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Windermere Vacation Rentals & Beach Rentals - 3410 Rentals Available

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3,410 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 18.6 miles to include more rentals

(1)

1 / 37

Orlando Townhouse - 5.4 miles away

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

Responds fast! Avg. 1 hour 26 minutes

$147.00

Excellent (1 reviews)

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from $147.00 / night

(21)

1 / 13

Four Corners Townhouse - 12.7 miles away

  • 4
  • 10
  • min stay varies
  • Nearest beach 70 mi
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 50 minutes

“Really enjoyed staying here! It was very spacious for us! Close to all the Disney parks and the area was also very peaceful! Will definitely be back...”
- Review left on 08/07/2017

$132.00

Excellent (21 reviews)

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from $132.00 / night

(41)

Certificate of Excellence

1 / 40

Orlando Townhouse - 15.3 miles away

  • 4
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 37 minutes

Certificate of Excellence

“Our stay was great, vacation home rentals was the right choice for where to stay while visiting the theme parks...”
- Review left on 10/28/2017

$114.00

Very Good (41 reviews)

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from $114.00 / night

1 / 56

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 49 minutes

$267.00

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from $267.00 / night

1 / 67

Kissimmee Villa - 15.9 miles away

  • 8
  • 20
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly

$229.00

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from $229.00 / night

1 / 24

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 49 minutes

$130.00

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from $130.00 / night

1 / 22

Orlando House - 5.4 miles away

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 49 minutes

$121.00

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from $121.00 / night

(2)

1 / 20

Kissimmee Villa - 13.1 miles away

  • 6
  • 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 17 minutes

“Our family rented this home and it was exactly what we hoped for. It was spacious, clean and nice place to relax. Thanks Gina for everything...”
- Review left on 08/20/2015

$189.00

Very Good (2 reviews)

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from $189.00 / night

(4)

1 / 36

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 49 minutes

“This was an amazing experience for my family! The house was beautiful! Everything was perfect. Management was on point and if I could give 10 stars I would...”
- Review left on 01/29/2018

$184.00

Excellent (4 reviews)

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from $184.00 / night

1 / 76

ChampionsGate Villa - 18.6 miles away

  • 11
  • 28
  • 3 nights min
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 18 minutes

$424.00

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from $424.00 / night

(1)

1 / 28

Old Town Townhouse - 11.4 miles away

  • 4
  • 10
  • 1 night min
  • Child friendly
  • Pet friendly

$114.00

Excellent (1 reviews)

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from $114.00 / night

1 / 29

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 44 minutes

$141.00

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from $141.00 / night

(1)

1 / 27

Four Corners Villa - 11.9 miles away

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

Responds fast! Avg. 1 hour 18 minutes

“Beautifully clean house. Clean neighborhood. Close to Wal Mart. High ceilings, spacious feel. Private pool. Bring a bed topper if you need a plush mattress. All light switches were labeled, a wonderful help. Directions to the DVD player would have...”
- Review left on 08/16/2015

$183.00

Very Good (1 reviews)

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from $183.00 / night

1 / 58

Kissimmee Villa - 15.9 miles away

  • 8
  • 18
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly

$229.00

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from $229.00 / night

(2)

1 / 32

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 44 minutes

$167.00

Excellent (2 reviews)

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from $167.00 / night

(1)

1 / 32

Loughman House - 18.4 miles away

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

Responds fast! Avg. 1 hour 44 minutes

$155.00

Average (1 reviews)

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from $155.00 / night

1 / 19

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 44 minutes

$104.00

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from $104.00 / night

1 / 33

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 44 minutes

$161.00

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from $161.00 / night

(3)

1 / 41

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 44 minutes

“House is great, plenty of room for our group of ten, great layout, nicely decorated, very nice kitchen which is sufficiently equipped, the resort itself was a lot of fun and the staff very friendly. Location is very convenient and quiet with easy...”
- Review left on 10/11/2016

$336.00

Very Good (3 reviews)

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from $336.00 / night

(1)

1 / 30

ChampionsGate Villa - 17.7 miles away

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

Responds fast! Avg. 1 hour 18 minutes

$297.00

Excellent (1 reviews)

