Winter Haven Vacation Rentals, Florida: Whole House to Yourself

Discover a selection of 102 homes, 18 apartments, and other vacation rentals in Winter Haven that are perfect for your trip. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the amenities you need and want for your stay, which might include air conditioning and a pool. No matter what you're looking for, you'll be able to choose a rental that has what everyone needs, including accessible or non-smoking choices.

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LEGOLAND® Florida

Find the best place to stay - Winter Haven

Lovely Condo Just 1 Mile From Disney w/ Resort Pool, WiFi & More

Sleeps 6 · 2 bedrooms · 2 bathrooms

Top rated rentals - Winter Haven

Enclosed patio to relax...entrance to guesthouse

Premier Host

Clean and quiet

Discovery & adventure for the whole family on Lake Idylwild! From the playground to the tiki bar & pool table inside, we have something for everyone!

Premier Host

Perfect!

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
All the privacy of home
Enjoy full kitchens, laundry, pools, yards and more
More for less
More space, more privacy, more amenities — more value
A place for everyone
We stand for diversity, inclusion and families everywhere.
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Wonderful times in Winter Haven

Let Winter Haven vacation rentals welcome you to this year-round destination. Let your imagination run wild in LEGOLAND Florida Resort or go wild in the water in one of Winter Haven’s 50 lakes. Catch the community theater bug by taking in a show at the Theatre Winter Haven. If you’re really looking for some retail therapy, step back in time and explore the many antiques stores that call Winter Haven home. However you want to spend your vacation, Winter Haven is sure to have something to satisfy everyone.

Theme park and theater thrills in Winter Haven

Adults and children alike will love LEGOLAND Florida Resort! This 150-acre theme park is dedicated to family-friendly fun and will delight children of all ages. Make a splash in the adjoining water park for an additional fee, and cool off in the Floridian sun. After a day of fun in the sun, returning to the Winter Haven vacation rentals will always be welcome; but how about an evening at the theater? Theatre Winter Haven is locally renowned for its top-quality community theater. The program will, of course, depend on when you visit, but you’re guaranteed a great evening.

Wild water and amazing antiques in Winter Haven

Winter Haven is also known as “The Chain of Lakes City” and for good reason. After getting settled in Winter Haven vacation rentals, break out your bathing suit and head for one of the city’s 50 lakes! Flyboarding is one of the area’s popular water pursuits and you can book a lesson with companies operating from different lakes. Want something a bit more sedate on the water? Charter a boat and spend an afternoon bobbing on the waves while bass fishing. On land, eagle-eyed antiques enthusiasts will love browsing for souvenirs and gifts in the many antiques stores here.

It’s not called Winter Haven for nothing!

If you’re looking for year-round sunshine and warm temperatures, Winter Haven is the perfect place for you. July through August see average highs in the low 90s but also a lot of rain owing to the humid, subtropical Floridian climate. For those looking to avoid the rain, come to Winter Haven from October through May as these are by far the driest months. Winters see average highs in the high 40s so you can expect to get your fill of this town’s average 242 days of sunshine.

Love the lakes in Winter Haven

Located between Tampa and Orlando within the Central Florida Highlands, Winter Haven is not your typical Floridian beach-side community. You’ll see flatland with rolling hills all around you, as well as the lakes this city is so famous for. The lakes are full of wildlife, and nature lovers may be able to spot bald eagles and alligators as well as the bass. To get a real sense of the natural world, sit back and relax on a guided river tour and learn all about the birds and creatures that call Winter Haven home.

Transportation to and around Winter Haven

Fly into Tampa Intl. Airport (TPA), the closest airport, located 49 mi (78.9 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Tampa, FL (TPF-Peter O. Knight), which is 44.4 mi (71.5 km) away.

If you're traveling by train, the main station serving the city is Winter Haven Station.

Frequently asked questions

What is the best area to stay in Winter Haven when booking a vacation rental?

Cypress Gardens is one of the more popular neighborhoods where you'll find a vacation property in Winter Haven. While here, drop by famous attractions such as LEGOLAND® Florida and Northgate Shopping Center.

What is the most popular type of vacation rental accommodation in Winter Haven?

The most popular types of vacation rentals in Winter Haven are houses. Ready for more choices? Vrbo has numerous options to match the needs of our guests, so you'll see vacation properties in all shapes and sizes. The perfect fit is ready and waiting for you — get yours today.

How much does it cost to rent a vacation rental in Winter Haven?

The average price for a vacation rental in Winter Haven is based on a number of factors, such as property type, length of stay and time of year. Whether you're looking for a sprawling villa with space for extended family or a cozy cabin ideal for just you and the kids, just add your dates of travel to find stays that offer great value.

How much does it cost to rent a beach house in Winter Haven?

Prices for beach houses in Winter Haven may differ depending on the style and size of the property and when you plan to travel. Just enter your travel dates into Vrbo and how many guests to view your rental options and prices. From there you can use our filters to narrow your search by ratings, nearby activities and more.

Are there pet-friendly vacation rentals in Winter Haven?

Pack a travel bag and a bone for the pup in your life because Winter Haven has 35 vacation rentals that throw open their doors to pets. Let your four-legged pal get in on the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates then check our "Pets allowed" filter box.

Can I rent a house with a pool in Winter Haven?

Add a new level of fun to your trip by booking your group into one of the 15 houses with a private pool in Winter Haven. Use our search filter to find the kind of property you want on Vrbo, and then spend leisurely days splashing and playing in a swimming pool that's only for you.

What are popular rental amenities in Winter Haven?

A nearby river, a fireplace and ski-in/ski-out facilities are the most popular rental amenities in Winter Haven. Whether you're traveling by yourself, with your better half or a group of friends, Vrbo will help you find a vacation rental that fits your tastes with all the options you need.

Are there large group vacation rentals in Winter Haven?

With five properties that can host 10 or more guests in Winter Haven, you won't have to hold back on your invites. From family vacations to special events like Christmas and birthday parties, Vrbo can help you find a large group rental to suit the occasion.

Are there vacation rentals in Winter Haven that welcome kids?

With 35 family-friendly vacation properties to select from in Winter Haven, now is the perfect time to introduce your kids to the magic of travel. Check our "Properties good for families" filter box to discover stays loaded with amenities perfect for vacationing families, such as dining rooms, outdoor spaces, entertainment areas and hot tubs.

What are the top attractions for families in Winter Haven?

There are tons of amazing things to do and see with the family in Winter Haven, including:

LEGOLAND® Florida
Chain Of Wakes
Indigos Billiards, Bowling & Games

Are there one-bedroom vacation rentals in Winter Haven?

Take your pick from 12 one-bedroom rentals in Winter Haven. Whether you're looking for a cozy cottage or an upmarket condo, Vrbo's one-bedroom rentals are just right if you don't need tons of space. One of the main perks of having your own digs? You won't ever need to share your vacation with strangers.

Can I find two-bedroom vacation rentals in Winter Haven?

You can pick from five two-bedroom vacation rentals in Winter Haven. Give the kids the second room or fill it with a couple of your best friends. There's space for whoever's fortunate enough to be joining in on the fun.