Winter Haven vacation rentals

We found 1,199 vacation rentals — enter your dates for availability

Discover a selection of 129 homes, 31 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.

Vacation rentals with weekly discounts - Winter Haven

Showing deals for:Dec 19 - Dec 26

Image gallery for Experience family fun! LEGOLAND® Florida just a 12-min drive

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9.2 out of 10 rating
Wonderful
(10 reviews)

Experience family fun! LEGOLAND® Florida just a 12-min drive

Winter Haven, FL

9% off
Price is $565
$3,953 for 7 nights
All fees included
Experience family fun! LEGOLAND® Florida just a 12-min drive

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Find out more about Winter Haven

Find out more about Winter Haven

Why visit Winter Haven

  • Family-Friendly Attractions: Winter Haven is home to exciting amusement parks and beautiful lakes, perfect for family outings.
  • Outdoor Adventures: Enjoy a variety of outdoor activities, from hiking to relaxing in inviting urban parks.
  • Charming Neighborhoods: Explore the vibrant local atmosphere, where friendly residents create a welcoming environment.
  • Comfortable Accommodations: Choose from a range of vacation rentals, including cozy homes and spacious villas for a relaxing stay.
  • Nearby City Exploration: Visit nearby cities like New Orleans for a unique cultural experience during your vacation.

Popular types of accommodation in Winter Haven

Looking for the perfect getaway in Winter Haven? You’re in the right place. Our vacation rentals feature a variety of popular accommodations, including houses, villas, and condos. Whether you’re seeking a cozy house rental or a spacious home with a dining area and side refrigerator, we have options that cater to your needs. Experience comfort and convenience while making unforgettable memories in Winter Haven.

  • Houses: This is the top choice for visitors to Winter Haven, offering spacious and comfortable accommodations perfect for families, friends, or couples.
  • Villas: A popular option for vacationers, villas provide luxury and relaxation with beautiful surroundings.
  • Condos: These well-appointed units offer convenience and amenities, making them a favored choice for travelers.
  • Apartments: Ideal for those seeking a home-like environment, apartments are a practical lodging option.
  • Cottages: These charming retreats offer a cozy atmosphere for a delightful getaway.**

Top attractions in and around Winter Haven

Winter Haven, Florida, is perfect for family-friendly outdoor adventures. Visitors can enjoy a variety of attractions, including beautiful lakes, thrilling amusement parks, and inviting urban parks. Whether you're seeking a beach experience or outdoor fun, Winter Haven has something for everyone, making it an ideal destination for travelers looking to create lasting memories with loved ones.

  • LEGOLAND® Florida: A vibrant amusement park that immerses families in a world of creativity and adventure. With themed rides, interactive attractions, and stunning LEGO displays, this park is perfect for kids and adults alike, ensuring a fun-filled day.
  • Auburndale City Park: Located 5 miles from Winter Haven, this urban park offers a serene escape with playgrounds, picnic areas, and walking trails. It's a great spot for families to relax and enjoy the outdoors in a friendly city atmosphere.
  • Peppa Pig Theme Park Florida: An enchanting theme park dedicated to the beloved children's show, featuring gentle rides and play areas designed for younger kids. Families can enjoy character meet-and-greets and immersive experiences in a delightful setting.

Things to do recommended for couples

Looking for a romantic getaway in Winter Haven? Dive into adventure at Chain Of Wakes for thrilling water sports, then savor the enchanting atmosphere at True Blue Winery, just 12 miles away, perfect for wine tasting and relaxation. Enjoy unforgettable moments together.

Things to do recommended for families

Your family will love exploring Chain of Lakes Park for sports fun, relaxing at Lions Park just 5 miles away, and enjoying games at Indigo's Billiards, Bowling & Games in Winter Haven. These spots offer a perfect blend of adventure, wellness, and family-friendly activities.

