Vacation Rentals & Villas in Windsor Hills Resort

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262 Houses

Windsor Hills 5BR/ 5BA SF Pool Villa,3MI to disney

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 33 minutes

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Price per night from

$247

MINUTES TO WALT DISNEY WORLD'S FRONT GATE

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$160

Pooh's Palace in Windsor Hills

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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$516

Windsor Hills Disney Townhouse, Newly Redecorated

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$160

Great rentals within 20 miles that match your search

Premium Kissimmee Timeshare rental

Kissimmee villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$328

Prestige 3: New Lux Home, South Fc Lake View, Pool

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 20

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Price per night from

$687

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

Windsor Palms 4/3 Pr. Pl., Hot Tub, Jacuzzi/Games

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Amazing house!” We have amazing family time! This house is excellent with great location! We'll be back soon! I recommend

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$177

Disney Pool Home in Gated Resort, Amenities for All

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 15

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$207

Disney Pool Home, Great view, Gated resort near Golf

Orlando villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

“Spacious and comfortable” Although this was not the home pictured in the photos of the home we chose and thought we were staying, it provided the same spacious and comfortable space needed for a family reunion. The lanai with the pool and hot tub was really nice with amazing sunsets in the evening and moonsets in the early morning. There was a resident Sandhill crane who meandered by for a visit each day. The location of this quiet resort community was pleasantly out of the way of the crowds, yet reasonably convenient to anything you would need or want to do. Our main concern was that we were unable to consistently lock the back sliding glass door and there was no bar to place to lock it. (And, the crumb tray on the toaster was broken.) Other than that, the home was a little tired, but more than adequate. Thank you for a delightful week!

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$189

Sunny Disney Pool Home in Gated Resort, Amenities for All

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

“Decent place but lacking in some areas” For one week in July 2014, my family from Alabama to Alaska (with us from Canada) all stayed at 928 Solona Circle. Overall we were happy with the house rental but do not stay here if you need assistance with anything. It took my 4 phone calls over 3 days to just find out what the Wi-Fi password had been changed to (the one that we were emailed was incorrect). It may not be the safest neighbourhood as there were police men in the gated area twice during our stay. And the house was filled with broken outlet covers and had very dirty couches, which needed steam cleaning. It was a spacious home and we loved the walk-in closets as well as the ease in which to find it and the easy drive to Disneyworld. But if you want to stray there, you need to supply everything- even your own toilet paper and Kleenex. The jets ion eth hot tub did not work and the game room had a broken foosball table. Overall we were mainly happy with our stay but were disappointed with a few things.

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Price per night from

$189

Disney Pool Home, Great view, Gated resort

Orlando villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

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$218

Sunny Disney Pool Home in Gated Resort, Amenities for All

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

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$212

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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$408

Upgraded 5-star Penthouse, Bahama Bay near Disney

Davenport apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Very comfortable stay - enjoyed every moment of it!” Very spacious accommodations. We stayed 2 families with little girls who were very anxious to see Disney World parks. The condo was perfect for our stay, we were just about 20 minutes from Magic Kingdom so we were there in a snap. The resort is beautiful and we can't wait to come back again. There are multiple swimming pools, one close to condo's building, another one - bigger and open until 10 pm - near the club house / reception. Another similar size pool at the restaurant area with little white sand beach, volleyball net and table tennis. Also we enjoyed playing tennis on the real hard court surface near reception, very good quality and with lighting. When you need a day off from visiting parks and all these crowds staying on the resort is the great option. Shopping is very close to the resort - 7 minutes drive to Walmart, so you could get anything you need, open 24 hours. We also recommend buying tickets to all attractions at the Walmart since there is a small discount vs buying at the gates. Overall - great experience, highly recommend to anyone. Will definitely come back again!

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$227

Reunion Resort-luxe 3BR/3BA Villa-Water Park

Reunion hotel apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Terrific Property” Dear Stacy and Craig, What a time we had! Expecting, as many Orlando-travelers do, that the theme parks would be our only major attractions, we were so pleased to be able to add our accommodations to this list as well. The Sagers have made it absolutely impossible for their guests not to have a first-class time in their condo on the Reunion property. And what an amazing property it is! Swimming pools galore (to include my daughter and son's favorite water park with a lazy river) and my personal favorite swimming and late-afternoon beverage/snacking pool area, Seven Eagles. It is here that we were able to really let-down after an amusement park day and relax only to go home to Stacy and Craig's little slice of heaven with beds that beacon even the most restless tourists. I loved the beds! So incredibly comfy with just the perfect linens making vacationers want to stay in bed just a little longer before heading back out to Sea World; Animal Kingdom; the Magic Kingdom, and the the like (all of which are not more than 15 minutes away). A true place of luxury, the Reunion four star hotel is always available to the Sager's guests serving up pub and kid fare all day and night; fine dining; and late night cocktails and sushi on the 11th floor where fireworks from local theme parks are a daily occurrence. Will we go back, yes! In fact, we have already booked again with the Sagers so we can dream away some of those cold winter days and nights looking forward to our next tip down. Thanks to you both for a wonderful stay. Jen and Dan Smith

