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Kissimmee Vacation Rentals

(197 rentals)
Kissimmee House
Sleeps 12, 6 bedrooms, 5 bathrooms
3 reviews

Key Amenities

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

About this property

Fantastic 2 KING bed EnSuite Villa w heated pool HOT TUB Mins to DisneyFamily-friendly Kissimmee vacation home in Four Corners with water parkContactless one time access code check in! All white linen! Private pool heat up to 104 degree. It’s like a 5 star hotel but better! Pet Friendly...

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Featured review

"Great place"

The owners were very easy to work with. The house was in perfect condition, very clean and well maintained. We had 9 people and plenty of room for everyone. Definitely would recommend the house.

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$294
avg per night
Kissimmee House
Sleeps 16, 8 bedrooms, 6 bathrooms
11 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to the Epic Universe House, an 8BR resort pool home that sleeps 22, and pays tribute to the new Epic Universal park, featuring a Ministry of Magic arcade, Nintendo World gaming room, & themed rooms including How To Train Your Dragon, Zelda and more! Located only minutes from Disney World,...

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$448
avg per night
Kissimmee House
Sleeps 10, 4 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

This is a NON SMOKING HOME *Community: Storey Lake Floors: 2 Floor, 4 Bedrooms on one level.Pets: Pets acceptable. limit 2.Minimum Stay: 2 nightsRooms: 4 Bedrooms, 2 Bath rooms. En-suite in Master bedroom.Bed Configuration:Bedroom 1: King size bed with en-suite Bedroom...

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Featured review

"Lovely place"

I love this place. It was nice, clean spacious and cozy I wish I could stay longer I would definitely rent this property again.

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$150
avg per night
Kissimmee Villa
Sleeps 12, 6 bedrooms, 3.5 bathrooms
1 review

Key Amenities

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

About this property

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

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Featured review

"Wonderful Stay!"

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

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$189
avg per night
Kissimmee House
Sleeps 14, 5 bedrooms, 5 bathrooms
11 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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$243
avg per night

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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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$106
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 Townhome
Sleeps 10, 5 bedrooms, 3 bathrooms
2 reviews

Distance to park: 6 miles to Disney kingdom

Key Amenities

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

About this property

Welcome to Coral Cay Resort! Coral Cay resort Situated 6 miles from Disney World, 1 mile to Walmart and target. 0.5 mile off highway 192.Seaworld and Convention Center are 8 miles away.Just minutes from Orlando's vast array of theme parks, fabulous dining options and world-class shopping.Our...

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Featured review

"Vacation was beautiful!"

We had an awesome week in Florida! The house was amazing! The owners were awesome!!!!’ 6 stars! My family and myself will book again very soon!!

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$139
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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$165
avg per night
Kissimmee Villa
Sleeps 14, 0 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

7 bedroom 4.5 bath waterfront home located in the highly desired Emerald Island resort close to Disney and Universal Studios. The ground floor of this villa is an open concept with a living area featuring a 65" Smart 4k tv. The granite countertop kitchen boasts all new 2022 stainless appliances....

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$301
avg per night
Kissimmee House
Sleeps 8, 3 bedrooms, 2 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This beautiful home is a 3-bedroom, 2-bathroom with its own private screened pool. The home is located in Lindfields; a peaceful subdivision situated approximately 10 minutes from the Walt Disney World entrance and is conveniently located for the other attractions. It is an ideal location with easy access...

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Featured review

"Cheap and cheerful"

Villa was easy to find, near plenty of shops and restaurants. Villa was nice and clean, could have done either a bit of tlc. Ad we entered the villa there were lots of bushes protruding over the path A...

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$130
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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$136
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 8, 4 bedrooms, 3 bathrooms
9 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

"Great Villa"

Had a fantastic stay in the villa. Would definitely stay again and highly recommend. It was extremely clean and in a great location near shops, resturaunts and 192 and Disney. Would highly recommend and...

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$152
avg per night
Kissimmee House
Sleeps 16, 7 bedrooms, 4 bathrooms
11 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Relax in the comfort of this luxurious, family friendly, seven bedroom, resort vacation home that sleeps 16-18 people. Featuring a private pool, Avengers movie room, themed rooms for the kids including Star Wars, Harry Potter and Pirates themes, and resort amenities included at the exclusive Terra Verde...

