What types of vacation rentals are available in Winter Haven?

There are loads of different property types that you can make your vacation home in Winter Haven. You’ll find apartments, campgrounds, chalets, condos, cottages, houses, homestays, houseboats and villas.

Are there any pet-friendly vacation rentals in Winter Haven?

There are a number of dog and pet-friendly Winter Haven vacation rentals, with around 10% allowing you to bring your pet along with you.

How much is a vacation rental in Winter Haven for tonight?

In the last 72 hours, users have found Winter Haven vacation rentals for tonight for as low as C$ 139.

How much is a vacation rental in Winter Haven for this weekend?

In the last 72 hours, users have found Winter Haven vacation rentals for this weekend for as low as C$ 163 per night.

How can I find vacation rentals near me in Winter Haven?

Take a look at our vacation rentals map to find the best vacation rental homes near you.

Winter Haven Vacation Rentals from C$ 55/night

Recommended by KAYAK

Best Winter Haven vacation rentals

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Winter Haven, FL, United States

9.2Wonderful(16)

House

Parking

Free Wi-Fi

Pet friendly

C$ 193+

Check availability

Modern Tiny Lake Cottageaceloc4mileslegoland

Winter Haven, FL, United States

9.3Wonderful(24)

Cottage

C$ 167+

Check availability

Stylish-N-Private 1br Retreat 2 Miles To Legoland

Winter Haven, FL, United States

8.1Very good(15)

House

Parking

Pet friendly

C$ 161+

Check availability

Cozy cove stay

Winter Haven, FL, United States

9.7Wonderful(11)

Apartment

Parking

Free Wi-Fi

Pet friendly

C$ 138+

Check availability

Winter Haven Apt 1 Mi to Polk State College!

Winter Haven, FL, United States

10Wonderful(6)

Apartment

Free Wi-Fi

Pet friendly

Spa

C$ 151+

Check availability

Unique cozy studio

Winter Haven, FL, United States

9.8Wonderful(7)

Apartment

Parking

Free Wi-Fi

C$ 156+

Check availability

Mco Tpa Lal Traveling Nurse Crashpad

Winter Haven, FL, United States

House

C$ 40+

Check availability

Large 3bedrooms 1 Bath Near Downtown Dining

Winter Haven, FL, United States

8.6Very good(11)

House

Parking

Pet friendly

C$ 243+

Check availability

Cheerful New Construction Home

Winter Haven, FL, United States

8.9Very good(25)

House

C$ 608+

Check availability

Peaceful Lakeside Retreat

Winter Haven, FL, United States

9.2Wonderful(14)

House

Parking

Free Wi-Fi

C$ 498+

Check availability

Charming 2-bedroom country house with AC, WiFi in Winter Haven

Winter Haven, FL, United States

6.8Okay(5)

House

C$ 233+

Check availability

1Bed 1Bath Container Home Centrally Located

Winter Haven, FL, United States

8.9Very good(23)

Chalet

Parking

Pet friendly

C$ 183+

Check availability

Oasis

Winter Haven, FL, United States

10Wonderful(1)

Campground

Free Wi-Fi

C$ 240+

Check availability

8 Mi to Legoland Winter Haven Home with Lanai!

Winter Haven, FL, United States

8.0Very good(1)

House

Free Wi-Fi

Spa

C$ 279+

Check availability

Central Private King Suit Washer Dryer 2 Miles to Hospital

Winter Haven, FL, United States

8.6Very good(23)

Apartment

Parking

Free Wi-Fi

Pet friendly

C$ 146+

Check availability

Historic home lake access, near parks and venues

Winter Haven, FL, United States

10Wonderful(6)

House

Parking

Free Wi-Fi

C$ 376+

Check availability

Booking Insights

KAYAK’s insights for vacation rentals in Winter Haven

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Winter Haven with confidence.

What is the cheapest day of the week to book a vacation rental in Winter Haven?

Thursday offers the lowest rates in Winter Haven, with an average nightly price of C$ 137. The highest prices are found on Wednesday, with average rates at C$ 377.

Find deals

Vacation rentals in Winter Haven are around 21% more expensive than hotels on average. Search here to compare prices for all accommodation types in Winter Haven.
The best vacation rental properties in Winter Haven are Soak up the charm of this cozy, recently remodel studio. (9.6, 28 reviews), Serenity Retreat, Confidently Clean (9.6, 22), and Hook, Line and Leisure Lakefront Gem with Porch! (9.6, 36), based on ratings and reviews from real travelers.
Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Winter Haven for 3 days.

What types of vacation rentals are available in Winter Haven?
There are loads of different property types that you can make your vacation home in Winter Haven. You’ll find apartments, campgrounds, chalets, condos, cottages, houses, homestays, houseboats and villas.
Are there any pet-friendly vacation rentals in Winter Haven?
There are a number of dog and pet-friendly Winter Haven vacation rentals, with around 10% allowing you to bring your pet along with you.
How much is a vacation rental in Winter Haven for tonight?
In the last 72 hours, users have found Winter Haven vacation rentals for tonight for as low as C$ 139. Search here for similar prices
How much is a vacation rental in Winter Haven for this weekend?
In the last 72 hours, users have found Winter Haven vacation rentals for this weekend for as low as C$ 163 per night. Search here for similar prices
How can I find vacation rentals near me in Winter Haven?
Take a look at our vacation rentals map to find the best vacation rental homes near you.

Winter Haven vacation rentals

KAYAK searches hundreds of travel sites at once for vacation home deals in Winter Haven

Best Winter Haven vacation rentals

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Most recommended vacation rentals in Winter Haven

KAYAK’s insights for vacation rentals in Winter Haven

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Winter Haven with confidence.

What is the cheapest day of the week to book a vacation rental in Winter Haven?

Thursday offers the lowest rates in Winter Haven, with an average nightly price of C$ 137. The highest prices are found on Wednesday, with average rates at C$ 377.

KAYAK's top tips for finding Winter Haven holiday rental deals

FAQs when booking a vacation home in Winter Haven

What types of vacation rentals are available in Winter Haven?

There are loads of different property types that you can make your vacation home in Winter Haven. You’ll find apartments, campgrounds, chalets, condos, cottages, houses, homestays, houseboats and villas.

Are there any pet-friendly vacation rentals in Winter Haven?

There are a number of dog and pet-friendly Winter Haven vacation rentals, with around 10% allowing you to bring your pet along with you.

How much is a vacation rental in Winter Haven for tonight?

In the last 72 hours, users have found Winter Haven vacation rentals for tonight for as low as C$ 139. Search here for similar prices

How much is a vacation rental in Winter Haven for this weekend?

In the last 72 hours, users have found Winter Haven vacation rentals for this weekend for as low as C$ 163 per night. Search here for similar prices

How can I find vacation rentals near me in Winter Haven?

Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Winter Haven?

Everything you need to know for your stay in Winter Haven

Hotels near airports in Winter Haven

Complete your trip to Winter Haven

Other popular hotel destinations