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Kissimmee Vacation Rentals with Private Pool

(177 rentals)
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
9 reviews

Distance to park: 8 miles to Disney

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Situated on the quiet Mediterranean styled High Grove Resort which is a gated community, close to the Disney World Theme Parks and attractions, with easy access to the fabulous beaches on the East and West coast and many fantastic golf courses.4 Bedrooms, 3 bathrooms, games room, air conditioning...

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Featured review

"Our stay for Disney trip"

The house was very comfortable and we were very pleased with all the options including the pool. We will definitely recommend and use this resort again. Thank you

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$150
avg per night
Kissimmee Villa
Sleeps 14, 7 bedrooms, 7.5 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This lake home is one of the larger homes on Lake Berkley and boasts 7 bedrooms 7.5 bathrooms. This really is the perfect place to unwind after a busy day visiting central Florida's attractions or just enjoying the home for everything it has to offer.This home is perfect for the larger families...

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Featured review

"Beautiful villa"

Great villa in a beautiful location. Villa was everything we hoped for and more. Booking was easy as was checking in. The villa itself was very clean with everything that you could need provided. I would...

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$230
avg per night
Kissimmee House
Sleeps 16, 8 bedrooms, 5 bathrooms
7 reviews

Distance to park: 6 miles to Disney world

Key Amenities

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

About this property

Welcome to our luxury finished 3600 Sq ft pool home at beautiful Crystal Cove Resort. It is conveniently located close to shopping and dining (less than 1 mile away). Disney is only 6 miles away. Just minutes from major attractions like Sea World, Universal Studios, Aquatica and the Convention Center...

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Featured review

"Pleasant Stay in Crystal Cove"

Large and spacious home in Kissimmee. Close to many attractions and restaurants. Bedrooms, kitchen and bathrooms. Pleasant and easy to maintain for extended stay. Washer and Dryer on site make vacation...

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$219
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Ideal for your next family vacation, this striking 4-bedroom, 3 bath Disney area vacation home is conveniently located just 10 minutes to the Walt Disney World Resort, 15-20 minutes from Universal Studios Florida and SeaWorld Orlando. Florida’s famous beaches are just a quick 45 minutes away. ...

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Featured review

"Ref Villa 26"

Lovely villa on Cumbrian Lakes gated community in Kissimmee. Very nice outlook, overlooking lake from the pool area. Close to parks and attractions, great support from management company and Stephen at...

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$170
avg per night
Kissimmee House
Sleeps 20, 9 bedrooms, 6 bathrooms
4 reviews

Distance to park: 2 miles to Disney’s Animal Kingdom Park

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. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, This 24 hour guard gated...

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Featured review

"Disney Vacation"

We enjoyed our stay. The owner was quick to respond to all my questions and issues we had . Great neighborhood and location to the parks!

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$312
avg per night

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Kissimmee Villa
Sleeps 6, 3 bedrooms, 2 bathrooms
18 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This is a beautiful professionally decorated and furnished 3 Bed, 2 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 sitting room has a Queen sofa sleeper bed so...

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Featured review

"We absolutely loved the villa."

The villa was perfect for our family. It was extremely spacious and well equipped. It had everything we needed.The pool was perfect for enjoying lazy mornings and there were lots of pool toys for the...

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$130
avg per night
Kissimmee Villa
Sleeps 11, 4 bedrooms, 3 bathrooms
5 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

"Amazing Serene stay"

This was a lovely clean and very modern designed residence with amazing amenities for each 1 of the family members to enjoy and plenty of space and room for everyone. 10 out of 10.

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$250
avg per night
Kissimmee House
Sleeps 8, 4 bedrooms, 3 bathrooms
24 reviews

Key Amenities

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

About this property

DISCOUNTED RATES FOR ALL REMAINING OPEN DATES IN 2026!Note: The availability calendar is only accurate up to 18 months in advance. If your desired dates are beyond that timeframe, please confirm availability.Luxury 4 BR / 3 Bath Villa with Private Pool and Spa in Guarded Gated Resort Close to...

