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Kissimmee Vacation Rentals with Private Pool

(167 rentals)
Kissimmee Villa
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our stunning 3 bed, 2 bath villa perfectly located just off Highway 27 in Davenport and is only 15 minutes from Disney main gate.It has an open, inviting floorplan with its own pool and gorgeous private pool, deck and spa; as well as a games room.This home is beautiful fresh and very...

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Featured review

"Great place to stay."

The villa is very convenient for shops and eating places - Walmart, Aldi and a large number of restaurants are less than 10 minutes away. The villa is also easily accessible to all the theme parks and shopping...

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$135
avg per night
Kissimmee House
Sleeps 16, 7 bedrooms, 4 bathrooms
11 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Relax in the comfort of this luxurious, family friendly, seven bedroom, resort vacation home that sleeps 16-18 people. Featuring a private pool, Avengers movie room, themed rooms for the kids including Star Wars, Harry Potter and Pirates themes, and resort amenities included at the exclusive Terra Verde...

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$320
avg per night
Kissimmee House
Sleeps 12, 6 bedrooms, 5 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Fantastic 2 KING bed EnSuite Villa w heated pool HOT TUB Mins to DisneyFamily-friendly Kissimmee vacation home in Four Corners with water parkContactless one time access code check in! All white linen! Private pool heat up to 104 degree. It’s like a 5 star hotel but better! Pet Friendly...

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Featured review

"Great place"

The owners were very easy to work with. The house was in perfect condition, very clean and well maintained. We had 9 people and plenty of room for everyone. Definitely would recommend the house.

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$366
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our superb 4-bedroom, 2.5-bathroom villa, located in the peaceful community of Eagle Pointe in Kissimmee, just minutes from Highway 192 and a short drive to Disney and other major Orlando attractions.The villa is spacious, comfortable, and well-equipped with everything you need for a relaxing...

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$160
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 2 bathrooms
11 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This fabulous 4 Bed Villa is located in secure gated Lake Berkley ResortThis fabulous 4 Bed Villa is located in a peaceful corner of Lake Berkley Resort with beautiful views to the Conservation Area and one on the lakes at Lake Berkley.The villa is fully equipped with everything you will need...

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Featured review

"2 week family vacation"

Our family had an amazing trip. It was as comfortable as being at home. Great communications with owner and management group if we had an issues or questions. Thank you.

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$120
avg per night

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Kissimmee Villa
Sleeps 14, 7 bedrooms, 4.5 bathrooms
3 reviews

Distance to park: 4 miles to Animal Kingdom

Key Amenities

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

About this property

Conveniently located on the Exclusive Emerald Island Resort. With 7 Bedrooms and 4.5 bathrooms, Berni’s Home from Home can easily accommodate two families travelling together or will give one family plenty of space.Enjoy relaxing by your very own private extended south facing pool or spend some...

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Featured review

"Very well maintained home"

This home was lovely and very well kept. Would rent again if the occasion arose that we needed a home this big again.

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$273
avg per night
Kissimmee House
Sleeps 18, 9 bedrooms, 6 bathrooms
5 reviews

Distance to park: 8 miles to Disney World

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Windsor at Westside Resort is one of the newest and most luxurious resort communities in the Orlando/Kissimmee,Developed by one of the nation's largest developer , the Pulte Homes. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, this...

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Featured review

"Great Vacation Home for Families"

We spent a great week in this home with our extended family. Tons of rooms and bathrooms and a nice big kitchen. Private pool and community water park were great for the kids. Location was convenient. We...

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$400
avg per night
Kissimmee Villa
Sleeps 10, 5 bedrooms, 3 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Your villa is located on the gated 5 Star Lake Berkley Resort in Kissimmee. 5 Beds, 3 Bath home that is beautifully furnished throughout (Big TV/Games Room/Heated Pool/Free Internet). Our villa is furnished to a very high standard and being all one level is ideal for one or two families. The villa...

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Featured review

"Lake Berkley Villa"

We have rented from this agent multiple times and are always beyond pleased. Each home we have rented were great and the location is perfect. Any communications before, during and after have always been...

