Winter Haven Vacation Rentals, Florida: house rentals & more

Discover a selection of 138 homes, 27 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

Charming 2-bedroom country house with AC, WiFi in Winter Haven

Sleeps 4 · 2 bedrooms · 1 bathroom

Nice Private Studio Room — 10 Minutes from the Legoland Park and Downtown

Sleeps 2 · 1 bedroom · 1 bathroom

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, yards and more
More for less
More space, more privacy, more amenities — more value

Find out more about Winter Haven

Why visit Winter Haven

Outdoor Adventures: Enjoy family-friendly activities in urban parks and scenic lakes, perfect for relaxation and fun.
Proximity to Disney: Experience the magic of Disney just a short drive away, ideal for a memorable family trip.
Charming Neighborhoods: Explore the delightful surroundings of Winter Park and South Haven for a taste of local culture.
Diverse Accommodations: Choose from private vacation homes, villas, and condos tailored to your needs for a comfortable stay.
Welcoming Atmosphere: Enjoy the friendly locals and vibrant community, making your visit truly enjoyable.

Popular types of accommodation in Winter Haven

If you're planning a getaway to Winter Haven, the excitement begins with selecting the perfect accommodation. Explore the most sought-after options, including houses, villas, and condos. Whether you're looking for short-term stays or monthly rentals, Winter Haven vacation rentals offer a variety of choices to suit your needs. Enjoy transparency, savings, and peace of mind as you find your ideal home away from home in this beautiful destination.

Houses: The top choice among visitors to Winter Haven, these homes offer spacious accommodations perfect for families or groups seeking comfort and privacy.
Villas: A close second, villas provide luxurious amenities and beautiful surroundings for those looking to indulge during their stay.
Condos: These modern, convenient options are ideal for travellers seeking a home-like experience with easy access to local attractions.
Apartments: A practical choice for individuals or couples, apartments offer a cozy atmosphere with the essentials for a comfortable visit.
Cottages: These quaint retreats are perfect for those desiring a charming and intimate getaway in a picturesque setting.**

Top attractions in Winter Haven

Winter Haven, Florida, is perfect for families seeking outdoor adventures and memorable experiences. With a variety of attractions like urban parks, lakes, and amusement parks, there's something for everyone, whether you're looking for relaxing family outings or romantic escapades. The area's diverse points of interest ensure that you'll enjoy a fun-filled vacation exploring the natural beauty and recreational activities available.

LEGOLAND® Florida: A fantastic amusement park brimming with adventure, LEGOLAND® Florida offers family-friendly rides, interactive attractions, and creative LEGO displays. It's perfect for visitors of all ages looking for outdoor fun and imaginative play.
Auburndale City Park: Located 8.0km away, this urban park features spacious green areas, playgrounds, and picnic spots. It’s an ideal place for families to enjoy outdoor activities in a vibrant city atmosphere.
The Circle B Bar Reserve: Approximately 14.5km away, this nature reserve provides an adventurous escape with scenic trails, diverse wildlife, and stunning landscapes, perfect for nature enthusiasts and those seeking tranquility.

Things to do recommended for couples

If you're seeking romance in Winter Haven, consider water sports at Chain Of Wakes for adventure, or take a thrilling leap with Jump Florida Skydiving, just 14.5km away. For a more laid-back experience, indulge in wine tasting at True Blue Winery, 19.3km from Winter Haven, perfect for couples.

Things to do recommended for families

Families in Winter Haven can explore the vibrant Chain of Lakes Park for sports fun, unwind at Lions Park for wellness and relaxation, and enjoy thrilling games at Indigo's Billiards, Bowling & Games for an adventurous family outing.

Things to do recommended for groups

Groups visiting Winter Haven can immerse themselves in local culture at Theatre Winter Haven, enjoy fun and entertainment at Indigo's Family Fun Center, and explore shopping at Northgate Shopping Center, which offers a vibrant atmosphere for family and group activities.

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

When planning your trip—whether you're traveling with friends, family, bringing along pets, or seeking extended accommodations—it's important to prioritize your needs through the right filters. Here are some helpful Vrbo booking tips to assist you.