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Featured review

"Fantastic Stay"

We had two wonderful weeks here in May and honestly could not have asked for a better place to stay. The location was fantastic, with so many great amenities, restaurants, and of course the parks all within...

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$202
avg per night
Kissimmee House
Sleeps 8, 4 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beautiful 4 bedroom villa which sits on a large corner plot at Lake Berkley. The villa benefits from a partial view of the lake, fishing is just a few yards away.The Lounge and very spacious dining area are of open plan design with high vaulted feature ceilings. Fully air conditioned with remote monitoring...

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Featured review

"Awesome stay in Davenport"

We rented a very beautiful home in Davenport. A 6 bedroom home that had everything that we could ever imagine. Security was top notch. We was in a gated community. I absolutely loved because I traveled...

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$155
avg per night
Kissimmee House
Sleeps 16, 8 bedrooms, 6 bathrooms
5 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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$308
avg per night
Kissimmee House
Sleeps 12, 6 bedrooms, 4.5 bathrooms
14 reviews

Key Amenities

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

About this property

Moran Disney Rentals would love to welcome you to our Luxury 6 bedroom house which is perfectly located on the exclusive Emerald Island Resort community less than 3 miles from the Walt Disney a world Parks in Florida. This property has 6 bedrooms two of which are master bedrooms with a further two and...

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Featured review

"Great location & spacious"

Great location for Disney, very generous sized bedrooms - had everything we required, would definitely return.

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$164
avg per night
Kissimmee Villa
Sleeps 12, 6 bedrooms, 5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Your vacation home from home! Our home is a 6-bedroom, 5-bathroom vacation villa, located on the desirable Highlands Reserve golf community.It has an open, inviting floorplan complemented by stylish, furnishing. A light and bright villa, allowing the Florida sun to brighten up your day.Our villa...

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Featured review

"Lovely stay at this villa"

Booking process very easy. Had lovely stay here with family. Villa is great location, is clean modern and well furnished/equipped. We will stay here again next visit to Micky. Stan

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$230
avg per night
Kissimmee Townhome
Sleeps 8, 3 bedrooms, 3 bathrooms
18 reviews

Key Amenities

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

About this property

Welcome to Toy Box Townhouse! A newly renovated townhome with modern touches, ensuites for each of the three bedrooms, and a Toy Story themed kids' bedroom that's only 10 minutes away from Walt Disney World.Enjoy some Resort Amenities: Water Park Zero Entry Pool Putting Green ...

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$190
avg per night
Kissimmee House
Sleeps 10, 5 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to this beautiful luxury villa on the gated 5 Star Resort of Lake Berkley. This villa has 5 bedrooms, 2 of which are on the ground floor and 3 are on the first floor. It can sleep up to 10 comfortably.This is a perfect location for fishing on 3 well stocked lakes. Fish all day long whilst...

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$200
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
19 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

"Another great stay"

Another year renting from Stephen and Co and another happy family holiday. Villa had everything we needed for our stay and was cleaned to a high standard. Accessing the house was easy, we felt safe with...

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$120
avg per night
Kissimmee Villa
Sleeps 6, 3 bedrooms, 2 bathrooms
6 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

"Eagle point villa ref 42"

My wife and I along with our 2 friends rented your villa for 4 weeks and had a relaxing time around the pool overlooking the lake full of wild life and the resident alligator The villa was so fully equipped...

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$140
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
3 reviews

Key Amenities

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

About this property

RECENTLY REFURBISHEDLuxurious Windsor Palms with an extra wide cul de sac lot and with a pool that is not overlooked. Our guests enjoy terrific privacy in one of the premier resorts in the Disney vicinity. We have a south facing pool with kiddy pool and stand alone hot tub. Numerous child friendly...

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Featured review

"Awesome vacation"

Everything was perfect from start to finish. House was better than we expected, owner was great to deal with and will for sure book this house again and have already referred friends to book this property...