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$130
avg per night
Kissimmee House
Sleeps 16, 8 bedrooms, 6 bathrooms
5 reviews

Distance to park: 8 miles to Disney World

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Windsor at Westside Resort is one of the newest and most luxurious resort communities in the Orlando/Kissimmee,Developed by one of the nation's largest developer , the Pulte Homes. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, this...

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Featured review

"Very nice"

We really enjoyed our stay. Community was really nice and house was huge. Had some good amenities and was a real easy drive to all the parks. Pool was nice… wish we paid for heat but we didn’t. ...

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$361
avg per night
Kissimmee House
Sleeps 16, 8 bedrooms, 6 bathrooms
6 reviews

Distance to park: 8 miles to Disney Animal Kingdom

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Windsor at Westside Resort is one of the newest and most luxurious resort communities in the Orlando/Kissimmee, Developed by one of the nation's largest developer , the Pulte Homes. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, this...

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Featured review

"Awesome"

Verry nice villa, warm jacuzzi. It was awesome. Bathrooms and bedrooms were good. Everthing was clean when we arrived. Great

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$360
avg per night
Kissimmee Villa
Sleeps 14, 7 bedrooms, 4.5 bathrooms
16 reviews

Key Amenities

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

About this property

This luxury villa is perfectly located on the exclusive Emerald Island Resort community less than 3 miles from Walt Disney World, Florida. The property has 7 bedrooms two of which are master bedrooms with en suite bathrooms and a further two and a half bathrooms.This stunning elegant and spacious...

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Featured review

"Great stay"

Great stay at this villa in Emerald Island, location is perfect for all the parks as well as going to the beaches. Katrina was very responsive12 in our party, 4 of which were children, the property...

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$143
avg per night
Kissimmee Villa
Sleeps 18, 8 bedrooms, 4.5 bathrooms
17 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

One of the closest communities to Walt Disney World (less than 3 miles away), Emerald Island Resort is a quiet oasis in which to spend your vacation. Emerald Island is an exclusive man gated resort community less than a mile from the world famous US Highway 192 where you will find shops, restaurants,...

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Featured review

"One of the best rentals to date"

Everything that was in house info was delivered. Safe neighborhood and close to everything. House was clean and well set up for our family. Pool and hot tub were our favorite with plenty of room for everyone.

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Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
15 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Your villa is located in an upscale gated community located just 8 miles from Walt Disney World. Terra Verde Resort is one of the most desired resorts in the Orlando area. Only a 25-minute drive from the Orlando International Airport and is situated central to all of Orlando’s famous attractions....

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Featured review

"Fantastic-Excellent."

IWe visited Orlando a lots of time,We are familiar with Lake Berkley.We had always very good impresion of staying in Lake Berkley.This time we stayed in Lake berkley drive 929.We arrived at almost 03;00...

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$155
avg per night
Kissimmee House
Sleeps 14, 7 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Enchanted Oasis at EmeraldOnly 15 minutes to Disney! Private Pool & Spa with heating available at the perfect vacation retreat in this stunning 7-bedroom, 6-bathroom home, located in the sought-after Emerald Island Resort. Designed for unforgettable stays, this property features covered poolside...

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$342
avg per night
Kissimmee House
Sleeps 8, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

This stunning Disney area pool villa offers your family comfortable and convenient accommodations that will make your next Florida vacation a memorable one.Ideal for your next family vacation, this attractive 4 bedroom, 2 bath Disney area vacation home is conveniently located just 10 minutes to the...

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$170
avg per night
Kissimmee House
Sleeps 20, 10 bedrooms, 7 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Exciting NEW 10 bedroom family vacation home Offering privacy and space for everyone 4300 square feet of awesomeness 2 separate large living areas Relaxing pool with spa Covered outdoor dining and seating Games loft with pool table and foosball Windsor Island Resort offers a wide variety of world...

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New
Kissimmee House
Sleeps 12, 0 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

a beautiful, private oasis offering 6 spacious bedrooms and 3.5 luxurious bathrooms.• Enjoy fast Wi-Fi throughout the home.• Relax by the pool and spa, drenched in sunlight all day long, with a stunning backdrop.• Conveniently located close to restaurants and amenities, just...

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