Vacation Rentals & Apartment Rentals in Winter Haven

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1,924 apartment rentals

Responds fast! avg. 6 minutes

Price per night from

$207

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

$306

Responds fast! avg. 6 minutes

Price per night from

$205

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

$129

Mints to Legoland

Winter Haven house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$167

Great rentals within 20 miles that match your search

Price per night from

$194

“Great Family Memories” We give this home an A+!! Everything about it from the appearance, to the owner (Liz), to the location, and the management company combine to give you unprecedented good customer service that insures a great experience. Everything is geared towards you! The house is actually even nicer than the pictures depict!! We had 5 adults and one child stay and there was plenty of room for everyone. We loved the layout. Our granddaughter squealed with delight when she saw the Mickey Mouse room. She even asked to go to bed several nights!! We enjoyed going to nearby outlet malls, Disney, Disney Springs, restaurants close by, and even grilling out on the patio while family members swam in the pool. The game tables in the garage provided some lively competition. The greatest compliment you can give a place is to say you would return again. When we come back to this area again, Pilgrim's Paradise will be at the top of our list to stay at again! Liz made everything run smooth and was a delight to work with!! Thanks for sharing your beautiful villa with our family!!

Responds fast! avg. 1 hour 56 minutes

Price per night from

$190

New cozy townhouse at Champions Gate resort

Davenport townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$138

7 Bedrooms / 5 Bathrooms / Solterra (4103 OD)

Davenport house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 22

Responds fast! avg. 3 hours 26 minutes

Price per night from

$214

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

$459

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 17 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. 2 hours 30 minutes

Price per night from

$137

Spacious, game room, theater loft, golf view, private pool & BBQ

Reunion house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Price per night from

$517

Price per night from

$190

ENCHANTING DISNEY VACATION RENTAL HOME

Davenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“A house that I could see living in permanently.” I can't think of anything negative to say, OK if I lived there I'd put a couple palm trees and a bar by the pool... I really liked the look of the tile floor in the living room and I really appreciated the fact that there is a DVR connected to the main TV. It is an awesome house.

Price per night from

$192

Disney Pool Home in Gated Resort, Amenities for All

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 15

Price per night from

$207

Disney Pool Home, Great view, Gated resort near Golf

Orlando villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

“Spacious and comfortable” Although this was not the home pictured in the photos of the home we chose and thought we were staying, it provided the same spacious and comfortable space needed for a family reunion. The lanai with the pool and hot tub was really nice with amazing sunsets in the evening and moonsets in the early morning. There was a resident Sandhill crane who meandered by for a visit each day. The location of this quiet resort community was pleasantly out of the way of the crowds, yet reasonably convenient to anything you would need or want to do. Our main concern was that we were unable to consistently lock the back sliding glass door and there was no bar to place to lock it. (And, the crumb tray on the toaster was broken.) Other than that, the home was a little tired, but more than adequate. Thank you for a delightful week!

Price per night from

$190

Tupelo Magic - Disney Orlando

Davenport house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Awesome Home” This home was beautiful! It was all the was described and more! My family and I had an amazing time! Our only regret was that we were so busy and did not get much time at the home relaxing.

Price per night from

$190

Price per night from

$229

AWARD WINNER, 5 STAR VILLA. Space, Luxury, Unique private sunny corner

Reunion villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

“Fabulous Location” From my initial contact with David I found that he responded promptly with any queries that I had and provided me with information on the Reunion Resort and the Kissimmee area. Arriving late on the Saturday evening, welcoming lights had been left on within the villa revealing a superbly decorated and immaculately clean home. The villa was suited to our family needs with 4 ensuite bedrooms. The provision of free wifi was a bonus for the younger family members. During our stay the well equipped kitchen with high quality utensils, including a kettle, was used to cook numerous meals. Our family did make use of items provided for guests such as sat-nav, beach towels and Tommy Bahama beach chairs which proved useful when we visited Clear Water beach. Craig from the Jeeves management team welcomed us on our first day and provided us with information on the Reunion Resort pointing out the community pools etc. The gym appealed to the enthusiastic among us. The Reunion Resort was easy to find with the instructions provided by David, unlike the 192, we experienced no traffic delays from the Disney Parks using the i 4. Publix supermarkets are located nearby. I can now understand why 7720 Link Side Loop, Patriots Landing is named 5* Villa Orlando. It certainly deserves the awards it has received. In my opinion there is a highly professional combination with David the owner and Jeeves the management team offering a high quality service and accommodation to renters. I recommend this villa and the Reunion Resort to any family contemplating a vacation in Orlando. I hope that when I return to Florida that this accommodation will be available on our chosen dates as I doubt if we will be able to find better. David thank you for all your help and playing your part in making our vacation to Florida successful and enjoyable.

Price per night from

$378

“Perfect Vacation Home” Great home, well laid out, perfect vacation home for the whole family. Clean, well equipped. Great location of Southern Dunes on a beautiful golf course. Had our family visit for two weeks and there was plenty of room for all our children and grand children. Would definitely recommend it to all my friends and would go back again.

Price per night from

$155

Lake View Dream Villa

Davenport villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 11

“Very family friendly house...” This was a very family-friendly house .We had a great stay and the kids loved the pool. The house was very clean and well managed. If we had any question we were able to get them without the long wait .Would highly recommend this house for any family looking for a wonderful stay minutes for Disney.

