Best Vacation Homes in Winter Haven
1469 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $246/Night
For 7 Nights US $1,725
1614.59 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- View
- Air Conditioner
US $188/Night
For 7 Nights US $1,318
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $438/Night
For 7 Nights US $3,068
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $246/Night
For 7 Nights US $1,720
796.53 ft²
5 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- View
- Pet Friendly
US $222/Night
For 7 Nights US $1,557
600 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $232/Night
For 7 Nights US $1,625
1279 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Fireplace/Heating
- Pool
- Ocean View
US $217/Night
For 7 Nights US $1,521
412 ft²
5 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $78/Night
For 7 Nights US $549
Winter Haven Luxury Rentals
1216.32 ft²
12 Guests
2 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $1,875/Night
For 7 Nights US $13,125
1184.03 ft²
10 Guests
3 Bedrooms
1 Bathroom
House
- Fireplace/Heating
- Parking
- Air Conditioner
US $1,875/Night
For 7 Nights US $13,125
2497.23 ft²
17 Guests
4 Bedrooms
3 Bathrooms
Free Cancellation
House
- Hot Tub
- Fireplace/Heating
- Pool
US $1,170/Night
For 7 Nights US $8,188
2900 ft²
18 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $998/Night
For 7 Nights US $6,985
10 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $941/Night
For 7 Nights US $6,585
10 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $941/Night
For 7 Nights US $6,585
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $939/Night
For 7 Nights US $6,570
10 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $889/Night
For 7 Nights US $6,225
Winter Haven Pet Friendly Vacation Rentals
540 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $104/Night
For 7 Nights US $725
1883.68 ft²
12 Guests
4 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $541/Night
For 7 Nights US $3,787
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $417/Night
For 7 Nights US $2,920
1279 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Fireplace/Heating
- Pool
- Ocean View
US $215/Night
For 7 Nights US $1,503
3304.52 ft²
22 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pet Friendly
US $491/Night
For 7 Nights US $3,437
800 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $293/Night
For 7 Nights US $2,048
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $131/Night
For 7 Nights US $915
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $322/Night
For 7 Nights US $2,253
Winter Haven Large Vacation Homes
1926 ft²
12 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $386/Night
For 7 Nights US $2,700
1878.3 ft²
14 Guests
6 Bedrooms
4 Bathrooms
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $200/Night
For 7 Nights US $1,400
2953 ft²
12 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $486/Night
For 7 Nights US $3,402
2949.31 ft²
12 Guests
4 Bedrooms
3 Bathrooms
House
- Hot Tub
- Fireplace/Heating
- Pool
US $315/Night
For 7 Nights US $2,205
3000 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $842/Night
For 7 Nights US $5,893
12 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Pool
US $437/Night
For 7 Nights US $3,056
11 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $487/Night
For 7 Nights US $3,412
1800 ft²
12 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $510/Night
For 7 Nights US $3,569
Why Choose Rent By Owner for your Winter Haven Vacation Rental Homes?
What makes our Vacation Rentals 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 Vacation Rentals
Where are the best neighborhoods to stay in Winter Haven?
When planning your stay in Winter Haven, Florida, choosing the right neighborhood can significantly enhance your vacation experience. Whether you're interested in exploring serene lakeside communities or vibrant city areas, Winter Haven offers a variety of neighborhoods that cater to different preferences. Each area provides convenient access to local amenities and outdoor activities, making it easy to enjoy all that this charming Florida town has to offer. Discover the ideal location for your needs and enjoy a seamless booking process for your vacation rentals in Winter Haven.
Winterset Gardens
In this tranquil neighborhood, you’ll find a variety of vacation rentals that offer easy access to local parks and outdoor activities. The area provides a peaceful retreat while still being close to the attractions that make Winter Haven a popular destination.
View 149+ Rentals in Winterset GardensBest Times to Visit Winter Haven
When should you plan your Vacation Rentals stay?
Timing your visit to this destination can enhance your experience, as the area offers ideal conditions for enjoying the local attractions and amenities throughout different seasons.
Peak Season Highlights
Winter (December to February)
During the winter months, the area experiences its peak season as visitors seek warm-weather escapes and outdoor activities in this destination.
Average Temperature Daytime: 75°F - Nighttime: 55°F
Spring (March to May)
Spring attracts tourists with pleasant weather and blooming landscapes, making it an ideal time for exploring and enjoying your stay here.
Average Temperature Daytime: 82°F - Nighttime: 60°F
Off-Season Highlights
Summer (June to August)
Summer tends to be less busy as humidity and heat increase, but it remains a good time for those looking for affordable rates and fewer crowds.
Average Temperature Daytime: 88°F - Nighttime: 70°F
Fall (September to November)
Autumn sees a dip in visitors as temperatures cool down, providing a relaxed atmosphere perfect for discovering the region at your own pace.
Average Temperature Daytime: 80°F - Nighttime: 58°F
Weekly Weather Forecast for Winter Haven
How to Book Your Winter Haven Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. 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 Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals 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 private swimming pool to unwind after exploring the region's attractions.
- Take advantage of a spacious outdoor patio or deck for hosting gatherings or relaxing in the sun.
- Benefit from well-maintained outdoor grilling areas perfect for barbecues with family and friends.
- Make use of lush, landscaped gardens that add to the charm and tranquility of your stay.
- Avail yourself of a dedicated outdoor dining space to savor meals while enjoying the fresh air.
- Explore nearby lakes or waterways with access to fishing or kayaking opportunities.
