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Kissimmee Vacation Rentals

(202 rentals)
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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$244
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 House
Sleeps 16, 9 bedrooms, 6 bathrooms
10 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

New! Did you say “let’s do Karaoke after Disney”? Then this house is for you! This 9BR resort pool home sleeps 24 people and features a Karaoke lounge! And also an arcade, a Nintendo gaming room, and themed bedrooms for the kids/adults including Sonic, Pokémon, and Pirates! Located...

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$581
avg per night
Kissimmee Townhome
Sleeps 8, 4 bedrooms, 3 bathrooms
6 reviews

Distance to park: 6 miles to Disney,Seaworld

Key Amenities

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

About this property

Welcome to the beautiful Coral Cay resort ! It is one of the most popular resort destinations in the Kissimee/Orlando area for its proximity to theme parks and other major attractions. Situated 6 miles from Disney,1 mile to walmart and target, 8 miles to seaworld and convention center.This 1500 sqft...

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Featured review

"Second stay"

This is a nice place. Well kept and clean. There is 3 pools but not enough lounge chairs. The room was nice. Needed to buy a frying pan there is not enough kitchen gadgets and the cups for coffee are very...

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$146
avg per night
Kissimmee Villa
Sleeps 10, 5 bedrooms, 3 bathrooms
11 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This fantastic 5 bedroom, 4 bath Vacation Villa offers all of the conveniences of home and everything you need for a fun family vacation including a Private Screened-In Pool, Outdoor Spa, Games Room, Fully Equipped Kitchen, Free Wireless High-Speed Internet, Full Size Washer/Dryer, Coffee Maker and Microwave....

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Featured review

"Amazing Villa and location"

Stayed at Emerald Island Resort in July. Villa was in an excellent location and was gorgeous, massive, real good value and helped made a holiday of a lifetime!

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$205
avg per night

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Kissimmee Villa
Sleeps 8, 3 bedrooms, 2 bathrooms
5 reviews

Key Amenities

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

About this property

Hello, Our vacation home is located in a gated community with a large swimming pool, playground for the children, shuffle board, pool table and a workout room. It’s a duplex with its own separate driveway. There are three bedrooms and two full baths. The kitchen was just fully remodeled in 2022...

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Featured review

"Clean and quiet retreat"

Nice, clean, and has all of the amenities necessary! I have enjoyed my stay in this quiet and peaceful vacation rental. Beautiful view of pond right outside of screened lanai. The home was clean, and Randy...

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$100
avg per night
Kissimmee House
Sleeps 10, 5 bedrooms, 4 bathrooms

Distance to park: 6 miles to Disney World

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This beautiful 5 bedroom house is located in Crystal cove gated community. Perfect vacation home for families with small children or large groups. This vacation villa offers a sunny private pool, relaxing spa overlooking the lake. There are 2 master suites, private pool, community pool / gym. Pool...

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$258
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 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 Townhome
Sleeps 10, 5 bedrooms, 3 bathrooms
3 reviews

Distance to park: 6 miles to Disney,Seaworld

Key Amenities

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

About this property

Welcome to the beautiful Coral Cay Resort. It is one of the most popular resort destinations in the Kissimmee/Orlando area for its proximity to the theme parks and other major attractions. Situated 6 miles from Disney World, 1 mile to Walmart and target. 8 miles to Seaworld and Convention center. Minutes...

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Featured review

"Comfortable place to stay....."

We stayed here while in Florida for my daughter's dance competition. It was so nice to come "home" after a long day of dance. I loved that the driveway was right up to the door. I also loved that it...

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$154
avg per night
Kissimmee Condo
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

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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Featured review

"Disney vacation"

We moved into the condo for 4 nights to finish out our vacation, after staying at a Disney Property for three nights. Wow, this property was fantastic, very clean. The two themed bedrooms were such a hit...

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$189
avg per night
Kissimmee House
Sleeps 14, 5 bedrooms, 5 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

This lakefront resort pool home sleeps 14 and is steps from the Paradise Palms clubhouse, and only minutes from Disney World, Universal, and all Orlando attractions. Featuring 5 bedrooms with three king beds, private pool, a Tron themed game & movie room, and themed rooms for the kids including Mickey...

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$236
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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$260
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 10, 5 bedrooms, 4.5 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our superb 5-bedroom 4.5-bathroom villa, located in the community of Solana in Davenport. It is fully gated for security.The villa is modern and very spacious with all the amenities you could want. It sleeps up to 10 guests.The villa benefits from 2 sitting rooms. One is classed as...

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Featured review

"Lovely house handy Disney andalltheattractions"

The location of this house was great for visiting all the attractions. There were 10 of us—9 adults and 1 child. We loved everything about this place. It was clean, everything we needed, pool and hot...

