Discover Your Perfect Winter Haven Resorts

Winter Haven Resorts

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10.0 (5 Reviews)
House
Getaway Clubhouse
  • Air Conditioner
  • View
  • Security/Safety
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Why Choose Rent By Owner for your Winter Haven Resorts?

What makes our Resorts special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Winter Haven Resorts

Where are the best neighborhoods to stay in Winter Haven?

When seeking the perfect place to stay in Winter Haven, Florida, exploring neighborhoods like Downtown Winter Haven offers a vibrant atmosphere close to local amenities and scenic views. Alternatively, the areas near Lake Henry provide tranquil surroundings ideal for relaxation and outdoor activities. Whichever neighborhood you choose, you'll find a welcoming environment that's tailored to make your visit comfortable and memorable.

Winterset Gardens

In this inviting neighborhood, you can enjoy a peaceful atmosphere that's perfect for relaxing stays. Its convenient location provides easy access to the area's attractions, making your visit both comfortable and memorable.

View 149+ Rentals in Winterset Gardens

Best Times to Visit Winter Haven

When should you plan your Resorts stay?

Choosing the right time to visit here can enhance your experience and ensure you enjoy the region's pleasant weather, making it an ideal destination for a relaxing getaway at the most favorable period of the year.

Peak Season Highlights

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Winter (December to February)

During this peak season, you’ll enjoy mild temperatures ideal for outdoor activities and relaxation, making it a popular time to visit the region's resorts.

Average Temperature Daytime: 75°F - Nighttime: 55°F
spring
Spring (March to May)

Springtime draws visitors seeking pleasant weather and blooming landscapes, which create a vibrant backdrop for your stay at the resorts here.

Average Temperature Daytime: 80°F - Nighttime: 60°F

Off-Season Highlights

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Summer (June to August)

In summer, the region experiences higher temperatures and humidity, leading to fewer crowds and more availability at resorts for those seeking a quieter retreat.

Average Temperature Daytime: 90°F - Nighttime: 70°F
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Fall (September to November)

Autumn offers cooler weather and fewer travelers, making it an excellent time to find great deals on resorts while still enjoying comfortable outdoor conditions.

Average Temperature Daytime: 78°F - Nighttime: 58°F

Weekly Weather Forecast for Winter Haven

How to Book Your Winter Haven Resorts

What's our booking process?

Our platform allows you to browse a curated selection of resorts. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Winter Haven

More Top-Rated Resorts in Winter Haven Area

Common Resorts Amenities

What amenities can you expect?

Our Resorts are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a refreshing swimming pool to relax after exploring the area’s attractions.
  • Take advantage of outdoor grilling areas for delicious meals outdoors with family and friends.
  • Make use of spacious patios or decks perfect for lounging and soaking up the sun.
  • Benefit from beautifully landscaped gardens that enhance your outdoor experience.
  • Stay active with access to tennis courts or other outdoor sports facilities.
  • Unwind by a private or community hot tub, ideal for relaxing under the stars.
  • Explore walking or biking trails nearby to enjoy the scenic surroundings of this destination.

Top Attractions Around Winter Haven

What attractions are nearby?

In this vibrant region, you can explore a variety of outdoor activities such as boating, fishing, and water sports on the scenic lakes, or enjoy nearby golf courses and nature trails that offer a perfect escape for outdoor enthusiasts visiting [Florida](#) to stay at comfortable resorts designed for relaxation and adventure alike.

