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Vacation Rentals & Apartment Rentals in Winter Haven

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4,482 apartment rentals

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

Winter Haven house

3 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$114

Legoland & Family Fun - Lake Silver Retreat in the Heart of Winter Haven

Winter Haven house

5 bedrooms / 3 bathrooms / sleeps 11

Price per night from

$353

Private Pool Paradise - 2.5 miles to Legoland & close to Disney! Contactless E

Winter Haven house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$186

Great rentals within 20 miles that match your search

Treetops Villa, Lake Wilson Preserve, Disney

Davenport house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$174

Unfurished 4/2.5/2 with Private Pool Weekly and Nightly rental available

Poinciana private room

4 bedrooms / 3 bathrooms / sleeps 20

Price per night from

$363

Lake Front Complex Motel & Villas Furnished 1 bedroom unit

Lake Wales lodge

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$98

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

$1,427

in the middle between Orlando and Tampa Florida

Lake Wales house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$619

Dream-Inn Villa Room 1, close to Disney, Shopping, Golf

Four Corners private room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$85

large vintage private safe apt near Lake Legoland

Lake Wales apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$116

4 bedroom, 3 bathroom, beautiful villa with pool and spa on the Solana resort

Four Corners villa

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$163

Vacation Rental in Grenelefe Country Homes

Haines City villa

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$108

SPACIOUS AND CLEAN DISNEY RENTAL VILLA IN FLORIDA

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$106

Lake front complex Motel & Villas

Lake Wales studio

Studio / 1 bathroom / sleeps 2

Price per night from

$91

5 bedroom vacation home with pool & game room near Disney

Four Corners house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$455

COMFORT 4200 sf 1 Level. 4 Q-BR, Library,TV Rm,Ofc

Davenport house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 32 minutes

Price per night from

$130

Immaculate secure, sanitized 6 bed/ 6 home, pool, theatre room, games room.

Davenport house

6 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 2 hours 56 minutes

Price per night from

$254

Responds fast! avg. 49 minutes

Price per night from

$135

WOW Brand new 4 bedroom 3 bath Champions Gate townhouse from $128nt

ChampionsGate townhouse

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 53 minutes

Price per night from

$155

Calabay Palms Villa - Luxury 5 Bed - Sleeps 10/2 - South Facing Pool - Hot Tub

Four Corners house

5 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$221

4 bed/3 baths 2 living rooms pool close to Disney

Four Corners house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$143

Stunning and Modern 4BR Villa Close to Disney

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$137

Beautiful 5BR/3BA (Sleeps 10) Pool & Game Room - close to Disney and Universal

Loughman villa

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$161

Modern 5 bed family friendly pool home

Loughman house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$167

Magic Villa Orlando Gated Community 4 Ensuite Bedrooms with Pool and Jacuzzi

Haines City villa

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$158

Golf views at Reunion Resort

Reunion apartment

3 bedrooms / 3 bathrooms / sleeps 6

“Relaxing at the Reunion” Beautiful three bedroom condo in Reunion. Great location to everything.Very spacious. Angela and Eileen were great to work with,we had never booked with anyone from the UK before they were very nice and ease of booking was great. Great view of golf course. Close to pool. Beds are very comfortable. Only downside is I wish they had a full size washer and dryer. Easy check in and checkout. We enjoyed having breakfast on the patio and watching the golfers everyday. Thank you for allowing us to enjoy your home.

Price per night from

$183

Upscale home w/ private pool and whirlpool spa - near lake, golf, & Disney!

Loughman house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$206

Enjoy a private pool & game room, shared tennis & gym - view Disney fireworks!

ChampionsGate house

5 bedrooms / 6 bathrooms / sleeps 10

Price per night from

$200

Family-friendly home w/ private pool, clubhouse access, and more!

Loughman house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$290

Spacious home in the Sunshine State w/ a covered lanai, private pool, & pool spa

Four Corners house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$168

Elegant home w/ private pool, spa pool & access to resort amenities!

Loughman house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$247

Contemporary family retreat, private pool close to Disney World & theme parks

Loughman house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$169

Gorgeous 4BD/3BA Reunion Resort Near DisneyLand

Reunion house

4 bedrooms / 5 bathrooms / sleeps 8

Price per night from

$146

Amazing 5 bedroom home - Champions Gate Resort

ChampionsGate house

5 bedrooms / 4 bathrooms / sleeps 11

Responds fast! avg. 2 hours 15 minutes

Price per night from

$287

Gorgeous 6-bedrooms 6-bathrooms home

Davenport house

6 bedrooms / 6 bathrooms / sleeps 14

Responds fast! avg. 2 hours 15 minutes

Price per night from

$323

6 bedrooms home - Champions Gate

ChampionsGate house

6 bedrooms / 6 bathrooms / sleeps 14

Responds fast! avg. 2 hours 15 minutes

Price per night from

$323

Modern 6-Bedroom Home

Four Corners house

6 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 2 hours 15 minutes

Price per night from

$323

Viewing 37 of 4,482
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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