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

$311

Responds fast! avg. 6 minutes

Price per night from

$229

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

Price per night from

$194

Southern Dunes Golf Vacation Villa

Orlando villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Visitor” Loved it. Great neighborhood. Clean house. Easy to get a hold of people if you had questions or needed help. Walmart right around corner. Had everything you need to cook with. Great place. Defiantly will come back and recommend to anyone.

Price per night from

$117

Beautiful Orlando Villa "Mags Den" Calabay Parc

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 44 minutes

Price per night from

$170

5 Star Luxury Resort Condo

Reunion condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$136

South-facing Pool Home near Disney World

Davenport house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$194

Disney pool home in gated resort near golf

Orlando house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

Responds fast! avg. 2 hours 48 minutes

Price per night from

$189

New cozy townhouse at Champions Gate resort

Davenport townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$138

Newly decorated at Reunion Resort with golf views

Reunion townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$160

7 Bedrooms / 5 Bathrooms / Solterra (4103 OD)

Davenport house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 22

Responds fast! avg. 2 hours 15 minutes

Price per night from

$213

Disney Area Villa in gated Aviana Resort

Orlando villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Mrs” This rental was clean and neat. It had great amenities and my kids love the pool and spa. The play room in the garage made it perfect for my kids when they ran out of energy from the pool. The staff was friendly and helpful. I would defiantly recommend this unit to anyone.

Responds fast! avg. 3 hours 28 minutes

Price per night from

$172

Luxury 6 Bed/5 Bath Villa near Disney on gated community with golf course

Davenport villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Price per night from

$458

A HOLIDAY HOME IN BEAUTIFUL LAKE MARION RESORT.

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 26 minutes

Price per night from

$135

Spacious, game room, theater loft, golf view, private pool & BBQ

Reunion house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Price per night from

$515

Price per night from

$189

Superb Orlando Holiday Villa Sanctuary Westhaven

Davenport villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Price per night from

$167

SPECIAL Fabulous Villa Sanctuary WestHaven

Davenport villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$160

Tower Lake Vista, pool villa 15 mins from Disney

Haines City villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$155

Most private backyard in Orlando! Minutes 2 Disney

Loughman villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$182

The House the Mouse would stay in

Davenport villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$182

Luxurious Villa at Calabay Parc, Haines City, FL

Haines City villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 48 minutes

Price per night from

$195

Orlando, Villa With south facing Private Pool, Close To Disney

Davenport villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$138

Regal Palms 539 La Mirage Sreet

Davenport condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$229

Spacious,Luxury,Comfy! Make Stay More Enjoyable!!

Davenport villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

“Vacation” We had a great time, we would stay there again. The house was very very spacious it worked out well for our trip.

Price per night from

$205

Exclusive Family Villa with Private Pool

Haines City house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$172

Holly's Lakeside Villa

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$183

SPACIOUS AND CLEAN DISNEY RENTAL VILLA IN FLORIDA

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$95

14 Room DisneyEstate by AmericanVacationLiving

Four Corners house

  • 12 bedrooms
  • 5 bathrooms
  • sleeps 24

Price per night from

$881

Beautiful and Spacious Orlando Pool Home

Davenport house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“Awesome Place to Stay!” Stayed there for a week and had an absolute ball. Villa is extremely clean and exactly as pictured on the website. We had so much fun in the pool we forgot the Villa had a pool table! Definitely booking this one again next vacation!

Price per night from

$138

Champions Gate #1 - Luxurious 8 Bedroom Pool Villa with Theater

Davenport villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

Price per night from

$399

Family & Friends Unite For Fun✩Amazing Villa w/ Unique Upscale Amenities

Davenport villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

“Amazing” We had a family of 10 and it was enough space for us. The kids loved the pool and movie room. I liked house to house was so updated and beautiful. We definitely would stay here again.

Price per night from

$330

Florida Delight at Watersong, Davenport, Orlando

Davenport villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Price per night from

$191

Doll House

Davenport house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$172

Price per night from

$335

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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