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Kissimmee Vacation Rentals with Private Pool

(167 rentals)
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 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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$345
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 12, 6 bedrooms, 3.5 bathrooms
1 review

Key Amenities

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

About this property

Bring your family to this stunning 6BR 3.5BA in the luxurious gated community just minutes from the world-famous Disney World. Have hours of fun in the game room and scenic pool backyard, or set out to explore local theme parks, golf clubs, restaurants, shops, and more!6 Comfy Bedrooms (2 Themed) ...

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Featured review

"Wonderful Stay!"

The house was lovely and had everything we needed for my family of 6 week long stay. Kitchen was well stocked with everything we needed, house and pool were clean, and the beds were comfortable. The 80s...

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$243
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
14 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

We invite you to stay at our villa which is a 4 Bedroom 3 Bathroom luxury vacation home.The villa is fully equipped with everything you will need including air con throughout, private pool, WiFi, fully equipped kitchen, laundry room, bed linens, towels etc.Full air con and hi-speed WiFi throughout.As...

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Featured review

"Beautiful villa with all you’ll need"

This is an excellent villa with absolutely everything you might need during your stay. Plenty of towels, kitchen utensils and lots of extras in the garage, like golf clubs and inflatables for the pool....

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$160
avg per night

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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
Kissimmee House
Sleeps 8, 4 bedrooms, 3 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

We welcome you to our beautiful professionally decorated and furnished 4 Bed, 3 Bath Villa located at Lake Berkley Resort. Have your vacation here in comfort and relaxation with air conditioning throughout.Full air con and hi-speed WiFi throughout.The spacious villa has two sitting room has comfortable...

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Featured review

"Great villa"

Recently had a family vacation it was an amazing villa. Clean and great location close to everything. Will definitely rent again.

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$160
avg per night
Kissimmee House
Sleeps 13, 5 bedrooms, 5.5 bathrooms
4 reviews

Distance to park: 12 miles to Disney's Magic Kingdom Park

Key Amenities

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

About this property

Welcome to Westside Villa! -20 minute drive to all Disney Parks -Private, heated pool; gas grill; EV charger on-site -Modern arcade: racing simulators, virtual reality, vintage games -3 king size suites with smart TVs -2 uniquely themed bunk rooms (Star Wars and Fairy Tale) -All bedrooms have ensuite...

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Featured review

"Amazing"

The house was simply amazing. The family could not believe what I had rented when we arrived, so spacious. So many things games/entertainment in the house. The house was very clean, the beds were really...

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$395
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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$144
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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$323
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 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 Villa
Sleeps 12, 6 bedrooms, 5 bathrooms
5 reviews

Distance to park: 4 miles to Disney

Key Amenities

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

About this property

We are only 3.5 miles from Disney!! So close to all the fun, Hollywood Studios, Sea World, beaches, walks, restaurants and shopping!! We are in the middle of it all! You will enjoy our lovely villa by yourself or with a group. Our pool is one of the biggest among the rental communities. When comparing...

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Featured review

"Wow!!!! Perfect 10 out of 10!!!!"

We stayed at the property for 6 nights during our recent family's Disney World vacation. Right from the start of the process, the owner was very courteous and prompt with her responses to our many questions....

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$429
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 2 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Luxury villa right on lake edge. Free fishing on 3 lakes. Gated 5 Star Resort.FREE Gas BBQ.Hi speed WiFi and air con throughout the villa.Our 4 Bed, 2 Bath villa is furnished to a very high standard and benefits from a perfect lake view position.Free fishing on 3 well stocked lakes. The...

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Featured review

"VIPVILLA"

Nice villa with wonderful lake view and very spacious booking was easy and efficient check in was great and super easy.

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$155
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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