Kissimmee Vacation Rentals

(405 rentals)
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9 BR | 5 BA | Sleeps 18 | Quick View

1
Owner special: SAVE Up to 35% off Nightly Rates during LOW (Sep 11-Nov 16) and MID (Nov 26- Dec 21) Seasons!

$430

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Be sure to visit our website to check availability on all our homes! Save our page for future vacations to the Orlando area!Visit us at lostinthemagic . comThe Retreat at Champions Gate - Kissimmee, Florida is a new upscale gated resort community located just 12 miles from Walt Disney World. ...

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Property Type

Kissimmee House

"Great family vacation home!"

We really enjoyed our time in this house! The few little glitches were handled immediately by the villatel staff. There was so much to do on our "house day" while we rested between long days at the parks. ...

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Studio | 5 BA | Sleeps 10 | Quick View

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Single family home fully furnished ready to welcome you on your short or long trip. We have everything you need. Just bring your bags & be ready to relax with our private heated pool. Sleep 10 people private parking, safe entrance, community pool with tennis court & playground for kids. We ...

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Property Type

Kissimmee House

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7 BR | 7 BA | Sleeps 14 | Quick View

Owner special: SAVE Up to 35% off Nightly Rates during LOW (Sep 11-Nov 16) and MID (Nov 26- Dec 21) Seasons!

$396

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Be sure to visit our website to check availability on all our homes! Save our page for future vacations to the Orlando area!Visit us at lostinthemagic . comReunion Resort -Kissimmee, Florida is only 15 minutes to the area's main attraction... Walt Disney World. This gated luxury resort sits nestled ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Immerse yourself in this much-beloved world and find the hidden easter eggs in the room as you open the door to Potter's Place. This charming open-concept themed home is ready to make you feel revitalized. From a cleaned, well-maintained space to a fully equipped kitchen to cozy beds and pillows, your ...

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Property Type

Kissimmee Townhome

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Located in popular Sonoma Resort, our home is the perfect place to stay for a care and stress-free holiday away. Whether you are looking to spend long days lounging by the pool, exploring the parks or stretching your legs on one of the surrounding golf courses, this is the perfect location. Guests benefit ...

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Property Type

Kissimmee Villa

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3 BR | 2.5 BA | Sleeps 8 | Quick View

$114

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Gorgeous 3 bedroom townhome in a gated resort community with many activities. The home is located right across the street from one of the pools and playground.

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Property Type

Kissimmee Townhome

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Storey Lake - Kissimmee is a brand new vacation community located just 4 miles from the magical world of Disney and just minutes to Universal, Sea World, and the many water parks in the area. Central Florida is also home to some of the nation's top-rated golf courses and many are within a 10-minute drive ...

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Property Type

Kissimmee House

"Great vacation"

Our family had a wonderful time staying at this home for our vacation! The personal pool was a great thing for the kids, and the staff were a pleasure to work with when we called for assistance with the ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

A fabulous home-base for your trip to Orlando! Just Minutes to Theme Parks.Home Features:* 3 Bedrooms* 1 King, 1 Queen, 2 Full, 1 Twin (Sleeps 7-8) * All New Mattresses * TV's in every bedroom * USBs & Outlets convenient for charging* 3 Bathrooms* All En-Suite * Hair ...

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Property Type

Kissimmee Townhome

"Loved it."

Beautiful House, and a wonderful experience from start to finish! Cant wait to go back! The home was spacious and beautifully decorated and Lisa was a Pleasure to work with, and very helpful.

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$160

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Welcome to Mickey’s townhouse!! This is not your regular, company managed Airbnb. This is a family owned, loved place. We poured so much effort in each detail of this house. We hope you feel the love and enjoy this place we call our home. The first floor has a roomy living room, kitchen, and dining; ...

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Property Type

Kissimmee Townhome

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Conservation View, Games Room & Outdoor Spa!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®. ...

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Property Type

Kissimmee Villa

"Excellent accomodation with everything you need for a great holiday"

Booking and communication before we arrived was faultless. The house was well equipped and pool area was magnificent. All in all a brilliant holiday accomodation.

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6 BR | 3.5 BA | Sleeps 14 | Quick View

4.8 rating on other travel sites

$401

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"Something for everyone - fun, beauty, and comfort. There's so much to love! Everyone will love the incredible Avengers game room; it is like no other. Plus, all will love the heated pool and spa. Kids will love the themed bedrooms. And, adults will love the professionally decorated beauty of the ...