Responds fast! avg. 20 minutes

Price per night from

$146

Disney Pool Home, Great view, Gated resort

Orlando villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

Price per night from

$218

Beautiful 3B/3B Penthouse Disney Vacation Condo

Reunion hotel apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Great Family Getaway” We really enjoyed our stay at Reunion Resort and actaully never left the property other than a quick trip to Downtown Disney. The waterpark was amazing and lots of fun for children and adults. The size of the park was perfect for our children, ages 8, 9 and 11 -- they had a great deal of freedom to explore and we were actually able to read a book while they played! The condo was lovely and I would definately stay there again. It had all of the modern conveniences and upgraded appliances. The large, flat screen TVs in each room were a hit for families. We really enjoyed being so close to the waterpark -- five minute walk. The view from the balcany was also -- over looks woods and gives you a tree house feel. Very nice not to look at another property. Disney less than 10 minutes away.

Price per night from

$228

Private one bedroom apartment at a great price

Lakeland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 36 minutes

Price per night from

$90

Sunny Disney Pool Home in Gated Resort, Amenities for All

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

Price per night from

$213

Spacious Disney pool home w/ Spa, near golf

Orlando villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

“PERFECT FAMILY VILLA!” This villa is HUGE and gorgeous! We were traveling with a large family and with 7 bedrooms and 9 beds plus a crib in the master there is more than enough room for your whole family to enjoy a get away! There are 2 rooms located down stairs so if anyone is disabled they can use these rooms. This home is beautifully decorated and so comfortable for us. We thoroughly enjoyed the screened in private pool -with a bathroom entrance right off the pool area! We felt very safe in the community this villa is in and the area surrounding it. Champions Gate is a gorgeous little community with everything you need within 10 minutes. We were visiting Disney and found this villa a wonderful option to staying in the parks. It took us 15 minutes to get to any park and we always parked and loaded a tram quickly and went right to the door. I don't know why people have always convinced me staying of property would be such a hassle..it was no hassle at all! A lovely bonus to this villa was an ice cream truck driver lives right down the street and hits the neighborhood 2 times a day. The kids LOVED that! The home came with all the comforts needed to make us feel at home. Including pool toys, 2 high chairs, iron/ironing board, hair dryers, big beach towels, bath towels and rags, kitchen towels and all the cooking utensils and appliances needed for cooking meals. We did have a dilemma with an odd shape staircase that our child gate would not fit and a toddler but we just moved a couch to block the entry from the livingroom to the front area and that worked well. The home is tiled so it was easy to keep the floors clean. The beds were comfortable and the pillows were mixtures of full and flat to suit all preferences. The home smelled nice and did not have the mild moldy smell many FL homes can have from the high humidity in the area. The owners were a pleasure to work with, very accommodating, helpful and prompt to answer my silly questions about where items in the house were and how to work locks etc We will for sure stay here the next time we visit orlando area. This villa felt like home and was hard to leave. It truly is so comfortable and I am a hard one to please! If you are reading this and considering this home...seriously do not continue your search. There is so much that can go wrong when renting homes on vacations. But this one does everything right!

Price per night from

$213

Lazy Days Villa

Davenport house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$161

Large Disney Pool Home w/ Resort Amenities

Orlando villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 19

Price per night from

$213

"HAROVIN" Disney-Family Vacation-Orlando-Florida

Davenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$148

Price per night from

$171

Large Sunny Pool Home Near Disney and Golf

Orlando villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

“Very Good” Nice quite location. It is close to the theme parks and all the family attractions. My family is well pleased with the spacious home, The children and adults are taking full advantage of the pool throughout the entire day prior to leaving the house and upon our return.

Price per night from

$182

Impressive Villa with Private Pool and Free WI-FI

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Beautiful Home-Definitely Recommend” This home is an amazing home away from home. Has everything available that you would need. Just bring your clothes and your good to go. Plenty of room and very comfortable seating and sleeping. The screened in pool was a wonderful place to spend some time outdoors without worrying about the insects. The owners are very quick to respond with any questions and are very kind! Very close to amenities and restaurants if you decide to eat out, but the home has a fully equipped kitchen to prepare your own meals!! Not a very far drive from the airport or amusement parks—very conveniently located. Close enough but not to close! We highly recommend and will definitely stay here again if the situations permits. We very much enjoyed our stay!!

Responds fast! avg. 1 hour 30 minutes

Price per night from

$144

Luxurious Villa in Marbella resort, Davenport, Fl

Davenport villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Birthday Trip” We were in Orlando celebrating my son's 4th birthday and it was great. The house was clean and very maintained. I spoke with the property manager once, and he gave us some great tips for travel and dealing with the heat. The instructions were clear and we enjoyed our visit.

Responds fast! avg. 1 hour 51 minutes

Price per night from

$207

Pluto's Palace Florida Villa "The Real One"

Davenport villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$259

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

Price per night from

$207

Luxury 4 Bedroom Condo, Terrace Ridge, Davenport.

Davenport apartment

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“Beautiful Condo” I recently stayed in this condo. We were a group of 6 (2 kids and 4 adults). This condo was perfect. It is bigger and nicer than it looks in the pictures. It is very well stocked. We had all the dishes we needed, dish soap, laundry detergent, there were even books and movies and toys for the kids. If we get to take another trip to orlando I am definitely gonna try to book this one again.

Price per night from

$115

Jenny's Disney Escape 5 miles from Disney!!

Reunion house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

“Wonderful home!” We can not say enough great things about this rental! The home is gorgeous, even nicer than pictured, the area is very quiet and safe, the drive to Disney is very convenient and the owner is wonderful! Every email I sent was answered right away by Jenny and she even checked in on us during the visit to make sure everything was ok! She even thought to include "essentials" that I didn't remember to buy. Our family will be staying here again (as soon as we save up for Disney again)! :0)

Responds fast! avg. 43 minutes

Price per night from

$138

Viewing 38 of 1,924
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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