Vacation Rentals & Apartment Rentals in Winter Haven

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1,931 apartment rentals

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Responds fast! avg. 6 minutes

Price per night from

$215

Lakefront Luxury: Boat Dock, Pet-Friendly, Close to LegoLand, Perfect for Family

Winter Haven house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 11

Responds fast! avg. 6 minutes

Price per night from

$289

Responds fast! avg. 6 minutes

Price per night from

$210

Cozy 1 BR Apt on Lake Howard with Lanai Patio, Dock & Kayaks

Winter Haven apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 6 minutes

Price per night from

$127

Mints to Legoland

Winter Haven house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$166

Peaceful Lakeside Retreat

Winter Haven house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$178

Great rentals within 20 miles that match your search

beautiful apartment with a pool view (RE7683)

Loughman house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$136

Cozy apartament with balcony

Loughman apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$104

Spacious home close to Disney w/Pool, lake view and golf course

Davenport house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$230

9 Bedrooms/ 5 Bathrooms/ Champions Gate (1301 DW)

ChampionsGate house

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 22

Responds fast! avg. 3 hours 26 minutes

Price per night from

$417

5 Bedroom / 5.5 Bathroom Festival Resort (446 CP)

Davenport townhouse

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 26 minutes

Price per night from

$167

4 Bathrooms/ 3 Bathrooms/ Cresent Lakes (5305 CV)

Intercession City house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 26 minutes

Price per night from

$143

5 Bedrooms / 4.5 Bathrooms / Solterra (7436 OL)

Davenport townhouse

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 3 hours 26 minutes

Price per night from

$190

7 Bedroom/ 5 Bathroom Champions Gate (9098 SH)

Four Corners house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

Responds fast! avg. 3 hours 26 minutes

Price per night from

$190

5 Bedroom/ 4.5 Bathroom Solterra Resort (7869 OR)

Loughman house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

Responds fast! avg. 3 hours 26 minutes

Price per night from

$167

5 Bedrooms/ 5 Bathrooms/ Solterra (7622 OL)

Davenport house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

Responds fast! avg. 3 hours 26 minutes

Price per night from

$190

9 Bedroom/ 5 Bathroom/ Champions Gate (9170SH)

Four Corners house

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 23

Responds fast! avg. 3 hours 26 minutes

Price per night from

$262

5 Bedrooms/ 3 Bathroom Hampton Lakes (573 BC)

Four Corners house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 16

Responds fast! avg. 3 hours 26 minutes

Price per night from

$167

3 Bedrooms / 2 Bathroom Champions Gate (1187 DL)

Four Corners townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 11

Responds fast! avg. 3 hours 26 minutes

Price per night from

$143

6 Bedrooms / 5 Bathrooms / Solterra (5220 OA)

Davenport house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 16

Responds fast! avg. 3 hours 26 minutes

Price per night from

$214

10 Bedroom/ 5 Bathroom Champions Gate (1405 WW)

Davenport house

  • 10 bedrooms
  • 5 bathrooms
  • sleeps 33

Responds fast! avg. 3 hours 26 minutes

Price per night from

$286

5 Bedrooms/4 bathrooms/ Solterra (7553OS)

Davenport townhouse

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

Responds fast! avg. 3 hours 26 minutes

Price per night from

$167

8 Bedrooms/ 6 Bathroom/ Champions Gate(1509 MB)

Davenport house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 27

Responds fast! avg. 3 hours 26 minutes

Price per night from

$226

3 Bedrooms / 2 Bathroom / Festival Resort (181 CD)

Davenport townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 26 minutes

Price per night from

$119

4 Bedrooms / 3 Bathrooms / Festival (232 CD)

Davenport townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 26 minutes

Price per night from

$143

9 Bedroom/ 5 Bathroom Champions Gate (9168 SH)

Four Corners house

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 27

Responds fast! avg. 3 hours 26 minutes

Price per night from

$262

8 Bedroom/ 5 Bathroom Champions Gate (1193 CD)

Four Corners townhouse

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 22

Responds fast! avg. 3 hours 26 minutes

Price per night from

$214

12 Bedrooms/ 11.5 Bathrooms/ Solterra (6052 BD)

Davenport house

  • 12 bedrooms
  • 10 bathrooms
  • sleeps 28

Responds fast! avg. 3 hours 26 minutes

Price per night from

$322

5 Bedroom/ 4.5 bathroom Solterra (7565 OS)

Davenport townhouse

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 26 minutes

Price per night from

$190

2 Bedroom/ 2 Bathroom Champions Gate (1113 CD)

Four Corners townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 26 minutes