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$165
avg per night
Kissimmee House
Sleeps 18, 9 bedrooms, 6 bathrooms
6 reviews

Distance to park: 8 miles to Disney World

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • 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 property!!"

What a great property! It was perfect for our family. Very spacious and clean. Definitely staying there again on our next stay in Florida.

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$417
avg per night
Kissimmee Apartment
Sleeps 4, 1 bedroom, 1 bathroom

Distance to park: 11 miles to Castaway Cove Adventure Park

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to this charming fully furnished one bedroom one bathroom apartment located in Heritage Key Villas, Kissimmee, Florida. This apartment is the epitome of convenience and comfort, offering a flexible lease term ranging from one month to twelve months, with a minimum stay of just 30 days, making...

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$106
avg per night
Kissimmee House
Sleeps 16, 6 bedrooms, 5 bathrooms
14 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to The Minions Mansion, a family fun, six bedroom resort vacation home that features a private pool, four KING bedrooms, a Minions themed bedroom, Star Wars themed arcade & movie theater, a billiards pool lounge with air hockey, a Super Mario gaming loft, and more! Located only minutes from...

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$311
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 House
Sleeps 8, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Want to enjoy a stay at a vacation home for you and your family? Our house offers a direct escape to a vacation paradise just for you! It offers 4 bedrooms and 2 bathrooms, and accommodates with a cozy living room. In the garage, there is also a game room for you or children to relax and have some fun....

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$165
avg per night
Kissimmee Condo
Sleeps 8, 4 bedrooms, 3 bathrooms
8 reviews

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

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to the Sun Lake Resort. We have 4 identical 1650 sqft units with 4 bedrooms and 3 bathrooms. The beautiful condo faces to sun lake and it has a spacious screened patio. It only takes 1 minute walk to a plaza for shopping and restaurants which is very convenient! More importantly, you are only...

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Featured review

"Awesome stay"

Beautiful resort and room was great. Great location and staff was very helpful. Would highly recommend this property.

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$145
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 Villa
Sleeps 16, 7 bedrooms, 4.5 bathrooms
13 reviews

Distance to park: 3 miles to Disney world

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Pool
  • WiFi

About this property

Newly furnished luxurious 2-story Villa home opens its door to welcome you! This villa is furnished with two master suite and one large bedroom with upscale King-size beds; two bedrooms with queen-size beds; and two bedrooms with two twin-beds each. All bedding and mattresses are Brand New with top quality...

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Featured review

"Once Again a Wonderful Vacation"

This is the third time we have rented a vacation home from Ann and Gary at Emerald Island Resort. The 7 bedroom home was perfect for our family of 12 people. Everyone commented how comfortable the beds...

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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
Kissimmee Villa
Sleeps 14, 7 bedrooms, 7.5 bathrooms
1 review

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

"Great pool!"

We stayed at the home for a week In March. Our kids loved the pool! Paying for the pool heating was a great decision.The home is big with lots of room for the kids to run around. It is close to the...

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$250
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 Villa
Sleeps 24, 9 bedrooms, 6 bathrooms
14 reviews

Distance to park: 2 miles to Sunday's Grill

Key Amenities

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

About this property

For last minute rentals or longer extended rentals, please inquiry about our discounted rates.This luxury vacation home is located in the Windsor at Westside upscale resort community - A perfect destination for DISNEY WORLD (10 minutes away), golf, and relaxing and celebrating with family and friends....

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Featured review

"Excellent"

Thank You Ann great service. Me and my family will be renting from you again in the future

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Kissimmee Townhome
Sleeps 10, 5 bedrooms, 3 bathrooms
4 reviews

Distance to park: 6 miles to Disney World,Seaworld

Key Amenities

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

About this property

Welcome to the beautiful Coral Cay Resort. It is one of the most popular resort destinations in the Kissimmee/Orlando area for its proximity to theme parks and other major attractions. Situated 6 miles from Disney,1 mile to Walmart and target, 8 miles to Seaworld and Convention Center.This gorgeous...

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Featured review

"Beautiful"

The apartment was beautiful My family and I really enjoyed this place If you are looking for a vacation rental please check this place out ️

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$153
avg per night
Kissimmee House
Sleeps 16, 6 bedrooms, 5 bathrooms
12 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Enjoy the sunrise & sunsets in this family friendly, lakefront, 6 bedroom resort vacation home featuring a private pool & spa, 2 king bedrooms, Minions themed arcade & game room, and themed kids rooms including Toy Story, Star Wars Mandalorian, and a Pacman gaming room! Located only 5 miles...

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$327
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Your family will be close to everything when you stay at this centrally-located gated Summerville Resort. It’s the perfect place for a trip!! The space is modern and stylish. This 4 bedroom (townhouse is Spacious enough to sleep 8.Access to resort, amenities, pool, gym, outdoor playground,...

