Winter Haven vacation rentals

We found 1,107 vacation rentals — enter your dates for availability

Discover a selection of 55 homes, 11 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:Jun 12 - Jun 19

Image gallery for Eagle Haven Lake House

Living area
10 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)

Eagle Haven Lake House

Eagle Lake

9% off
Price is $403
$2,822 for 7 nights
All fees included
Eagle Haven Lake House

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Find out more about Winter Haven

Why visit Winter Haven

  • Beautiful Lakes: Winter Haven is known for its stunning lakes, perfect for outdoor activities like fishing, boating, and picnicking.
  • Amusement Parks: Enjoy family-friendly fun at popular attractions like Legoland Florida, offering rides and entertainment for all ages.
  • Charming Downtown: Explore the vibrant downtown area filled with local shops, dining options, and a friendly atmosphere.
  • Outdoor Adventures: Take advantage of mild winters with outdoor activities such as hiking and biking in urban parks.
  • Variety of Accommodations: Choose from vacation rentals like private homes and condos, catering to every budget and preference.

Popular types of accommodation in Winter Haven

Planning a getaway to Winter Haven? You're in for a treat. This charming destination offers a variety of vacation rentals to suit your needs, including houses, villas, and condos. Whether you're looking for a cozy retreat or a spacious family home, you'll find the ideal spot to unwind. Explore the best Winter Haven vacation rentals and enjoy your stay in the heart of Florida.

  • Houses: The top choice for visitors in Winter Haven, these spacious homes offer comfort and privacy for families or groups.
  • Villas: Elegant and often luxurious, villas provide a stylish retreat with ample amenities and beautiful surroundings.
  • Condos: A popular option, condos offer convenient access to local attractions while providing a home-like experience.
  • Apartments: Ideal for solo travelers or couples, apartments deliver a cozy atmosphere with essential amenities.
  • Cottages: Charming and quaint, cottages provide a unique, rustic escape in a serene setting.**

Top attractions in Winter Haven

Winter Haven, Florida, is a fantastic destination for family and outdoor adventures. You'll find plenty of attractions, including beautiful lakes, urban parks, and amusement parks that cater to all ages. Explore the charming downtown area for local shops and dining options. Whether you're seeking outdoor activities or a fun beach experience, Winter Haven offers something for everyone, making it an ideal vacation spot for families and adventure seekers alike.

  • LEGOLAND® Florida: This vibrant amusement park offers a unique blend of family fun and adventure with thrilling rides, interactive exhibits, and beautifully crafted LEGO displays, perfect for kids and the young at heart.
  • Peppa Pig Theme Park Florida: Dive into a world of entertainment designed for young children, featuring rides and attractions themed around the beloved Peppa Pig characters, ensuring a delightful experience for families.
  • Winter Haven Hospital: While primarily a medical center, Winter Haven Hospital embodies a community-focused atmosphere, offering essential services and a welcoming environment for families in need of care.

Things to do recommended for couples

For a romantic getaway in Winter Haven, consider a visit to Ridgewood Lakes Golf and Country Club, just 14 miles away. Enjoy the luxurious atmosphere while playing a round of golf or relaxing in the serene surroundings, perfect for couples seeking a memorable experience.

Things to do recommended for families

Families visiting Winter Haven can have a thrilling day at LEGOLAND Florida Resort, featuring rides and attractions for all ages. Explore the beautiful Bok Tower Gardens, where kids can enjoy nature and play, making lasting memories together in this charming Florida destination.

Things to do recommended for groups

Explore the beautiful Chain of Lakes with a scenic boat tour, or enjoy a day of fun at LEGOLAND Florida Resort. For a unique experience, try paddleboarding at Lake Eloise or gather for some friendly competition at the local escape rooms.