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$205

1.5 M to Disney,From $100/nt,3BR 1600 sqft Townhome

Kissimmee apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Spacious family friendly condo close to Disney.” Perfect location to visit Disney. Very spacious with a full kitchen . A great family friendly condo.

Responds fast! avg. 1 hour 27 minutes

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$115

The Ever After Estate - 13BR Sleeps 45 People & Has 62 Private Acres

Clermont house

  • 11 bedrooms
  • 10 bathrooms
  • sleeps 43

“Everything you could ever imagine !!!” My new Wife and I just got back from our stay. We held our Wedding there. We had both our immediate families stay with us during 3 days of our 4 day stay. Plenty of room for all, we had 15 adults and 8 kids total. This place is just so amazing. My wife and I toured it prior to our stay and missed so many things because there is so much detail. Our favorite place was the pool area. The day after our wedding some of us hung out at the pool for a couple of hours. The kids all had a blast between the pool slide, video games, ball pit, mini golf, and movie room. This made it easy for us to focus on set up and tear down for the wedding. We had 220 guest during our day and everyone loved the place. Biggest question was how did you find this place. Great photos from our day hit facebook immediately with babies on the Carousels,kids playing mini golf, and people around the tropical pool setting. Andrew, Felicia, and his staff were very helpful. Andrew answered all our questions with fast response times through out the planning. Felicia was there when we checked in and ensured we were settled and answered any last minute questions. The detail andrew put into his Estate is amazing. Every thing out there takes you away from your everyday. We are so lucky that such an awesome place was shared with our family and friends to enjoy. It was the perfect place to hold our special day. The last day I spent an hour taking photos of the Estate in which I noticed the incredible landscape,a touch that just simply takes your breath away on the beauty of life. Andrew thought of it all. The only down fall, which was our fault, is that we did not have enough time to enjoy everything. This was due to a short stay, wedding set up and tear down. Our next stay will be longer. My older Sister from Philly was talking about a family meet up next year. Boy I Hope so. All our Wedding dreams came true. Thank you Ever after Estate and Thank you andrew.

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Price per night from

$1,985

YOLO HOUSE, WINDSOR WHERE LUXURY MEETS ADVENTURE : POOL / SPA INCLUDED

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 13

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$571

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$241

Disney Vacation Condo - stay 6 days get 7th FREE

Four Corners condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Owner is awesome. Goes beyond to satisfy guest” This is a 3 bedroom 2 bath unit. Unit has everything you need. It was clean except for the carpets. I called the owner and she asked what did she need to do to make this better. I said clean carpets. She sent Stanley Steamer out to clean them! That was awesome! Loved that we had washer and dryer in the unit. The unit does need some TLC. Deck attached to the master is in need of repair and the bathroom could use and update for sure. We enjoyed our stay and it was very comfortable! Owner is fabulous to work with...best ever!

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$100

Sunny Pool Home, Gated Resort near Disney

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 16

Responds fast! avg. 2 hours 48 minutes

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$184

✦Comfortable 4 Bedrooms Town Home - Nearby Disney World✦

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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$117

Scotty's Luxury Orlando Villa - Snowbirds welcome

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$172

“Vacation Florida” Great place to stay and will recommend. The accommodation was perfect and my needs was met. Great service, amenities and security. Perfect place for single family.

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$250

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

$487

Home Away Villa

Davenport house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

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$229

✧Good Location - Spacious and Comfortable 8 Bedrooms Villa w/ Private Pool✧

ChampionsGate villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

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$401

⭐Spacious 7 Bedrooms Villa w/ Private Pool - Nearby Disney World⭐

Kissimmee villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

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$265

XMAS AT DISNEY WORLD- 54 ACRE RESORT W/WATERPARK

Orlando hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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$287

Stunning 5 Bed/3bath with Pool/Spa + Games Room

Kissimmee villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

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Price per night from

$218

“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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$458

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Price per night from

$117

⭐Great Value Villa w/ Private Pool - Nearby Disney Resort⭐

Kissimmee villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

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$265

⭐ 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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$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

Orange Lake Resort Kissimee FL

Kissimmee townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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$377

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Price per night from

$164

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