10 Vacation Rentals In Winter Haven, Florida - Updated 2021

vacation rentals in winter haven fl

The appropriately-named town of 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 - the temperature rarely drops below 11 degrees Celsius (51 Fahrenheit), 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, found just 51 miles (82 km) to the east of Tampa Bay, will enjoy going for long walks 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, if you have an eye for the quirky, 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’ll want to check out these great vacation rentals in Winter Haven, Florida, USA.

1. Stunning lakeside getaway for large parties (from USD 425)

This incredible lakeside property is the perfect choice for those seeking a winter haven vacation home for a large group of people. The property is set across 2,500 square feet (232m2) and offers four bedrooms, three bathrooms, a 26 foot (6 metre) 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 Home with Dock & Hot Tub!
29 reviews
House 4 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
read one of the provided books 5
It fit four couples with room to spare and the kids enjoyed the game room
you hardly want to leave
the baths were roomy and the kitchen and living areas were the tops
Kitchen was well equipped plenty of towels available
The home was very clean and had great bath towels and linens
The house was super clean and perfect for a family
They were all nice and huge
paddle boarding pool table arcade game and smart TVs everywhere
And did I mention the arcade game
The dock with the bar and Bluetooth speakers was awesome
This was the perfect vacation home for our family reunion during the holidays
Location is also great supermarket across the street and lots of restaurants near by
Everything 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 easy
we never left the property
We 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 Lakeland
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2. Luxury rental for up to 18 guests (from USD 364)

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.

Relaxing luxury and lakeside living. Come! Enjoy our dream home for few days.
63 reviews
House 5 Bedrooms 5 Bathrooms
Top guest reviews
Amenities & Room:
The kitchen dining room and living room were so inviting
The home is spacious and has plenty of parking space
The TV channels were excellent for the boys who wanted to watch the UK premiership football games
but 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
The house is clean abd spacious with a great back yard
Eric and Dee are the best and their house is top shelf
The owner was very responsive and extremely helpful
Owners were available and quick to respond to any needs
Honestly a bit nervous about the check out my family
Quiet private peaceful Good place for a big family with children
The owner's have thought of just about everything
disappointingly strict and scary check out
It was no where to be found
only netflix etc Missed FOX NEWS and other TV shows A few suggestions: get a garbage disposal
There were plenty of supplies and linens
The ONLY issue we had was the television in the master suite did not work and the projector was no where to be found
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3. 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.

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
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4. Space for seven guests with a lake view (from USD 82)

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
193 reviews
Entire house 3 Beds 3 Bedrooms 2 Bathrooms
Top guest reviews
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
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
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
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
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5. Magical villa with swimming pool close to Legoland (from USD 115)

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.

Florida Oasis w/ Pool near LEGOLAND
Winter Haven, Florida, United States
135 reviews
Entire house 4 Beds 3 Bedrooms 1 Bathrooms
Top guest reviews
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
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
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
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
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6. Lovely lakeside property with free parking (from USD 86)

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 States
129 reviews
Entire house 3 Beds 3 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
incredible amenities cozy and comfortable
the tv sets were great
the king bed was amazingly comfortable
so comfortable my sister is buying the same mattress for her room
the beds were super comfortable and my daughter loved her room with games and toys
everything was clean and spacious
great clean place to stay
the place is very clean and nice
everything was amazing clean and quick respond
an amazingly beautiful clean and great local place to stay
jin and pedro very nice hosts
jin as the host is very responsive
very responsive hosts
great and quick communications with owner
jin and pedro are awesome hosts
super close to legoland
great location for legoland
great location for anyone visiting legoland
nice place that is close to legoland
great place and close to all winter haven activities
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7. Wonderful condo near all amenities (from USD 106)

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.

FALL/WINTER SPECIAL RATES Mid-century Mod w/ Fireplaces - Downtown Near Legoland
72 reviews
townhome 2 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
The bed in the master was incredibly comfortable
the rooms are filled with light thanks to the lovely courtyards in both front and back
it was nice to come back to a comfortable living room where we could stretch out
We were so comfortable there and enjoyed the two courtyards After a long day of baseball
The townhouse had everything we needed for an extended stay and the owners were only a phone call away if we needed anything
The condo was very clean and nicely decorated
The condo was very clean and spacious
The condo was very clean
It was very clean and had everything you need
Place was clean and close to restaurants
She responds very quickly to emails or calls Everything we needed was available at the condo
We had all the conveniences of being at home
Owners are very friendly and respond quickly
This location was so comfortable and quiet that our hectic trip was made even more peaceful
My experience was good staying in Winterhaven cute little condo close to all the downtown
The location was so convenient to downtown Winter Haven
Convenient to the city proper but not much shopping Lots of stores closed
you have to check out Country Primitives Vintage Market
try out the many different restaurants and relax at Richard's Coffee Shop
You can't beat the downtown location which is a short walk to shops coffee and restaurants
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8. Stunning Art Deco property 10 minutes from Legoland

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.

★ Family-Friendly House With Art Deco Style ★
Winter Haven, Florida, United States
28 reviews
Entire house 4 Beds 3 Bedrooms 2 Bathrooms

9. 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.

2 Bedroom Luxury Lake house -Unique vacation experience close to Legoland and Central Florids Chain of Lakes. Under an hour drive to Orlando.
2600 West Lake Eloise Drive #17
villa 2 Bedrooms 2 Bathrooms

10. 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.

1920's Vintage Updated 3/2 Pet Friendly Minuts From Legoland. Minutes to Disney
24 reviews
House 3 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
I appreciate you renting to me during a very difficult time
All the amenities provided with personal touches all around right down to hand crocheted afghans on your couches and chairs
it was like being home
With 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
Large washer and dryer to wash clothes
The house is extremely neat and clean
The house has 3 good sized bedrooms and 2 full bathrooms
The house is beautiful and we had everything we needed
The house was very roomy and the decor and style of the home
Every convenience available So handy with a washer dryer and even dishwasher
The owner Mark could not have been more responsive or concerned for me during my stay
We always hate to leave there
the owners very responsive and the location was great
If you love the historical period of the 1920's antiques and the movie "
It's 10 minutes from the Chain of Lakes sports complex and 15 minutes from the Lake Myrtle complex in Auburndale
My aunt was able to locate this cute house for me
The 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 much
We traveled to the Kissimmee and Orlando areas daily meeting friends and visiting the parks all within 45mins of the house location
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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.

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

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Antonia Kelly is a freelance writer based in Leicester, UK and she enjoys European travel as well as road trips closer to home. Her favourite domestic destinations include Snowdonia and the Brecon...Read more

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