Vacation Rentals & Apartment Rentals in Winter Haven

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1,334 apartment rentals

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$206

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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$261

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$190

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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$129

Great rentals within 20 miles that match your search

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$194

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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$172

Large Sunny Pool Home Near Disney and Golf

Orlando house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

Responds fast! avg. 2 hours 48 minutes

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$181

5 Star Luxury Resort Condo

Reunion condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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$137

South-facing Pool Home near Disney World

Davenport house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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$194

Disney pool home in gated resort near golf

Orlando house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

Responds fast! avg. 2 hours 48 minutes

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$189

“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

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$189

New cozy townhouse at Champions Gate resort

Davenport townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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$138

Newly decorated at Reunion Resort with golf views

Reunion townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$161

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

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$172

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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$458

A HOLIDAY HOME IN BEAUTIFUL LAKE MARION RESORT.

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 38 minutes

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$136

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$189

SPACIOUS AND CLEAN DISNEY RENTAL VILLA IN FLORIDA

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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$96

14 Room DisneyEstate by AmericanVacationLiving

Four Corners house

  • 12 bedrooms
  • 5 bathrooms
  • sleeps 24

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$882

Beautiful and Spacious Orlando 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!

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$138

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

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$138

Family & Friends Unite For Fun✩Amazing Villa w/ Unique Upscale Amenities

Davenport villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

“Amazing” We had a family of 10 and it was enough space for us. The kids loved the pool and movie room. I liked house to house was so updated and beautiful. We definitely would stay here again.

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$330

⭐Deluxe Villa+Private Pool+Hot Tub+Theatre Room+Pool with Waterslides⭐

ChampionsGate villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 18

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$401

Florida Delight at Watersong, Davenport, Orlando

Davenport villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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$192

Doll House

Davenport house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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$172

⭐Comfy Villa w/ Golf Clubhouse - Adventure & Thrills For Everyone⭐

Davenport villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

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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

DisneyMansion /11BR/30 Beds Golf Pool Tennis Villa

Davenport house

  • 12 bedrooms
  • 5 bathrooms
  • sleeps 24

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$653

DisneyEstate /11King/30 Bed Golf Pool Tennis Villa

Davenport house

  • 12 bedrooms
  • 6 bathrooms
  • sleeps 24

“Best Vacation EVER!!!” I booked this Villa through flip key. I was very impressed by the owners fast response to ALL and ANY questions prior to our much needed vacation. Upon arrival we were warmly welcomed at the villa by our host Mike. Mike gave us a tour of this beautiful and Big home. He even had Fresh Strawberries, chocolate, water and champagne over ice. And had the fridge stocked with breakfast! As for the villa itself, from the kind, courteous, and friendly Host Mike, to the meticulous, comfortable rooms with very well equipped kitchen, cosy common areas - Our experience was nothing less than exceptional. Bonus-The supermarket, restaurants, and shopping is less than 5miles down the road (just a few minutes). We had 5 families (total of 25 people) staying at this villa and Never felt like we were on top of each other. Thank you again to the owners and Our Awesome Host Mike for going above and beyond to make their guests feel Extra special!!! We definitely recommend this place

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$653

Jenny's Disney Retreat 5 miles from Disney

Reunion townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 43 minutes

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$115

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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$158

28 Room DisneyMansionEstate by AmericanVacationLiving

Davenport house

  • 20 bedrooms
  • 11 bathrooms
  • sleeps 50

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$2,256

5 bed luxury villa in Champions Gate Florida

Davenport villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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$215

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$338

The Villa on the Lakes

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$201

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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$189

DisneyByTheLake

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$123

Viewing 38 of 1,334
rentals in Winter Haven

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