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Vacation Rentals & Apartment Rentals in Winter Haven

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4,404 apartment rentals

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

Winter Haven house

3 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$132

Lakeviews, Legoland, Foosball & Kayaks ~ Family Fun!

Winter Haven house

5 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 2 hours 12 minutes

Price per night from

$241

Lake Silver Retreat III * Lakeviews~Legoland~Foosball & Kayaks ~ Family Fun

Winter Haven house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 2 hours 12 minutes

Price per night from

$241

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

Winter Haven house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 12 minutes

Price per night from

$173

Great rentals within 20 miles that match your search

BROOKS RETREAT

Haines City villa

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$147

Minnies Florida Villa

Haines City house

5 bedrooms / 4 bathrooms / sleeps 10

“Wonderful Home and Host” Nice home in a nice neighborhood. Reasonable price. Owner was easy to deal with and very hospitable. Overall a nice experience. The only draw back is that 6 of the 7 mattress sets are low grade and in need of upgrading which I'm guessing is in the near future.

Price per night from

$237

Beautiful Private Villa Close To Disney Parks

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 59 minutes

Price per night from

$174

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

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

$328

Luxury 6-Bedroom Lakeside Villa near DisneyWorld

Davenport villa

6 bedrooms / 5 bathrooms / sleeps 14

“Vacation” The house was clean and spacious, it was perfect for my family and I to enjoy each other and rest. Thanks

Responds fast! avg. 3 hours 38 minutes

Price per night from

$206

Reunion Resort - Golf views private pool and summer kitchen

Reunion villa

5 bedrooms / 6 bathrooms / sleeps 10

“Excellent location and great house” We (two families) selected the house from a wide list and we where very pleased with the property, the location, cleanliness, facilities and service. Its ideal for the usual mix or Orlando resorts and days out plus it was also excellent to use the giant BBQ each night for dinner while the kids messed around in the pool. The beds and bedding where very comfy and also very quiet.

Price per night from

$400

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

$175

Rivendell Villa Holiday Rental Davenport Orlando

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$127

Just Bring Your Toothbrush

Lake Wales house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$172

✧Near to All Orlando Parks and Attractions! - 7BR Spacious Villa✧

Davenport villa

7 bedrooms / 6 bathrooms / sleeps 14

“My stay at Solona” House was very nice! Had w issue with ants. Nd dusty other than that it was worth it. They did what they could to help in any way! Loved the heated pool

Price per night from

$189

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

Price per night from

$111

Beautiful Solana villa near Disney and Universal

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 59 minutes

Price per night from

$103

Oleander Villa - Luxury 4 Bedroom Villa, 2.5 miles from Champions Gate.

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 3 minutes

Price per night from

$218

8br Luxury Vacation Home, Disney World, Golf

Davenport villa

8 bedrooms / 5 bathrooms / sleeps 18

Price per night from

$401

SPACIOUS AND CLEAN DISNEY RENTAL VILLA IN FLORIDA

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$106

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

$103

⭐Spacious 7 Bedrooms w/ Private Pool - 6 miles to Walt Disney World⭐

Davenport villa

7 bedrooms / 6 bathrooms / sleeps 14

“Great place for gathering” We chose this home for our big family reunion. It was comfortable and the layout of this home was perfect for everyone. Everyone had their own privacy. Everything in this home was like the pictures. This home is going to be our go-to home next time we come back to Florida. The home was clean and had everything we were looking for. We enjoyed our stay tremendously and would love the opportunity to book this home again.

Price per night from

$195

Exclusive Home Within High Grove Gated Community

Clermont house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$161

Solana Resort Villa

Davenport villa

4 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$166

Beautiful and peaceful house with pool

Davenport house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 18 minutes

Price per night from

$153

South-facing Pool Home near Disney World

Davenport house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$137

Bright, Spacious, Immaculate Villa, Large Pool/Spa

Davenport house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$195

large vintage private safe apt near Lake Legoland

Lake Wales apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$102

Forest View Villa

Davenport house

5 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$214

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 20 minutes

Price per night from

$343

Treetops Villa, Lake Wilson Preserve, Disney

Davenport house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$174

1400MV

Davenport house

8 bedrooms / 5 bathrooms / sleeps 19

“Great place for a large family ,we had a wonderful time will visit again.” The kitchen had all the necessary utensils for our vacation.The house was very clean there was clean towels available for our use.

Responds fast! avg. 3 hours 25 minutes

Price per night from

$295

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

$1,260

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

$172

in the middle between Orlando and Tampa Florida

Lake Wales house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$547

Golf house

Reunion house

5 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 46 minutes

Price per night from

$344

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

$149

Stunning and Modern 4BR Villa Close to Disney

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$126

Viewing 38 of 4,404
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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