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Property Type

Kissimmee House

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8 BR | 6 BA | Sleeps 16 | Quick View

5.0 rating on other travel sites

$441

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"Professionally decorated, classy and full of fun vacation home with a beautiful waterfront view from the pool area. The inside movie theater and game room have a Jurassic Park theme - both of which make you feel like you are in Jurassic Park. You will find the poolside to be a huge hit at night ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Imagine a vacation like no other spent in a 9 bedroom, 10 bath custom luxury lakefront pool villa. The Formosa Grand is located in the exclusive gated community of Formosa Gardens Estates and one of the closest communities to Disney (less than 10 minutes!!) No expense was spared in the gorgeous estate ...

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Property Type

Kissimmee Villa

"West Family Reunion"

We had a great time at the mansion. Only a few things I would change. The hot tub price should have been included in the rental agreement.

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5 BR | 5 BA | Sleeps 10 | Quick View

4.8 rating on other travel sites

$346

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"We loved staying at this house, it is in a convenient location to the parks, and groceries are nearby. The house was clean and well-equipped. Our grandkids really enjoyed the themed rooms, the game room, and of course the pool! The gated resort community is awesome, and the water park/big pool were ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Property Reference EMI_1700RA perfect size vacation home for families who wish to stay close to Disney and come home to their own private pool to cool off after a long day at the parks. The decor was professionally updated in June 2022 aand again with further updates such as new flooring, new beds ...

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Property Type

Kissimmee House

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Key Amenities

  • Private pool

About this property

Bring the whole family to this great place with lots of room for fun. Come visit our luxury 7 bedroom/5.5 baths with a Private Heated Pool home with all the amenities necessary for your family and friends to spend a precious and memorable vacation in Orlando. Inside the Luxurious Windsor at Westside ...

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Property Type

Kissimmee House

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3 BR | 3 BA | Sleeps 9 | Quick View

2

Distance to park: 5 miles to Animal Kingdom Lodge

$142

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

**The private pool is not heated unless requested by the guest. Pool heating is available for an additional fee of $10.00 per day.**Create unforgettable memories in this beautifully decorated townhouse, located in the lovely Windsor Palms Resort, just minutes from Disney parks and Universal. This ...

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Property Type

Kissimmee Townhome

"Perfect place to stay and close to the theme parks"

The unit was super clean and the kitchen was supplied with everything you need to prepare meals when dining in. It is great location to Disney as well as our go-to restaurant – Bahama Breeze! There ...

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$114

avg/night

View Details

Key Amenities

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

About this property

CHEERY AND BRIGHT. Just what a vacation home should be. 4 bedrooms, 2 bathrooms, great views and just minutes from all the fun. Fully furnished , just bring personal items or things you cannot live without. Located in Eagle Pointe, a well sought-after vacation home community. Just minutes from what ...

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Property Type

Kissimmee House

"Vacation"

The house was perfect for our family’s size and the location was great. We enjoyed the large pool and the kids loved it.

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4 BR | 2.5 BA | Sleeps 8 | Quick View

6

Distance to park: 4 miles to Disney World

$150

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Great vacation home just three miles from the gates of Disney! Flat screen TV's in living room and all 4 bedrooms. Free wireless hi-speed internet and cable TV. HD TV in living room and all bedrooms. King bedroom has a flat screen 50" TV and 2 additional bedrooms have a built in DVD player in the ...

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Property Type

Kissimmee House

"Fantastic!"

The description of the home is everything it says it is. There are no exaggerations or stretching of the truth. If I were to go to Disney again, I would first look to see if Kay was renting her home. ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"Kids and adults love the game room. Really cool. Movie theater in the converted garage is incredible - better than being at a regular movie theater. And, maybe your biggest treat will be the poolside theater. Very pretty and comfortable home and full of fun." Keith C.LOOKING for an incredibly ...

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Property Type

Kissimmee House

"Great spot! Exactly as described!"

Terrific house. Has everything you need. All the electronics were working as they should. The theatre room and the outdoor pool/tub were the highlights. When I had question about the place while I was there, ...

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6 BR | 4 BA | Sleeps 12 | Quick View

9

Distance to park: 2 miles to Disney World

$358

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Welcome to Oasis by KLMJ Sunshine! Completely renovated (2022), this villa is in the #1 location in the beautiful gated community of Windsor Hills, just two miles from Disney. Enjoy complimentary pool & spa heat, themed rooms, and the only private Virtual Reality studio in the area! This is the 2nd ...