- Utilize community amenities such as tennis courts or walking trails, common in many rental properties here.
Top Attractions Around Winter Haven
What attractions are nearby?
Enjoy a variety of outdoor activities nearby, including boating, fishing, and exploring scenic parks, making your stay in this destination a memorable adventure in the heart of Florida’s region.
Family Activities
- Legoland Florida Resort: Experience a fun-filled day exploring the themed rides and attractions designed for families, making it a perfect activity for those seeking adventure in this region.
- Haines City Water Sports & Adventures: Enjoy water-based activities such as kayaking and paddleboarding on nearby lakes, offering a refreshing way to explore the area's natural beauty.
- Winter Haven Historical Museum: Discover the history of the region through engaging exhibits, ideal for family outings that combine education with enjoyment.
- Chain of Lakes Park: Relax or play at this scenic park featuring playgrounds, walking trails, and picnic areas, providing a great outdoor experience for all ages here.
Adult Activities
- Visit the Chain of Lakes Park: Enjoy outdoor concerts, sports facilities, and scenic walking trails in this popular park that offers a relaxing escape for adults seeking leisure activities.
- Explore the Winter Haven Museum of Art: Immerse yourself in local culture and discover inspiring exhibitions at this charming art museum located within the region.
- Tour the Legoland Florida Resort: Experience the variety of attractions, including themed rides and shows, ideal for adults who appreciate entertainment and creative displays in this family-friendly destination.
- Enjoy boating and fishing on the lakes: Take advantage of the area's abundant freshwater lakes for a day of tranquil boating or fishing adventures tailored to your relaxation needs.
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?
- Explore Local Attractions: Take advantage of the nearby attractions to immerse yourself in the region’s unique charm and natural beauty while staying within your vacation rental.
- Plan Outdoor Activities: Make the most of the area’s pleasant climate by scheduling outdoor activities such as boating, fishing, or walking around local parks near your rental property.
- Choose Your Location Carefully: Select a vacation rental in a convenient part of the destination to easily access popular spots and maximize your time exploring here.
- Experience Seasonal Events: Check for seasonal festivals or events happening during your stay to enjoy authentic local culture without straying far from your accommodation.
Transportation Options
- Rental Car Services: Several major rental car companies operate here, offering convenient transportation to explore the area's attractions and scenic spots with ease.
- Public Transit Systems: The local bus system provides an affordable and accessible way to get around the region without the need for personal transportation.
- Taxi and Ride-Sharing Services: Taxis and ride-sharing options like Uber and Lyft are readily available, providing quick and reliable transit for your travel needs within the area.
- Bike Rentals and Pedestrian Pathways: Biking is an eco-friendly option here, with bike rentals and dedicated pathways allowing you to enjoy the region’s natural beauty at a leisurely pace.
Local Customs Options
- Holidays and Parades: You can experience local festivities during regional parades and holiday celebrations, which are cherished traditions here.
- Waterfront Customs: Embrace the area's love for lakeside living through boating, fishing, and picnicking along the scenic waterways.
- Farmers’ Markets: Visiting the local farmers' markets allows you to enjoy fresh produce and handmade goods rooted in this destination's agricultural heritage.
- Community Events: Participating in community festivals and outdoor concerts provides authentic insight into the friendly spirit that defines this region.
Frequently Asked Questions About Winter Haven?
1. What are the top vacation rentals 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 Vacation Rentals in Winter Haven:
- Private pool lake house with game room—just 4 minutes from LEGOLAND
- Waterfront Winter Haven Home with Dock & Hot Tub!
- Winter Haven, FL Pet Friendly Residential Retreat
- 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
2. How many vacation rentals have private pools in Winter Haven?
There are 38 vacation rentals with private pools near Winter Haven. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Winter Haven are best for families?
If you are looking for a family-friendly vacation home in Winter Haven, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winter Haven:
4. How many Rentbyowner vacation rentals are available in Winter Haven?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 408 in the Winter Haven area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Winter Haven.
5. What is the cancellation policy for vacation rentals in Winter Haven, Florida?
Cancellation policies vary by property; please review the specific listing details or contact the owner directly to understand the terms applicable to your booking in this area.
6. How do I confirm the availability of a vacation rental in Winter Haven?
Availability depends on the dates you select; use the booking platform’s calendar feature to check current availability or reach out to the property owner for real-time updates.
7. Are there any additional fees I should be aware of when booking vacation rentals here?
Additional fees such as cleaning fees, service charges, or taxes are typically listed during the booking process; verify these details on the particular listing before confirming your reservation.
8. What amenities should I expect from vacation rentals in this destination?
Amenities can vary, so review each property’s listing for details on features like Wi-Fi, pools, or kitchen facilities to ensure it meets your needs.
9. How can I ensure my stay in this region complies with local regulations?
It’s advisable to read the property description carefully and communicate with the owner about local rules or restrictions to ensure a smooth and compliant stay.
Winter Haven Top Rated Vacation Rentals
2300 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $364/Night
For 7 Nights US $2,548
3045 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $432/Night
For 7 Nights US $3,024
4732 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $612/Night
For 7 Nights US $4,282
11 Guests
4 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $529/Night
For 7 Nights US $3,706
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $401/Night
For 7 Nights US $2,809
7 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $388/Night
For 7 Nights US $2,714
1800 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $235/Night
For 7 Nights US $1,643
1760 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Kitchen
US $371/Night
For 7 Nights US $2,595
