Vacation Rentals & Apartment Rentals in Winter Haven

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2,268 apartment rentals

Disney 45 minutes away! LegoLand 10 minutes away!!!

Winter Haven house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$137

Sunrise on Lake Idylwild~Chain of Lakes w Tiki Bar, Dock and Kayaks~Legoland

Winter Haven house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 1 hour 48 minutes

Price per night from

$229

10% Off Thru 2/28~Lake Silver V~Gorgeous Sunset~Boat Dock~Pristine Lake Water &

Winter Haven house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 11

Responds fast! avg. 1 hour 48 minutes

Price per night from

$306

10% Off Thru 2/28~Lake Silver V~Gorgeous Sunset~Boat Dock~Pristine Lake Water &

Winter Haven house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 1 hour 48 minutes

Price per night from

$261

Responds fast! avg. 1 hour 48 minutes

Price per night from

$116

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

ENCHANTING DISNEY VACATION RENTAL HOME

Davenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“A house that I could see living in permanently.” I can't think of anything negative to say, OK if I lived there I'd put a couple palm trees and a bar by the pool... I really liked the look of the tile floor in the living room and I really appreciated the fact that there is a DVR connected to the main TV. It is an awesome house.

Responds fast! avg. 5 minutes

Price per night from

$191

“Spacious and comfortable” Although this was not the home pictured in the photos of the home we chose and thought we were staying, it provided the same spacious and comfortable space needed for a family reunion. The lanai with the pool and hot tub was really nice with amazing sunsets in the evening and moonsets in the early morning. There was a resident Sandhill crane who meandered by for a visit each day. The location of this quiet resort community was pleasantly out of the way of the crowds, yet reasonably convenient to anything you would need or want to do. Our main concern was that we were unable to consistently lock the back sliding glass door and there was no bar to place to lock it. (And, the crumb tray on the toaster was broken.) Other than that, the home was a little tired, but more than adequate. Thank you for a delightful week!

Price per night from

$188

Luxury Villa in Hampton Lakes near Disney

Davenport villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

“Peacefull and relaxing” Great family condo, good pool, relaxed neighourhood. Plenty of space, offers privacy and yet a family and home feeling

Responds fast! avg. 3 hours 30 minutes

Price per night from

$212

Orlando Magic - Disney Orlando

Davenport house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Awesome Home” This home was beautiful! It was all the was described and more! My family and I had an amazing time! Our only regret was that we were so busy and did not get much time at the home relaxing.

Price per night from

$154

Responds fast! avg. 2 hours 31 minutes

Price per night from

$227

Upscale 2BR Condo at Terrace Ridge near Disney FL

Davenport apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Very Nice Location, Property, and Experience” The booking process was very easy and straightforward. It was much easier than bookings I have done on other sites. I felt my payment and information was secure. The process of checking in and getting access to the condo was very efficient as well. There was a minor hiccup with the entry code, but the customer service line was able to correct it right away. The house was nice and spacious. It had everything we needed to ensure we had a proper vacation. While there were some initial headaches, the owner and customer support line were always there to ensure we were satisfied. The location was great. it seems that there is a lot of development going on in this location. There were multiple places to eat, and shop. It was not far from all of the main attractions. Because of its proximity to I-4, there was minimal traffic. The pool and facilities were clean and comfortable. I met a lot of nice people there. I would recommend this condo to anyone looking for a peaceful vacation that is close to all the great things in Orlando.

Price per night from

$89

Luxury pool home near Disney

Four Corners house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

“Lovely home..” My family and i enjoyed the heated pool very much. My mother really loved the master bedroom and leather furniture.

Responds fast! avg. 2 hours 30 minutes

Price per night from

$149

AWARD WINNER, 5 STAR VILLA. Space, Luxury, Unique private sunny corner

Reunion villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

“Genuinely 5 star accommodation” Just returned from a really lovely holiday in this accommodation. We travelled with our 3 children and one set of grandparents. There was plenty room in the house for the 7 of us and we didn't feel like we were living on top of each other. It is truly beautiful inside and out. It is immaculate and very spacious and there is nothing that we could mark it down for. Although it is immaculate, it still feels very homely. All the bedrooms are beautiful and lots of care has been taken in the furnishings of each room. The kitchen is very well appointed and there are ample utensils/crockery for eating in should you wish to do so. The outside/pool area is so private and relaxing that you almost forget that you are actually in a very busy Orlando!! We enjoyed a few BBQ's in the outside kitchen area too. Reunion itself is beautiful and is very well maintained. The gents of our party enjoyed some golf on resort and they were very well looked after by the staff at the golf courses. Would most definitely return if we were on holiday in Orlando again! All communications with the owner David Prescott were dealt with very quickly and to our satisfaction.

