COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

Vacation Rentals & Apartment Rentals in Winter Haven

Updating...

age 0-16
5123 Results

Relevance

Price: low to high

Price: high to low

Number of reviews

5,123 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. 2 hours 29 minutes

Price per night from

$151

Snowbird - Central Florida - Waterfront / Bord de lac

Winter Haven house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$81

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

Winter Haven house

3 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$113

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

Winter Haven house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$78

Charming Lake Eloise Home w/Boat Ramp Access!

Winter Haven house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 29 minutes

Price per night from

$78

Modern Home w/Porch & Private Canal to Lake Eloise

Winter Haven house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$95

Stylish Home w/ Private Canal Access to Lake Eloise

Winter Haven house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 29 minutes

Price per night from

$78

Newly Listed! Private Pool Paradise 2.5 miles to Legoland & close to Disney! Co

Winter Haven house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$185

Great rentals within 20 miles that match your search

Lake View Retreat in Historic District

Lake Wales house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$170

Executive Vacation Villa by Disney

Davenport house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$162

Disney, Sea World, Universal, Legoland, Golf Condo

Haines City condo

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$89

Treetops Villa, Lake Wilson Preserve, Disney

Davenport house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$175

Stunning brand new 6 bed, 4 bath, 3 living areas, games room, south facing pool

Davenport house

6 bedrooms / 4 bathrooms / sleeps 14

Price per night from

$279

Disney Pines

Davenport house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$131

Lake View at Terrace Ridge

ChampionsGate condo

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$111

2 Bed / 2 Bath Resort Condo near Disney

Davenport condo

2 bedrooms / 2 bathrooms / sleeps 4

“Wonderful, amazing” The condo was huge and beautiful, it had everything we needed and then some. The owner was very helpful and went beyond expectation to meet our needs and make our vacation awesome. Shops and fun excitement was just a 15-20 min drive. The pool was wonderful.

Price per night from

$196

Florida Vacation Rental Home | Play Under the Palm

Haines City house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$157

Festival Resort - Huge Villa close to all Orlando attractions

ChampionsGate villa

5 bedrooms / 6 bathrooms / sleeps 14

Responds fast! avg. 34 minutes

Price per night from

$196

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

$365

Just Bring Your Toothbrush

Lake Wales house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$196

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

$1,437

in the middle between Orlando and Tampa Florida

Lake Wales house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$624

Large 4 bed home close to Disney World Orlando

Haines City house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$157

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

Orlando Area 4BR,3B Rental Villa

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 10

“Wonderful house” Such an amazing house, great location and wonderful amenities. The place is beautiful, me and my family had a wonderful time there. I recommend renting this house with my eyes closed

Responds fast! avg. 2 hours 16 minutes

Price per night from

$262

The Florida Hotel & Conference Center, BW Premier Collection

Orlando private room

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$262

large vintage private safe apt near Lake Legoland

Lake Wales apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$117

Watersong Dream Villa

Davenport villa

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$242

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

$164

Brand New ChampionsGate 8br/5ba 12 min to Disney

ChampionsGate villa

8 bedrooms / 5 bathrooms / sleeps 18

Responds fast! avg. 47 minutes

Price per night from

$914

Stunning Executive 6 bed Villa 15mins from Disney

Orlando villa

6 bedrooms / 6 bathrooms / sleeps 14

“A spacious home away from home!” From the first contact with Mr Vaughan, we were pleasantly surprised at the prompt response and attention he took with the details of our rental. We found the realty agent in Orlando also as quick to handle our requests and ready to make our stay as comfortable as possible. Our family gathered from alabama and Colorado with up to 12 people in and out of the house at times, enjoying the spacious and well appointed villa. The kitchen has a great quantity of dishes, glasses, silverware, pots, pans, even down to a hot water pot for hot tea or cocoa! I was expecting to have to buy paper plates/cups etc, as we usually do, but not so at this house!! It seems they have thought of everything! The rooms and baths are so plentiful that each person had their own space, without having to double up or be uncomfortable sleeping on a couch. The house was clean and had a huge amount of towels for bathing and swimming. Although the January temps were chilly, the heated swimming pool gave the children hours of entertainment and the balmy spa was enjoyed by some of the adults. The game room kept the rest of the crew having fun together with it's large assortment of game tables. Haines City is about a 25 minute drive to the Disney parks and the roads are excellent. There are grocery stores within minutes of this house, so shopping is very convenient. The fact that the home is in a gated community made it feel very safe. We highly recommend it to anyone planning an Orlando vacation!

Price per night from

$374

Golf house

Reunion house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$392

Beautiful and Spacious Orlando Vacation Pool Home

Davenport house

4 bedrooms / 3 bathrooms / sleeps 10

“Awesome Place to Stay!” Stayed there for a week and had an absolute ball. Villa is extremely clean and exactly as pictured on the website. We had so much fun in the pool we forgot the Villa had a pool table! Definitely booking this one again next vacation!

Price per night from

$118

Vacation Rental in Grenelefe Country Homes

Haines City villa

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$109

ORLANDO LUXURY GOLF FRONT HOME 5 BED/4 BATH + POOL

Davenport house

5 bedrooms / 4 bathrooms / sleeps 10

“Fantastic Villa” We really enjoyed our stay at this lovely villa. The owners were very friendly and helpful and the villa is in excellent condition and very well equiped. It is about 20-30,ins drive from the parks which we really liked as it was nice to drive away from that area after a busy day !

Price per night from

$249

Florida Paradise

Davenport house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$195

Viewing 37 of 5,123
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