Winter Haven vacation rentals

We found 1,215 vacation rentals — enter your dates for availability

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.

Vacation rentals with weekly discounts - Winter Haven

Showing deals for:Aug 1 - Aug 8
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Find out more about Winter Haven

Find out more about Winter Haven

Why visit Winter Haven

  1. Thrilling attractions: Visit exciting theme parks and enjoy a variety of rides, perfect for family fun.
  2. Scenic lakes: Experience the beauty of Winter Haven's lakes, ideal for relaxing and outdoor activities.
  3. Family-friendly atmosphere: Enjoy a welcoming environment that caters to families and vacationers alike.
  4. Cozy accommodations: Choose from a range of vacation rentals, including private homes and stylish condos.
  5. Nearby beaches: Explore beautiful Clearwater Beach for a perfect day trip to soak up the sun.

Popular types of accommodation in Winter Haven

If you're exploring vacation rentals in Winter Haven, you'll find a variety of appealing options. The most popular types of accommodations include Houses, Apart Hotels, and Condos. Whether you’re searching for a cozy retreat with a private pool, pet-friendly rentals, or units equipped with a dryer, Winter Haven has something to suit every traveler’s needs. Enjoy your stay with transparency, savings, and the reassurance you deserve!

  • Houses: The top choice for visitors, these spacious homes offer comfort and privacy, perfect for families or groups.
  • Condos: A popular option, condos provide convenient amenities and often stunning views, ideal for a relaxed stay.
  • Apartments: Offering a home-like atmosphere, apartments are great for those looking for flexibility and a local experience.
  • Villas: Known for their luxury and spaciousness, villas are perfect for a lavish getaway in Winter Haven.
  • Cottages: Quaint and charming, cottages provide a cozy retreat, perfect for couples or solo travelers.**

Top attractions in Winter Haven

Winter Haven, Florida, is a fantastic destination for families and outdoor enthusiasts alike. With its mix of theme parks, scenic lakes, and urban parks, there's no shortage of entertainment and adventure. Whether you're looking to enjoy thrilling rides or relax by the water, Winter Haven offers a variety of attractions that cater to every traveler's desire for outdoor fun and beautiful scenery. Plan your visit for an unforgettable experience!

  1. LEGOLAND® Florida: This vibrant theme park offers a world of imagination with LEGO-themed rides, attractions, and interactive experiences perfect for families. Explore colorful lands, enjoy live shows, and build your own creations in a fun-filled environment.
  2. Auburndale City Park: Just 5 miles from Winter Haven, this urban park features lush greenery, playgrounds, and picnic areas, making it an ideal spot for family outings and outdoor activities amid a city vibe.
  3. The Circle B Bar Reserve: Located 9 miles away, this natural preserve is perfect for adventure seekers. Enjoy scenic trails, diverse wildlife, and opportunities for birdwatching in a serene and picturesque setting.

Things to do recommended for couples

For a romantic getaway in Winter Haven, try water sports at Chain of Wakes for adventure, experience the thrill of Jump Florida Skydiving nearby, or enjoy a luxurious day at Ridgewood Lakes Golf and Country Club. Each offers unique experiences perfect for couples seeking fun and excitement.

Things to do recommended for families

Explore Chain of Lakes Park for sports fun, unwind at Lions Park just 5 miles away for wellness and relaxation, or enjoy family-friendly games at Indigo's Billiards, Bowling & Games in Winter Haven. Each destination offers a unique experience perfect for creating lasting memories.

Things to do recommended for groups

Experience the vibrant culture at Theatre Winter Haven, enjoy shopping at Northgate Shopping Center, and hit the greens at Cypresswood Golf and Country Club. These activities offer a perfect blend of entertainment, family fun, and outdoor enjoyment for your group in Winter Haven.

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, pets, or seeking extended stays—be sure to prioritize your preferences when filtering your options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Winter Haven with a group: Think about how many bedrooms you'll require, along with additional features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Winter Haven with young kids: Traveling with young kids can be a bit of a challenge. It’s important to prioritize their comfort and safety, along with finding amenities that are suitable for their age, like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Winter Haven: For many families, a vacation just wouldn’t feel right without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone, including your pet, 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 month-long stays, 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 amenities like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay in Winter Haven

Winter Haven, Florida, is a fantastic destination for families seeking entertainment and outdoor adventures. With its friendly atmosphere and sunny weather, visitors can explore nearby attractions like the beautiful Clearwater Beach and enjoy quiet neighborhoods perfect for relaxation. Whether indulging in excursions or soaking up the local vibe, Winter Haven offers the ideal experience for snowbirds and vacationers alike, ensuring a memorable getaway in a family-friendly environment.

  • Kissimmee: Located 27 miles from Winter Haven, Kissimmee is a vibrant city that serves as a gateway to Florida's famous attractions. Known for its family-friendly environment, Kissimmee offers a plethora of entertainment options, including world-renowned theme parks, shopping malls, and resort experiences. Visitors can explore various activities such as dining, shopping, and live entertainment. Notable landmarks nearby include iconic theme parks, a film studio, and beautiful beaches, making it an ideal destination for families seeking adventure and relaxation.
  • Eagle Lake: Only 3 miles from Winter Haven, Eagle Lake is a charming small city that captures the essence of outdoor family fun. Known for its serene environment, it offers a variety of recreational activities, including golfing and resort experiences. Eagle Lake is the perfect spot for those looking to unwind while enjoying nature. With proximity to beautiful beaches and family-friendly attractions, this city is ideal for travelers wanting both adventure and relaxation in a picturesque setting.
  • Cypress Gardens: Nestled in the Winter Haven area, Cypress Gardens is a delightful destination known for its lush landscapes and outdoor activities. This area is perfect for families seeking entertainment and adventure, featuring golf courses and resort-style amenities. The nearby theme parks, pristine beaches, and tranquil lakes add to the allure of Cypress Gardens, making it a must-visit for anyone looking to enjoy Florida's natural beauty and recreational options.