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Property Type

Kissimmee House

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5 BR | 5 BA | Sleeps 12 | Quick View

5.0 rating on other travel sites

$315

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"Spacious, well-equipped, clean and a quick drive to the Disney parks. Great game room. You couldn't ask for anything more!" Melissa MARE YOU LOOKING for a vacation home with an incredible game room, a private south facing pool and SPA, totally renovated home, in Windsor Hills Resort with ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Property Reference #RVH_1008RWelcome to Fairway Dream! This beautiful property is located at Reunion Resort in the Fairway Ridge neighborhood, close to Orlando's world-class attractions.Through the foyer, you have access to the second floor and the game room, before it leads you into the spacious ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool

About this property

2bd/2ba with the Best View in the amazing community of Storey Lake. Located 10 minutes from Disney Come in and enjoy a unique experience. There is a beautiful waterpark in the community center for you to enjoy. It is the perfect place to relax, have a good time and enjoy all that Orlando has to offer. This ...

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Property Type

Kissimmee House

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8 BR | 6 BA | Sleeps 16 | Quick View

4
LAST MINUTE DEAL 9/19 - 10/31: Special Discount 15-35% Off this Gorgeous 8 Bed Pool Home in Windsor at Westside - Don't Miss Out!

$300

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Windsor at Westside - Kissimmee, Florida is an upscale gated community located just 10 minutes from Walt Disney World. This luxury home sits nestled just outside of Orlando, Florida, and has quickly become one of the most desired locations in the Orlando area. During your stay, you will enjoy this well-appointed ...

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Property Type

Kissimmee House

"Champion gates"

Beautiful house, nice and spacious Clean, private, easy to book. Had 13 people there, 3 families, could have stayed longer

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DEAL

6 BR | 4 BA | Sleeps 14 | Quick View

4.9 rating on other travel sites

$348

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"When you walk through the front door, you immediately walk into fun with the adult area's pool table and large TV. And that's just the beginning. There's an awesome game room, 3 themed bedrooms, and in the pool area are a poolside theater and bar counter with TV. You will be totally entertained ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Welcome to a magnificent 5-bedroom, 5-bathroom in the prestigious Storey Lake community. As you step into this stunning home, prepare to be captivated by its elegant design and exceptional features, promising an unforgettable vacation experience.The ground floor invites you into a spacious bedroom ...

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Property Type

Kissimmee House

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5 BR | 4 BA | Sleeps 12 | Quick View

7

Distance to park: 6 miles to Disney Animal Kingdom

$230

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

***FREE WIRELESS INTERNET JUST BRING YOUR MOBILE DEVICES**. (Please note - there is no landline in the home)Sleeps a maximum 12 guests, with a maximum of 8 guests over the age of 14 years old.As you enter our lovely home, you will be impressed with the soaring 17ft high ceilings in the spacious ...

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Property Type

Kissimmee House

"Wonderful place to stay !!!"

House was located as stated ,15 minute access to all of our Disney visits,shopping and dining . Pool was great for relaxing afterwards,plenty of bedrooms was very nice that they had things set up for ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Sunset Lakes is ideally situated, just 4 miles from Disney World and a short drive from other popular attractions like Universal Studios, Sea World, and more. The proximity to Orlando and other destinations makes it a prime choice for travelers. The gated community offers various amenities such as a community ...

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Property Type

Kissimmee House

"Home away from home!"

We are regular Airbnb travelers and would rate this stay one of the nicest, best located, and real value of all the places we have stayed. The place was very clean, modern, had everything we needed to feel ...

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3 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to park: 1 miles to Disney Animal Kingdom

$97

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Come and enjoy your vacation in this comfortable condo, right by Disney. Yes Enjoy Three large screen TV's, DVD and free Wi-FI.Yes Beautiful/alluring condo, 1 mile from Disney world and minutes from other attractions, Such as sea world and Universal studio. In Celebration area Florida. Walking distance ...

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Property Type

Kissimmee Condo

"Recommended"

This is a beautiful property to stay in. Very clean and neat. I truly recommend it to anyone who wants to be near the main attractions. Everything is very close. You have gift shops, souvenirs shops, target ...

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3 BR | 2.5 BA | Sleeps 6 | Quick View

Distance to park: 2 miles to Disney Animal Kingdom

Inquire for rates

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Rentals by owner

About this property

Touches of Disney around every corner make this town home a fun spot to stay during your Florida adventure! Enjoy Orlando, Florida, home to Disney World and a lot of other AMAZING attractions! This property is located on the Exclusive Emerald Island Resort and is inviting and convenient for any planned ...

