Winter Haven, Florida, is a blissful getaway for holidaymakers keen to enjoy a bit of sunshine at any time of the year. As the name suggests, even in the coldest months of the year it’s worth visiting, and in the summer it’s a positively tropical location with the mercury shooting into the high 30s (around 100 degrees). Visitors to this charming, quiet city enjoy fun things to do by its lakes. There are more than 50 within the city, leading to its nickname the “City of the Chain of Lakes”. Shoppers will enjoy a chance to visit the many stores and restaurants and you’ll love the fact that Winter Haven is home to the Florida branch of Legoland. If you’re planning a visit to the city, you should look for the best Airbnb vacation rentals in the area. Read on our list of the best vacation rentals in Winter Haven, Florida, USA.
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.
1. Well-furnished lakehouse with scenic views (from USD 1541)
Large families or groups of friends will enjoy staying at this spacious and newly-restored 1937 lakehouse. With 3 spacious bedrooms and 8 beds, this home can comfortably sleep 12 guests. It also boasts a strategic location, just a 15-minute walk to downtown.
Inside, the house exudes a cozy and bright interior that offers beach views. For entertainment, guests can avail of free wifi and TV to catch up on their favorite shows. There is a fully equipped kitchen to prepare your meals, and also an office room with its own bathroom so you can get needed work done while on vacation. Music lovers will enjoy the grand piano in the Sitting Room. Guests with cars can park for free on the premises.
Located just a few steps from Lake Otis, guests can spend their afternoons enjoying various watersports with their pets and loved ones. Adventure lovers can also rent a jet-ski from the hosts. Simply inform them in advance, and they’ll kindly prepare them for you.
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Winter Haven, Florida, United StatesSuperhost
Accommodates: 12
Top guest reviews
Read more reviewsHost:
patrick was extremely responsive and helpful in his conversations about the place
2. Space for seven guests with a lake view (from USD 238)
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 StatesAccommodates: 7
Top guest reviews
Host:
the hosts were very kindjin and pedro were great hostsjin and pedro were wonderful hoststhe kind of place you feel like home away from homethe host was able to respond quickly to make sure everything was fineLocation:
great location close to legolandperfect location for visiting legolandfamily friendly so close to legolandvery nice house close to legolandsuch a wonderful house and very close to legolandCleanliness:
house was clean and the beds were comfortablevery quiet and very clean place to staybeautiful home everything was clean and tidy great accommodationsthe place was clean and had adequate towels and anything else that you may needthe place was immaculate clean and beautifulRead more reviewsAmenities & Room:
plenty of sleeping options lots of kitchen amenities nice touches throughoutit’s very nicely designed full of comfortable furniture and has a lot of nice amenities from the hostsit’s a place with lots of space very comfortable with a full kitchen washer and dryer dishwasher etcthe house includes additional amenities and extra touches that made our stay more comfortablethe beds are really comfortable there were great extra touches like coffee bottled water and snacks
3. Magical villa with swimming pool close to Legoland (from USD 428)
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 StatesAccommodates: 6
Top guest reviews
Host:
owners are very responsiveour hosts were wonderful to work withchad and catherine’s have a such a beautiful home and were very helpful throughout our tripfabulous hosts couldn’t ask for betterresponsive accessible even swing by half way through our stay make sure the pool was cleanLocation:
great location as wellthe location is very close to everything you need and the neighborhood is very safe and quietthe location is perfect for a visit to legolandlocation is close to everything would definitely stay again thanks so muchit was a great value and super close to legolandCleanliness:
very clean and comfy bedssparkling clean warm & invitingthe house was very clean and invitingwe enjoyed the pool everyday and was also very cleanit was sparkling clean and insanely accommodatingRead more reviewsAmenities & Room:
the pool was well kept and the amenities were even better than expectedthe pool and the grill were great to haveawesome they had a high-chair and bunk beds for kidsmy family loved the back patio and pool areapool and patio relaxing
4. Lovely lakeside property with free parking (from USD 251)
This stunning Lake Mariam duplex accommodation is suitable for up to six guests across three bedrooms, helping to ensure that large parties can enjoy the convenient location and stunning lakefront views. All modern conveniences have been supplied, as well as luxury linens, Wi-Fi access, entertainment options, and much more besides. If travelling by car, you’ll enjoy free parking on the premises, and also be able to explore further afield: Legoland is just four miles away (6.4 km), while Seaworld, Disney/Universal, and downtown Orlando are all within an hour’s drive of this delightful accommodation.
Winter Haven, Florida, United StatesAccommodates: 6
Top guest reviews
Host:
jin and pedro very nice hostsjin as the host is very responsivevery responsive hostsgreat and quick communications with ownerjin and pedro are awesome hostsLocation:
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 activitiesCleanliness:
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 stayRead more reviewsAmenities & 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 toys
5. Stunning Art Deco property 10 minutes from Legoland (from USD 62)
Perfect for large families and mixed travelling parties, this chic house has everything you could need for a family break. Two bedrooms with king-size beds are located at opposite ends of the house and the property is within walking distance of a plethora of local play parks. Not only that, but with Legoland 10 minutes away by car, and Disney just 35 minutes away, it’s right where you need to be for what the kids really want. A fully-stocked kitchen means that home-cooked family meals are a possibility.
