Windermere Rentals

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294 Houses

Private Home in the Heart of Orlando!

Windermere guest house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$115

Great rentals within 20 miles that match your search

Cozy One Bedroom Villa in Gorgeous Resort & Spa

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$180

1 Week Rental in Orlando, FL 2 Bdm Deluxe Villa Close to Theme Parks

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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$196

“Excellent and convenient choice to visit WDW.” Location was superb, had all conveniences of home. Kids enjoyed the pool after a long day at the park. Wish we could have stayed longer. We will rent here again.

Responds fast! avg. 3 minutes

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$224

Spacious 4-bed lakeside pool villa near Disney

Kissimmee villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“Great Location” We stayed from Saturday to Saturday. Overall the house was good. Pros: Clean, spacious, close to Disney Parks, close to stores, very quite place, easy access, comfortable furnitures, Cons: master bedroom was hot, internet service went down mostly at night time like it has a timer at night, and odd times during day time only for few minutes, the pool only the first day when we arrived pool was with cloudy water and water very hot all the time, we think the heater was on. Cable TV, we had two afternoons that we had no signal. The house has two blenders both not working. No raw meat knife, we had to buy our own for cooking. We wanted to use the garage to place our car, it has many objects we could not use it.

Responds fast! avg. 1 hour 57 minutes

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Price per night from

$162

Doc's Magical Escape, Sleeps 14, Wireless Internet

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

“Family Vacation” The house was nice. The grandkids loved the pool. The house was close to all the attractions. We enjoyed our vacation. We will book again

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$201

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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Price per night from

$146

The Peninsula Clermont, Orlando

Clermont villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Excellent Vacation! Can't wait to go back” We absolutely loved your villa and the resort it was situated in. From the moment we arrived we enjoyed every minute. The house was very quiet and spacious. It can easily fit in two families of 4. The house was clean inside out. The mattresses were plush and bedding soft. The Mickey/Minnie room was super cute and my kids' favorite! We all slept like babies every night. The furniture was solid wood and looked brand new. It was also nice to have a kitchen with anything and everything we needed. It's a paradise to have that much space for a vacation. All theme parks including the Lego land were easy to access. There were Publix, McDonald, Danny's close by with plenty of choices to eat out. We were not able to swim in the pool or check the clubhouse. Will try out next time. The view from the backyard was gorgeous! We would definitely be back again soon. I would be happy to refer any friends thinking of travelling to Orlando area.

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$131

Westgate Lakes, Orlando Florida - 4 Bedroom Villa - Huge Resort with everything

Orlando hotel apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

“Worth It!!!” Our family stayed at Westgate Lakes for one week during Spring Break. We had a four bedroom condo and the space was fabulous!!! We were more than impressed with the resort staff and all the ammenities. The location was also very excellent and so easy to find and so close to the attractions we wanted to visited. The resort was very clean in all areas and very safe and secure for our family.

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$409

Lakefront Townhouse 5 Star LOCATION

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Lakefront Townhouse Review” Centrally located to everything. Place very clean and well kept.Enjoyed our stay there and would recommend the place to anyone. The agent was very helpful and polite. We are going back in 2011.

Responds fast! avg. 36 minutes

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Price per night from

$109

Beautiful 2 Bedroom Condo on the Lake

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$343

Sunset Dream, Lake Views, Hot Tub, Disney 4 Miles

Kissimmee house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$327

“Perfect, as seen on the pics” Was a great pleasure to be there and very helpful information from the owners side. Easy to book and friendly service. We will be back one day, for sure.

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$327

From $110/nt,4br/3ba townhome with lake view,Near Disney,Seaworld

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

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Price per night from

$132

Discount.. Waterview - 3BR Water View Villa

Davenport villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$102

Luxury 6-Bedroom Lakeside Villa near DisneyWorld

Davenport villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

“Vacation” The house was clean and spacious, it was perfect for my family and I to enjoy each other and rest. Thanks

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$207

Luxury Lakeside House with private solar heated pool and spa

Kissimmee villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

“Very nice.” We had a great time. The house was clean, accommodations were very nice. The kitchen light started to burn out. One call & it was fixed quickly. We would go back.

Responds fast! avg. 3 hours 25 minutes

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Price per night from

$160

From $100/NT,1.5 Mile to Disney ,1808 sq ft 4br/3ba townhome with lake view

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Great location” We had great times in Oakwater, all was perfect! The house is fully equipped, all is clean, new and works perfect!It is an ideal location, close to everything. Near the home are so many great restaurants such as: Bonefish, Longhorn, Golden Corral, Ihop, Bahama Breeze, Buffalo Wild Wings, Flippers Pizza*, Red Lobster and lots more! The super target is within 2 min as well as the Publix.It is also located in very quiet area. There are great sports facilities, tennis court, and the pool area itself is fantastic. We enjoyed it very much and the pool s huge and warm !!! We loved it and will definitely recommend to our friends and family!

