Vacation Rentals & Apartment Rentals in Winter Haven

/ Home
/ Vacation Rentals
/ United States
/ Florida
/ Central Florida
Book with confidence.

Updating...

age 0-16
2403 Results

Relevance

Price: low to high

Price: high to low

Reviews

Why am I receiving these results?

2,403 apartment rentals

Why am I receiving these results?

Responds fast! avg. 6 minutes

Price per night from

$206

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

$261

Responds fast! avg. 6 minutes

Price per night from

$186

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

$105

Mints to Legoland

Winter Haven house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$166

Peaceful Lakeside Retreat

Winter Haven house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$178

Great rentals within 20 miles that match your search

Price per night from

$194

New cozy townhouse at Champions Gate resort

Davenport townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$138

The Great Titan

Orlando villa

  • 14 bedrooms
  • 16 bathrooms
  • sleeps 30

Responds fast! avg. 2 hours 20 minutes

Price per night from

$4,008

7 Bedrooms / 5 Bathrooms / Solterra (4103 OD)

Davenport house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 22

Responds fast! avg. 3 hours 6 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. 2 hours 52 minutes

Price per night from

$172

♥EEV♥ South-facing Pool & Spa - Gated Resort - Games Room

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$198

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

$361

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 8 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. 1 hour 39 minutes

Price per night from

$140

Solterra Resort 5 Bedroom Home with Pool (1604)

Davenport house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 59 minutes

Price per night from

$195

Doll House

Davenport house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$172

⭐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

Jenny's Disney Retreat 5 miles from Disney

Reunion townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 40 minutes

Price per night from

$138

Orlando villa with a conservation view Sandy Ridge

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$163

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

$222

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. 3 hours 7 minutes

Price per night from

$189

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. 41 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

$132

Newly Renovated and Furnished Private South Facing Villa near Disney

Orlando villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 52 minutes

Price per night from

$130

Stunning 4 bedroom pool villa sitting on a lake

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$172

♥EEV♥ Resort Home with Sunny Pool & Spa - Games Room

Davenport villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$212

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. 3 hours 7 minutes

Price per night from

$189

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

Davenport villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 13

Price per night from

$443

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

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$132

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

Price per night from

$177

Large Sunny Pool Home Near Disney and Golf

Orlando house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

Responds fast! avg. 3 hours 7 minutes

Price per night from

$181

5 Star Luxury Resort Condo

Reunion condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$137

Viewing 38 of 2,403
rentals in Winter Haven

×

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!

Also consider