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Winter Haven Apartments & Homes - 1307 Rentals Available

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1,307 Vacation rentals

1 / 6

Winter Haven House

  • 3
  • 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 59 minutes

$144.00

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from $144.00 / night

Your search has been expanded 19.8 miles to include more rentals

(5)

1 / 41

Orlando Villa - 19.2 miles away

  • 7
  • 20
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 17 minutes

“We loved it here. It was a nice to be able to use the club house. Lots of stores by for shopping. We would go there again...”
- Review left on 09/06/2016

$184.00

Very Good (5 reviews)

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from $184.00 / night

(2)

1 / 22

ChampionsGate Townhouse - 17.2 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 51 minutes

“House was decorated well, very clean, and spacious. Was nice having these accommodations versus a hotel. Highly recommended...”
- Review left on 10/31/2017

$147.00

Very Good (2 reviews)

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from $147.00 / night

(85)

1 / 101

Davenport Villa - 16.7 miles away

  • 4
  • 10
  • 3 nights min
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 4 minutes

“We stayed here for 16 nights in October 2018 as a family of 5 and had a fantastic time. The villa is very spacious and was like a home from home. The pool and spa are great with a nice seating area for outdoor dining and the area is quiet so no...”
- Review left on 10/28/2018

$129.00

Excellent (85 reviews)

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from $129.00 / night

(6)

1 / 43

Reunion Villa - 19.8 miles away

  • 4
  • 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Beautiful!lots of room for all 4 families . Nicely decorated and great amenities. Very nice to have the pool and hot tub heated to use everyday at the end of the day at the parks...”
- Review left on 01/29/2015

$385.00

Very Good (6 reviews)

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from $385.00 / night

(12)

Certificate of Excellence

1 / 55

Davenport Villa - 12.3 miles away

  • 7
  • 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 17 minutes

Certificate of Excellence

“We really enjoyed the week we spent at the house. It has all we needed: a room that was big enough for each family. It was easy to get to malls, parks, etc. The kids had a lot of fun in the game room, and, of course, the pool. Parents enjoyed the...”
- Review left on 12/12/2016

$172.00

Excellent (12 reviews)

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from $172.00 / night

1 / 45

Davenport House - 12.3 miles away

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 51 minutes

$279.00

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from $279.00 / night

(5)

1 / 24

Davenport Villa - 16.4 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“My family of four took our first Disney vacation and rented this beautiful home. The decor was beautiful and it was spotless. Everything you can need on your trip is available to you in this home. They even had stuff for the beach. My kids loved...”
- Review left on 03/16/2017

$120.00

Excellent (5 reviews)

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from $120.00 / night

(6)

1 / 16

Davenport Villa - 18.8 miles away

  • 5
  • 12
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Love this place, the house its big, rooms are nice. I loved everything about this house. I just wished that they have more kitchen supplies like bigger pots, bigger tupperwares etc...”
- Review left on 03/17/2016

$252.00

Very Good (6 reviews)

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from $252.00 / night

1 / 28

Davenport House - 19.6 miles away

  • 5
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 46 minutes

$107.00

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from $107.00 / night

(2)

1 / 26

Davenport House - 19.3 miles away

  • 7
  • 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$258.00

Very Good (2 reviews)

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from $258.00 / night

(10)

1 / 14

Davenport Villa - 18.5 miles away

  • 4
  • 10
  • 5 nights min
  • Nearest beach 100 mi
  • Swimming pool
  • Ask about children
“From the moment I made an enquiry regarding the villa, the owners responded immediately to any questions I asked and when it came to us going on holiday we were given all the information we needed on how to get to the villa to how to get to...”
- Review left on 03/01/2015

$115.00

Very Good (10 reviews)

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from $115.00 / night

(8)

1 / 17

Haines City Villa - 10.3 miles away

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“A fine place near Southern Dunes Golf Course. Backs up to an orange grove so is peaceful and quite. Nice floor plan. Pool and lanai were great. Owner replace pool heater when I arrived. comfortable for a good size group. May rent again next year”
- Review left on 04/03/2016

$109.00

Very Good (8 reviews)

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from $109.00 / night

(3)

1 / 42

Haines City Villa - 9.9 miles away

  • 6
  • 12
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

Responds fast! Avg. 2 hours 39 minutes

“Wonderful home in pristine condition. A few things already broken/needing repair but call to management company was handled quickly. The home could use more towels, etc. but otherwise great house! Pool heat a MUST in Spring...”
- Review left on 04/12/2016

$205.00

Very Good (3 reviews)

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from $205.00 / night

(6)

Certificate of Excellence

1 / 20

Davenport House - 19.1 miles away

  • 4
  • 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 20 minutes

Certificate of Excellence

“Myself, my fiancee, and two other adults all stayed in this beautiful modern house. It was the perfect place to relax after a long day at the parks. The location is perfectly outside Orlando so there's no craziness but its only a 20 minute drive(with...”
- Review left on 10/20/2017

$115.00

Very Good (6 reviews)

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from $115.00 / night

(4)

1 / 91

Davenport Villa - 17.3 miles away

  • 8
  • 18
  • min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
“We had a really great time here, the house is beautiful and so comfortable, best place I rented, our kids loved it! It had everything we needed and more, loved the area and its close to theme parks (15 min) We would stay here again for sure...”
- Review left on 04/01/2016

$306.00

Excellent (4 reviews)

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from $306.00 / night

(4)