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$214
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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$165
avg per night
Kissimmee House
Sleeps 8, 4 bedrooms, 3 bathrooms
10 reviews

Distance to park: 4 miles to Disney World

Key Amenities

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

About this property

Welcome to La Casita on the Island (The Little House on the Island) "Our house, our casita" If you want a place to relax and enjoy the beautiful weather of Florida, I invite you to see the "encanto" (charm) that you can experience during your stay at La Casita on the Island.Enjoy...

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Featured review

"La Casita on the island"

My wife and I rented this property from January through April 2026. The property is in a nice resort Emerald Island. The the house when we entered with clean, so there was hardly anything we need to do...

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$141
avg per night
Kissimmee Villa
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This well maintained 3 bedroom 2 baths home located in the renowned Lindfields Estate.It is perfectly placed to maximize your family’s vacation fun here in the entertainment capital of Florida!You will not want to miss this lovely vacation home close to Disney and on the doorsteps of local...

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Featured review

"Lovely home from home"

An Amazing House located superbly close to Disney Land, Malls. and Old town. Karen is a lovely host.

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$140
avg per night
Kissimmee Villa
Sleeps 6, 3 bedrooms, 2 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to our 3-bedroom, 2-bathroom villa, with private pool. The villa is in a quiet neighbourhood located in the popular Lindfields subdivision close to highway 192, I-4 and the 429. It is an ideal location with easy access to the Disney World attractions and Margaritaville resort.There is a fully...

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Featured review

"Wonderful vacation spot"

The home is beautiful and cozy. Although we only used part of the house it was perfect. Everything was clean and in good shape. We spent almost everyday in the pool and jacuzzi . The pond was right behind...

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$130
avg per night
Kissimmee House
Sleeps 12, 6 bedrooms, 6 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Vacation in style with this luxurious family-friendly villa with your very own pool, spa and lake view. Family games room.The villa is located on the 5 Star safe gated Bella Vida Resort in the heart of Kissimmee, close to shops, restaurants and bars, and is only 15 minutes from Disney.Offering...

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Featured review

"Beautiful"

Beautiful home and spacious with all the things you would need to enjoy your stay . After out all day come back and relax in the roomy and comfortable home.The weather did't pan out while we were there...

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$230
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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$168
avg per night
Kissimmee Villa
Sleeps 9, 4 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Luxury villa right on lake edge. South facing poolNestled in the heart of Kissimmee, this large 4 bedroom lake front Villa is the perfect blend of relaxation, adventure, and convenience for an unforgettable getaway. Upon entering, guests are greeted with stunning views of the tranquil lake, setting...

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Featured review

"Very nice villa"

We had a lovely vacation at this very nice villa. It has everything you would need. Clean and modern, We will book again. David and family

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$155
avg per night
Kissimmee House
Sleeps 16, 8 bedrooms, 5 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This spacious home is designed to impress with top-tier amenities and elegant touches, making it ideal for families or groups craving an unforgettable escape. Enjoy the ultimate blend of comfort and excitement ensuring your stay is spectacular.Bedroom 1: (3) Twin Beds, Bathroom Attached Bedroom 2:...

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Featured review

"My excited vacation home"

It was everything a family could want. Good location,spacious home nice game room beautiful decoration . I WOULD BE MORE THAN WILLING TO STAY THERE AGAIN. The host went above and beyond for my family .

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$315
avg per night
New
Kissimmee House
Sleeps 10, 4 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to The Blinking Alligator Bungalow... Your family’s Disney getaway starts here! Our spacious 4-BR 3BA home is tucked inside a secure, gated resort community in Kissimmee—right in the Golden Triangle of Disney World, bordered by I-4, Route 192, and Route 27. Minutes from Disney parks,...

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New
Kissimmee Villa
Sleeps 14, 6 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Magic Palms Villa — Your Perfect Orlando Getaway Located just 10 minutes from Disney, Universal, Old Town, Walmart, and Publix, Family‑friendly 6BR home. Private pool + jacuzzy game room, fast WiFi, Smart TVs, full kitchen, and free parking. Gated community with clubhouse, gym, and...

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