Price per night from

$302

“Perfect Vacation Home” Great home, well laid out, perfect vacation home for the whole family. Clean, well equipped. Great location of Southern Dunes on a beautiful golf course. Had our family visit for two weeks and there was plenty of room for all our children and grand children. Would definitely recommend it to all my friends and would go back again.

Price per night from

$154

Lake View Dream Villa

Davenport villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 11

“Very family friendly house...” This was a very family-friendly house .We had a great stay and the kids loved the pool. The house was very clean and well managed. If we had any question we were able to get them without the long wait .Would highly recommend this house for any family looking for a wonderful stay minutes for Disney.

Responds fast! avg. 44 minutes

Price per night from

$145

“Decent place but lacking in some areas” For one week in July 2014, my family from Alabama to Alaska (with us from Canada) all stayed at 928 Solona Circle. Overall we were happy with the house rental but do not stay here if you need assistance with anything. It took my 4 phone calls over 3 days to just find out what the Wi-Fi password had been changed to (the one that we were emailed was incorrect). It may not be the safest neighbourhood as there were police men in the gated area twice during our stay. And the house was filled with broken outlet covers and had very dirty couches, which needed steam cleaning. It was a spacious home and we loved the walk-in closets as well as the ease in which to find it and the easy drive to Disneyworld. But if you want to stray there, you need to supply everything- even your own toilet paper and Kleenex. The jets ion eth hot tub did not work and the game room had a broken foosball table. Overall we were mainly happy with our stay but were disappointed with a few things.

Price per night from

$188

Private one bedroom apartment at a great price

Lakeland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$89

Price per night from

$188

Stunning 5/6BR/3BA Pool Home Disney Golf! Luxury!

Davenport house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 12

Price per night from

$193

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. 1 hour 36 minutes

Price per night from

$110

Exclusive Home Within High Grove Gated Community

Clermont house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$160

Responds fast! avg. 15 minutes

Price per night from

$112

Cloud Nine Villa - The Finest Villa In The Disney Area

Davenport house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Fabulous. Just as advertised.” The pool was amazing, having in stayed in various villas at Highlands over the years, this was the winner. So clean, no nasty chemicals and just beautiful. Villa was very clean and spacious and had everything we needed. perfect location overlooking the Golf Course, lots of sun all day almost and great to be at the top of a cul de sac with no passing traffic. Not overlooked at all and very private. Great location for the Orlando parks and not too far from Bush Gardens our favourite park ever over the years. Have no doubts! Book this villa.Great contact from Owners when we asked any questions.

Responds fast! avg. 2 hours 59 minutes

Price per night from

$219

Price per night from

$149

Stunning and Modern 4BR Villa Close to Disney

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$126

Double Lot! No Carpet! 8 bedroom home with private pool/spa!

Davenport house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 18

Price per night from

$399

1058 Reserve Place, town centre, davenport, Florida

Davenport villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$156

Fresh and Relaxing Home

ChampionsGate house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 40 minutes

Price per night from

$159

Tuscan Sunsets . . . Stunning Views! Romantic Reatreat 2 or Family Fun for 10

ChampionsGate house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$193

Lovely Villa 15 Minutes from Disney

Four Corners villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$160

Spacious Vacation Apartment (266651)

Reunion condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$112

Gorgeous Vacation Home with Pool RT1170

Loughman house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$122

Responds fast! avg. 2 hours 34 minutes

Price per night from

$170

UNIQUE LUXURY POOL VILLA - Private Pool/Golf View/Fully Refurbished Aug 2017

Haines City villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 34 minutes

Price per night from

$170

♥ Orlando ChampionsGate Disney Golf 8BR/5BTH(1430)

ChampionsGate house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 18

Responds fast! avg. 2 hours 37 minutes

Price per night from

$547

sunset hideaway

Davenport house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$171

Summertime with a PRIVATE POOL at Solterra! 4606

Davenport townhouse

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$170

Viewing 38 of 2,268
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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