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$150
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 Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
5 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

"Very comfortable villa with a great pond view and beautiful sunsets!"

We stayed in this villa for 20 nights. Upon arrival the house was spotless and we found the furniture to be very comfortable. We used the hot tub and pool a lot and were glad that we could find shade...

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$170
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 Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our beautiful 4-bedroom, 3-bathroom villa, located in the gated community of Lake Berkley Resort in Kissimmee, just off US-192 and close to all of Orlando’s top attractions.The villa is spacious, bright, and thoughtfully furnished to make your stay as comfortable as possible. It can...

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Featured review

"Emerald Island Resort"

Enjoy my 12 days stay with family kids had a blast at the theme parks. There were some minor problems but they were very responsive and was dealt with in a timely manner.

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$160
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 House
Sleeps 18, 9 bedrooms, 6 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • 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 View"

Fantastic time. Pool overlooks the lake. We had an issue with a burner on the stove the first day and the owner had a brand new stove delivered the next day. The owner has similar properties also. We have...

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$409
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 2 bathrooms
14 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

he villa is situated within Lake Berkley, Kissimmee, one of the most sought after locations for people wanting to rent a villa. For those visiting Disney it is just 5 miles away--approximately 10 minutes drive. All the other major theme parks are also very close by. For convenience and very cheap shopping...

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Featured review

"rental at Lake Berkeley"

We spent 2 weeks in this home and enjoyed our visit. Was easy access to areas where we wanted to go and the community was lovely. I would rent this property again.Elizabeth :)

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$155
avg per night
Kissimmee Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

This is a NON SMOKING condo *Community: Secret LakeFloors: Ground Floor Condo.Pets: Pets OK.Rooms: 2 Bed rooms, 2 Bath rooms. En-suite in Master bedroom.Bed Configuration: King (1), Two Queen Beds (2). Sleeps 6Flooring: Carpet throughout with tile in bath and kitchen.General:...

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$120
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...

View all property information

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 House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This unique 4-bedroom, 3-bathroom luxury Town home is situated on the new community of Tuscan Hills. Tuscan Hills is a new secure gated community, with extensive oak landscaping, located in Davenport on highway 27, close to highway 192, and only minutes from interstate 4.The town house is on over...

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$110
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 4 bathrooms
27 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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Featured review

"Amazing rental"

This place was very clean and well put together. The themed rooms were amazing and the location to the Disney parks couldn't get any better than here. It felt safe and clean with all staff in the gated...

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$343
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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$406
avg per night
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 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 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 House
Sleeps 16, 7 bedrooms, 6 bathrooms
16 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Enjoy the family fun in this 7BR resort vacation home that sleeps 17 people and features 3 KING bedrooms, a private pool w/ spa, an Avatar arcade game room, a FROZEN Castle room, and more themed rooms including Star Wars, Lion King, Monsters Inc, and Moana! Located only minutes from Disney World, Universal...

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$465
avg per night
Kissimmee Villa
Sleeps 16, 7 bedrooms, 5.5 bathrooms
1 review

Distance to park: 3 miles to Disney World

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

"Dory's Magic" is our Emerald Island Resort 7 bed/5.5 bath vacation home offering a fully air-conditioned games room in addition to a south-facing pool/spa and multiple living areas. It offers several complimentary amenities such as a BBQ grill, free full-size crib, pack 'n play, stroller,...

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Featured review

"7 bedroom house 8460 Secret Key Cove"

Sri was an outstanding contact ready to help all the time. Place was fantastic for our group of 8. Minor issues where Sri handled. Definite return next year.

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$323
avg per night
Kissimmee Townhome
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Modern 3-Bedroom Townhome – Near Disney!Enjoy the best of Orlando in this spacious and cozy home just minutes from Disney! Located in a gated community right next to the new Dollar Tree in Kissimmee, our home comfortably sleeps up to 8 guests.Bedrooms:Suite 1: King bed + private bathroomSuite...

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$139
avg per night
Kissimmee House
Sleeps 12, 6 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

A Truly Luxurious Executive Retreat, Main Level Features: Quality Ceramic Tile Flooring throughout. Spacious Family Room with Vaulted Ceiling and Corner Leather Sofa.70″ TV with 5.1 surround sound with blue tooth capabilities. Formal Dining Room/ Sitting Area with table for six, Fabulous Kitchen...

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$364
avg per night
Kissimmee House
Sleeps 18, 8 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Windsor at Westside Resort features a large 10,000 sq.ft. clubhouse which includes a resort-style pool, lazy river, water slide, & hot tub. Other amenities include a gym, beach volleyball, cabana rentals, basketball court, game room, tiki bar and concierge desk.Location is great with a Kissimmee...

