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Vacation Rentals & Apartment Rentals in Winter Haven

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7,393 apartment rentals

Saltwater Pool Villa Next to Legoland and Near All Disney Attractions

Winter Haven villa

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 15 minutes

Price per night from

$151

45 Min to Disney 15 Min to Legoland on chain of la

Winter Haven house

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$262

Lakeview Tiny Home by Legoland/Disney w/ boats!

Winter Haven house

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 19 minutes

Price per night from

$76

NEW! Winter Haven Home w/Lake Access - 33Mi to WDW

Winter Haven house

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 4 minutes

Price per night from

$75

Snowbird - Central Florida - Waterfront / Bord de lac

Winter Haven house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$72

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

Winter Haven house

3 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$104

Winter Haven Family Home - Walk to 2 Lakes!

Winter Haven house

3 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 4 minutes

Price per night from

$113

NEW! Winter Haven Home: Near Fishing & Family Fun!

Winter Haven house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 4 minutes

Price per night from

$70

Charming Lake Eloise Home w/Boat Ramp Access!

Winter Haven house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 4 minutes

Price per night from

$79

Modern Home w/Porch - Steps from Lake Eloise!

Winter Haven house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 4 minutes

Price per night from

$96

Lake Lucerne Villa

Winter Haven house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$174

Stylish Home w/ Lake Eloise Boat Ramp Access!

Winter Haven house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 4 minutes

Price per night from

$79

*3/2*GorgeousLakeHome1*AceLoc*4miles*LEGOLAND*1722

Winter Haven house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$87

*3/2*GorgeousLakeHome2*AceLoc*4miles*LEGOLAND*1724

Winter Haven house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$87

Great rentals within 20 miles that match your search

Luxury Six Bedroom Home - Close to Disneyworld

Four Corners villa

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$198

477-ORLANDO-15 Min FROM DISNEY & OMNI RESORT

Four Corners house

8 bedrooms / 6 bathrooms / sleeps 26

Price per night from

$314

ORLANDO-CHAMPIONS GATE-15 Min FROM DISNEY & OMNI RESORT

ChampionsGate house

4 bedrooms / 1 bathroom / sleeps 11

Price per night from

$116

1580-ORLANDO-15 Min FROM DISNEY & OMNI RESORT

ChampionsGate house

8 bedrooms / 6 bathrooms / sleeps 17

Price per night from

$279

730-ORLANDO-CHAMPIONS GATE-15 Min FROM DISNEY & OMNI RESORT

Four Corners house

4 bedrooms / 1 bathroom / sleeps 11

Price per night from

$116

Warmescape

Haines City house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$187

Beautiful Private Villa Close To Disney Parks

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$184

1570-ORLANDO-CHAMPIONS GATE-15 Min. da DISNEY & OMNI RESORT-

ChampionsGate house

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$149

At Last You can Rent the Perfect Luxury Villa on Solterra Resort, minutes from

Loughman villa

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$251

How to Rent Your Own Private Luxury Holiday Villa on Champions Gate Resort

Loughman villa

8 bedrooms / 5 bathrooms / sleeps 16

Price per night from

$387

Stunning 4 bed villa with south facing pool and spa

Davenport house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$139

Gorgeous 6BR 6Bth Champions Gate Home with Private Pool, Spa and Gameroom

ChampionsGate house

6 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 1 hour 4 minutes

Price per night from

$269

An amazing 4 bedroom house with ots own swimming pool.

ChampionsGate villa

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$158

Joy Palace - Luxury new home in Champions Gate, South facing,Disney,Golf

Davenport villa

9 bedrooms / 5 bathrooms / sleeps 24

Responds fast! avg. 2 hours 56 minutes

Price per night from

$329

Gorgeous, newly refurbished throughout 3 bed 2 bath private pool home

Four Corners villa

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 21 minutes

Price per night from

$162

5 Star Villa for rent in Orlando, Solterra Resort, Villa Orlando 1510

Loughman villa

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$292

✿Near Disney / SeaWorld / Universal - Affodrable 8 Bedrooms w/ Private Pool✿

Davenport villa

8 bedrooms / 5 bathrooms / sleeps 18

Price per night from

$173

“You have Found the Perfect Orlando Villa” Villa 1408

ChampionsGate villa

9 bedrooms / 5 bathrooms / sleeps 21

Price per night from

$483

House Inn Orlando - Amazing private bedroom at this beautiful house - 44-03

ChampionsGate house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$58

⭐7 Bedrooms 6 Bathrooms Villa w/ Private Pool - Near Disney World⭐

Davenport villa

7 bedrooms / 6 bathrooms / sleeps 14

Price per night from

$144

✦Spacious & Luxurious✦Perfect for Large Group w/ Private Pool✦

ChampionsGate villa

8 bedrooms / 5 bathrooms / sleeps 20

Price per night from

$173

Festival Resort-422ACDIL

Davenport house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$273

Disney Sanctuary Villa

Davenport villa

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$151

Watersong Resort-670AOCJGIL

Davenport house

7 bedrooms / 4 bathrooms / sleeps 14

Price per night from

$215

Viewing 38 of 7,393
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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