Vacation Rentals & Apartment Rentals in Winter Haven

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1,923 apartment rentals

Responds fast! avg. 6 minutes

Price per night from

$215

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

$347

Responds fast! avg. 6 minutes

Price per night from

$223

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

$137

Mints to Legoland

Winter Haven house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$166

Great rentals within 20 miles that match your search

Price per night from

$194

Terrace Ridge condo ideal for Disney and I4

Davenport apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“AMAZING Condo!” This was by far, hands down, the best place to stay! This condo is set up well, decorated adorably and fully equipped with anything you can imagine you would need. The kitchen is completely stocked with any cookware or gadget you may need. I highly recommend this condo. It was much closer to all of the Disney parks than I expected it to be.

Price per night from

$126

“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

$189

New cozy townhouse at Champions Gate resort

Davenport townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$138

Newly decorated at Reunion Resort with golf views

Reunion townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$161

“Disney vacation” Beautiful vacation home! We loved the spacious living arrangement and proximity to a shopping center. Only about 15-20 minutes to Disney parks. Would certainly recommend this house and stay again!

Responds fast! avg. 30 minutes

Price per night from

$170

The Great Titan

Orlando villa

  • 14 bedrooms
  • 16 bathrooms
  • sleeps 30

Responds fast! avg. 2 hours 21 minutes

Price per night from

$4,008

The Golden Bear

Orlando villa

  • 10 bedrooms
  • 11 bathrooms
  • sleeps 24

Responds fast! avg. 2 hours 21 minutes

Price per night from

$2,497

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

$213

Disney Area Villa in gated Aviana Resort

Orlando villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Mrs” This rental was clean and neat. It had great amenities and my kids love the pool and spa. The play room in the garage made it perfect for my kids when they ran out of energy from the pool. The staff was friendly and helpful. I would defiantly recommend this unit to anyone.

Responds fast! avg. 3 hours 28 minutes

Price per night from

$172

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

$458

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

Solterra Resort 5 Bedroom Home with Pool (1604)

Davenport house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 59 minutes

Price per night from

$157

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

Reunion house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Price per night from

$516

Price per night from

$189

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

$189

Luxury Villa in Hampton Lakes near Disney

Davenport villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

“Peacefull and relaxing” Great family condo, good pool, relaxed neighourhood. Plenty of space, offers privacy and yet a family and home feeling

Responds fast! avg. 3 hours 52 minutes

Price per night from

$259

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

$189

Price per night from

$228

Upscale 2BR Condo at Terrace Ridge near Disney FL

Davenport apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Very Nice Location, Property, and Experience” The booking process was very easy and straightforward. It was much easier than bookings I have done on other sites. I felt my payment and information was secure. The process of checking in and getting access to the condo was very efficient as well. There was a minor hiccup with the entry code, but the customer service line was able to correct it right away. The house was nice and spacious. It had everything we needed to ensure we had a proper vacation. While there were some initial headaches, the owner and customer support line were always there to ensure we were satisfied. The location was great. it seems that there is a lot of development going on in this location. There were multiple places to eat, and shop. It was not far from all of the main attractions. Because of its proximity to I-4, there was minimal traffic. The pool and facilities were clean and comfortable. I met a lot of nice people there. I would recommend this condo to anyone looking for a peaceful vacation that is close to all the great things in Orlando.

Price per night from

$109

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

$377

“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

Sunny Disney Pool Home in Gated Resort, Amenities for All

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

“Decent place but lacking in some areas” For one week in July 2014, my family from Alabama to Alaska (with us from Canada) all stayed at 928 Solona Circle. Overall we were happy with the house rental but do not stay here if you need assistance with anything. It took my 4 phone calls over 3 days to just find out what the Wi-Fi password had been changed to (the one that we were emailed was incorrect). It may not be the safest neighbourhood as there were police men in the gated area twice during our stay. And the house was filled with broken outlet covers and had very dirty couches, which needed steam cleaning. It was a spacious home and we loved the walk-in closets as well as the ease in which to find it and the easy drive to Disneyworld. But if you want to stray there, you need to supply everything- even your own toilet paper and Kleenex. The jets ion eth hot tub did not work and the game room had a broken foosball table. Overall we were mainly happy with our stay but were disappointed with a few things.

Price per night from

$189

Disney Pool Home, Great view, Gated resort

Orlando villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

Price per night from

$218

KISSIMMEE'S KNIGHT CASTLE

Kissimmee house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 20

“Absolutely outstanding!” Our family of 8 adults, 2 children aged 4 years, and 3 infants under 15 months of age, had an outstanding vacation in this home. Only a short drive to all the amenities (including Magic Kingdom) was exactly what was advertised. This home was immaculate, and extremely comfortable. I would highly recommend this property for anyone traveling with family! J. Macpherson, Whitby, Ontario, Canada

Price per night from

$463

Price per night from

$275

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

$227

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

$212

Viewing 38 of 1,923
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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