Vacation Rentals & Apartment Rentals in Winter Haven

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1,924 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

$310

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

$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

The Golden Bear

Orlando villa

  • 10 bedrooms
  • 11 bathrooms
  • sleeps 24

Responds fast! avg. 2 hours 21 minutes

Price per night from

$2,497

7 Bedrooms / 5 Bathrooms / Solterra (4103 OD)

Davenport house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 22

Responds fast! avg. 2 hours 14 minutes

Price per night from

$213

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

Family Golf Resort 'Villa Bonita' Southern Dunes

Haines City villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“nice house” everything was updated and nice ,except for the mattress they are very old every time we when to sleep and got up we had back paint everybody, and everyroom they need to updated...other then that it was very nice

Responds fast! avg. 1 hour 17 minutes

Price per night from

$121

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

$136

Solterra Resort 5 Bedroom Home with Pool (1604)

Davenport house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 50 minutes

Price per night from

$157

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

Reunion house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Price per night from

$516

Price per night from

$189

Price per night from

$336

⭐Comfy Villa w/ Golf Clubhouse - Adventure & Thrills For Everyone⭐

Davenport villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

Price per night from

$336

The Ultimate Florida Vacation

Poinciana villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great place” Very cozy, out in suburbs. Neighborhood clean and friendly. Pools and outdoor basketball courts and activities for the kids.

Price per night from

$110

DisneyMansion /11BR/30 Beds Golf Pool Tennis Villa

Davenport house

  • 12 bedrooms
  • 5 bathrooms
  • sleeps 24

Price per night from

$653

DisneyEstate /11King/30 Bed Golf Pool Tennis Villa

Davenport house

  • 12 bedrooms
  • 6 bathrooms
  • sleeps 24

“Best Vacation EVER!!!” I booked this Villa through flip key. I was very impressed by the owners fast response to ALL and ANY questions prior to our much needed vacation. Upon arrival we were warmly welcomed at the villa by our host Mike. Mike gave us a tour of this beautiful and Big home. He even had Fresh Strawberries, chocolate, water and champagne over ice. And had the fridge stocked with breakfast! As for the villa itself, from the kind, courteous, and friendly Host Mike, to the meticulous, comfortable rooms with very well equipped kitchen, cosy common areas - Our experience was nothing less than exceptional. Bonus-The supermarket, restaurants, and shopping is less than 5miles down the road (just a few minutes). We had 5 families (total of 25 people) staying at this villa and Never felt like we were on top of each other. Thank you again to the owners and Our Awesome Host Mike for going above and beyond to make their guests feel Extra special!!! We definitely recommend this place

Price per night from

$653

Orlando villa with a conservation view Sandy Ridge

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 41 minutes

Price per night from

$158

28 Room DisneyMansionEstate by AmericanVacationLiving

Davenport house

  • 20 bedrooms
  • 11 bathrooms
  • sleeps 50

Price per night from

$2,256

5 bed luxury villa in Champions Gate Florida

Davenport villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$215

Price per night from

$338

The Villa on the Lakes

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$201

DisneyByTheLake

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$123

3 bedroom home private pool near Disney I4 & shops

Davenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Supervisor” It was really nice. We stayed for three nights and we enjoyed it. It was close to the parks, to publix, restaurants, and gas stations. Only one negative was that there were no phone signal.

Responds fast! avg. 44 minutes

Price per night from

$121

BEAUTIFUL 4 BEDROOM VILLA - NEAR DISNEY

Davenport villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 48 minutes

Price per night from

$126

Stunning 4 bedroom pool villa sitting on a lake

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$172

Beautiful 6 Bedroom Home in Reunion Resort and Spa

Reunion house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 16

Responds fast! avg. 14 minutes

Price per night from

$487

Denmark Villa

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$126

Large Disney Pool Home w/ game room, near golf

Orlando villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 20

Responds fast! avg. 2 hours 48 minutes

Price per night from

$189

Immaculate Spacious Villa

Orlando villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 1 minutes

Price per night from

$218

Watersong Luxurious Villa 6 Bed, 5 Bath + 2 x1/2b

Davenport villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 13

Price per night from

$430

Southern Comfort

Davenport villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 16

Price per night from

$430

SUNSET at SOLTERRA Large 7 Beds / Private Pool / Game Room / Grill

Davenport house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 22

“Great” GREAT!!! Let me first start off by saying that there were issues that had occurred, such as the power went off, and the alarm beeped all day, the toilet had issues, which is normal, but Luciana made sure that each and everything was resolved immediately. My only suggestion would be is, if your undecided on paying for the heated pool and jacuzzi, which doesn't get to warm, let her know immediately, if not your responsible for paying for it if management keeps it on. Bring your own dish towels and a can opener, and your all set to enjoy this beauty. So I would have to say that my overall experience was GREAT, perfect loved it!!! Would stay again.

Responds fast! avg. 3 hours 48 minutes

Price per night from

$251

Florida Home near Disney with Private Pool

Four Corners house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$195

Reserve at Town Center Lake View Disney Villa with free Wi-Fi and Netflix

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 7 minutes

Price per night from

$132

BigDisneyVilla 4 Bed Executive Orlando Pool Home Sleeps up to 8 - Golf

Davenport house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$172

Viewing 38 of 1,924
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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