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Family Activities

  • LEGOLAND Florida Resort: Experience a day of family fun with exciting rides, interactive attractions, and immersive Lego-themed experiences suitable for all ages.
  • Hollis Garden: Enjoy a relaxing stroll through this beautifully maintained botanical garden, perfect for family picnics and exploring vibrant plant displays.
  • Chain of Lakes: Take advantage of the area's scenic lakes for boating, fishing, or simply enjoying peaceful waterfront views with your loved ones.
  • Theatre Winter Haven: Catch family-friendly performances and live shows that offer entertainment for children and adults alike in this charming regional theatre.
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Adult Activities

  • Lake Mirror Civic Center: Experience the vibrant arts and cultural scene through engaging performances and exhibits in this central venue.
  • Chain of Lakes: Enjoy kayaking, paddleboarding, or simply relaxing lakeside while taking in the scenic views of this popular waterway.
  • LEGOLAND Florida Resort: Discover family-friendly adventures, interactive rides, and themed attractions that offer fun for adult visitors as well.
  • Historic Downtown Winter Haven: Stroll through charming streets featuring boutique shops, art galleries, and delightful dining options to explore here.

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Winter Haven Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit During Off-Peak Seasons: Visiting during less busy times allows you to enjoy the area’s natural beauty and attractions with fewer crowds, enhancing your overall experience.
  • Explore Local Dining and Entertainment Options: Take advantage of nearby restaurants and entertainment venues to immerse yourself in the regional culture and make your stay more memorable.
  • Take Advantage of Water Activities: The region offers numerous opportunities for boating, fishing, and other water-based recreation that you can conveniently access from your accommodation.
  • Utilize Concierge Services or Local Guides: Seek assistance from local experts to discover hidden gems and personalized experiences that elevate your trip here.

Transportation Options

  • Winter Haven Trolley: This convenient trolley service offers easy transportation around the area, making it simple to explore the region’s popular attractions and relax during your stay.
  • Rental Car Services: Numerous rental agencies are available in the vicinity, providing flexible options to navigate here at your own pace and access nearby destinations comfortably.
  • Taxi and Rideshare Options: Reliable taxi and rideshare providers operate throughout the region, offering quick and hassle-free transportation tailored to your schedule.
  • Public Bus Transit: The local bus system connects key points across the destination, enabling budget-friendly travel for exploring the region with ease.

Local Customs Options

  • Hammock Culture: You’ll find that relaxing in hammocks is a cherished local custom here, embodying the region’s laid-back atmosphere and appreciation for leisure.
  • Florida Citrus Traditions: Engaging in seasonal citrus festivals and enjoying fresh fruit is a common practice that celebrates the area's historic citrus industry.
  • Waterway Etiquette: Respect for boating and fishing customs along the lakes and canals is essential, reflecting the community's close relationship with its waterways.
  • Community Festivals: Participating in lively local festivals offers a glimpse into the area's vibrant cultural expressions and welcoming spirit.

Frequently Asked Questions About Winter Haven Resorts

1. What are the top Resorts in Winter Haven?

There are a lot of options in Winter Haven. If you plan on staying in the Winter Haven area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Resorts in Winter Haven:

2. How many Resorts are available in Winter Haven?

Currently, the total number of properties listed by RBO in 2026 is over 2 in the Winter Haven area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Winter Haven. 

3. What is the cancellation policy for resorts in this area?

Cancellation policies vary depending on the specific resort you choose. You should review the property's cancellation terms directly on the listing or contact the owner for detailed information.

4. Are there any additional fees or charges I should be aware of when booking a resort here?

Additional fees such as resort fees, cleaning charges, or taxes may apply. Please check the booking details for a complete breakdown of costs before confirming your reservation.

5. What amenities are typically included with resorts in this destination?

Resorts here often offer amenities like swimming pools, fitness centers, on-site dining, and recreational activities. Specific features can vary, so it's best to review each property's listing for exact details.

6. How do I confirm my reservation and what is the payment process?

Reservations are confirmed through the booking platform upon payment completion. Payment methods and confirmation procedures are outlined in each listing, so review these details before finalizing your booking.

7. Is it possible to get assistance or make special requests during my stay?

Yes, many properties accommodate special requests or provide assistance. Contact the host or property manager directly through the booking platform to discuss any specific needs or arrangements.

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