Vacation Rentals & Apartment Rentals in Winter Haven

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1,927 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

$261

Responds fast! avg. 6 minutes

Price per night from

$190

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

$129

Mints to Legoland

Winter Haven house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$166

Great rentals within 20 miles that match your search

20% OFF | Paradise Gem Villa |5BR| Private Pool

Reunion villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Price per night from

$252

Price per night from

$286

6 Bedroom/ 5 Bathroom/ Champions Gate (530SS)

Four Corners house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 18

Responds fast! avg. 3 hours 26 minutes

Price per night from

$189

20% OFF | Lakeview Home | 3BR (1 En-Suite) | Foosball | Pool | Tennis

Reunion townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$172

6 Bedrooms /5 Bathrooms / Champions Gate (8997 PT)

Four Corners house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 15

Responds fast! avg. 3 hours 26 minutes

Price per night from

$153

Gorgeous Home with Golf Course View Championsgate

ChampionsGate house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 16

Price per night from

$400

Brand new lux townhome close to Disney

ChampionsGate townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$160

Paradise Home Close To Disney and other parks

ChampionsGate apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$183

Resort style villa close to Disney and other parks

ChampionsGate villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 16

Price per night from

$297

Stunning 5 bedroom house near Disney

ChampionsGate townhouse

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Price per night from

$229

6 Bedrooms/ 5 Bathrooms/ Champions Gate (9039 PT)

Four Corners house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16

Responds fast! avg. 3 hours 26 minutes

Price per night from

$189

Kingfisher at Watersong (Disney Area)

Orlando villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$201

Luxurious 4-Bedroom Orlando Villa, Sleeps 11 - Perfect Family Getaway

Loughman villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

Price per night from

$177

5 Bedroom/ 4 Bathroom/ Champions Gate (9033PT)

Four Corners house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

Responds fast! avg. 3 hours 26 minutes

Price per night from

$166

6 Bedrooms/ 5 Bathrooms/ Champions Gate (590 SS)

Four Corners house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Responds fast! avg. 3 hours 26 minutes

Price per night from

$189

9 Bedroom/ 5 Bathroom/ Champions Gate (771PB)

Four Corners house

  • 9 bedrooms
  • 7 bathrooms
  • sleeps 25

Responds fast! avg. 3 hours 26 minutes

Price per night from

$201

Cozy Vacation Home near Disney World

ChampionsGate townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$155

Vibe Time Private Resort Villa • Close to Disney • Resort Amenities

ChampionsGate house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Price per night from

$252

7 Bedrooms/ 5 Bathrooms/ Champions Gate (8916 TW)

Four Corners house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 18

Responds fast! avg. 3 hours 26 minutes

Price per night from

$189

9 Bedrooms/ 5 Bathrooms/ Champions Gate (9017 ST)

Davenport house

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 24

Responds fast! avg. 3 hours 26 minutes

Price per night from

$261

Reunion Retreat w/ Community Perks: 8 Mi to Disney

Reunion apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$166

5 Bedrooms/ 4.5 Bathrooms/ Solterra (7548 OS)

Davenport townhouse

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 26 minutes

Price per night from

$159

Peaceful 3-bedrooms villa/Beautiful view and paver

Davenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$172

9 Bedrooms/ 5 Bathrooms/ Champions Gate (9013ST)

Davenport house

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 20

Responds fast! avg. 3 hours 26 minutes

Price per night from

$261

9 Bedrooms/ 5 Bathrooms/ Champions Gate (9037 ST)

Davenport house

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 20

Responds fast! avg. 3 hours 26 minutes

Price per night from

$261

7 Bedrooms/ 5 Bathrooms/ Champions Gate (9009 ST)

Davenport house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 20

Responds fast! avg. 3 hours 26 minutes

Price per night from

$213

Pluto's Palace Florida Villa South Facing Pool

Loughman house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

Price per night from

$271

Entire home in Davenport, Florida

ChampionsGate house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 17

Responds fast! avg. 1 hour 26 minutes

Price per night from

$286

Spacious 4-bedroom 3 bathroom villa just 15 minutes from Disney!

ChampionsGate villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Price per night from

$137

Private Suite 15 Mins to Disney

ChampionsGate hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$86

Luxury Solterra Resort Home

ChampionsGate house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Price per night from

$262

Disney Dream Home: 5BR/5BA, Resort & Waterpark Fun | Sleeps 14

Orlando house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

Price per night from

$287

Cozy Home w/Private Pool and Game Room

Orlando house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$200

Viewing 38 of 1,927
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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