Vacation Rentals & Apartment Rentals in Winter Haven

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1,440 apartment rentals

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$207

Lakefront Luxury: Boat Dock, Pet-Friendly, Close to LegoLand, Perfect for Family

Winter Haven house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 11

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$306

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$205

Great rentals within 20 miles that match your search

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$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!!

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$190

New cozy townhouse at Champions Gate resort

Davenport townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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$138

Luxury 6 Bed/5 Bath Villa near Disney on gated community with golf course

Davenport villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

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$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

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$121

A HOLIDAY HOME IN BEAUTIFUL LAKE MARION RESORT.

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$137

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$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.

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$192

Disney Pool Home in Gated Resort, Amenities for All

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 15

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$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!

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$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.

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$190

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$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.

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$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.

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$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.

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$146

Disney Pool Home, Great view, Gated resort

Orlando villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

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$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.

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$228

Sunny Disney Pool Home in Gated Resort, Amenities for All

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

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$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!

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$213

Lazy Days Villa

Davenport house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$161

Large Disney Pool Home w/ Resort Amenities

Orlando villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 19

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$213

"HAROVIN" Disney-Family Vacation-Orlando-Florida

Davenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$148

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$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.

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$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

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$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

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$207

Pluto's Palace Florida Villa "The Real One"

Davenport villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$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

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$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.

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$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

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$138

Luxury Florida Villa (Pool, FREE Wi-Fi, Gameroom)

Davenport villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“Fantastic place to stay!!!” The owner and property manager are courteous and prompt to our inquiries. The villa was in great shape.

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$144

"Beautiful Disney Home"

Davenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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$114

Luxury 4 bedroom villa in Davenport, near Disney,

Davenport villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“Great family home close to everything” We were a group of 4 adults and 3 kids. This house was perfect and room to spare for additional people if needed. Very well maintained, equipped home. Location was a plus, close to everything, quiet neighborhood. The owner and management team was very quick to respond. Only had to contact them once the morning after arrival, for nothing more than something minor with WiFi. The private pool was a big hit with our grandkids, once the water was warm enough to get in. Definitely would stay here again. Great week.

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$173

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.

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$401

Willow View Villa 5+ Bed, 3xKing Master 2xTwin + Den

Davenport villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

“Willow View Villa” First, let me say the home is not what you see in the pics. The home has flat screen throughout. The home was convenient to parks, outlets and restaurants. My family and I stay in Davenport a few times a year but this was a last minute trip and based on pics we were really nervous. The home was clean and kids loved the pool. We cooked out and enjoyed the patio. I had 2 problems that was unfortunately fixed the day we were leaving but it was nature not the owner!. The other was the downstairs bedroom smelled like smoke, we sprayed but was in the linen. Again, it was clean but smelled like smoke and being non smokers it was annoying. We spent most of our time on the comfy recliners or at the pool so it was ok. Thank you Martin!

Responds fast! avg. 2 hours 12 minutes

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$276

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