Winter Haven holiday rentals

We found 1,189 holiday rentals — enter your dates for availability

Discover a selection of 133 homes, 26 apartments and other holiday rentals in Winter Haven that are perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the amenities that you need and want for your stay, which might include cable TV and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including accessible or non-smoking choices.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Delight in the lakeside landscape of Winter Haven

Enjoy the entertainment and other features of Winter Haven. This city's lake, gardens and baseball games draw many visitors. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Winter Haven

Are you looking for attractions to visit during your stay? Venture out of your holiday home and experience everything that makes Winter Haven a fun place to get away to. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • LEGOLAND® Florida (3.2 mi / 5.2 km)
  • Southern Dunes Golf Club (9.8 mi / 15.8 km)
  • Southern Dunes Golf and Country Club (9.9 mi / 15.9 km)
  • Mountain Lake (10.2 mi / 16.5 km)
  • Ridgewood Lakes Golf and Country Club (13.6 mi / 21.8 km)
  • The Club at Eaglebrooke (14 mi / 22.6 km)

Exploring the natural landscape of Winter Haven

Travellers enjoy Winter Haven for its lakeside setting and gardens. Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Winter Haven is a great place to get outside. These are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Auburndale City Park (4.5 mi / 7.3 km)
  • The Circle B Bar Reserve (8.8 mi / 14.2 km)
  • Sanlan Bird and Wildlife Sanctuary (10.2 mi / 16.5 km)
  • Bok Tower Gardens (11.2 mi / 18 km)
  • Lewis W Mathews Memorial Sports Complex (12.9 mi / 20.8 km)
  • Lake Mirror (13.5 mi / 21.8 km)

Transport to and around Winter Haven

Fly into Lakeland Intl. Airport (LAL), the closest airport, located 17.3 mi (27.8 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Kissimmee, FL (ISM-Kissimmee Gateway), which is 26 mi (41.9 km) away.

If you'd prefer to travel by train, you can make your way to Winter Haven Station.

Frequently asked questions

What is the best area to stay in Winter Haven when booking a holiday home?
Cypress Gardens is one of the more popular neighbourhoods where you’ll find a holiday property in Winter Haven. While here, drop by famous attractions such as LEGOLAND® Florida and Northgate Shopping Centre.
What is the most popular type of holiday home accommodation in Winter Haven?
The most popular types of holiday homes in Winter Haven are houses. Ready for more choices? Stayz has numerous options to match the needs of our guests, so you’ll see holiday 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 holiday home in Winter Haven?
The average price for a holiday home 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 cosy 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 Stayz and how many guests to view your home options and prices. From there you can use our filters to narrow your search by ratings, nearby activities and more.
Are there pet-friendly holiday homes in Winter Haven?
Pack a travel bag and a bone for the pup in your life because Winter Haven has 35 holiday homes that throw open their doors to pets. Let your four-legged pal get in on the family fun at one of our pet-friendly holiday homes on Stayz. 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 Stayz, and then spend leisurely days splashing and playing in a swimming pool that’s only for you.
What are popular home amenities in Winter Haven?
A nearby river, a fireplace and ski-in/ski-out facilities are the most popular home amenities in Winter Haven. Whether you’re travelling by yourself, with your better half or a group of friends, Stayz will help you find a holiday home that fits your tastes with all the options you need.
Are there large group holiday homes 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 holidays to special events like Christmas and birthday parties, Stayz can help you find a large group home to suit the occasion.
Are there holiday homes in Winter Haven that welcome kids?
With 35 family-friendly holiday 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 holidaying 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 holiday homes in Winter Haven?
Take your pick from 12 one-bedroom homes in Winter Haven. Whether you’re looking for a cosy cottage or an upmarket condo, Stayz’s one-bedroom homes 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 holiday with strangers.
Can I find two-bedroom holiday homes in Winter Haven?
You can pick from five two-bedroom holiday homes 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.
Are there holiday homes with WiFi in Winter Haven?
There are 18 holiday homes with WiFi in Winter Haven. If you want to disconnect from the world during your escape, but still want to be connected to the internet, these properties have what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Winter Haven?
You’ll have a choice of 34 holiday homes with air conditioning in Winter Haven giving you that cooling breeze and extra comfort level. Just enter your preferred travel dates and then make use of our filter tool to locate stays with air conditioning.
How old do you have to be to rent a holiday home in Winter Haven?
The minimum required age is generally 16, 18 or 21. It can change across properties on Stayz, so check the rules of your chosen Winter Haven holiday home before booking your stay.
How long can I rent a holiday home in Winter Haven for?
It really depends on the Winter Haven property. To view all available options offering extended stays, simply enter your travel dates and number of people into Stayz. Look forward to having the whole property to yourself, along with home comforts such as a fully-equipped kitchen, air conditioning and a yard where the little ones can play. Keep your eyes peeled for any long-term stays that offer discounted weekly or monthly prices.

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