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Windsor Hills Resort (Kissimmee, Florida) Vacation Rentals

(14 rentals)
Kissimmee Villa
Sleeps 8, 4 bedrooms, 4 bathrooms
12 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

NEW TO MARKET!!! "Summer House" at Windsor Hills is an extra clean vacation home - recently upgraded with new floors, paint, decor, furniture and brand new Stearns & Foster mattresses in every room. The villa is a 4 Bedroom 4 Bathroom Ensuite property with an attached bathroom on every bedroom! ...

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Featured review

"Best place to stay EVER!!!!"

This villa was perfect for our family of 8. Everything was extremely clean and Kim was so wonderful to work with. The heated pool and spa was so refreshing after a long days at the parks. The kitchen is ...

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$241
avg per night
Kissimmee Villa
Sleeps 14, 6 bedrooms, 4 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Crush's Crash Pad WDW and M&M Legacy Rentals LLC would Love to welcome your family and friends to our Luxurious 6 bedroom 4-bathroom Oasis at Windsor Hills resort. We are located within the World-Renowned Windsor Hills Resort in Kissimmee, FL, just 2 miles to Walt Disney World. We overlook the ...

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Featured review

"We had a great holiday at Crushes Crash Pad."

We had a great holiday at Crushes Crash Pad. The villa is very well equipped and has everything you could possibly need (and more) to make your stay enjoyable. The location couldn’t be better, being ...

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$363
avg per night
Kissimmee House
Sleeps 14, 6 bedrooms, 4 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to your ultimate themed vacation experience in the heart of Kissimmee, Florida! Prepare to embark on an extraordinary journey as you step into this spectacular 6-bedroom, 4-bathroom house in the prestigious Windsor Hills community. This newly listed paradise has been meticulously designed to immerse ...

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Featured review

"Amazing"

This was an amazing experience for my kids and I. I would definitely choose again!!!!!!!!!!!!!!!!!!!

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$271
avg per night
Kissimmee House
Sleeps 14, 6 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

If you're bringing a big group with you on your next trip to Florida, you're probably looking for a luxurious vacation rental with plenty of room for everyone. This 6-bedroom Orlando vacation rental fits the bill! Windsor Hills Dream Private Screened Pool Home is an absolute dream come true ...

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$309
avg per night
Kissimmee Townhome
Sleeps 8, 3 bedrooms, 3 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

A fabulous home-base for your trip to Orlando! Just Minutes to Theme Parks.Home Features:* 3 Bedrooms* 1 King, 1 Queen, 2 Full, 1 Twin (Sleeps 7-8) * All New Mattresses * TV's in every bedroom * USBs & Outlets convenient for charging* 3 Bathrooms* All En-Suite * ...

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Featured review

"Loved it."

Beautiful House, and a wonderful experience from start to finish! Cant wait to go back! The home was spacious and beautifully decorated and Lisa was a Pleasure to work with, and very helpful.

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$199
avg per night

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Kissimmee Townhome
Sleeps 8, 3 bedrooms, 3 bathrooms
2 reviews

Distance to park: 6 miles to Walt Disney World

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Name Of Home: Ohana Mouse HouseLocation: Windsor Hills Resort (24/7 guard gated community - Disney World only mins away!)Home Highlights: Recently Renovated Home - Private Pool - Bunk Bedroom with PS4Property Type: Townhouse, Two Stories (1,437 SF)Bedrooms: 3 Total - 1 Master w/ King Bed, ...

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$147
avg per night
Kissimmee Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Distance to park: 2 miles to Disney

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Our exquisite, tastefully decorated and perfectly maintained 2-bedroom and 2 full bath condo is perfect for your family and friends up to 6 people. We are on the top floor, and you will hear no noise from above! There are two double beds in the Master Bedroom with a walk-in closet and ensuite. The ...

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Featured review

"5 star"

Super clean and tidy with lots to do around the property. Definitely Woukd stay again , beautiful layout of pool area

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$140
avg per night
Kissimmee Villa
Sleeps 10, 4 bedrooms, 4 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Name Of Home: Walking on Sunshine VillaLocation: Windsor Hills Resort (24/7 guard gated community - Disney World only mins away!)Home Highlights: Recently Renovated Home - Incredible Air Conditioned 80s Game Room - Private South Facing Pool/Spa - Bunk Bedroom with PS5Property Type: Single ...

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$265
avg per night
Special Offer
Kissimmee Villa
Sleeps 12, 5 bedrooms, 5 bathrooms
2 reviews

Distance to park: 5 miles to Disney World/Animal Kingdom

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Our Disney vacation villa is furnished to the highest standard and offers your family the luxury of a Five star hotel combined with the relaxed atmosphere of a family vacation home. Soak up the Florida sun on our extended deck where you can relax in the pool and spa, or simply enjoy the shade of the lanai ...

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Featured review

"Fantastic Stay"

We loved staying at this house it was truly amazing. There were 9 of us altogether, 6 adults and 3 children aged 10,8 & 4. The kids loved the games room and the pool, everything you could wish for in ...

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$300
avg per night
Kissimmee Villa
Sleeps 10, 5 bedrooms, 5 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to Minnie's Mansion! A 5 bd/ 5 bth pool home located in the closest community to Disney World-Windsor Hills Resort!This resort features, $2.1 mil Lagoon Style pool with Zero Depth Entry and Water Slides. Also, with a Water Park for the littles! Clubhouse has Sundry Shop /Deli, Games Room, ...

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Featured review

"Home away from home"

The house was beautiful. Heated pool was so nice. Thank you for providing swim towels. Kids spent a lot of time playing ping pong on the one rainy day. Location was great. Could use new mattresses ...

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$232
avg per night
Kissimmee Condo
Sleeps 7, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This condo is one of our most highly sought-after Orlando vacation rentals, and for a good reason. This beautiful property is equipped for up to seven guests between its three bedrooms and two bathrooms. Those who stay in this rental will be able to take full advantage of every amenity and feature that ...

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$135
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 4 bathrooms
21 reviews

Distance to park: 2 miles to Disney

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Wonderfully Themed villa in the beautiful gated community of Windsor Hills, just two miles from Disney. Enjoy complimentary pool & spa heat, themed rooms, and a fun games room in the garage (air hockey, ping ping, foosball)! This is one of very few 4-bedroom units on the resort. We're nice and ...

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$286
avg per night
Kissimmee Townhome
Sleeps 7, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Just 5 minutes away from Disney World, this Cozy, Lux, themed townhouse will be your perfect getaway from Disney while being your neural operation center to Disney, Golf and Orlando itself. Equipped with everything you need to have unforgettable vacations, from a fully equipped Kitchen to cook the best ...

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$155
avg per night
Kissimmee Condo
Sleeps 8, 3 bedrooms, 2 bathrooms

Distance to park: 3 miles to Disney World

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to Surrounded in Magic! Please check your spam for any quotes.Kids of all ages will love this magical, bright and spacious Disney & Universal Studios themed (1400 sq ft), 3-bedroom, 2-bath, 1st floor condo. Set in a quiet location at the renowned Windsor Hills Resort within walking distance ...

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$134
avg per night
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