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Kissimmee Vacation Rentals with Private Pool

(167 rentals)
Kissimmee House
Sleeps 10, 5 bedrooms, 5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our superb 5-bedroom, 5-bathroom villa, located in Highgate Park, a gated community on the villages of Legacy Park close to Disney and other major Orlando attractions.The villa is spacious, comfortable, and well-equipped with everything you need for a relaxing family getaway. It can sleep...

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Featured review

"very nice villa"

Headline sums it up, this is a very nice villa. No negative comments as the villa is just as described and seen in the photos. We will definitely book this villa again. James

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$150
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

At Calabay near Disney- This 4 bedroom 3 bath home is well maintained and cared for. It is a perfect vacation rental getaway. The spacious foyer leads to a well equipped kitchen/dining room. The master bedroom has a king bed; master bath has double sinks, garden tub, privacy toilet & shower. A second...

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Featured review

"Perfect serene environment"

My family and I thoroughly enjoyed our stay at the villa. It’s truly one of the best private rental properties in Florida, and we would rate it over 100%!

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$155
avg per night
Kissimmee Villa
Sleeps 11, 4 bedrooms, 3 bathrooms
4 reviews

Key Amenities

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

About this property

Magic Lake View Villa near Disney- Totally private (no neighbors looking in either side) heated PRIVATE South pool with hot tub facing a 14 acre natural fishing lake on a prestigious Lake Berkley Resort, 24/7 Security - gated territory, 100% SAFE! Just 7.8 miles to DISNEY! The villa has everything...

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Featured review

"Lovely sunny villa in a great location."

We visited this villa for 2 weeks in October 2025. We loved the outdoor space and the villa had everything we needed. The location is perfect for visiting parks and local restaurants. Walmart is close by....

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$250
avg per night
Kissimmee Villa
Sleeps 10, 5 bedrooms, 4 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

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

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Featured review

"Family vacation"

Our family were there for 2 1/2 weeks and everyone loved it. Location very close to parks,restaurants and stores.Grandkids loved the time in the pool. House was big enough for the family and clean.Screens...

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Kissimmee House
Sleeps 15, 5 bedrooms, 5 bathrooms
10 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Enjoy this family friendly, five bedroom Orlando vacation home that sleeps 15 people and features a private pool, a Super Mario game and movie room, and themed rooms for the kids including a Beauty and The Beast castle room and Transformers! The entire interior of this home is brand new, so you'll...

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$239
avg per night

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Kissimmee Villa
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Located in the prestigious, gated Windsor Palms resort community in Kissimmee, this privately owned 3-bedroom, 3-bathroom vacation villa comfortably sleeps up to 6 guests. Featuring a private south-facing splash pool with full privacy, spacious en-suite bedrooms, and just a 4-minute walk from world-class...

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$120
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 8, 4 bedrooms, 3.5 bathrooms
10 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our beautiful villa situated in Veranda Palms, ideally located close to US-192 and only a 10-minute drive from I-4Our home boasts peaceful water views at the back with no rear neighbours plus the front is situated across from open countryside.The villa has also been professionally decorated...

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Featured review

"Comforts of Home"

The mattresses and blankets were fantastic. Everything was very clean, and I loved the themed rooms. The pool was great too, with floats and towels for everyone. The only thing I think could have been improved...

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$185
avg per night
Kissimmee House
Sleeps 12, 6 bedrooms, 6 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Our 6 Bedrooms 6 Bathroom, luxury villa ideal for you and your families / friend’s vacation.As you enter the home you are greeted with a large living room area. Towards the back of the villa there is an open plan living/dining/kitchen area. There are tri-sliding doors to the pool area where...

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Featured review

"Stunning villa"

Let me start by saying location was Ok.South of I-4 not so good. Traffic very bad to theme park near I-4. Gated community nice. Guards were very nice and pleasant. Now for the Villa. Villa was beautiful.Entry...

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$185
avg per night
Kissimmee Villa
Sleeps 6, 3 bedrooms, 2 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Luxury Screened-In, Lake Front, Private Pool Home! This amazing 3 bedroom, 2 bathroom, Disney Area Vacation Rental Home is located in the family-friendly residential community of Eagle Pointe. Just a few short miles from Orlando's World-Renowned Theme Parks including the Walt Disney World Resort,...

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Featured review

"soaring eagle lane"

tidy villa nice views our small lake ducks will come up to be fed nice size pool overall good villa games room in garage

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$140
avg per night
Kissimmee House
Sleeps 16, 9 bedrooms, 5 bathrooms
11 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to your 9-bedroom lakefront villa with a private pool, just minutes from Disney! Race in the Mario Kart room, sleep in a Princess Castle, explore the glowing Avatar game room, and relax in the vibrant Coco loft. Packed with luxury amenities, themed fun, and endless photo ops—this is the...

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$400
avg per night
Kissimmee Villa
Sleeps 10, 5 bedrooms, 4 bathrooms
22 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our stunning, larger than average, 5 Bed 4 Bathroom villa with a beautiful view of the conservation area at the rear as background of our private pool. All rooms in the villa are spacious. The villa is furnished and maintained to a very high standard.The villa is located just off US 192...

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Featured review

"Fabulous Villa on Bellavida Resort"

All I can say is fabulous, the villa was everything you promised and more, absolutely superb. Cleaning was done to a high standard throughout. Pool was enjoyed by all, multi coloured pool light at night...

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$160
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
17 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

A stunning, larger than average 4 Bed 3 Bathroom villa.There are 2 sitting rooms both with lots of comfortable seating. Both rooms have large screen TVs, ideal for when the adults want to watch the latest sports programme whilst the kids enjoy the latest Disney film. Netflix subscription is also included...

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Featured review

"Highly recommend this villa"

We have just returned home after spending two great weeks at this amazing villa.It was spacious,spotlessly clean, with very comfortable beds and all the amenities you need for a relaxing, enjoyable holiday. The...

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$120
avg per night
Kissimmee House
Sleeps 8, 4 bedrooms, 3 bathrooms
3 reviews

Distance to park: 12 miles to Disney World

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beautiful lakeside home with a private south facing pool in a gated community 12 miles from Disney. Enjoy fishing in the lake behind the house. Game room with pool table, skeet ball, foosball table and a gaming system with hundreds of old favorites like Pac Man and Mario Brothers. 4 bedrooms and 3 bathrooms....

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Featured review

"Vacation home"

It was a very relaxing vacation home. Everything was clean and dust free. No complaints at all. It’s a very nice community.

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$170
avg per night
Kissimmee House
Sleeps 12, 6 bedrooms, 4 bathrooms
7 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Our fabulous 6-bedroom, 4.5-bathroom luxury vacation villa is set in the tranquil location of beautiful Watersong and the property overlooks a conservation area at the rear.The villa sleeps 12 guests and boasts a private pool as well as a games room.Situated at the front of the house as you enter,...

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Featured review

"Family vacation/daughter celebration"

My family and i had a wonderful time at this home. Everything was great, the pool was wonderful and the property manager was amazing the wholw time. Will book again.

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$185
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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