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Kissimmee Weather

 | 

7222°  489°
JANUARY
7323°  499°
FEBRUARY
7725°  5312°
MARCH
8228°  5814°
APRIL
8731°  6418°
MAY
9032°  7021°
JUNE
9233°  7222°
JULY
9233°  7222°
AUGUST
9032°  7122°
SEPTEMBER
8429°  6518°
OCTOBER
7926°  5714°
NOVEMBER
7323°  5010°
DECEMBER

FAQ

Proximity to Attractions

How close are Kissimmee rentals to the main entrance of Walt Disney World versus Orlando rentals?

Some Kissimmee vacation rentals are only 12 miles from Walt Disney World. Orlando rentals are a little further away from the amusement park at around 20 miles.

What is the average drive time from Kissimmee to Universal Studios or SeaWorld?

The average drive time from Kissimmee to Universal Studios is 23 minutes, while the average drive to SeaWorld takes 25 minutes.

Are there Kissimmee communities that offer shuttle services to the theme parks?

Yes. Encore Resort Condo, Wyndham Bonnet Creek Resort Condo, and Champions Gate Condo are some of Kissimmee’s vacation rentals offering shuttle service to Walt Disney World, Universal Studios, SeaWorld, and other attractions.

How bad is the traffic on US-192 or I-4 when driving from Kissimmee to the parks?

Both US-192 and I-4 are busy roadways leading to the parks. Traffic is heavier or lighter depending on the day of the week and the time of day. Weekday mornings, early evenings, and Saturdays are especially crowded.

Property Type & Communities

What are the most popular resort communities in Kissimmee (e.g., Reunion, ChampionsGate, Windsor Hills)?

Champions Gate, Reunion, Emerald Island, Windsor Hills, and Indian Creek are all popular resort communities in Kissimmee.

What kind of exclusive amenities do these large resort communities offer?

Some exclusive amenities include a clubhouse, tennis courts, a fitness center, a movie theater, a sauna, and a marketplace to purchase food.

Is it better to stay in a large resort or a smaller, non-gated community in Kissimmee?

The answer depends on your preferences. A smaller, non-gated community in Kissimmee offers fewer amenities than a large resort but still has a collection of fun activities nearby.

What are the main differences between staying in Kissimmee versus staying in Orlando?

Orlando is a large, bustling city full of restaurants, shops, and attractions, while Kissimmee is less crowded with a more family-friendly atmosphere. Though both cities are close to the major parks, Kissimmee is closer to Disney World, whereas Orlando is closer to Universal Studios.

Amenities & Features

What size homes are typically available for rent in Kissimmee?

The typical Kissimmee vacation home has four bedrooms and ranges from 1,980 to 2,000 square feet.

Do most house rentals come with a private, screened-in pool and lanai?

Though most house rentals come with a private, screened-in swimming pool, not all of them have a lanai.

Are multi-generational homes with multiple master suites common?

Yes, multiple master suites are common in Kissimmee vacation homes for rent.

What are some unique amenities to look for in Kissimmee homes, like private movie theaters or elaborate game rooms?

Check listings for unique amenities in Kissimmee house rentals such as EV chargers, gardens, balconies, ping pong tables, pool tables, game rooms, and heated pools.

Booking & Cost

Is it generally more affordable to rent a large house in Kissimmee compared to a similar one in Orlando?

Yes, when comparing similar homes in these two Florida cities, Kissimmee house rentals are the more affordable option.

What are the typical resort fees or community access fees I should budget for?

The typical resort fee is around $40 per day.

Are there any "hidden costs" associated with Kissimmee rentals, like pool heating or BBQ grill rental?

Studying the “Fees” section of a Kissimmee rental’s listing can help you avoid any surprise costs. Some owners list fees for services like pool heating, damage protection, and pets.

What is the best time of year to find deals on Kissimmee vacation homes?

September and October are the best times to find deals on Kissimmee vacation homes because fewer people are booking rentals.

Kissimmee Specifics

What attractions are there to see in Kissimmee itself, outside of the major theme parks?

Boggy Creek Airboat Adventures, Gatorland, Shingle Creek Regional Park, Congo River Golf, and Lake Tohopekaliga (Lake Taho) are all unique attractions in Kissimmee.

What are the best places for shopping and dining in the Kissimmee area?

The Promenade at Sunset Walk, The Crosslands, and Universal CityWalk are some of the best places for shopping, dining, or both.

How does the vibe of Kissimmee differ from the International Drive area in Orlando?

Orlando’s International Drive has a high-energy vibe with dozens of shops, restaurants, shows, spas, and other attractions. While Kissimmee has its own collection of shops, eateries, and attractions, the city’s vibe is more laid-back.

Are there any good nature-based activities, like airboat tours, that are easily accessible from Kissimmee?

Yes. Wild Florida Adventure Park, Gatorland Bird Rookery, and horseback riding sessions at Lazy H Ranch give visitors the opportunity to admire Kissimmee’s natural environment.