*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 traveling with a group, family, pets, or planning an extended stay, it's important to filter your options based on your specific needs. 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, as well as any additional features like a full kitchen or outdoor area for group activities. Luckily, you can easily apply filters for these options and many more on Vrbo.
  • Traveling to Winter Haven with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, thinking about how close you are to family-friendly attractions is a smart move.
  • Taking your pets with you to Winter Haven: For many families, a vacation wouldn't feel complete without their furry companion along for the fun. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Winter Haven: If you're in search of vacation rentals offering 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 features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Winter Haven

Winter Haven, Florida, offers a delightful vacation experience perfect for families and outdoor enthusiasts. Explore the beautiful waterfront, enjoy mild winters, and immerse yourself in the friendly atmosphere of the city. Nearby regions provide additional opportunities for adventure and relaxation, making Winter Haven an ideal base for your getaway. Discover charming neighborhoods and attractions that cater to every budget, ensuring a memorable trip for all.

  • Cypress Gardens: Nestled within Winter Haven, Cypress Gardens is a charming village that invites travelers to indulge in a family-friendly, outdoor adventure. Known for its lush landscapes and recreational opportunities, visitors can enjoy a variety of activities at nearby resorts, amusement parks, and golf courses. The area features local landmarks such as a renowned theme park, beautiful beaches, and a sports facility stadium, making it an ideal spot for both relaxation and excitement. Whether you're looking to spend a day soaking up the sun or exploring thrilling rides, Cypress Gardens provides a delightful escape.
  • Eagle Lake: Located just 3 miles from Winter Haven, Eagle Lake is a vibrant city perfect for those seeking outdoor and family adventures. This picturesque destination offers easy access to resorts, amusement parks, and golf, catering to all ages. Nature lovers will appreciate the scenic beauty of the nearby lake and urban parks, which provide ample opportunities for picnicking, hiking, and wildlife watching. With its friendly atmosphere and exciting attractions like a theme park, Eagle Lake is a great place to create lasting memories with loved ones.
  • Jan Phyl Village: Situated within Winter Haven, Jan Phyl Village is a quaint community that appeals to families and business travelers alike. The village boasts an array of amenities, including resorts, educational institutions, and shopping malls, ensuring visitors have everything they need at their fingertips. Local highlights include a nearby theme park, beautiful beaches, and a modern college university, providing both entertainment and learning opportunities. Jan Phyl Village is an excellent choice for those looking to mix leisure with a touch of city life.

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

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Additionally, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and receive all the OneKeyCash associated with your booking. Being the planner certainly has its rewards. When you join our travel rewards program, One Key, you'll gain immediate access to exclusive member discounts and the ability to earn and redeem OneKeyCash on eligible reservations. Sign up today to start 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 travel arrangements, or review your bookings. Your saved and booked properties are neatly organized into categories: Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please 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, Florida, United States of America when booking a vacation rental?
When looking for the best area to stay in Winter Haven, Florida, consider the charming neighborhood surrounding Lake Eloise. This picturesque area is known for its scenic views and proximity to top attractions such as Legoland Florida Resort, which offers a fantastic experience for families with its rides and interactive exhibits. Additionally, the nearby Bok Tower Gardens provides a serene escape with its beautiful landscapes and stunning carillon, making it a superb spot for nature lovers.

Another great option is the downtown area, where visitors can engage in the local culture. This vibrant neighborhood boasts a variety of shops, restaurants, and cafes, superb for enjoying a leisurely stroll. The downtown area is also close to the Chain of Lakes, where outdoor enthusiasts can enjoy various water activities, including boating and fishing.

In terms of vacation rentals, both neighborhoods offer a diverse selection of properties, ensuring that you can find something that fits your needs, whether you're looking for a cozy retreat or a spacious family home.
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, the area surrounding Lake Howard is a great choice. This picturesque lake offers various vacation rental options with easy access to waterfront activities. Many properties here come with amenities such as private docks, spacious decks for outdoor dining, and scenic views of the lake, making it superb for families or groups looking to enjoy a relaxing getaway.

Another appealing area is near the Chain of Lakes, where travelers can find charming properties with direct access to multiple lakes for boating, fishing, and swimming. Rentals in this vicinity often feature modern amenities like full kitchens, barbecue grills, and large backyards, suitable for gatherings or enjoying the warm Florida sun.

