Winter Haven Resorts
383.19 ft²
25 Guests
380 Bedrooms
5 Bathrooms
Ocean View
Resort
- Oceanfront
- Fireplace/Heating
- Pool
AU $371/Night
For 7 Nights AU $2,600
376.74 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Free Cancellation
Resort
- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $112/Night
For 7 Nights AU $782
2497.23 ft²
12 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Pool
- Ocean View
AU $635/Night
For 7 Nights AU $4,447
1469 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $349/Night
For 7 Nights AU $2,440
1614.59 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- View
- Air Conditioner
AU $266/Night
For 7 Nights AU $1,864
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $620/Night
For 7 Nights AU $4,340
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
AU $348/Night
For 7 Nights AU $2,433
796.53 ft²
5 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- View
- Pet Friendly
AU $315/Night
For 7 Nights AU $2,203
600 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
AU $328/Night
For 7 Nights AU $2,299
2497.23 ft²
17 Guests
4 Bedrooms
3 Bathrooms
Free Cancellation
House
- Hot Tub
- Fireplace/Heating
- Pool
AU $1,655/Night
For 7 Nights AU $11,583
1279 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Fireplace/Heating
- Pool
- Ocean View
AU $307/Night
For 7 Nights AU $2,152
1883.68 ft²
12 Guests
4 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Balcony/Terrace
- View
AU $765/Night
For 7 Nights AU $5,357
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Why Choose Rent By Owner for your Winter Haven Resorts?
What makes our Resorts special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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 GardensBest 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
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 (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
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
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
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.
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.
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.
Other Places to Stay in Winter Haven, FL
Polk County
Lake Henry Golf Club
Theatre Winter Haven
Baycare Womens Hospital
Chain of Lakes Park
Winter Haven Women's Hospital
Indigo's Family Fun Center
Indigo's Billiards
Rotary Park
Inwood
Jan Phyl Village
Cypress Gardens
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:
- Private pool lake house with game room—just 4 minutes from LEGOLAND
- Waterfront Winter Haven Home with Dock & Hot Tub!
- Waterfront Lakehouse, Private Dock, Tiki Bar, Playground, Near Legoland | Lake Idylwild Delight
- Lake Rochelle Rental Lakefront
- Hot Tub & Fire Pit: Lakefront Home on Lake Eloise
- 3/2 kid friendly home, only minutes to Legoland.
- Spectacular Waterfront Home in Winter Haven
- Fantastic Water Front Home on the Chain of Lakes
- Cheerful 4 Bed, 3 Bath Home with Screened Pool
- Large Family Home, Legoland, Pet Friendly, 7 Beds
2. How many Resorts are available in Winter Haven?
Currently, the total number of properties listed by RBO in 2026 is over 3 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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