Vacation Rentals & Apartment Rentals in Winter Haven

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1,949 apartment rentals

Responds fast! avg. 1 hour 35 minutes

Price per night from

$284

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

Winter Haven house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 11

Responds fast! avg. 1 hour 35 minutes

Price per night from

$243

Responds fast! avg. 1 hour 35 minutes

Price per night from

$197

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

Winter Haven apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 35 minutes

Price per night from

$152

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

$218

Price per night from

$182

Champions Gate1568MVD Town Houese 4BD/3BA/Pool,Golf,near Disney

Davenport house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“Disney Adventure” My family and I drove from NY to this lovely house and felt right at home. We were a total of 11 and stayed for 10 days. Since the first day we booked the house the owner was attentive and responded very quickly when I wrote to him. The house was well equippped, clean and beautifully decorated. We all loved it so much!!!!

Price per night from

$1,259

2 Bed / 2 Bath Resort Condo near Disney

Davenport condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Wonderful, amazing” The condo was huge and beautiful, it had everything we needed and then some. The owner was very helpful and went beyond expectation to meet our needs and make our vacation awesome. Shops and fun excitement was just a 15-20 min drive. The pool was wonderful.

Price per night from

$172

“Quick Disney Ger Away” The house was just as it was described & it was very clean. The pool was great for our 5 yr old grandaughter to play in with a shallower area at one end & lots of pool toys. Our 12 yr old son loved the basketball hoop for pool & hot tub was great for us, the adults. The location of house was about 20 min to the Magic Kingdom & 1-1/2 hr to Cocoa Beach. There were many restaurants, shops & things to do nearby. Beds were very comfortable & neighborhood was nice & quiet. We had a great stay with no problems. Janet was very accomodating & friendly when we booked our reservation. We will definately be back!

Price per night from

$189

Near to Disney with Private Pool/Spa and Game Room

Davenport villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$198

Beautiful Villa in the community of Solterra

Loughman villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$297

in the middle between Orlando and Tampa Florida

Lake Wales house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$547

5 Suites Luxury Single Home with private pool RE1492

Kissimmee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

Price per night from

$1,234

5 Bed/3 Bath Orlando Dream Holiday Home

Loughman house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

Price per night from

$206

Large Disney Pool Home w/Game Room, Resort Amenities

Orlando house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 20

Price per night from

$212

ChampionsGate Best Florida Vacation Home

Orlando house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$217

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

$161

“Disney vacation” Beautiful vacation home! We loved the spacious living arrangement and proximity to a shopping center. Only about 15-20 minutes to Disney parks. Would certainly recommend this house and stay again!

Price per night from

$170

The Golden Bear

Orlando villa

  • 10 bedrooms
  • 11 bathrooms
  • sleeps 24

Responds fast! avg. 2 hours 8 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. 1 hour 50 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 16 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

$373

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

The Sanctuary at West Haven. South-facing pool, overlooking nature reserve.

ChampionsGate house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$344

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

$138

Solterra Resort 5 Bedroom Home with Pool (1604)

Davenport house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 54 minutes

Price per night from

$138

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

$194

⭐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.

Responds fast! avg. 22 minutes

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 54 minutes

Price per night from

$160

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

$218

Viewing 38 of 1,949
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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