Things to do recommended for groups

Experience the vibrant culture at Theatre Winter Haven, enjoy a fun night at Indigo's Family Fun Center, or explore the Northgate Shopping Center for shopping and entertainment. These local spots promise a memorable time for your group in Winter Haven, Florida.

*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

If you're planning a trip with a group, family, pets, or seeking extended stays, it's important to apply the right filters to meet your needs. Here are some helpful booking tips for Vrbo.

  • Traveling to Winter Haven with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Winter Haven with young kids: Traveling with little ones can be quite a journey. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Winter Haven: For many families, a vacation isn’t truly fulfilling without their furry companion by their side. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winter Haven: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Also, think about including features like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in and around Winter Haven

Winter Haven, Florida, offers a delightful mix of family-friendly adventures and charming neighborhoods. Explore the vibrant atmosphere where friendly locals welcome you, and enjoy relaxing moments in stylish settings. Nearby cities, like New Orleans, add a unique flair to your vacation, making it a perfect blend of fun and tranquility. Whether you seek outdoor activities or a quiet retreat, Winter Haven provides an unforgettable experience for all types of travelers.

  • Eagle Lake: Located a mere 3 miles from Winter Haven, Eagle Lake is a charming city known for its family-friendly atmosphere and outdoor entertainment. This destination is perfect for those seeking a blend of leisure and adventure. Visitors can enjoy various resort options and thrill-seeking at nearby amusement parks. Local attractions like theme parks and family-friendly beaches offer plenty of activities for all ages, making it an ideal spot for a fun-filled day out.
  • Cypress Gardens: Nestled within Winter Haven, Cypress Gardens is a delightful village that invites families and adventure seekers alike. Known for its lush landscapes, this area features a blend of outdoor activities and entertainment options. Whether you’re teeing off at the local golf courses or enjoying the thrills of amusement parks, Cypress Gardens provides a vibrant experience. The proximity to beautiful beaches and a film studio adds to its allure, making it a must-visit for those looking for both adventure and relaxation.
  • Inwood: Inwood is a picturesque village also located in the Winter Haven area, celebrated for its outdoor adventures and family activities. With access to resorts, amusement parks, and golf, there's something for everyone to enjoy. Local landmarks like scenic lakes and a stadium enhance the experience, providing plenty of opportunities for outdoor recreation and entertainment. Inwood's welcoming atmosphere makes it a great spot to explore the natural beauty of Florida while enjoying various fun activities.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
February64.4°F (18.0°C)No Rain (Dry)Mostly SunnyAverageSlightly Low
March67.5°F (19.7°C)Light RainMostly SunnySlightly HighAverage
April72.9°F (22.7°C)Light RainMostly SunnySlightly HighSlightly High
May77.2°F (25.1°C)Light RainMostly SunnyAverageAverage
June80.6°F (27.0°C)Moderate RainMostly SunnyAverageAverage
July81.7°F (27.6°C)Moderate RainMostly SunnyAverageSlightly High
August81.9°F (27.7°C)Moderate RainMostly SunnySlightly LowAverage
September79.5°F (26.4°C)Moderate RainMostly SunnySlightly HighSlightly Low
October74.7°F (23.7°C)Light RainMostly SunnySlightly LowSlightly Low
November68.0°F (20.0°C)No Rain (Dry)Mostly SunnySlightly LowAverage
December64.2°F (17.9°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming adventure? Staying flexible with your travel dates can really help, as prices can vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on the full booking amount. Taking on the planning role truly has its benefits. When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides you with a convenient platform to plan new trips, manage your existing plans, or review and organize your bookings. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To check out Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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?
When planning a vacation in Winter Haven, Florida, one of the best areas to consider for your stay is the downtown district. This vibrant neighborhood offers a charming atmosphere with a mix of shops, restaurants, and cultural attractions. Staying in downtown Winter Haven puts you in close proximity to the beautiful Chain of Lakes, where you can enjoy scenic views, walking trails, and various water activities. The area is also home to the popular LEGOLAND Florida Resort, making it an ideal spot for families looking for fun and excitement.

