean and perfect fit for what we neededthe house was very clean and owners were very kindHost:
walter was an excellent host and we really enjoyed our stayRead more reviewsLocation:
cute house in a very quiet neighborhoodpark nearby too which was greatnice place for the pricethis place was wonderful to stay at
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 StatesTop guest reviews
Amenities & Room:
we loved the amenities: the lake wifi netflixthank goodness the small space heater workedthe beds are on the floor in the loft & of average comfortthe bathroom was a good size and the water pressure and temperature proved to stay consistently comfortableCleanliness:
very clean and accommodatingvery clean very nicely decoratedclean quiet and scenic areathe space was clean and comfortableeverything was clean and well suppliedHost:
she is very attentive and helpfulkeypad access was convenient and the host was very helpful and quick to answer questions through textsuch a fun place to stay anna is a great host and replied to every message really quickthe tiny home was great anna was easy to get in touch with and very responsiveshe was very responsive and offered excellent suggestions for things to do and see while in the areaRead more reviewsLocation:
perfect distance to legoland and close attractionsi loved the locationthis place is super cutethe location was perfect for my flight training at the airport across the streetwe enjoyed the experience and greatly appreciated how close the tiny house was in location to legoland
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.
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