Price per night from

$119

3 Bedrooms/ 3 Bathrooms Champions Gate (1143 CD)

Four Corners townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 3 hours 26 minutes

Price per night from

$130

9 Bedrooms/ 5 Bathrooms/ Champions Gate (8892 CD)

Reunion house

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 26

Responds fast! avg. 3 hours 26 minutes

Price per night from

$262

3 Bedrooms/ 2.5 Bathrooms/ Festival (812 LD)

Davenport townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 3 hours 26 minutes

Price per night from

$119

4 Bedrooms / 3 Bathrooms / Champions Gate (1571 SD)

Davenport townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 26 minutes

Price per night from

$178

7 Bedrooms/ 5 Bathrooms/ Solterra (7684 OL)

Loughman house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

Responds fast! avg. 3 hours 26 minutes

Price per night from

$226

6 Bedrooms/ 4.5 Bathrooms/ Solterra (7639 OL)

Davenport house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 26 minutes

Price per night from

$190

4 Bedrooms/ 3 Bathrooms Festival Resort (305 CD)

Davenport townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

Responds fast! avg. 3 hours 26 minutes

Price per night from

$143

7 Bedroom/ 5 Bathroom Champions Gate (9246 SH)

Four Corners house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

Responds fast! avg. 3 hours 26 minutes

Price per night from

$202

Viewing 38 of 1,931
rentals in Winter Haven

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About Winter Haven

Whether you're in Winter Haven because of the kids (hello, Legoland!) or flying solo, there is something for everyone in this city! Why not visit FlipKey for the perfect Winter Haven vacation rental that you can relax in when you're done exploring?

About Winter Haven

The earliest people known to what is now Winter Haven were the Timucua and the Calusa. In the 1860s, the first settlers came to Winter Haven and it wasn't named Winter Haven until 1885 by P.D. Eycleshimer.

Winter Haven has a myriad of interconnected lakes. Started in 1915 and completed by the early 1920s, be sure to check out the Chain of Lakes!

Winter Haven has a long history which you can find out about at the Museum of Winter Haven.

The second largest city in Polk County, Winter Haven is home to a variety of cultural experiences. Located between Tampa and Orlando, there is plenty to do in this fabulous city!

Whether you want to discover your inner water baby by checking out the watersports Winter Haven has to offer, or you'd rather just relax and enjoy the eclectic food scene, Winter Haven is for everybody!

What to do

Why not start your day off by exploring Downtown Winter Haven? Full of great shops and restaurants, you will really get a feel of Winter Haven here!

When you're done exploring, head on over to The Chain of Lakes so you can take part in a spot of fishing. Too boring? Then there are many watersports you can enjoy, such as jet skiing, water tubing, and boating.

Make sure to check out the fountain in Central Park, which changes its colors during holidays!

Winter Haven holds many events throughout the year. Enjoy local musicians at Pickin in the Park held the first Friday of the month.

Check out the local produce at the Farmer's Market, which is held every Thursday 8 am - 5 pm.

Last but not least, be sure to check out Legoland which is the second-largest Legoland in the world. The kids will be sure to enjoy it!

Top Winter Haven travel tips

Winter Haven enjoys a mild climate throughout most of the year, so you can mostly get away with a light sweater. Be aware of the occasional shower during the summer months, though!

You'll be able to get to Winter Haven quite easily from Orlando. Orlando International Airport is only 45 minutes away. You can also access Winter Haven via Tampa International Airport. However, this is slightly further away.

You can easily get around Winter Haven by bus using the two bus services on offer: Winter Haven Area Transit and Citrus connection.

Winter Haven is the perfect vacation spot as there are so many things to do! Whether you're an art lover or a watersports enthusiast, Winter Haven doesn't turn anybody away. Find the perfect Winter Haven vacation rental FlipKey!

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