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Property Type

Kissimmee Townhome

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

This fabulous 4 Bed Villa is located in secure gated Lake Berkley ResortThis fabulous 4 Bed Villa is located in a peaceful corner of Lake Berkley Resort with beautiful views to the Conservation Area and one on the lakes at Lake Berkley.The villa is fully equipped with everything you will need ...

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Property Type

Kissimmee Villa

"Great company to use"

This is our 3rd visit to Orlando in 7 years. We used Stephen and VIP Villa on all occasions and have stayed at different Villas each time. The location of the lake Berkley resort is perfect for the theme ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Huge South Facing Rear Deck The Most Exclusive Home in Reunion ResortThis unique, one of a kind, beautiful, private custom Estate Home features over 8,200 sq/ft of luxury accommodation and balconies. This 'WOW!' factor home is private, quiet and not overlooked.Soak up the Florida sun on the biggest ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Private pool

About this property

Beautiful south facing Villa with private pool and hot tub overlooking a peaceful lake.This private gated community is 20 minutes to Disney’s Magic Kingdom and 20 minutes to Universal Studio and 45minutes to the gorgeous Daytona beach where you can actually drive your car onto this huge beach.A ...

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Property Type

Kissimmee House

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6 BR | 4 BA | Sleeps 14 | Quick View

5.0 rating on other travel sites

$329

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"We have stayed in many Windsor hills homes and this is THE one to stay in! Beautifully decorated, fun and so comfortable!" Beth MARE YOU LOOKING for a very special vacation home? This is it . . . Totally renovated by a professional decorator and includes an incredible game room, a private ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"This home is so much fun and is the best we have ever stayed in! The 2 theaters were a hit, and my kids could not get enough of the game room. So much to do in there- play pool, foosball, air hockey, shuffleboard, arcade style video games and PS4 games. We also spent so much time enjoying the private ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"Have lots of fun and relax in this beautifully renovated vacation home in Windsor Hills Resort! The air conditioned Star Wars themed game room (with a life-size Storm Trooper) and the poolside movie theater and bar make this home a one-of-a-kind." Cindy CARE YOU LOOKING for lots of fun ...

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Property Type

Kissimmee House

"Endless FUN"

From the pool with a movie projector to the games room this house was amazing!!! Would highly recommend and will definitely be using again.Close to Disney and Universal is a bonus.

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3 BR | 2.5 BA | Sleeps 6 | Quick View

1

Distance to park: 5 miles to Disney Animal Kingdom

$142

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Our Disney World themed townhome is located in the beautiful Emerald Island Resort. It is a gated community minutes from Disney and all of the main attractions in Kissimmee and Orlando. You will see we have decorated the home with Mickey Mouse and Animal Kingdom (we even have the same carpet upstairs ...

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Property Type

Kissimmee Townhome

"Great stay!"

We had a great stay at this home. Great location, beds were comfortable, and everything was well stocked to make this our home for the week.

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6 BR | 4 BA | Sleeps 13 | Quick View

1

$327

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Guests: 12 / Bedrooms: 6 / Bathrooms: 4 / Community: Indian Creek / Type: Villa6 LARGE BEDROOMS, 4 FULL BATHS A King Size Master Bedroom with TV, walk-in closet, a private pool/spa access door, a large en-suite master bathroom consisting of a large walk in shower and separate tub,his & hers ...

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Property Type

Kissimmee Villa

"Fantastic trip!! Wonderful property management."

My family and I had a great Christmas vacation. We were very close to Disney and the house was clean, quiet and well cared for. We were very pleased with the communication from the property management team ...

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$389

avg/night

View Details

Key Amenities

  • Private pool

About this property

Bring the whole family to this great place with lots of room for fun. You will love it

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Property Type

Kissimmee House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Our luxury Kissimmee vacation villa will comfortably sleep 10 people. It is fully air-conditioned for your comfort, and has a very roomy and spacious floor plan. It has 2 lounge areas (one with 2 full sofas, and a ceiling fan, the other with a love seat and a sofa bed), both have cable T.V. The kitchen ...

