Winter Haven vacation rentals

We found 1,119 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

10% off
Price is CA $464
CA $4,181 total
includes taxes & fees
Eagle Haven Lake House

Find spaces that suit your style

Find out more about Winter Haven

Why visit Winter Haven

  • Picturesque lakes: Winter Haven boasts beautiful lakes perfect for relaxation and outdoor activities.
  • Thrilling amusement parks: Experience family fun at nearby amusement parks that offer rides and entertainment for all ages.
  • Serene urban parks: Enjoy the peaceful atmosphere of local parks, ideal for picnics and leisurely strolls.
  • Charming neighborhoods: Explore friendly communities that reflect the warmth and hospitality of the region.
  • Variety of accommodations: Choose from budget-friendly rentals, including homes, villas, and condos tailored to family needs.

Popular types of accommodation in Winter Haven

Planning a getaway to Winter Haven, Florida? You're in for a treat. Discover the most sought-after vacation rentals, including private homes, villas, and condos that cater to your needs. Whether you're looking for family-friendly accommodations or properties with convenient laundry facilities, Winter Haven has it all. Explore your options and find the perfect stay that offers comfort and savings for your trip.

  • Houses: The top choice for visitors to Winter Haven, these homes offer spacious, comfortable accommodations perfect for families or groups.
  • Villas: These luxurious properties provide a blend of elegance and relaxation, ideal for those seeking a premium experience.
  • Condos: A convenient option, condos often come with shared amenities and are great for short stays.
  • Apartments: Offering a homey feel, apartments are perfect for solo travelers or couples looking for a local experience.
  • Cottages: These quaint and charming spaces provide a cozy atmosphere, perfect for a peaceful getaway.**

Top attractions in and around Winter Haven

Winter Haven is an ideal destination for families and outdoor enthusiasts, offering a variety of activities that include exploring picturesque lakes, thrilling amusement parks, and serene urban parks. Visitors can enjoy a blend of adventure and relaxation, making it perfect for those seeking memorable experiences in a beautiful setting. Whether you're looking for family fun or a beach-like atmosphere, Winter Haven has something for everyone.

  • LEGOLAND® Florida: This vibrant amusement park offers a fantastic experience with its creative LEGO-themed attractions, rides, and shows. Perfect for families, it features interactive adventures and beautiful outdoor spaces, making it a delightful day out for visitors of all ages.
  • Auburndale City Park: Located 8.0km away, this urban park provides a serene escape with lush green spaces, picnic areas, and playgrounds. It's ideal for families looking to enjoy outdoor activities amidst a charming city atmosphere.
  • The Circle B Bar Reserve: About 14.5km from Winter Haven, this nature preserve offers an adventurous experience with hiking trails, wildlife viewing, and scenic landscapes. It's a perfect spot for nature enthusiasts and those seeking a bit of wilderness.

Things to do recommended for couples

Planning a romantic getaway in Winter Haven? Enjoy thrilling water sports at Chain Of Wakes, where adventure awaits. Then, indulge in a delightful wine tasting at True Blue Winery, located 19.3km away, perfect for a cozy evening filled with romance and entertainment.

Things to do recommended for families

During your family vacation in Winter Haven, explore Chain of Lakes Park for sports fun, unwind at Lions Park for relaxation, and enjoy a thrilling time at Indigo's Billiards, Bowling & Games, where adventure awaits for all ages.

Things to do recommended for groups

In Winter Haven, groups can enjoy a captivating performance at Theatre Winter Haven, have fun at Indigo's Family Fun Center, or hit the greens at Lake Henry Golf Club for a day of outdoor sports. These experiences ensure a memorable time for everyone in the group.

*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

When planning your trip—whether you're traveling with friends, family, bringing along your pets, or seeking extended stays—it's important to refine your search based on what matters most to you. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Winter Haven with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas suitable for group gatherings. Thankfully, you can easily apply filters for all these options and more on Vrbo.
  • Traveling to Winter Haven with young kids: Traveling with little ones 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 attractions that are great for families.
  • Taking your pets with you to Winter Haven: For many families, a trip feels incomplete without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Most 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 seeking vacation rentals with special offers for stays of a month or more, you've come to the right spot. By utilizing 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 as well.