Winter Haven, Florida, United States
6. Cosy nest on Lake Mariana (from USD 50)
This house is referred to by its owner as a “tiny house”, and while that’s an entirely accurate description it shouldn’t put off any parties of four or fewer. It’s a joy to look at and to spend time in, with a fully-equipped kitchen and full bathroom. Sleeping quarters are in two loft rooms joined by a bridge, while downstairs there is a pull-out couch on which one adult, or two kids, can comfortably sleep. You’re also right on the shore of Lake Mariana, and with canoes and a kayak laid on as part of the rental, you can have a lot of fun on the river when you’re not exploring nearby attractions, such as Disneyworld and Legoland.
Winter Haven, Florida, United StatesTop guest reviews
Host:
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 areaLocation:
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 legolandCleanliness:
very clean and accommodatingvery clean very nicely decoratedclean quiet and scenic areathe space was clean and comfortableeverything was clean and well suppliedRead more reviewsAmenities & 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 comfortable
7. Lakefront vacation home
Set on peaceful lakefront property, this vacation home offers accommodation that is close to Orlando’s famous attractions. With its four bedrooms and two full bathrooms, this home can cater six guests comfortably. It comes with a large, fully equipped kitchen and dining, and a spacious living area with a wall-mounted TV. You can prepare your meals in the kitchen and you can also make use of the grill outdoors.
In the afternoon, you can head to the patio with outdoor furniture and enjoy beautiful lake views.
Winter Haven, Florida, United States
Top guest reviews
Host:
easy check in process and owner very easy to respond withCleanliness:
very nice clean well equippedthe unit was clean when we checked in and during our entire stay it was very quietclean spacious and quiet perfect for the night before my weddingthis property was very clean and spacious and was very close and convenient to legolandthe home was clean filled with everything and felt like homeRead more reviewsAmenities & Room:
was very comfortable; however needs a little work - some painting
8. Stunning lakeside getaway for large parties
This incredible lakeside property is the perfect choice for those large groups of people seeking a Vrbo rental in Winter Haven, Florida. The property is set across 2,500 square feet (232m2) and offers four bedrooms, three bathrooms, a 26-foot (6-meter) dock, a hot tub, swimming pool, a game room, and much more.
For groups looking to explore the local area, there is plenty to enjoy also: the house is located close to the Chain of Lakes, next to Legoland, as well as a number of restaurants that can be reached by boat with ease.
Winter Haven, Florida, United States
Top guest reviews
Host:
They were all nice and hugepaddle boarding pool table arcade game and smart TVs everywhereAnd did I mention the arcade gameThe dock with the bar and Bluetooth speakers was awesomeThis was the perfect vacation home for our family reunion during the holidaysLocation:
Location is also great supermarket across the street and lots of restaurants near byEverything you would need is near by like grocery restaurants- if you are coming here for Legoland it was 5 minutes away and flying into and out of Tampa was so easywe never left the propertyWe were there just a few days and still made it to Universal Studios rented a pontoon and made it for a charity event in near by LakelandCleanliness:
The home was very clean and had great bath towels and linensThe house was super clean and perfect for a familyRead more reviewsAmenities & Room:
read one of the provided books 5It fit four couples with room to spare and the kids enjoyed the game roomyou hardly want to leavethe baths were roomy and the kitchen and living areas were the topsKitchen was well equipped plenty of towels available
9. Luxury rental for up to 18 guests
For large parties looking for a convenient, luxurious place to stay in Central Florida, this incredible 6,000 square foot (557m2) property is definitely worth considering. Five and a half bedrooms, five bathrooms, a kitchen, dining and living room, a private deck, and two spacious loft areas allow up to 18 guests to stay at once, with incredible lake views that are sure to delight all. Outside the property, you’ll have the opportunity to explore the lake itself, bask in the pool, enjoy the paved deck area, and generally bask in the stunning surroundings of this truly beautiful property.
Winter Haven, Florida, United States
Top guest reviews
Host:
The owner was very responsive and extremely helpfulOwners were available and quick to respond to any needsHonestly a bit nervous about the check out my familyQuiet private peaceful Good place for a big family with childrenThe owner's have thought of just about everythingLocation:
disappointingly strict and scary check outIt was no where to be foundonly netflix etc Missed FOX NEWS and other TV shows A few suggestions: get a garbage disposalThere were plenty of supplies and linensThe ONLY issue we had was the television in the master suite did not work and the projector was no where to be foundCleanliness:
The house is clean abd spacious with a great back yardEric and Dee are the best and their house is top shelfRead more reviewsAmenities & Room:
The kitchen dining room and living room were so invitingThe home is spacious and has plenty of parking spaceThe TV channels were excellent for the boys who wanted to watch the UK premiership football gamesbut I just hated feeling like if the bean bag chair was not lined up in the exact direction it should have faced or the blinds werent facing up or the floor wasnt swept and mopped meant I was getti...With large size 5 bedrooms and plenty of bathrooms
10. Wonderful condo near all amenities
This stunning 1,200 square foot (111m2) townhouse was designed by renowned architect Gene Leedy and those seeking beautiful accommodation in Winter Haven will definitely want to consider the delights the property can provide. Suitable for up to six guests, you will have access to both storeys, which include two bedrooms, two and a half bathrooms, a living room, a well-equipped kitchen, and two walled courtyards. In addition, the townhouse’s downtown location means you will enjoy easy access to parks, the city library, restaurants, shops, watersports on the ‘Chain of Lakes’, and much more.