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Property Type

Kissimmee Villa

"Excellent villa"

Very clean and central to all theme parks, it was well cleaned for our arrival and the pool was cleaned twice a week during our stay. Would highly recommend this villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

and enjoy all that Florida has to offer? Look no further, introducing Villa Mickey Lakeview, the spacious 8 bedroom, 6 bathroom vacation home with beautiful lake views where the entire group can make memories to last a lifetime!Enter through the front door into the inviting foyer, make your way down ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Property Reference RVH_1018RMajor Excitement is situated in the Liberty Bluff neighborhood of Reunion Resort, this luxurious 6-bedroom, 6 bath home offers a private pool and much more!With an open-planned floor plan, the living area is bright and spacious with an "L-Shaped" sofa before ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

NO Party’s but Our mission is to provide excellent service and guest relations for every guest that comes to stay in our home. we wish to provide a fabulous experence of relaxation and comfort thoughout your time with us. But above all, we want to give you the chance to create the great memories ...

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Property Type

Kissimmee House

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5 BR | 3.5 BA | Sleeps 12 | Quick View

$299

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

This newly remodeled 5bd/3.5bath gated community home is waiting for you to visit! Saltwater pool, game room IN the house, all new flooring, granite countertops in kitchen, new pool furniture, new decorations, community playground and SO much more! This home is located only 5 miles from Disney World and ...

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Property Type

Kissimmee Villa

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3 BR | 2 BA | Sleeps 9 | Quick View

Distance to park: 10 miles to Disney World

$135

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Designed to seamlessly merge comfort and convenience, this two-story vacation home is an ideal retreat for remote workers and business travelers in search of a welcoming home away from home. With access to resort amenities including a well-equipped gym, refreshing pool, and more, this cozy townhome offers ...

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Property Type

Kissimmee Apartment

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Beautiful south facing lakeside villa with electrically heated pool option. Great location for all the theme parks, Disney 20 mins, Seaworld 15mins, Universal 30 mins and Cocoa Beach/Kennedy Space Centre 45 mins. Local English management contact and fully inspected/licensed by the Florida Hotels Board. ...

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Property Type

Kissimmee Villa

"Family Vacation"

We loved our stay at Alan’s house. It was clean and comfortable. He was very quick with any questions we had. The manager, Robert, was very prompt also. We had a problem with the pool heater but he took ...

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Inquire for rates

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

A beautiful vacation condo located in a prestigious gated and guarded community, for you to relax and spend time with your family and friends. With the prime location in Kissimmee near Disney World, major parks and restaurants, shops and so much more, this 3BD/2BA condo unit is designed for your best ...

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Property Type

Kissimmee Villa

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5 BR | 5 BA | Sleeps 12 | Quick View

4
LAST MINUTE DEAL 9/13 - 9/30: Price reduced for the month of September

$283

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

☆☆ HIGHLIGHTS ☆☆✹ 3 fun kids’ bedrooms; Pirate room, Choo-Choo Train room + Princess room ✹ 2 master suites ✹ 8 beds; 3 kings, 1 queen + 4 twins ✹ 5 full bathrooms; essential toiletries provided ✹ Full kitchen w/ modern appliances + coffee bar ✹ Huge kitchen island ...

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Property Type

Kissimmee House

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DEAL

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Ready for an ultra-special Disney area vacation? You’ll have everything you dreamed of in this luxury villa with 12 bedrooms! The large screened lanai with a built-in pool and hot tub will fast become one of everyone’s favorite gathering spaces, along with the dedicated theater room with seating ...

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Property Type

Kissimmee Villa

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Kissimmee Vacation Rentals

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

Soak up the Sun on Your Next Trip to Kissimmee Vacation Rentals


There’s nothing quite like a vacation to sunny Florida, a unique and inviting state with a huge variety of distinctive cities and natural areas to explore. One popular vacation destination in Florida is Kissimmee, a charming city with plenty to see and do just south of the Orlando metropolitan area. 

Kissimmee has a lot more to offer visitors than just excellent weather year-round. With a huge variety of scenic nature, shopping opportunities, and outdoor activities, Kissimmee itself has lots to offer every member of the family, not to mention its extremely close proximity to some of Orlando’s biggest amusement parks. 

You could stay in a busy hotel during your trip to Kissimmee, but then you wouldn’t be able to get a truly immersive experience of local city life. Kissimmee vacation rentals allow you to enjoy Kissimmee from inside its authentic residential neighborhoods. Additionally, having your own home to live in rather than a jam-packed hotel will provide some much-needed peace and quiet during your vacation. It will also offer plenty of space for the whole family to spread out.  