Traveling to Winter Haven with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group get-togethers. Luckily, you can easily filter for all these options and more on Vrbo.
Traveling to Winter Haven with young kids: Travelling with young children can present its own set of challenges. It’s important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
Taking your pets with you to Winter Haven: For many families, a vacation isn’t truly fulfilling without their furry companions. If that resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
Planning for a long term stay visiting Winter Haven: If you're searching for vacation rentals that offer 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 include preferences like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay in Winter Haven

Winter Haven, Florida, offers a delightful blend of family-friendly activities and outdoor adventures. Explore the nearby charm of Winter Park, relax in the scenic beauty of South Haven, or embark on a magical Disney vacation just a short drive away. With friendly locals and a welcoming atmosphere, you'll find the perfect balance of relaxation and excitement in this vibrant region. Don't miss the opportunity to experience the enchanting Florida Keys as part of your journey!

Cypress Gardens: Nestled in the Winter Haven area, Cypress Gardens is a delightful village renowned for its family-friendly outdoor adventures. This charming locale offers access to various activities, including a resort, amusement park, and golf facilities. Visitors can explore the nearby theme park, relax on the beach, or take a peek behind the scenes at a film studio. The lush landscapes and serene surroundings make it an ideal spot for families seeking both relaxation and excitement.
Jan Phyl Village: Also situated in the Winter Haven area, Jan Phyl Village is a vibrant community perfect for families looking for outdoor entertainment. The village boasts easy access to resorts, an amusement park, and thrilling motor racing experiences. Nearby attractions include a theme park, a stadium, and beautiful beaches. This welcoming neighbourhood provides an engaging atmosphere for tourists eager to explore and enjoy various activities in the Florida sun.
Eloise: Eloise, another charming village in the Winter Haven vicinity, is ideal for families seeking adventure and outdoor fun. Visitors can enjoy access to a resort, amusement park, and shopping centre. The area is close to a theme park, picturesque lakes, and a stadium, making it a fantastic destination for those wanting to combine leisure with excitement. Eloise’s inviting atmosphere and diverse attractions ensure a memorable vacation experience for all.

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. Peak season runs in March to April and September, while off-peak times, like August and October to November tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	60.4°F (15.8°C)	Light Rain	Mostly Sunny	Average	Average
February	64.4°F (18.0°C)	No Rain (Dry)	Mostly Sunny	Average	Slightly Low
March	67.5°F (19.7°C)	Light Rain	Mostly Sunny	Slightly High	Average
April	72.9°F (22.7°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
May	77.2°F (25.1°C)	Light Rain	Mostly Sunny	Average	Average
June	80.6°F (27.0°C)	Moderate Rain	Mostly Sunny	Average	Average
July	81.7°F (27.6°C)	Moderate Rain	Mostly Sunny	Average	Slightly High
August	81.9°F (27.7°C)	Moderate Rain	Mostly Sunny	Slightly Low	Average
September	79.5°F (26.4°C)	Moderate Rain	Mostly Sunny	Slightly High	Slightly Low
October	74.7°F (23.7°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
November	68.0°F (20.0°C)	No Rain (Dry)	Mostly Sunny	Slightly Low	Average
December	64.2°F (17.9°C)	No Rain (Dry)	Mostly Sunny	Average	Slightly High

Booking with Vrbo is simple

Are you hoping to save on your upcoming travel plans? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for an extended stay. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect option for your needs!

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a user-friendly platform to help you plan your trips, resume your previous bookings, and manage your travel arrangements with ease. You'll discover your saved or booked properties neatly organized into categories such as Potential, Upcoming, and Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/en-ca/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. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation 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

Do you want to find top things to see and do during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Winter Haven has to offer. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

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

Travelers enjoy Winter Haven for its lakeside setting and gardens. Whether you're an active traveler or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Winter Haven. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

Auburndale City Park (4.5 mi / 7.3 km)
The Circle B Bar Reserve (8.8 mi / 14.2 km)
Bok Tower Gardens (11.2 mi / 18 km)
Lake Parker (12.5 mi / 20.1 km)
Lewis W Mathews Memorial Sports Complex (12.9 mi / 20.8 km)
Lake Mirror (13.5 mi / 21.8 km)

Transportation to and around Winter Haven

Fly into Lakeland Intl. Airport (LAL), the closest airport, located 17.3 mi (27.8 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Kissimmee, FL (ISM-Kissimmee Gateway), which is 26 mi (41.9 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.

Are there vacation rentals with WiFi in Winter Haven?

There are 18 vacation rentals 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 Vrbo.

How can I find vacation rentals with air conditioning in Winter Haven?

You’ll have a choice of 34 vacation rentals 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 vacation rental in Winter Haven?

The minimum required age is generally 16, 18 or 21. It can change across properties on Vrbo, so check the rules of your chosen Winter Haven vacation home before booking your stay.

How long can I rent a vacation rental 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 Vrbo. 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.