1 / 12

Davenport Villa - 17.5 miles away

  • 4
  • 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Our experience renting this home was great Al took great care of us from the first day. The house was very clean along with the pool and the house is huge pictures do not do a justice. We look forward to renting again in the future. Once again thank...”
- Review left on 03/28/2016

$229.00

Excellent (4 reviews)

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from $229.00 / night

(15)

1 / 30

Reunion Hotel apartment - 19 miles away

  • 3
  • 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 2 hours 8 minutes

$183.00

Very Good (15 reviews)

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from $183.00 / night

(2)

1 / 71

Loughman Villa - 18.4 miles away

  • 4
  • 8
  • 1 night min
  • Nearest beach 126 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 28 minutes

$172.00

Excellent (2 reviews)

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from $172.00 / night

1 / 8

Davenport Villa - 19.1 miles away

  • 7
  • 17
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$287.00

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from $287.00 / night

(3)

1 / 25

Davenport Villa - 19.2 miles away

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“We have had a beautiful time in a nice place near the Disney Parks. All things you need are in the house or garage. Clean and quiet...”
- Review left on 12/17/2016

$123.00

Very Good (3 reviews)

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from $123.00 / night

(55)

1 / 14

Davenport Villa - 14.3 miles away

  • 4
  • 10
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 33 minutes

“Our stay here at the property was more than what we imagined! The owners made sure their guests felt comfortable and at home! The property is very clean, and comes with all needed amenities. The kids loved the pool and the adults enjoyed being able...”
- Review left on 01/06/2017

$95.00

Excellent (55 reviews)

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from $95.00 / night

(2)

1 / 30

Davenport Condo - 18.6 miles away

  • 2
  • 4
  • 1 night min
  • Swimming pool
  • Air conditioning

Responds fast! Avg. 58 minutes

“Clean, comfortable and very well equipped with everything we needed for our 3 month stay. Great location - close to major highways, shopping, good restaurants and area attractions. A very nice pool area complete with a poolside bar and grill which...”
- Review left on 04/14/2018

$172.00

Excellent (2 reviews)

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from $172.00 / night

(11)

1 / 27

Davenport Villa - 19.3 miles away

  • 4
  • 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 56 minutes

“We arrived at the home at 2am. There was a light on for us and easy access. The place was exactly as the photos showed. It was very clean. We comfortable seating in living room and breakfast nook. Pool was right out the back door very private. The...”
- Review left on 09/26/2016

$104.00

Excellent (11 reviews)

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from $104.00 / night

(3)

1 / 24

Loughman House - 17.5 miles away

  • 5
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 11 minutes

$120.00

Very Good (3 reviews)

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from $120.00 / night

1 / 5

Davenport Villa - 16.5 miles away

  • 4
  • 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$163.00

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from $163.00 / night

1 / 16

ChampionsGate House - 16.8 miles away

  • 14
  • 30
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 25 minutes

$800.00

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from $800.00 / night

(1)

1 / 52

Sand Lake House - 16.7 miles away

  • 8
  • 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 18 minutes

“I highly recommend this vacation rental, it was absolutely beautiful, just like the photos. It was very comfortable and spacious, management was very accommodated to my daughter and myself. Thank you for making my birthday wonderful...”
- Review left on 01/26/2017

$302.00

Excellent (1 reviews)

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from $302.00 / night

1 / 34

Davenport Villa - 12.7 miles away

  • 9
  • 24
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$343.00

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from $343.00 / night

(3)

1 / 38

Davenport Villa - 12.7 miles away

  • 9
  • 22
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Big beautiful, comfortable home. Everyone was happy to be there and everyday we had fun. The upstairs family room was a huge hit. We watched movies, played games and filled the room with lots of laughter. Because the house was brand new some of the...”
- Review left on 07/12/2016

$373.00

Very Good (3 reviews)

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from $373.00 / night

1 / 21

Davenport House - 17.1 miles away

  • 5
  • 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$229.00

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from $229.00 / night

(1)

1 / 56

Reunion Villa - 19.7 miles away

  • 4
  • 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$289.00

Very Good (1 reviews)

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from $289.00 / night

(1)

1 / 32

Loughman House - 17.7 miles away

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 51 minutes

$155.00

Average (1 reviews)

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from $155.00 / night

(5)

Certificate of Excellence

1 / 31

Four Corners House - 14.6 miles away

  • 4
  • 11
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 11 minutes

Certificate of Excellence

$113.00

Excellent (5 reviews)

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from $113.00 / night

1 / 39

Orlando Townhouse - 18 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 51 minutes

$147.00

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from $147.00 / night

1 / 11

Lake Alfred Studio - 4.5 miles away

  • -1
  • 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning

Responds fast! Avg. 3 hours 59 minutes

$52.00

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from $52.00 / night

1 / 38

Davenport House - 17.2 miles away

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 51 minutes

$361.00

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from $361.00 / night

1 / 19

Davenport Villa - 12 miles away

  • 6
  • 12
  • 5 nights min
  • Child friendly

Responds fast! Avg. 5 minutes

$212.00

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from $212.00 / night

(1)

1 / 17

Four Corners Villa - 19.2 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 5 minutes

$149.00

Excellent (1 reviews)

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from $149.00 / night

(8)

1 / 19

Reunion Apartment - 19 miles away

  • 3
  • 6
  • 4 nights min
  • Swimming pool
  • Air conditioning

$175.00

Very Good (8 reviews)

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from $175.00 / night