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 iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
February64.4°F (18.0°C)No Rain (Dry)Mostly SunnyAverageAverage
March67.5°F (19.7°C)Light RainMostly SunnySlightly HighSlightly High
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 SunnyAverageAverage
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 LowSlightly Low
December64.2°F (17.9°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is simple

Are you eager to save on your upcoming travel adventure? Being flexible with your travel dates can lead to great savings, as prices often fluctuate. Additionally, booking a longer stay can offer substantial discounts. To discover a Vrbo property that aligns with your budget, feel free to use our filters to refine your search by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your booking. Being the planner truly has its rewards! When you join our travel rewards program, One Key, you’ll gain immediate access to exclusive member savings and the ability to earn and redeem OneKeyCash™ on eligible reservations. Sign up now and begin enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo's user-friendly Trip Board offers you a convenient way to plan new trips, pick up right where you left off, or manage your travel arrangements. You can easily access the properties you’ve saved or booked, all organized into categories like Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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?
Among the more sought-after neighborhoods to book a vacation property in Winter Haven is Cypress Gardens. Find your dream stay on Vrbo and explore this area as a local.
What is the most popular type of vacation rental accommodation in Winter Haven?
Apartments are the most popular style of vacation rental in Winter Haven, according to our data. Even if you’ve got something different in mind, Vrbo has vacation homes in many sizes and shapes. Look over our options to find your ideal fit.
How much does it cost to rent a vacation rental in Winter Haven?
Length of stay, property type and time of year are some things that can influence the price of a vacation home. Simply enter your dates of travel to find your perfect escape. From homey country cottages to sprawling luxury villas, all Vrbo vacation rentals provide unbeatable value.
How much does it cost to rent a beach house in Winter Haven?
When you travel and the style and size of the property will help determine the cost of your beachside vacation rental. Put in your Winter Haven travel dates to view your options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use our filters to pick the amenities and features you need.
Are there pet-friendly vacation rentals in Winter Haven?
Pack a suitcase and a bone for the pup in your life because Winter Haven has 84 properties that open their doors to pets. Let your happy hound get in on the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates and destination, then check our “Pets allowed” filter box.
Can I rent a house with a pool in Winter Haven?
Add an extra layer of fun to your adventure by staying in one of the 40 houses with a private pool in Winter Haven. Use our handy search filter to find the kind of property you want on Vrbo, and then spend leisurely days splish-splashing around in a swimming pool that’s just for you.
What are popular rental amenities in Winter Haven?
When it comes to rental amenities that guests search for in Winter Haven, ski-in/ski-out facilities, a barbecue grill and a nearby river rank highest. With Vrbo vacation rentals, you’ll enjoy choices to match your style and taste, whether you’re taking a trip with your partner, your friends or even pets.
Are there large group vacation rentals in Winter Haven?
Winter Haven has 15 vacation rentals that can fit 10 or more people. These stays come with the space you need to enjoy good times with your favorite people.
Are there vacation rentals in Winter Haven that welcome kids?
Bring the entire family together for an adventure in Winter Haven at one of our 80 family-friendly vacation rentals. A lot of these stays come with conveniences that are ideal for getaways with youngsters, such as dining rooms, living rooms and pools. Just click on the “Properties good for families” filter and pick out your favorite.
What are the top attractions for families in Winter Haven?
Keep the kids amused at these fun family-friendly attractions in Winter Haven:

  • Indigo’s Family Fun Center
  • Lake Henry Golf Club
  • Cypresswood Golf and Country Club

Are there one-bedroom vacation rentals in Winter Haven?
You’ll find 24 one-bedroom properties in Winter Haven to select from. A one-bedroom vacation home is an excellent option if it’s just you and your sweetheart or if you’re traveling alone. Throw in more privacy, convenience and space than a hotel, and you’re bound to have an unforgettable break.
Can I find two-bedroom vacation rentals in Winter Haven?
You can pick from 12 two-bedroom rentals in Winter Haven. Give your little ones the second room or maybe fill it with a couple of your besties. There’s ample space for whoever’s fortunate enough to be joining in on the fun.
Are there vacation rentals with WiFi in Winter Haven?
Take your pick of 49 vacation rentals with WiFi in Winter Haven. If you want to disconnect from daily life on your trip, but still need to be connected to the internet, these properties are for you. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Winter Haven?
Winter Haven has 76 vacation rentals where you’ll be able to relax in air-conditioned comfort. To book a property on Vrbo featuring this perk, enter your preferred travel dates and use the handy filter tool to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Winter Haven?
The minimum age allowed can vary across properties on Vrbo, so double-check the rules of the vacation home in Winter Haven you’re considering. But usually, it’s 16, 18 or 21.
How long can I rent a vacation rental in Winter Haven for?
The amount of time you can book a Winter Haven vacation home for is up to the property. Just tap in your preferred travel dates to see options that offer long-term stays. They include all you need to make your extended vacation more comfortable and convenient, such as air conditioning and kitchens. Some Vrbo vacation homes may also offer weekly or monthly discounted prices, so you can hang around longer for less.
Does Vrbo offer discounts for vacation homes in Winter Haven?
Whether you’ve got your eye on one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to score some incredible deals and discounts on Vrbo. From mini stays to extended getaways, we’ve got the ideal space for your next Winter Haven escape.

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