Accommodates: 6
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Host:
She responds very quickly to emails or calls Everything we needed was available at the condoWe had all the conveniences of being at homeOwners are very friendly and respond quicklyThis location was so comfortable and quiet that our hectic trip was made even more peacefulMy experience was good staying in Winterhaven cute little condo close to all the downtownLocation:
The location was so convenient to downtown Winter HavenConvenient to the city proper but not much shopping Lots of stores closedyou have to check out Country Primitives Vintage Markettry out the many different restaurants and relax at Richard's Coffee ShopYou can't beat the downtown location which is a short walk to shops coffee and restaurantsCleanliness:
The condo was very clean and nicely decoratedThe condo was very clean and spaciousThe condo was very cleanIt was very clean and had everything you needPlace was clean and close to restaurantsRead more reviewsAmenities & Room:
The bed in the master was incredibly comfortablethe rooms are filled with light thanks to the lovely courtyards in both front and backit was nice to come back to a comfortable living room where we could stretch outWe were so comfortable there and enjoyed the two courtyards After a long day of baseballThe townhouse had everything we needed for an extended stay and the owners were only a phone call away if we needed anything
11. Spacious rental near Lake Eloise
Up to seven guests are able to enjoy this accommodation, which is located close to Lake Eloise in Winter Haven. You will have the use of two bedrooms, as well as a sleeper in the lounge, a modern kitchen, two full bathrooms that are complete with walk-in showers, and a living and dining room. When looking to explore the surrounding area, you have the option of visiting the world-famous Legoland resort, as well as the fishing-friendly Chain of Lakes. For those looking to venture further afield, the Orlando theme parks are less than an hour away, so you can be sure of a host of incredible options should you choose this villa for your vacation to central Florida.
2600 West Lake Eloise Drive #17
12. Newly-renovated luxury home near Legoland
This stunning, recently-updated accommodation is suitable for up to six guests and offers a modern, luxurious space for those seeking to visit Winter Haven, FL. The property offers a formal dining room, a screened front patio, a well-stocked kitchen, two large queen bedrooms, one double bedroom, and two full baths. In terms of location, you couldn’t be better served: Disney World is just 40 minutes away, there’s a public boat ramp less than half a block away, and the nearby Lake Howard offers walking, cycling, and fishing opportunities that you’re sure to love.
Top guest reviews
Host:
Every convenience available So handy with a washer dryer and even dishwasherThe owner Mark could not have been more responsive or concerned for me during my stayWe always hate to leave therethe owners very responsive and the location was greatIf you love the historical period of the 1920's antiques and the movie "Location:
It's 10 minutes from the Chain of Lakes sports complex and 15 minutes from the Lake Myrtle complex in AuburndaleMy aunt was able to locate this cute house for meThe house is situated within the lakes of Florida and we would have loved to spend some more time just in that area (maybe our next trip)I was mainly out all day due to my father being sick and did not get to enjoy the house too muchWe traveled to the Kissimmee and Orlando areas daily meeting friends and visiting the parks all within 45mins of the house locationCleanliness:
Large washer and dryer to wash clothesThe house is extremely neat and cleanThe house has 3 good sized bedrooms and 2 full bathroomsThe house is beautiful and we had everything we neededThe house was very roomy and the decor and style of the homeRead more reviewsAmenities & Room:
I appreciate you renting to me during a very difficult timeAll the amenities provided with personal touches all around right down to hand crocheted afghans on your couches and chairsit was like being homeWith 3 bedrooms (single queen bed in each) and 2 bathrooms it was a perfect fit Big living room with a HUGE flat screen tv nice screened in porch on the front and covered back porch (with a gas g...I spent some nights in a hotel once he was admitted but soon realized that I would need something more permanent than just one room with a mini fridge
Winter Haven - a name well chosen for a sunny getaway
If you’re looking for the ideal location for a family holiday, Winter Haven - far enough from the big cities to be secluded, but close enough to make for an easy trip - really is perfect. These accommodations are also just right for big-ticket trips to Disney and Lego theme parks - more than a few of them allow you to collaborate with friends and family for a trip you’ll never forget. In short, whatever you want your holiday to be, you can have it at Winter Haven - and, more importantly, so can your family.
History
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