Additionally, the nearby Lake Eloise area provides options for those seeking a more tranquil setting. Here, vacation homes often come with private pools, outdoor lounges, and landscaped gardens, allowing guests to unwind in a serene environment after a day of exploring the local attractions.
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 about 110 available throughout the area. These houses typically offer spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or gardens—ideal for families and groups. Many properties are located near points of interest like Legoland Florida and the Chain of Lakes, providing convenient access to local attractions. Additionally, there are around 25 apartments and 16 cottages for those seeking smaller accommodations, often featuring cozy living areas and essential amenities.
Are there any family house rentals in Winter Haven?
In Winter Haven, Florida, there are numerous family-friendly house rentals available, with around 101 options to choose from. This area is well-known for its beautiful Chain of Lakes, offering plenty of opportunities for water-related activities such as fishing and boating. Many of the homes feature spacious living areas, full kitchens for preparing family meals, and outdoor spaces where children can enjoy playing.

Visitors can also find amenities like game rooms, private pools, and fenced yards, making these properties ideal for families. Additionally, the close proximity to attractions like LEGOLAND Florida Resort and the scenic parks in the region ensures that families will have plenty to explore and enjoy during their stay.
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 include pools and hot tubs, with around 61 options to choose from. This charming city, located in Central Florida, is famous for its Chain of Lakes and offers a variety of neighborhoods where these properties can be found. Families and groups can expect amenities such as private pools, relaxing hot tubs, spacious outdoor patios, and fully equipped kitchens, which make these rentals great for both leisure and entertainment.
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 any remote work vacation rentals in Winter Haven?
In Winter Haven, Florida, there are numerous vacation rentals suitable for remote work, with around 143 options available. This area is known for its beautiful lakes and outdoor recreational opportunities, making it a pleasant environment for those balancing work and leisure. Many properties come equipped with essential amenities for remote work, such as high-speed Wi-Fi, dedicated workspaces, and in some cases, computer monitors and printers to enhance productivity.

Travelers can expect a variety of accommodations, from cozy apartments to spacious homes, often featuring comfortable living areas and full kitchens for meal preparation. The proximity to local attractions, including the scenic Chain of Lakes and nearby parks, provides a refreshing break from work. 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 typically include a fully equipped kitchen, making it easy for guests to prepare meals during their stay. Many rentals also offer onsite parking for convenience. For those who enjoy a warm beverage, coffee and tea makers are commonly found in these properties. Outdoor spaces are a highlight as well, with many rentals featuring decks or patios where guests can relax and enjoy the pleasant Florida weather.
When is the best time to visit Winter Haven for a vacation rental?
The best time to visit Winter Haven for a vacation rental is during the peak season from February to April, with March standing out as the most popular month. This period attracts a vibrant mix of travelers eager to enjoy the warm, sunny climate and the array of outdoor activities available in the area. Average temperatures range from the low 50s to mid-80s Fahrenheit, creating ideal conditions for exploring the beautiful lakes, parks, and attractions that Winter Haven has to offer.

During this peak season, visitors can take advantage of various recreational opportunities, including boating, fishing, and relaxing at Legoland Florida. The pleasant weather also makes it superb for leisurely strolls along the scenic Chain of Lakes, where you can soak in the stunning views and enjoy the local wildlife.

If you're looking for a more budget-friendly time to visit, consider planning your trip in November. During this time, this month offers a lovely experience with mild temperatures and fewer crowds, allowing for a more relaxed exploration of the area's charming attractions.
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, Florida, United States of America?
In Winter Haven, visitors can enjoy a range of attractions that cater to various interests. Central Florida's famous Legoland Florida Resort is a major highlight, located just off Cypress Gardens Boulevard, offering a family-friendly atmosphere with rides, shows, and interactive experiences. The nearby Chain of Lakes provides scenic views and opportunities for outdoor activities, including fishing, boating, and picnicking along the waterfront.

The historic downtown area features charming shops, local eateries, and events throughout the year, making it a great place to explore on foot. Additionally, the Bok Tower Gardens, located a short drive away, showcases beautiful gardens, walking paths, and a stunning carillon tower, all set in a peaceful environment superb for relaxation and nature walks.
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 cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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