Vacation Rentals & Apartment Rentals in Winter Haven

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775 apartment rentals

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$186

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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$277

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$198

Cozy 1 BR Apt on Lake Howard with Lanai Patio, Dock & Kayaks

Winter Haven apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$133

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!!

Responds fast! avg. 2 hours 12 minutes

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$190

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

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$121

A HOLIDAY HOME IN BEAUTIFUL LAKE MARION RESORT.

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 26 minutes

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$136

No Rear Neighbors/SW Pool/Close to Disney/Game Rm

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$138

Champions Gate #1 - Luxurious 8 Bedroom Pool Villa with Theater

Davenport villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

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$400

Doll House

Davenport house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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$172

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$336

The Ultimate Florida Vacation

Poinciana villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great place” Very cozy, out in suburbs. Neighborhood clean and friendly. Pools and outdoor basketball courts and activities for the kids.

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$110

Orlando villa with a conservation view Sandy Ridge

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 41 minutes

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$157

28 Room DisneyMansionEstate by AmericanVacationLiving

Davenport house

  • 20 bedrooms
  • 11 bathrooms
  • sleeps 50

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$2,258

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$339

Disney pool home, Great view, Gated resort

Orlando villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

“Iraq Home Coming” Excellent vacation home for a visiting family. It was the easiest check in process I have ever done since I’ve been traveling. Just to come back from a war zone and visit family and friends along with eating at different restaurants and amusement parks was very enjoyable. I would recommend renting a vacation home before renting a hotel room any day if it’s as pleasant as this trip has been for me. I want to personally thank the home owner and the company for such an easy process of communication and updates.

Responds fast! avg. 2 hours 48 minutes

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$190

DisneyByTheLake

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$123

3 bedroom home private pool near Disney I4 & shops

Davenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Supervisor” It was really nice. We stayed for three nights and we enjoyed it. It was close to the parks, to publix, restaurants, and gas stations. Only one negative was that there were no phone signal.

Responds fast! avg. 44 minutes

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$121

Newly Renovated and Furnished Private South Facing Villa near Disney

Orlando villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 4 minutes

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$148

Beautiful 6 Bedroom Home in Reunion Resort and Spa

Reunion house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 16

Responds fast! avg. 14 minutes

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$488

Large Disney Pool Home w/ game room, near golf

Orlando villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 20

Responds fast! avg. 2 hours 48 minutes

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$190

Immaculate Spacious Villa

Orlando villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 1 minutes

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$218

Watersong Luxurious Villa 6 Bed, 5 Bath + 2 x1/2b

Davenport villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 13

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$428

BigDisneyVilla 4 Bed Executive Orlando Pool Home Sleeps up to 8 - Golf

Davenport house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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$172

Southern Dunes Golf Vacation Villa

Orlando villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Visitor” Loved it. Great neighborhood. Clean house. Easy to get a hold of people if you had questions or needed help. Walmart right around corner. Had everything you need to cook with. Great place. Defiantly will come back and recommend to anyone.

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$117

Beautiful Orlando Villa "Mags Den" Calabay Parc

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 44 minutes

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$171

South-facing Pool Home near Disney World

Davenport house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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$194

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

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

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$257

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$228

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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$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.

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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.

Responds fast! avg. 20 minutes

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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

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.

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$190

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