Where to stay in and around Winter Haven

Winter Haven, Florida, is an ideal destination for families seeking a lakeside getaway in Central Florida. With its friendly atmosphere and abundance of outdoor activities, visitors can enjoy a relaxing vacation filled with adventure. Explore nearby attractions and discover charming neighborhoods that embody the warmth of friendly people and budget-friendly options, making it a perfect spot for creating memorable experiences with loved ones.

  • Eagle Lake: Located a mere 4.8km from Winter Haven, Eagle Lake is a charming city that offers a delightful family-friendly atmosphere and a variety of outdoor activities. Visitors can enjoy an array of entertainment options, including a nearby amusement park and shopping mall. The area is also home to beautiful local landmarks, including a scenic beach and a popular theme park, making it a perfect destination for those seeking both relaxation and excitement. With its quaint charm and accessible amenities, Eagle Lake is an ideal spot for families looking to create lasting memories.
  • Cypress Gardens: Nestled in the Winter Haven area, Cypress Gardens is a picturesque village known for its adventurous spirit and family-oriented experiences. The village boasts a selection of resorts and an amusement park, ensuring that visitors have ample opportunities for fun and relaxation. Golf enthusiasts will also find several excellent courses nearby. Attractions such as a renowned theme park, a stunning beach, and a film studio provide unique experiences for travelers. With its blend of adventure and leisure, Cypress Gardens is a must-visit for families and thrill-seekers alike.
  • Inwood: Also located in the vicinity of Winter Haven, Inwood is a delightful village that embraces outdoor adventures and family-friendly fun. The area features a variety of resorts and amusement parks, as well as golf courses for those looking to enjoy a round in the sun. Visitors can explore local attractions such as a beautiful lake, an exciting theme park, and a stadium that often hosts events. Inwood offers a welcoming atmosphere for families and outdoor enthusiasts, making it a fantastic destination for those seeking adventure and relaxation.

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 a breeze

Are you hoping to save on your next getaway? Being flexible with your travel dates can lead to better deals, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even greater savings. To discover a Vrbo property that aligns with your budget, feel free to utilize our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides you with a convenient platform to plan new adventures, manage your ongoing travel arrangements, or review and organize your reservations. Your saved or booked properties are thoughtfully categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please 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)
  • Peppa Pig Theme Park Florida (3.6 mi / 5.8 km)
  • Lake Myrtle Sports Complex (7.4 mi / 12 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)

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)
  • Sanlan Bird and Wildlife Sanctuary (10.2 mi / 16.5 km)
  • Bok Tower Gardens (11.2 mi / 18 km)
  • Twin Lakes (11.9 mi / 19.2 km)
  • Lake Parker (12.5 mi / 20.1 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?
When considering a vacation rental in Winter Haven, Florida, a popular area to stay is the downtown vicinity. This charming neighbourhood offers a delightful mix of local shops, restaurants, and a vibrant setting. One of the top attractions here is the beautiful Chain of Lakes, where visitors can enjoy scenic views, boating, and picnicking along the waterfront. Additionally, the nearby LEGOLAND Florida Resort provides a fun-filled experience for families and those young at heart, featuring rides, shows, and interactive attractions.

Another great option is the picturesque Cypress Gardens area, known for its stunning botanical gardens and serene landscapes. This area, steeped in history, is superb for those looking to unwind amidst nature while still being close to various amenities.
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 travelling 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.
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.
What is the most popular type of vacation rental accomodation in Winter Haven?
In Winter Haven, vacation houses are the most popular type of vacation rental, with around 440 available throughout the area. These properties typically offer spacious living arrangements, multiple bedrooms, and fully equipped kitchens, making them ideal for families or larger groups. Many also feature outdoor spaces such as private gardens or patios, great for enjoying the warm Florida weather. Additionally, there are about 100 apartments, which provide a more compact option for couples or solo travellers, often including amenities like pools and fitness centres. Cottages and villas, with 64 and 16 options respectively, offer a more quaint and relaxed atmosphere, while several condos can also be found, providing yet another alternative for visitors.
Are there any family house rentals in Winter Haven?
In Winter Haven, Florida, there is a substantial selection of family-friendly houses available, with around 101 options to choose from. This charming city is renowned for its beautiful chain of lakes, making it an appealing destination for families looking to enjoy water-based activities. Many of the homes feature spacious living areas, full kitchens, and outdoor patios or gardens, great for barbecues or simply unwinding after a day of adventure.

