Winter Haven holiday lettings

We found 1,236 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 106 homes, 20 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, 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)
  • Safari Wilderness (17.1 mi / 27.5 km)
  • Providence Golf Club (17.3 mi / 27.9 km)
  • ChampionsGate Golf Club (18.1 mi / 29.1 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:

  • The Circle B Bar Reserve (8.8 mi / 14.2 km)
  • Bok Tower Gardens (11.2 mi / 18 km)
  • Lake Mirror (13.5 mi / 21.8 km)
  • Disney Wilderness Preserve (19.2 mi / 30.8 km)
  • Northeast Regional Park (21.4 mi / 34.5 km)
  • Lake Davenport (22 mi / 35.4 km)

Transport to and around Winter Haven

Fly into Kissimmee, FL (ISM-Kissimmee Gateway), the closest airport, located 26 mi (41.9 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Avon Park, FL (AVO-Avon Park Executive), which is 32.1 mi (51.7 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 rental?

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 rental accommodation in Winter Haven?

The most popular types of holiday 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 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 rental in Winter Haven?

The average price for a holiday 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 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 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 holiday rentals in Winter Haven?

Pack a travel bag and a bone for the pup in your life because Winter Haven has 35 holiday 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 holiday 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 travelling by yourself, with your better half or a group of friends, Vrbo will help you find a holiday rental that fits your tastes with all the options you need.

Are there large group holiday 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 holidays to special events like Christmas and birthday parties, Vrbo can help you find a large group rental to suit the occasion.

Are there holiday rentals 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 rentals in Winter Haven?

Take your pick from 12 one-bedroom rentals in Winter Haven. Whether you're looking for a cosy 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 holiday with strangers.

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

You can pick from five two-bedroom holiday 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.

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