Winter Haven holiday homes

We found 1,093 holiday rentals — enter your dates for availability
Discover a selection of 56 homes 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.

Holiday rentals with weekly discounts – Winter Haven

Showing deals for:6 Nov - 13 Nov

  • 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

Why visit Winter Haven

  • Scenic lakes and water sports: Winter Haven boasts beautiful lakes perfect for water sports and leisurely boat rides, offering a refreshing escape.
  • Vibrant urban parks: Enjoy relaxed strolls and picnics in the city's inviting parks, ideal for families and outdoor enthusiasts.
  • Family-friendly amusement parks: Experience thrilling rides and fun activities, making it a top choice for family adventures.
  • Active neighbourhoods: Explore the welcoming community vibes and local events that capture the winter garden spirit.
  • Nature trails: Discover scenic walks and nature trails that showcase the beauty of central Florida.

Top attractions in and around Winter Haven

Winter Haven, Florida, is a fantastic holiday destination for families and outdoor enthusiasts alike. With its beautiful lakes, inviting urban parks, and thrilling amusement parks, there's no shortage of activities to enjoy. Whether you're keen on water sports, exploring nature trails, or delighting in fun-filled adventures, Winter Haven offers a vibrant mix of experiences that cater to all ages and interests, making it an ideal spot for your next getaway.

  • LEGOLAND® Florida: Situated in Winter Haven, this amusement park offers an outdoor adventure full of family fun, interactive rides, and creative experiences unique to its theme.
  • Peppa Pig Theme Park Florida: Located in Winter Haven, this theme park delivers entertaining attractions and family-friendly activities inspired by the beloved character.
  • Auburndale City Park: Just 8km from Winter Haven, this urban park provides a city vibe with outdoor family fun and scenic walks.

Things to do recommended for couples

Discover Winter Haven’s charm with romantic activities perfect for couples. Delight in local experiences, scenic walks, and intimate moments that capture the essence of a Kiwi holiday in the USA.

Things to do recommended for families

Families in Winter Haven can explore LEGOLAND® Florida Resort, enjoy paddle boating on chain of lakes, and discover wildlife at local parks, ensuring a memorable Kiwi holiday experience.

Things to do recommended for groups

Explore the stunning Chain of Lakes with a group paddleboarding adventure, or visit LEGOLAND Florida for exhilarating rides and attractions. For a unique experience, enjoy a guided airboat tour through nearby wetlands, where you can spot native wildlife.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Winter Haven

Whether you’re travelling as a group, with family, alongside your pets or for an extended stay, be sure to use the appropriate filters to match your needs. Here are some handy Vrbo booking tips for you.

  • Traveling to Winter Haven with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for socialising with your group. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Winter Haven with young kids: Traveling with little ones can be a challenge. You must prioritise their comfort and safety, as well as ensure there are age-appropriate facilities like a private pool. It’s also wise to consider how close you are to attractions that are family-friendly.
  • Taking your pets with you to Winter Haven: For many, a family getaway isn't truly enjoyable without their furry companion by their side. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Winter Haven: If you're in search of holiday rentals with discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or even a private pool to your search criteria.

Where to stay in and around Winter Haven

Winter Haven, Florida offers a delightful blend of family-friendly attractions and outdoor adventures in central Florida. Enjoy a relaxed holiday amidst active neighbourhoods and a welcoming community that embraces the winter garden vibe. Perfect for a family getaway, the city invites visitors to explore its parks, scenic lakes, and local events, creating an ideal base for a memorable adventure holiday.

  • Davenport: Situated 21km from Winter Haven, Davenport is a charming city that offers a delightful blend of family-friendly activities and outdoor adventures. Known for its entertainment-themed attractions, visitors can explore nearby golf courses and resorts that cater to all ages. Davenport is also close to exciting landmarks such as theme parks and film studios, providing ample opportunities for fun-filled days. The city’s welcoming atmosphere and convenient access to recreational activities make it a great option for those seeking both relaxation and excitement during their holiday.
  • Cypress Gardens: Nestled within the Winter Haven area, Cypress Gardens is a picturesque village renowned for its family-oriented outdoor adventures. Visitors flock to this beautiful locale to enjoy its amusement parks, golf venues, and stunning natural scenery. The area is also home to popular attractions such as theme parks and beaches, making it an ideal spot for those looking to immerse themselves in both adventure and relaxation. With its vibrant community and plethora of activities, Cypress Gardens promises a delightful experience for tourists of all ages.
  • Auburndale: Located just 8km from Winter Haven, Auburndale is a lively city that offers a wonderful mix of family-friendly entertainment and outdoor experiences. Known for its charming atmosphere, visitors can enjoy access to various amusement parks, golf facilities, and urban parks. The city is also in proximity to beautiful beaches and theme parks, providing endless opportunities for exploration and leisure. Auburndale’s inviting environment and diverse range of attractions make it a great choice for those seeking a memorable holiday experience.

Best time to go to Winter Haven

If you're planning a trip to Winter Haven, it's a good idea to check both the weather and property rates. The warmest month is August.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January60.4°F (15.8°C)Light RainMostly SunnyAverage
February64.4°F (18.0°C)No Rain (Dry)Mostly SunnyAverage
March67.5°F (19.7°C)Light RainMostly SunnySlightly High
April72.9°F (22.7°C)Light RainMostly SunnySlightly High
May77.2°F (25.1°C)Light RainMostly SunnyAverage
June80.6°F (27.0°C)Moderate RainMostly SunnyAverage
July81.7°F (27.6°C)Moderate RainMostly SunnyAverage
August81.9°F (27.7°C)Moderate RainMostly SunnySlightly Low
September79.5°F (26.4°C)Moderate RainMostly SunnySlightly High
October74.7°F (23.7°C)Light RainMostly SunnySlightly Low
November68.0°F (20.0°C)No Rain (Dry)Mostly SunnySlightly Low
December64.2°F (17.9°C)No Rain (Dry)Mostly SunnyAverage

Booking with Vrbo is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate quite a bit. Plus, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental. We're here to help you find the perfect spot for your getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo's clever Trip Board offers you a dedicated space to plan new adventures, pick up where you last stopped, or manage your travel arrangements with ease. You can easily access the properties you've saved or booked in the Potential, Upcoming, or Current Trips sections. To start using Trip Boards, simply visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

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. LEGOLAND® Florida and Reunion Resort Golf Course are just a couple of the must-see attractions in the area. 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)
  • Reunion Resort Golf Course (19.3 mi / 31 km)
  • Peppa Pig Theme Park Florida (3.6 mi / 5.8 km)
  • Chain Of Wakes (4.1 mi / 6.6 km)
  • Lake Myrtle Sports Complex (7.4 mi / 12 km)
  • Southern Dunes Golf and Country Club (9.9 mi / 15.9 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)
  • Star Lake (10.1 mi / 16.3 km)
  • Mary Holland Park (10.5 mi / 16.8 km)
  • Bok Tower Gardens (11.2 mi / 18 km)
  • Lake Parker (12.5 mi / 20.1 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? Bookabach 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 Bookabach 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 Bookabach. 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 Bookabach, 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, Bookabach 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, Bookabach 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, Bookabach'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 Bookabach.
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 Bookabach, 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 Bookabach. 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.