Families will find amenities such as Wi-Fi, air conditioning, and laundry facilities common in these properties, ensuring a comfortable and convenient stay. Additionally, the locale is near popular attractions like LEGOLAND Florida, which offers fun for all ages, and the serene Bok Tower Gardens, where visitors can explore lush landscapes and enjoy the famous carillon music.
Can I rent a vacation home with a pool or hot tub in Winter Haven?
In Winter Haven, there are many vacation homes available for rent that come with pools and hot tubs, with approximately 61 options to choose from. This picturesque city, known for its chain of lakes and pleasant weather, features various neighbourhoods where these rentals can be found, including the tranquil areas near Lake Eloise and the more vibrant spots close to Lake Howard.

Travellers can expect a range of amenities in these properties, such as private swimming pools, relaxing hot tubs, spacious outdoor patios, and fully equipped kitchens, ideal for enjoying both relaxation and social gatherings. 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. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Winter Haven?
In Winter Haven, there is a wide selection of pet-friendly house rentals available, with around 54 options to choose from. These vacation homes often come equipped with amenities such as spacious backyards, modern kitchens, and comfortable living areas, making them ideal for families or groups travelling with pets. Many properties feature additional conveniences like laundry facilities, outdoor seating areas, and even private pools, enhancing the overall experience for pet owners.

The area is known for its beautiful lakes and parks, providing ample opportunities for outdoor activities with pets. Nearby, you can explore the scenic Chain of Lakes, which offers walking trails and picnic spots, superb for enjoying the Florida sunshine with your four-legged friends. Additionally, local pet-friendly cafes and shops contribute to a friendly setting for those travelling with pets. See all pet-friendly rentals in Winter Haven.
Are there any remote work vacation rentals in Winter Haven?
In Winter Haven, there are numerous options for remote work vacation rentals, with around 572 available throughout the area. Many of these properties cater specifically to those needing a productive work environment, featuring amenities such as high-speed Wi-Fi, dedicated work desks, and comfortable chairs to ensure an efficient workspace.

The city is known for its picturesque Chain of Lakes, offering opportunities for outdoor activities during breaks from work. Additionally, many rentals include fully equipped kitchens, allowing guests to prepare meals conveniently. For those seeking a balanced work-life experience, the nearby attractions, such as Legoland Florida Resort and beautiful parks, provide ample opportunities for relaxation after a day of remote working. 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 travellers 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 well-equipped kitchens, ensuring guests can prepare their own meals. Onsite parking is typically available, making it convenient for those travelling with cars. Many rentals also feature coffee and tea makers, allowing visitors to enjoy a warm drink at their leisure. Additionally, outdoor spaces like decks or patios are common, providing a pleasant area to relax and unwind after a day of exploring the local attractions.
When is the best time to visit Winter Haven for a vacation rental?
The ideal 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 vibrant period attracts visitors looking for warmer weather and an abundance of outdoor activities. With temperatures typically ranging from 15 to 28 degrees Celsius, it's superb for enjoying the area's famous attractions, including the stunning Legoland Florida Resort and the beautiful Chain of Lakes.

During these months, you can expect a buzzing atmosphere filled with travellers, all eager to partake in the numerous recreational opportunities. From boating and fishing to exploring the local parks, there's something for everyone to enjoy in the mild sunshine.

If you're looking for a more budget-friendly option, November is a wonderful time to visit Winter Haven. This month offers a quieter experience, allowing you to explore the area's charming attractions without the crowds. The weather remains pleasant, making it a great time for leisurely strolls and enjoying the scenic views.

Ultimately, the best time to book your vacation rental in Winter Haven depends on your preferences for social atmosphere and outdoor activities.
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 highlight the area's unique charm. The most top is Legoland Florida Resort, a family-friendly set-up park that offers rides, shows, and interactive experiences based on the popular LEGO toy brand. This park is a major draw for families staying in the area and is located near several rental options.

For those interested in nature, the Chain of Lakes provides opportunities for boating, fishing, and scenic walks along the water. The surrounding parks, such as Lake Howard Nature Park, feature walking trails and picnic areas, superb for outdoor enthusiasts.

Additionally, downtown Winter Haven boasts a selection of shops, cafes, and restaurants, allowing visitors to experience local cuisine and culture. The historic area is also home to the beautiful theatre, which often hosts community events and performances.
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 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 travellers 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 cosy cabin or a beach house, 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.

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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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