Responds fast! avg. 1 hour 27 minutes

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Price per night from

$121

Lake View Villa Orlando

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“Lovely, relaxing holiday” My wife and I stayed here for 2 weeks to celebrate our silver wedding anniversary in Jan/Feb 15. The villa is beautifully furnished and equipped. The pool and pool area is very large but the weather wasn't quite hot enough for us to brave the pool itself. The view from the pool over the lake is really spectacular. The Hampton Lakes area is nice and quiet and is conveniently situated within a very short drive of some great restaurants and supermarkets. It's also very easy to reach Clermont, straight up the US27 or Orlando/Kissimmee via the I4. Kan and Myat were extremely good at providing us with all the information we needed and the booking process was straightforward and very efficient. I would highly recommend the villa to either couples or families.

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Price per night from

$180

2 miles to Disney,1650 sqft 4BR/3BA big Condo from $80/nt

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Excellent location and all the comforts of home.” Condo was within walking distance of a Winn Dixie grocery store, Fridays, Cracker Barrel, and Outback. The community pool and hot tub were excellent. The condo was equipped with everything we needed. The only negatives were the fact that we were a little disappointed that the ice maker didn't work and definitely dismayed by the fact that the smoke alarms were disconnected. We also had some periodic problems with the cable TV and wi-fi. Those are the things that caused a very good rating instead of an excellent rating. But other than those we would highly recommend the place and definitely stay again, especially if the smoke alarms are fixed.

Responds fast! avg. 1 hour 27 minutes

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Price per night from

$127

9 Br/6 Ba luxurious Pool House from $380/nt, Close To Disney

Kissimmee house

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

“Great time!” House was a perfect fit for my family. We had a great time and plan on making this a yearly trip. Central to everything, but far enough away you didn’t feel trapped. Would highly recommend it!

Responds fast! avg. 1 hour 27 minutes

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$344

“Good price for family of 10” With 5 bedrooms, fits 10 comfortably. Owner is very helpful and location is 20mins from the parks. Walmart and restaurants are very close.

Responds fast! avg. 1 hour 27 minutes

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Price per night from

$149

A Lakeside Luxury

Kissimmee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

“Outstanding Villa in a beautiful surroundings.” We are a family of 5, stayed at the this Lakeside Luxury Villa for 9 weeks total. The house is so beautiful with all that is needed when staying with kids. Very spacious house and lots of things to do, table tennis, soccer game and Playstation game console where everybody can play. Giant TV with hundreds of satelite tv-channels. The pool area is simply fantastic, big south facing screen and large pool - sitting out there and watch the sunset is so lovely. We have rented lots of houes before in Florid and this is simply the best one we have rented. The house is close to supermarkets, mall, Disney and all kinds of activities and shopping. Do spare the words: This house is beautiful, with outstanding surroundings. Grade: 10 out of 10. Best Wishes for great stays. Stefan

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Price per night from

$308

Tropical Lakefront Villa, Gated, Pet-Friendly, less than 10 mins to Disney!

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Excellent location!” The house was very clean and well maintained. It was a short and easy drive to the Disney parks and Universal. We enjoyed relaxing in the pool after a long day of walking in the heat. It was a perfect size for my husband and I,our two grown sons and their fiancés. A great alternative to staying on Disney property because it was like being in our own home. Laree is fantastic to work with!

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Price per night from

$178

Responds fast! avg. 33 minutes

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Price per night from

$253

Disney is SUPER close, Pool, Spa, Game room, Free WiFi, Private backyard, Lake

Four Corners house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 17

Responds fast! avg. 2 hours 40 minutes

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Price per night from

$488

Disney Area Villa with Pool

Davenport villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

“Wonderful home” My family and I had an awesome trip and this wonderful home was certainly a highlight. Very clean, spacious and a great location. We would love to stay again!

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Price per night from

$127

Fabulous 3B Condo Bahama Bay Resort

Davenport apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Loved it!” It was perfect accommodations for our family. We loved the resort. Also being from the Bahamas we loved the theme of the resort.

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$230

Fabulous 3B Condo Bahama Bay Resort 10 min Disney

Davenport apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$230

The House the Mouse would stay in

Davenport villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$183

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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Price per night from

$138

Lovely 3BR/3BH New Pool& Slide, 3 Miles to Disney

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Amazing” Townhouse was perfect..walking distance to Old Town..and the heated pool, AMAZING!!Inquiring about purchasing a unit, that’s how nice this place is..

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Price per night from

$138

LAKESIDE HAVEN, Windward Cay, The "hidden jewel" of Kissimmee

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$207

“Very welcoming and worth it !” Me and my family absolutely loved this vacation house everything was so welcoming and near perfect ! This house is definitely something we will never forget and hopefully when we come back we will be able to rent from kim molnar again ! Everything was to a T ! Thank you so much kim !

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$459

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Price per night from

$257

4BR/3BA 1650 sqft Condo from $100/nt, 2 Miles to Disney

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Excellent Location” THis place was great for our family we stayed for 12 days and have no complaints. We will try to stay next year as well. Thank you

Responds fast! avg. 1 hour 27 minutes

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Price per night from

$115

⭐ Spacious and Comfortable Villa - Near Theme Parks ⭐

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

“Fantastic Stay” The home was in a beautiful community and there was a huge resort pool with all the things one would look for in a resort setting. The home itself was immaculate and very clean upon arrival. The beds were all comfortable and the rooms were spacious. We enjoyed the home and the resort so much that we actually spent a few days less at the parks. The reservation process was simple and straightforward. All in all a great vacation!

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Price per night from

$265

1 week Westgate Resort Studio in Orlando_Sleeps 4

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$107

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