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Windermere Vacation Rentals & Beach Rentals - 2698 Rentals Available

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2,698 Vacation rentals

1 / 25

Windermere House

  • 4
  • 10
  • 30 nights min
  • Swimming pool
  • Ask about children

$1,000.00

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from $1,000.00 / night

Your search has been expanded 18.3 miles to include more rentals

1 / 28

Four Corners Villa - 13 miles away

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

Responds fast! Avg. 1 hour 13 minutes

$321.00

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from $321.00 / night

(9)

1 / 12

Kissimmee House - 10.7 miles away

  • 2
  • 6
  • 1 night min
  • Nearest beach 95 mi
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 15 minutes

“I stayed for 5months at this house and it was great. Had everything needed to cook, fenced in backyard for my dog, neighbors were great and I was only 10 minutes from give kids the world where I volunteered. Lots of places to eat and close to all...”
- Review left on 04/11/2016

$98.00

Excellent (9 reviews)

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from $98.00 / night

(3)

1 / 25

Davenport Villa - 16.1 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

1 / 10

Davenport Villa - 15 miles away

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

$196.00

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from $196.00 / night

(20)

1 / 17

Four Corners Villa - 12.3 miles away

  • 4
  • 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“The house was fantastic. The kitchen was well equipped with everything you would need to cook with. The pool was very nice. The community was quiet which was nice to sit out by the pool and read. All the beds were comfortable. Plenty of towels...”
- Review left on 07/14/2016

$144.00

Excellent (20 reviews)

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from $144.00 / night

1 / 16

Old Town Townhouse - 13.1 miles away

  • 3
  • 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 15 minutes

$149.00

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from $149.00 / night

(3)

1 / 26

Davenport House - 17.8 miles away

  • 8
  • 18
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“The house that we rented was by far more than what we expected. Champions Gates is a great community for visiting families. We had four different families stay within the home without anyone feeling like they were stepping on anyone toes. The...”
- Review left on 07/16/2015

$321.00

Excellent (3 reviews)

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from $321.00 / night

(24)

1 / 37

Four Corners Villa - 12.4 miles away

  • 6
  • 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Our family of 11 took a first time ever family vacation and through extensive internet searching found this awesome villa. It couldn't have been any nicer. Six kids, 4 girls & 2 boys & 5 adults. There was so much room for everyone to hang out. The...”
- Review left on 07/27/2016

$223.00

Excellent (24 reviews)

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from $223.00 / night

(31)

1 / 31

Orlando Townhouse - 5.4 miles away

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

Responds fast! Avg. 1 hour 30 minutes

“Excellent place to spend your vacation in. I am glad we stayed!There was one little issue with the heater not on but I called and they came right out and fixed it. We had a great time and enjoyed the home a lot! I hope to use again in the future...”
- Review left on 11/26/2017

$130.00

Very Good (31 reviews)

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from $130.00 / night

1 / 55

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 30 minutes

$267.00

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from $267.00 / night

(6)

1 / 12

Kissimmee Condo - 13.1 miles away

  • 3
  • 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“the location was great, and being without steps was a plus, but I believe that it needs the kitchen to be up-dated. Over all, I really liked everything about the place, except I felt a little up-date for the kitchen would have been better...”
- Review left on 06/28/2015

$102.00

Very Good (6 reviews)

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from $102.00 / night

(18)

1 / 27

Four Corners Villa - 13.1 miles away

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

Responds fast! Avg. 41 minutes

“The house was extremely clean, very comfortable and perfect for our family. It was ready when we got to Florida and it had everything we needed while we were on vacation. I received my deposit back as soon as I got home and the owner was very nice...”
- Review left on 02/17/2017

$149.00

Excellent (18 reviews)

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from $149.00 / night

1 / 27

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 30 minutes

$153.00

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from $153.00 / night

(43)

1 / 57

Clermont House - 12.1 miles away

  • 6
  • 12
  • 4 nights min
  • Nearest beach 113 mi
  • Swimming pool
  • Child friendly

$252.00

Excellent (43 reviews)

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from $252.00 / night

(3)

1 / 24

Kissimmee Villa - 12.9 miles away

  • 4
  • 10
  • 3 nights min
  • Nearest beach 72 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 22 minutes

$137.00

Very Good (3 reviews)

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from $137.00 / night

(2)

1 / 30

Davenport Condo - 16.3 miles away

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

1 / 16

Four Corners Townhouse - 12.4 miles away

  • 3
  • 8
  • 3 nights min
  • Ask about children
  • Air conditioning

$98.00

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from $98.00 / night

(1)

1 / 25

Kissimmee Villa - 14.5 miles away

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

Responds fast! Avg. 1 hour 13 minutes

$167.00

Excellent (1 reviews)

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from $167.00 / night

(13)

1 / 93

Loughman Villa - 17.4 miles away

  • 4
  • 8
  • min stay varies
  • Nearest beach 126 mi
  • Swimming pool
  • Child friendly
“The villa is perfect for a family to stay in to make the most of their Orlando vacation. We loved having the freedom to be on our own schedule, to visit more attractions than just Disney, and to keep the food budget in check. Robert provides...”
- Review left on 02/16/2016