Top Tips for Traveling to Kissimmee Rentals


Like most other Florida cities, Kissimmee enjoys sunshine and clear skies throughout the majority of the year. However, the tropical climate of the state means that bouts of rain can occur throughout the seasons, particularly during the summer months, peaking in August. 

In addition to a higher likelihood of rain, the summer season in Kissimmee tends to be the most humid time of year. That’s why most vacationers choose mid to late spring or early autumn to make their trip to the city. At those times of the year, vacationers can enjoy great weather and lots of outdoor activities. 

Though the Kissimmee Gateway Airport is located centrally within the city, most vacationers taking commercial flights will fly into Orlando International Airport. It is located roughly 17 miles northeast of the city center, about halfway between Kissimmee and Orlando. Vacationers coming in from elsewhere in Florida can access Kissimmee by road using U.S. Route 192 and U.S. Route 441.

Things to Do Nearby Kissimmee House Rentals


Some of the most popular natural areas around Kissimmee are the swamps, which are located in major local bodies of water like Lake Tohopekaliga (known around town as Lake Toho). At Boggy Creek Airboat Adventures, you can experience the swamps from the water and get the thrill of a lifetime on an airboat driven by a local wetlands expert. Get up-close views of gator ponds, discover precious gemstones, and then grab a delicious lunch with the family at Boggy Bottom BBQ! 
Looking to explore a piece of history during your trip to Kissimmee? Medieval Times Dinner & Tournament allows visitors to step into the 11th century for an evening of authentic feasting, jousting, and sword fighting in true medieval style! Enjoy a delicious four-course meal, incredible performances, and a truly unforgettable experience for the entire family. 
Any vacation to Kissimmee isn’t complete without a trip or two to Old Town, a popular outdoor attraction with opportunities for shopping, dining, and family fun. Old Town is made up of an 18-acre stretch of classic city attractions, including the Old Town Ferris Wheel, the Great Magic Hall, and Mortem Manor, a year-round haunted house that is open for visitors to explore.

Kissimmee Annual Events


Kissimmee is a vibrant area with lots of annual festivals and events to enjoy in and around the city throughout the year. Kissimmee locals and visitors alike flock to the Ford Cuban Sandwich Festival each May near downtown Kissimmee, which celebrates the colorful history of Cuban cuisine in the area. Watch as local dining professionals attempt to build the world’s biggest Cuban sandwich during the event! 
The Ford Taste of Latino Festival is another local opportunity to celebrate and experience the best in authentic Latin cuisines in Kissimmee. The event features a contest to find the Top Latino Chef as well as plenty of live music and dance performances to enjoy as you taste a variety of Latin dishes. 
Not sure if you’ll be in town for any of Kissimmee’s larger annual events? You can enjoy Show Car Saturday Nights every Saturday night in the city on Margaritaville Boulevard. Check out the city’s best classic cars from a variety of eras and enjoy the plethora of delicious eateries and exciting shops located along the boulevard.

Wining and Dining in Kissimmee  


Between your outdoor activities and trips to local amusement parks while in Kissimmee, you’re sure to need some satisfying food and refreshing drinks to complete your perfect day. Luckily, Kissimmee is home to some of the best restaurants that Florida has to offer, combining authentic local flavors with worldly cuisine. 

To start your day off right with a delicious and hearty breakfast, look no further than Woodsby’s Countryside Café. This spot has authentic, cozy diner vibes to spare, not to mention a stacked menu of classic breakfast favorites, coffee bar items, and unique dishes you won’t want to miss out on. 

Tarantino’s Italian Restaurant is a great choice for a vacation date night or simply a nice dinner out with the family. A hearty Italian meal is a great way to finish a fun day of activities, and you’re sure to get that and more at Tarantino’s. If you bring the family along, you can take advantage of the takeout dinner special, which feeds four and includes a massive entrée, salad, and garlic bread.


FAQ

How many vacation rentals are there in/around Kissimmee?

There are 405 Kissimmee vacation rentals available on FloridaRentals.com. From house rentals to villa rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Kissimmee?

There are vacation rentals available in Kissimmee for as low as $95 per night with an average price per night of $227.

Can I rent a house in Kissimmee?

Yes, you can find house rentals in Kissimmee close to Lakefront Park, Monument of States, and Old Town. Don't forget to stop in to Shingle Creek Park or the nearby theme parks!

Do any vacation rentals in Kissimmee have a pool?

Yes, there are 340 vacation rentals in Kissimmee with a pool on FloridaRentals.com. Search using our filters and book one for your next vacation!