351+ Private Villas and Holiday Rentals in Winter Haven |
  1. USA
  2. Florida
  3. Lakeland - Winter Haven
  4. Winter Haven

Winter Haven Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Winter Haven

Discover more than 351 vacation rentals available in Winter Haven. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Winter Haven.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winter Haven, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Winter Haven. On average, places to stay near Winter Haven offer 873.1 ft², with nightly prices averaging GB £197.

With Casai, finding and comparing holiday rentals in Winter Haven is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Winter Haven

Type Count
Vacation Homes 234
Holiday Apartments 48
Cottages 10
Villas 3

Use these Quick Filters to Find a Holiday Rental in Winter Haven

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Winter Haven.

Weather in Winter Haven, FL

View the weather forecast for Winter Haven before booking your Winter Haven Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Winter Haven, FL

Casai offers a large selection of top attractions around Winter Haven . Research things to do on your vacation before you visit Winter Haven.


Legoland Florida
Chain of Lakes Park
Theatre Winter Haven
Chain Of Wakes
Indigo's Family Fun Center
Northgate Shopping Center
Cypresswood Golf and Country Club
Inman Park
Sertoma Park
Rotary Park
Willowbrook Golf Course
Lake Henry Golf Club
Lake Conine
Lake Region Golf Club
Indigo's Billiards
Baytree Golf Club
Winter Pines Golf Course
Winter Haven Hospital
Baycare Womens Hospital
Winter Haven Women's Hospital

Other Places to Stay in Winter Haven, FL


Polk County 15,911 Properties
Lake Henry Golf Club 518 Properties
Baycare Womens Hospital 229 Properties
Winter Haven Women's Hospital 229 Properties
Theatre Winter Haven 229 Properties
Indigo's Billiards 228 Properties
Indigo's Family Fun Center 226 Properties
Chain of Lakes Park 224 Properties
Rotary Park 208 Properties
Inwood 126 Properties
Cypress Gardens 81 Properties
Jan Phyl Village 66 Properties

Frequently Asked Questions About Winter Haven?

What are the top holiday rentals in Winter Haven?

With numerous options available in Winter Haven, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Winter Haven:

How many holiday rentals have private pools in Winter Haven?

Discover a selection of holiday rentals with private pools near Winter Haven with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Winter Haven are best for families?

If you're searching for a family-friendly holiday home in Winter Haven, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Winter Haven:

How many Casai.uk holiday rentals are available in Winter Haven?

As of 2025, Casai boasts over 351 properties listed in the Winter Haven area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winter Haven.

Nearby Neighborhood (1) 
Neighborhood Property Count
Winterset Gardens Vacation Rentals in Winter Haven, Florida 106

People Also Ask

There are 351 Winter Haven, FL Holiday Rentals

Recently Booked Holiday Rentals in Winter Haven