Vacation Rentals & Apartment Rentals in Winter Haven

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1,928 apartment rentals

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

$215

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

$167

Great rentals within 20 miles that match your search

South-facing Pool Home near Disney World

Davenport house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$195

“Great Family Memories” We give this home an A+!! Everything about it from the appearance, to the owner (Liz), to the location, and the management company combine to give you unprecedented good customer service that insures a great experience. Everything is geared towards you! The house is actually even nicer than the pictures depict!! We had 5 adults and one child stay and there was plenty of room for everyone. We loved the layout. Our granddaughter squealed with delight when she saw the Mickey Mouse room. She even asked to go to bed several nights!! We enjoyed going to nearby outlet malls, Disney, Disney Springs, restaurants close by, and even grilling out on the patio while family members swam in the pool. The game tables in the garage provided some lively competition. The greatest compliment you can give a place is to say you would return again. When we come back to this area again, Pilgrim's Paradise will be at the top of our list to stay at again! Liz made everything run smooth and was a delight to work with!! Thanks for sharing your beautiful villa with our family!!

Responds fast! avg. 2 hours 12 minutes

Price per night from

$190

New cozy townhouse at Champions Gate resort

Davenport townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$138

The Golden Bear

Orlando villa

  • 10 bedrooms
  • 11 bathrooms
  • sleeps 24

Responds fast! avg. 2 hours 21 minutes

Price per night from

$2,507

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

Price per night from

$190

No Rear Neighbors/SW Pool/Close to Disney/Game Rm

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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

$402

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

$332

Florida Delight at Watersong, Davenport, Orlando

Davenport villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Price per night from

$192

Doll House

Davenport house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$173

Price per night from

$337

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

Davenport villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

Price per night from

$337

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

$111

DisneyMansion /11BR/30 Beds Golf Pool Tennis Villa

Davenport house

  • 12 bedrooms
  • 5 bathrooms
  • sleeps 24

Price per night from

$656

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

$656

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

$157

Price per night from

$340

Disney pool home, Great view, Gated resort

Orlando villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

“Iraq Home Coming” Excellent vacation home for a visiting family. It was the easiest check in process I have ever done since I’ve been traveling. Just to come back from a war zone and visit family and friends along with eating at different restaurants and amusement parks was very enjoyable. I would recommend renting a vacation home before renting a hotel room any day if it’s as pleasant as this trip has been for me. I want to personally thank the home owner and the company for such an easy process of communication and updates.

Responds fast! avg. 2 hours 48 minutes

Price per night from

$190

DisneyByTheLake

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$123

Newly Renovated and Furnished Private South Facing Villa near Disney

Orlando villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 4 minutes

Price per night from

$137

Stunning 4 bedroom pool villa sitting on a lake

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$173

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

$489

Denmark Villa

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$127

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

$190

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

Davenport villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 13

Price per night from

$428

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

$118

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

$171

Large Sunny Pool Home Near Disney and Golf

Orlando house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

Responds fast! avg. 2 hours 48 minutes

Price per night from

$182

5 Star Luxury Resort Condo

Reunion condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$137

House near Mickey

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$136

Pluto's Palace Disney Villa

Davenport villa

  • 3 bedrooms
  • 8 bathrooms
  • sleeps 8

Price per night from

$242

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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