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from $297.00 / night

(2)

1 / 25

Kissimmee House - 13.5 miles away

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 20 minutes

$101.00

Excellent (2 reviews)

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from $101.00 / night

(7)

1 / 20

Davenport Villa - 15.7 miles away

  • 7
  • 18
  • 3 nights min
  • Nearest beach 130 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 25 minutes

“Super happy with our stay!!! Metboyr expectations and necessity!!! The owner was very kind and extremely helpful in answering each of our worries and inquiries quickly!!! I would definitely stay here again and highly recommend the home!!! Txu so much...”
- Review left on 06/15/2016

$218.00

Very Good (7 reviews)

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from $218.00 / night

(13)

1 / 17

Davenport Villa - 14.7 miles away

  • 8
  • 18
  • min stay varies
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 59 minutes

“We had a group of 11 golfers and had no problem finding plenty of space fro all in this wondeful house. Everything was in great condition and there is no complaint at all with this home. Communication with the owners was better than any other of...”
- Review left on 03/06/2017

$217.00

Excellent (13 reviews)

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from $217.00 / night

(15)

Certificate of Excellence

1 / 28

Kissimmee House - 15.1 miles away

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

Certificate of Excellence

“The property is perfect. The pictures don't do the pool justice. It is one of the nicest pools you'll see on a vacation property. We had 3 children all 3 and under and it was no problem at all. The drive to Disney was a very quick and easy drive and...”
- Review left on 12/02/2017

$98.00

Excellent (15 reviews)

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from $98.00 / night

1 / 55

Orlando House - 5.4 miles away

  • 9
  • 18
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 44 minutes

$330.00

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from $330.00 / night

1 / 39

Orlando House - 5.4 miles away

  • 7
  • 14
  • min stay varies
  • Child friendly

Responds fast! Avg. 1 hour 44 minutes

$201.00

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from $201.00 / night

1 / 44

Kissimmee Villa - 14.1 miles away

  • 7
  • 18
  • min stay varies
  • Nearest beach 97 mi
  • Swimming pool
  • Child friendly

$144.00

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from $144.00 / night

1 / 30

Orlando Townhouse - 5.4 miles away

  • 4
  • 8
  • min stay varies
  • Child friendly

Responds fast! Avg. 1 hour 44 minutes

$129.00

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from $129.00 / night

(1)

1 / 19

Kissimmee Villa - 13.6 miles away

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

Responds fast! Avg. 5 minutes

$161.00

Excellent (1 reviews)

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from $161.00 / night

1 / 59

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 44 minutes

$353.00

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from $353.00 / night

(35)

1 / 19

Kissimmee House - 15.1 miles away

  • 4
  • 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“We had a last minute vacation opportunity and Sheryl was so accommodating and excellent and we loved her place! We had 5 kids and 2 adults and there was tons of space to relax and have private space. The pool was amazing!! It was the perfect temp and...”
- Review left on 07/07/2018

$137.00

Very Good (35 reviews)

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from $137.00 / night

(14)

1 / 42

Davenport Villa - 15.6 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“The villa offers a plethora of amenities with convenience stores located nearby. It is fully furnished, well maintained and in a golf community. No complains, 5 stars...”
- Review left on 06/01/2016

$133.00

Excellent (14 reviews)

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from $133.00 / night

1 / 26

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 44 minutes

$284.00

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from $284.00 / night

1 / 45

Orlando Townhouse - 5.4 miles away

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

Responds fast! Avg. 1 hour 44 minutes

$147.00

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from $147.00 / night

(2)

1 / 49

Kissimmee House - 12.6 miles away

  • 6
  • 16
  • min stay varies
  • Nearest beach 114 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 23 minutes

“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

1 / 36

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 44 minutes

$132.00

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from $132.00 / night

1 / 20

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 44 minutes

$187.00

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from $187.00 / night

1 / 48

Orlando Townhouse - 5.4 miles away

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

Responds fast! Avg. 1 hour 44 minutes

$147.00

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from $147.00 / 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