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$248
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 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our idyllic 3 bed, 2 bath villa at Indian Ridge in the heart of Kissimmee. Because it is close to both the US192 and the I-4 it is a perfect place in which to enjoy Disney (10 minutes away) and Universal which is 20-25 minutes away.You are greeted by an airy, open plan living space creating...

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$145
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 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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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 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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$313
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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$382
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 Villa
Sleeps 8, 4 bedrooms, 4 bathrooms
29 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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$311
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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$521
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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$281
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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$396
avg per night
New
Kissimmee Townhome
Sleeps 8, 3 bedrooms, 3 bathrooms

Distance to park: 9 miles to Epcot

Key Amenities

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

About this property

Welcome to your perfect Orlando retreat! Located in the heart of the action, our spacious 3-bedroom, 3-bathroom townhome is just minutes from Disney World, Universal Studios, and other top theme parks — and only 30 minutes from Orlando International Airport (MCO).

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$143
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 Villa
Sleeps 14, 6 bedrooms, 5.5 bathrooms
2 reviews

Distance to park: 3 miles to Disney World

Key Amenities

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

About this property

This "Tropical Magic" villa is proudly offered to you by "Emerald Island Rentals"Air Conditioning • Free Wi-Fi • Free Internet • Outdoor Grill • Parking Included • Pool • SMART TVs through-out • Full-size laundry facilities • Children Welcome...

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Featured review

"Excellent vacation & house"

we were a family of 10 staying in this beautiful house was well equipt with everything we needed room was a big hit ..The heated pool was sure a big catcher the 4 children loved it so did the adults.....

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$298
avg per night
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 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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$141
avg per night
Kissimmee House
Sleeps 12, 6 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Situated on the very popular well maintained and long-established peaceful golfing Highlands Reserve community on the US27 in Davenport is this beautiful, well-presented villa with 6 bedrooms and 3 bathrooms. It can accommodate up to 12 guests very comfortably.The spacious open-plan villa is a great...

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Featured review

"Great location"

We very much enjoyed our stay. Villa was clean, well equipped and close to Disney. Management company was quick to respond to any questions.

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$220
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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$319
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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$346
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 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 Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
7 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our fabulous 4-bedroom, 3-bathroom family villa, located in the highly sought-after community of Orange Tree in Clermont, just off Highway 27.This spacious and fully air-conditioned home is ideal for families or groups of up to 8 guests. With two living areas, a fully equipped kitchen,...

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Featured review

"AWESOME!!!!"

This home is just as described. It is clean, well kept, beautifully decorated and spacious with plenty of kitchen utensils. The game room was so much fun. We had a few hiccups but the property management...

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$140
avg per night
Kissimmee House
Sleeps 15, 5 bedrooms, 5 bathrooms
15 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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$202
avg per night
Kissimmee House
Sleeps 10, 5 bedrooms, 4 bathrooms
12 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our stunning spacious 5 bedroom, 4 bath home located in the much sought after community of Tuscan Hills near DisneyThis beautiful home offers 2 masters en-suite bedrooms and 3 sitting rooms.Full air con and hi-speed WiFi throughout.The villa uniquely has 3 sitting rooms, two of...

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Featured review

"Amazing villa"

My family and I stayed at this wonderful villa for 5 nights. The house is very spacious,.clean and in a secured gated community. Watersong community is the best area for villa rentals close to Disney. We...

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$200
avg per night
Kissimmee House
Sleeps 8, 4 bedrooms, 3 bathrooms
7 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

"Nice"

Nice location nice place nice ppl. Will continue to rent with Florida rentals on every vacation my family decides to take.

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$165
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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$238
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 House
Sleeps 14, 7 bedrooms, 4 bathrooms
1 review

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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Featured review

"Best Christmas vacation ever"

Thank you so much for making our family Christmas vacation the best one ever. The home was absolutely what you stated, no hiccups whatsoever. The location was perfect. Absolutely what me and my family...

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$219
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 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 House
Sleeps 20, 10 bedrooms, 7 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Exciting NEW 10 bedroom family vacation home Offering privacy and space for everyone 4300 square feet of awesomeness 2 separate large living areas Relaxing pool with spa Covered outdoor dining and seating Games loft with pool table and foosball Windsor Island Resort offers a wide variety of world...

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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.