Another great neighborhood to consider is the Lake Howard area. This picturesque part of Winter Haven features lovely waterfront properties and offers easy access to some of the region's best parks, such as Lake Howard Park, which is superb for picnicking, fishing, or simply enjoying the outdoors. The Lake Howard area is known for its serene environment and is a fantastic choice for those seeking a peaceful retreat while still being close to local attractions.

Overall, Winter Haven has a variety of vacation rental options available, particularly in these neighborhoods, making it easy to find the superb place to relax and enjoy your stay.
How much does it cost to rent a vacation home in Winter Haven?
Prices for vacation rentals in Winter Haven vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winter Haven to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winter Haven vacation house rentals?
You can find great discounts on house rentals in Winter Haven on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Winter Haven?
For renting a beach house in Winter Haven, Florida, travelers should explore the picturesque areas surrounding the chain of lakes that the city is famous for. Although Winter Haven is not directly on the coast, it offers beautiful lakefront properties along Lake Eloise and Lake Howard. Many of these rentals come with convenient amenities such as private docks for boating, outdoor grills for entertaining, and spacious patios for enjoying the sunset views over the water.

The nearby Legoland Florida Resort also caters to families, making it an ideal area for those looking to combine beach house rentals with fun attractions. For those seeking a bit more activity, the neighborhood around Lake Silver features homes with access to public beaches and recreational areas, where travelers can enjoy swimming, fishing, and picnicking.

Additionally, the scenic Bok Tower Gardens is a short drive away, providing a beautiful backdrop for nature enthusiasts. Rentals in this area often feature outdoor spaces that are great for relaxation after a day of exploration, and some may include amenities like fire pits or hot tubs to enhance the experience. Find your rental near the beach in Winter Haven.
What is the most popular type of vacation rental accomodation in Winter Haven?
In Winter Haven, vacation houses are the most popular type of rental, with around 121 available throughout the area. These houses typically provide spacious rooms with multiple bedrooms, full kitchens, and outdoor spaces for relaxation, making them ideal for families or larger groups. Many are located near the Chain of Lakes, allowing easy access to various water activities and scenic views. Additionally, there are about 26 apartments, which offer a more compact living option with essential amenities like kitchenettes and comfortable living areas, often situated in convenient neighborhoods close to local dining and shopping options. For those seeking a quaint experience, approximately 15 cottages are available, featuring cozy interiors and outdoor seating, superb for enjoying the pleasant Florida weather. While villas and cabins are also present, their numbers are fewer, providing unique stays for travelers looking for something special.
Are there any family house rentals in Winter Haven?
In Winter Haven, Florida, travelers will find a wealth of family-friendly house rentals, with around 125 options available throughout the area. This charming city is well-known for its picturesque lakes, including the famous Chain of Lakes, making it a great destination for families seeking outdoor adventure. Many properties offer spacious living rooms, fully equipped kitchens for meal preparation, and private outdoor spaces for relaxation or play.

Visitors can enjoy amenities like Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable stay for everyone. The locale is close to family-friendly attractions, such as LEGOLAND Florida Resort, which features rides and activities suitable for children of all ages. Additionally, nearby parks and recreational areas provide opportunities for hiking, picnicking, and enjoying the natural beauty of the region. See all family-friendly rentals in Winter Haven.
Can I rent a vacation home with a pool or hot tub in Winter Haven?
In Winter Haven, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 73 options to choose from. This charming city, known for its picturesque chain of lakes, offers a variety of neighborhoods where these properties can be found, including areas close to Lake Eloise and Lake Howard, ideal for those looking to enjoy waterfront views and recreational activities.