$137.00

Excellent (13 reviews)

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from $137.00 / night

(1)

1 / 37

Kissimmee House - 14.3 miles away

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

Responds fast! Avg. 1 hour 13 minutes

$136.00

Excellent (1 reviews)

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from $136.00 / night

(9)

1 / 24

Davenport Villa - 17 miles away

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“The house was nice and clean ,the kitchen had everything we need ,the baby staff was so helpful with my little daughter .my kids enjoyed the pool it was interesting.i forget our passports in the house and I called the office and they send them to us...”
- Review left on 02/11/2016

$148.00

Excellent (9 reviews)

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from $148.00 / night

(2)

1 / 49

Kissimmee House - 12.6 miles away

  • 6
  • 16
  • min stay varies
  • Nearest beach 114 mi
  • Swimming pool
  • Child friendly
“We loved our recent trip to Florida with family. Some flew in and some drove. We loved the nice and clean big house with lots of space for everyone to retreat to if they wanted. The pool was great and very well used for the 10 days we were there. We...”
- Review left on 03/24/2016

$264.00

Excellent (2 reviews)

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from $264.00 / night

(42)

1 / 15

Davenport Villa - 15 miles away

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

$184.00

Excellent (42 reviews)

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from $184.00 / night

(15)

1 / 59

Kissimmee Villa - 11.7 miles away

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 1 hour 20 minutes

$81.00

Very Good (15 reviews)

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from $81.00 / night

1 / 35

Kissimmee Villa - 14.3 miles away

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

Responds fast! Avg. 1 hour 13 minutes

$138.00

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from $138.00 / night

(76)

1 / 27

Davenport Villa - 15.2 miles away

  • 3
  • 7
  • 4 nights min
  • Ask about children
  • Air conditioning
“The summer bay resort through Exploria is amazing. The one bedroom condos are beautiful and I would recommend them to anyone. So thankful they were able to accommodate us and move us into the resort and we're so thankful...”
- Review left on 03/20/2017

$137.00

Very Good (76 reviews)

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from $137.00 / night

1 / 30

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 34 minutes

$170.00

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from $170.00 / night

(1)

1 / 56

Reunion Villa - 15.5 miles away

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

$272.00

Very Good (1 reviews)

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from $272.00 / night

(4)

1 / 12

Davenport Villa - 17.6 miles away

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

Responds fast! Avg. 2 hours 16 minutes

“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

(3)

1 / 23

Kissimmee Apartment - 13.4 miles away

  • 3
  • 8
  • 3 nights min
  • Nearest beach 72 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 22 minutes

$91.00

Excellent (3 reviews)

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from $91.00 / night

1 / 5

Davenport Villa - 18.3 miles away

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

Responds fast! Avg. 58 minutes

$154.00

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from $154.00 / night

1 / 56

ChampionsGate House - 18.3 miles away

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

Responds fast! Avg. 54 minutes

$914.00

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from $914.00 / night

1 / 20

Davenport House - 17.8 miles away

  • 5
  • 10
  • 7 nights min
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly

$201.00

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from $201.00 / night

(52)

1 / 26

Four Corners Villa - 12.7 miles away

  • 4
  • 10
  • 5 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
“We thoroughly enjoyed our stay at this home. Quick drive to all parks. We paid extra for pool heat and it was So worth it!! House has Lots of towels for guests and most everything u could need. House and pool very clean and neighborhood very quiet....”
- Review left on 12/18/2016

$161.00

Excellent (52 reviews)

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from $161.00 / night

(5)

1 / 50

Kissimmee House - 11.6 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 34 minutes

$233.00

Excellent (5 reviews)

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from $233.00 / night

(9)

1 / 24

Davenport House - 17.2 miles away

  • 4
  • 8
  • 6 nights min
  • Beach/lakeside relaxation
  • Nearest beach 137 mi
  • Swimming pool
“The location and pool were great. We were traveling between Orlando and Tampa and it had great access to Rt-4. It would have been nicer if the garage was actually a garage, instead of game room, and having slightly better supplies of paper products...”
- Review left on 07/05/2016

$183.00

Excellent (9 reviews)

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from $183.00 / night

(21)

1 / 24

Four Corners Villa - 13 miles away

  • 7
  • 16
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“We were very pleased with our rental !! If we vacation to Florida again we would definitely stay here again !! Convenient location to local stores and attractions”
- Review left on 07/04/2016

$343.00

Very Good (21 reviews)

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from $343.00 / night

1 / 42

Four Corners Villa - 13 miles away

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

$207.00

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from $207.00 / night

(4)

1 / 31

Kissimmee House - 13 miles away

  • 4
  • 10
  • 3 nights min
  • Nearest beach 72 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 22 minutes

“This home is both beautiful and clean with plenty to do. It was so nice to relax while the children played pool and air hockey. We all loved the pool and hot tub! It was also nice having two bedrooms with bathrooms in them! The other two bedrooms...”
- Review left on 09/03/2015

$137.00

Very Good (4 reviews)

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from $137.00 / night