Vacation Rentals & Apartment Rentals in Winter Haven

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1,928 apartment rentals

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Responds fast! avg. 6 minutes

Price per night from

$186

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

$297

Responds fast! avg. 6 minutes

Price per night from

$186

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

$133

Mints to Legoland

Winter Haven house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$167

Great rentals within 20 miles that match your search

6 Bdrm Chic home Heated Salt Water Pool and Spa

ChampionsGate house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 28 minutes

Price per night from

$214

4 Bedroom Villa With Private Pool & Golf Course View

Davenport house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$155

Home 15 minutes from Disneyworld

Davenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$344

Private Luxury Getaway w/ Garage minutes from Hollywood Studios

ChampionsGate apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$114

Family Friendly Condo Near Walt Disney World

Davenport condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$161

Rolling Skies | Poolside Cinema and Spa Near Disney

ChampionsGate house

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 26

Price per night from

$574

Luxury 4bd villa in Champions Gate resort near Disney (CG215)

ChampionsGate villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$1,146

Premium 4bd villa close to Disney (CG652)

ChampionsGate villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,146

Premium 5bd villa close to Disney (ST392)

Davenport villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$1,146

Awesome 4bd home near Disney (ST396)

Davenport villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,146

NEWLY UPDATED< THEMED ROOMS<4 BDRM

ChampionsGate house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$174

Price per night from

$167

3 Bedroom Villa with Pool and Game Room

Davenport villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$145

Luxury 5 bedroom Villa near Disney & Golf

Haines City villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$214

Robert's Southern Dunes Vacation Home

Haines City house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$145

>2/2 apt home w pool, great amenities near Disney, Universal, theme parks, etc

Davenport apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$183

5 BD Exquisite summer home with PRIVATE POOL - 131

Davenport house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$194

Luxury Pebble Beach Champions Gate Close To Disney

ChampionsGate house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$201

Solterra Resort - Orlando, Florida

ChampionsGate house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$728

Ultimate privacy with lake view! large pool ! in gated community

Loughman villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$258

Incredible & Beautiful 5BR/4.5BA Home w/Private Pool *4590*

Loughman house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 16

Price per night from

$206

Grand Holiday 4BD Pool Home* Disney & Universal

Loughman house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

Price per night from

$154

SOLANA- 7 Bedrooms Family Vacation Villa with Private Pool & Spa

ChampionsGate house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

Price per night from

$373

Grand Executive 3BD Condo Apartment near Disney #8

Reunion apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$917

South facing pool, themed bedrooms and Game room on property with 6 beds

Davenport house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Price per night from

$379

1Treasure Point Villa

Loughman house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$144

*4722TD* Modern Paradise 4BR/3BA w/Private Pool - Great Amenities!

Loughman house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$194

Price per night from

$194

Luxurious 7 beds , 6 baths villa

ChampionsGate house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 12

Price per night from

$458

4 bedroom 2 bath near all theme parks and near champion gate are

ChampionsGate house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$224

NEWLY 6 BR/4BA LUXURY VACATION HOUSE 10 MINS FROM DISNEY

Reunion house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

Price per night from

$458

A DISNEY REUNION! FIVE Heated Pools, Near Disney, Views, Sleeps 8!

Reunion condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 12 minutes

Price per night from

$229

Beautiful Villa. Nice house. Great pool all in one

ChampionsGate villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$229

Viewing 38 of 1,928
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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