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Kissimmee Vacation Rentals

(216 rentals)
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 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 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 House
Sleeps 12, 4 bedrooms, 3 bathrooms
13 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • WiFi

About this property

This 4 bedroom Themed Orlando vacation home sleeps 12, and features a Ratatouille themed living area, two master suites, a Guardians of the Galaxy themed room, a Toy Story themed room, and a Star Wars themed room! Located only minutes from Walt Disney World, Universal Studios, and all Orlando attractions!The...

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$209
avg per night
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

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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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$349
avg per night
Kissimmee Villa
Sleeps 10, 5 bedrooms, 4 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Our fabulous 5-bedroom, 4-bathroom luxury vacation villa is set in the tranquil location of beautiful Watersong, with no rear neighbours the property overlooks a conservation area at the rear.The villa sleeps 10 guests and boasts a private south facing pool/spa as well as a games room.At the rear...

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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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$185
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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$321
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
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 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 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 14, 7 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This 7 bedroom/4½ bathroom private house features a huge 10' x 40' covered lanai, with ceiling fans, extra patio furniture and a large flatscreen TV (accessed only by Netflix/Hulu, etc). Nice pool area in general. Interior furnishings are nice (certainly not spectacular). This is...

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$224
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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$386
avg per night
Kissimmee Villa
Sleeps 6, 3 bedrooms, 2 bathrooms
2 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

"Great"

A great family vacation rental.booking was easy and check in process was flawless. We had an issue with the internet but the manager resolved it as soon as possible.The rental was safe clean and convenient...

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$110
avg per night
Kissimmee House
Sleeps 14, 5 bedrooms, 4 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to The Marvel Mansion, a spacious five bedroom Orlando vacation home that sleeps 14 and features a large private fenced backyard with pool & spa, a Super Smash Bros movie theater & game room, TWO king bedrooms, and themed rooms for the kids and adults including Spider Man, Guardians of...

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$224
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 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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$148
avg per night
Kissimmee Villa
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This is a NON SMOKING condo *Community: Sweetwater Club VillasFloors: Ground Floor Condo.Pets: NOT PET FRIENDLY.Rooms: 3 Bed rooms, 2 Bath rooms. En-suite in Master bedroom.Bed Configuration: King bed (1) Queen bed (1), Full Bed (2). Sleeps 6.Flooring: Hard wood throughout with...

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$120
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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$346
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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$268
avg per night
Kissimmee House
Sleeps 16, 8 bedrooms, 5 bathrooms
15 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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$424
avg per night
Kissimmee Townhome
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Distance to park: 5 miles to Disney,Seworld

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to our new opening 4 Bedroom/3 bathroom Townhouse in CLUB CORTILE,This gated-community is close to every major Orlando attraction: Disney's Magic Kingdom, Epcot, Animal Kingdom, Universal Studios (Harry Potter), Sea World, and many more. Club Cortile is also conveniently close to WalMart,...

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Featured review

"Well located safe townhouse on a lake with good club facilities"

We are a pensioned couple from the Netherlands and in Florida to play golf in the sunshine. We have rented from the owner on several occasions over the last 15 years. This was our first time in the Club...

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$135
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, 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 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
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 House
Sleeps 7, 3 bedrooms, 2 bathrooms
8 reviews

Distance to park: 12 miles to Disney

Key Amenities

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

About this property

Heavenly Retreat, a designated rental vacation home, was just remodeled in a casual and comfortable style. It is a complete turn key ready vacation home with a full equipped kitchen, three bedrooms, and two bathrooms for up to 6 guests. The pool offers lots of privacy and relaxing atmosphere.This...

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Featured review

"Large well kept house"

very nice house. Clean, spacious rooms, nice pool, quiet neighborhood. Very nice owner, she helped several times with tv operation. Enjoyed staying there very much. Good location. Near major roads.

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$162
avg per night
Kissimmee Condo
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

My place offers all you need for a perfect family vacation. Minutes to Disney World, close to all the other attractions. Gated community Villas at Island Club. Two large saltwater swimming pools (my unit is steps from the swimming pool), a tennis court, a volleyball court, and two clubhouses with exercise...

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$110
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 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 Townhome
Sleeps 8, 4 bedrooms, 3 bathrooms
3 reviews

Distance to park: 6 miles to Disney,Seworld

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 1500...

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Featured review

"Wonderful location"

Very nice home, close to Disney and shopping places. Very quiet friendly neighborhood. Def will be booking again in the future

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$144
avg per night
Kissimmee Villa
Sleeps 12, 5 bedrooms, 3 bathrooms
16 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This villa is a stunning 5 Bed 3 Bath villa that can comfortably sleep 12 guests.A stunning, larger than average, 5 Bed 3 Bathroom villa with a fantastic private pool. All rooms in the villa are spacious. The villa is furnished and maintained to a very high standard.The villa is spaciously arranged...

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Featured review

"Our great vacation"

My family and I have stayed at this home twice and it has been great. The home is clean and very comfortable. We love to cook and the kitchen was well stocked with cooking utensils. Rent here you will...

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$130
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, 3.5 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 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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$390
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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$348
avg per night
Kissimmee House
Sleeps 12, 6 bedrooms, 4 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beautiful two-story home with 6 bedrooms and 4 bathrooms.This home is situated on a quiet street within the Solterra Resort. It boasts modern open plan living. It has an additional outdoor balcony space along with a large private pool and spa, loungers, outdoor table and chairs with an optional BBQ...

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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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$200
avg per night
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 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 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 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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$302
avg per night
Kissimmee House
Sleeps 16, 7 bedrooms, 6 bathrooms
14 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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$401
avg per night
Kissimmee House
Sleeps 8, 4 bedrooms, 3 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Bring your family and stay at this beautiful vacation home in the Emerald Island Resort community. You will be just minutes away from Walt Disney World® Resort, and all of the nearby theme parks and attractions of Orlando, Florida. This home has 1 King en-suite, 1 queen en-suite and 2 sets of twins.This...

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Featured review

"Great stay at a lovely villa"

We are just back from 2 weeks here, we had a fabulous time making use of the games room and the pool. Thank you

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$165
avg per night
Kissimmee House
Sleeps 16, 8 bedrooms, 6 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Located on Windsor Island Resort, an exclusive gated community in Kissimmee, this privately owned vacation villa is perfect for you and your family. 8 good-sized bedrooms, 2 lounge areas, an air-conditioned games room area and a private pool and spa with no rear overlooking neighbours.The resort...

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Featured review

"Rental home"

The home felt like home away from home. House was clean and the host was very attentive and friendly.

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$275
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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$355
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Our luxury 4 bedroom home is located within the top rated community of Indian Creek. 2 of the bedrooms have ensuite bathrooms.The villa is furnished to a very high standard and is fully Air-conditioned throughout keeping the villa cool in the warm Florida weather.Full hi-speed WiFi throughout...

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Featured review

"Excellent Vacation"

Great family-friendly house with a stunning pool and wonderful hot tub. Close to all major theme parks, many restaurants & stores. Neighborhood is super quiet with walking paths & nearby park.

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$160
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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$136
avg per night
Kissimmee Villa
Sleeps 14, 6 bedrooms, 4 bathrooms

Key Amenities

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

About this property

****CONTACT US FOR SPECIAL RATES & DISCOUNTED QUOTES***Central Breeze Villa located in the popular Windsor Hills Resort. Just 3 miles from Disney. Cozy, quiet & filled with fun to entertain everyone. Enjoy the saltwater pool, spa tub or just lounge on your private lanai. Head inside for a...

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$383
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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$217
avg per night
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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.