Travelers can expect a range of amenities in these rentals, including private swimming pools, relaxing hot tubs, outdoor patios for al fresco dining, and fully equipped kitchens superb for family meals. Many homes also come with spacious living areas, game rooms, and sometimes even access to communal amenities like clubhouses or fitness centers, enhancing the overall vacation experience. Find your rental in Winter Haven with a pool or a hot tub.
Can I find long-stay vacation rentals in Winter Haven?
A long-stay vacation rental in Winter Haven is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Winter Haven?
In Winter Haven, there are numerous pet-friendly house rentals available, providing a welcoming environment for travelers with furry companions. Many of these properties feature amenities such as spacious backyards, fully equipped kitchens, and cozy living areas, making them suitable for families or groups.

The area is known for its beautiful chain of lakes, which offers opportunities for outdoor activities like boating and fishing. Additionally, nearby parks such as Lake Howard Park and the scenic Circle B Bar Reserve allow for enjoyable walks and exploration with pets. These parks often have trails and open spaces, great for letting dogs roam while enjoying the natural surroundings. See all pet-friendly rentals in Winter Haven.
Are there any remote work vacation rentals in Winter Haven?
In Winter Haven, Florida, there are numerous options for remote work vacation rentals, with approximately 151 available throughout the area. Many of these properties cater specifically to remote workers, offering amenities like Wi-Fi, dedicated desk spaces, and comfortable office setups that include desk chairs and laptop workspaces. Some rentals also feature additional conveniences such as computer monitors and safes, ensuring a productive work environment away from home.

The location of these rentals often allows for easy access to local attractions, including the beautiful Chain of Lakes and nearby Legoland Florida Resort, which can provide a fun break from work. Additionally, with various shops and restaurants nearby, you can easily find dining options or take a leisurely stroll during your downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winter Haven vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winter Haven with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Winter Haven?
In Winter Haven, popular vacation rental amenities include WiFi, kitchens, and patios, making stays comfortable and convenient for guests. Many rentals come equipped with coffee and tea makers, as well as blenders, suiting those who appreciate preparing their own meals or enjoying a morning beverage in a relaxed setting.
When is the best time to visit Winter Haven for a vacation rental?
The most popular time to visit Winter Haven for a vacation rental is from February to April, when temperatures are pleasantly warm, typically ranging from the mid-50s to the low 80s Fahrenheit. This peak season attracts travelers eager to enjoy outdoor activities, including visits to the famous LEGOLAND Florida Resort and the picturesque Chain of Lakes, which offers a variety of water sports and scenic parks. The vibrant atmosphere during these months makes it an ideal time for sightseeing and enjoying the beautiful Florida sunshine.

March, in particular, stands out as a prime month to experience Winter Haven's charm. With blooming flowers and plenty of sunshine, it's superb for leisurely strolls or picnics at Lake Howard Park. Visitors can also expect a range of events and activities that cater to travelers.

For those looking for a more budget-friendly option, consider planning your visit in November. While this month may be quieter, it allows for a relaxing experience with mild temperatures, typically in the mid-60s to low 70s Fahrenheit.
How early should I book a Winter Haven vacation rental?
Book your Winter Haven vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Winter Haven?
In Winter Haven, visitors can enjoy a variety of attractions that cater to different interests. The city is famous for its chain of lakes, making it a great destination for those who love water activities such as boating, fishing, and kayaking. The historic downtown area features charming shops, restaurants, and the beautiful Lake Silver, which provides picturesque views and walking paths.

One of the main highlights is Legoland Florida Resort, located in the nearby Cypress Gardens area, which offers a fun-filled experience for families with its rides, attractions, and interactive exhibits based on the popular toy. Another must-see is the Bok Tower Gardens, located just a short drive away, where guests can explore lush gardens and enjoy the stunning Singing Tower, providing a tranquil escape.

Additionally, the nearby Chain of Lakes Park offers recreational opportunities, including walking trails, picnic areas, and playgrounds, ideal for those looking to enjoy the outdoors.
Can I change or cancel my Winter Haven home rental booking on Vrbo?
To find Winter Haven vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Winter Haven vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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