Located in Central Florida, Winter Haven is home to 50 lakes, making it an ideal destination for waterskiing and fishing enthusiasts. So if you are visiting for some fun on the lake, there is a broad range of vacation homes to choose from in Winter Haven. Depending on your budget, you can get a luxury condo, villa or an apartment that offers the ultimate comfort and convenience. There are vacation houses that feature spectacular lakeside views while providing welcoming neighborhood charm.

Choose the perfect vacation rental
Best Vacation Home Deals in Winter Haven
Save up to 41%
Find a rental that fits your preferences among the 284 fantastic options from more than 7 partner websites in Winter Haven. The website HomeToGo instantaneously compares all of these rentals so you can save up to 33%!
Top-Rated Rentals and Accommodations in Winter Haven
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Recommended Vacation Rentals in Winter Haven
Find your perfect vacation rental in Winter Haven: from $47 per night
Budget-friendly Vacation Rentals in Winter Haven
Find Fantastic yet Inexpensive Offers
Vacation rentals with Wi-Fi
Stay connected while traveling and book a Winter Haven accommodation with high-speed internet.
Apartments and vacation rentals with a kitchen
Cook up a feast on your next vacation and book a Winter Haven rental with full kitchen.
Vacation rentals and apartments with air conditioning
Keep cool during your trip to Winter Haven and book a vacation rental with air conditioning.
Popular Rental Amenities in Winter Haven
Select a filter to find an accommodation meeting your criteria among the 284 properties in Winter Haven. Many vacation rentals in Winter Haven offer "Pool" or "Pets allowed," which makes it a great vacation spot if you want a rental with a pool or you travel with your pet. You could even look for accommodations if you want a rental providing a crib (54 rentals include "Crib" in Winter Haven) or if you need a fenced-in backyard (13 rentals in Winter Haven include "Fenced").
The Weather in Winter Haven
Check out the climate diagram for Winter Haven. The highest average temperatures are in the month of June. Conversely, January is the coolest month in Winter Haven, with temperatures going under 52° The rainiest month is July while the driest month is March.
7-Day Weather Forecast in Winter Haven
Accommodations for your vacation in Winter Haven
Information about vacation rentals in Winter Haven
🏡 Vacation rentals available | 284 homes |
---|---|
💳 Possible discounts | up to 33% |
🌙 Nightly prices starting at | $47 |
⭐ Popular amenities | Pool, Pets allowed and Internet |
🐾 Pet friendly homes | 34 homes |
🏊 Vacation rentals with pools | 166 homes |
Frequently Asked Questions
What is the nightly price for a vacation home in Winter Haven?
The nightly price of accommodations in Winter Haven starts at $47. If you are looking for a house rental, the nightly price is $291 on average. A apartment rental Winter Haven will cost $154 per night on average.
How many vacation homes are available for booking in Winter Haven?
Currently there are 284 vacation rentals in Winter Haven to browse and book for your next trip.
What amenities are most popular for vacation rentals in Winter Haven?
Travelers search for Pool, Pets allowed, and Internet when booking a vacation rental in Winter Haven.
How many vacation rentals with a pool are there in Winter Haven?
Check out 166 vacation rentals available in Winter Haven for renting.
Are pets allowed in vacation homes in Winter Haven?
Finding a vacation home in Winter Haven that allows pets is easy, with 34 pet-friendly available.
What's the best time to travel to Winter Haven?
Winter Haven has its warmest time of year around June and July, with average nightly prices around $47.
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