Kissimmee Vacation Rentals

(288 rentals)

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Our beautiful FOUR-BEDROOM, THREE-BATHROOM, luxury home is located at the gated community of Emerald Island Resort, surrounded by lush Florida vegetation, is the one of the latest full-facility resort in the Disney area. The winding, palm-lined road that leads to the impressive entry to the resort gives ...

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Property Type

Kissimmee House

"BGG"

Excellent location and very comfortable accommodations. Loved the pool and jacuzzi. Game room was enjoyable.

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4 BR | 3 BA | Sleeps 8 | Quick View

4

$161

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • 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 Townhome

"Beautiful, clean, great location!"

This townhouse was beautiful, clean, nicely decorated and in a great location in regards to DisneyWorld, SeaWorld, Discovery Cove, NASA etc. The community area (waterslides, pools etc) was fun, clean and ...

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3 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to park: 1 miles to Disney Animal Kingdom

$109

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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4 BR | 3 BA | Sleeps 10 | Quick View

2

Distance to park: 3 miles to Walt Disney Animal Kingdom

$162

avg/night

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Key Amenities

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

About this property

Star Lake Villa has 4 Bedrooms & 3 Bathrooms (2 master suites) – a beautiful pool – on a Lake with a games room.  This is a beautiful lakeside home is in the peaceful exclusive community of Rolling Hills Estates in Kissimmee off of Formosa Gardens Dr. It is close to everything, ...

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Property Type

Kissimmee Villa

"Great Home!"

From before booking and after David was GREAT! Quick responses and very detailed answers to questions asked. The home was great for our week stay, many things to do and eat nearby and the pool was the cherry ...

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Key Amenities

  • Air conditioning
  • Pool
  • Private pool

About this property

Modern Happy Vacation Home!!!The patio/deck area is completely screened in with a large pool. Have a relaxing meal and overlook the beautiful landscape. Families can splash around and lounge by the pool while soaking up the Florida sun. The pool area features a safety fence for extra added protection ...

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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

"Love the place!"

We absolutely loved this villa! We enjoyed sitting by the pool watching the sun set every evening. Keeping the kids away from all the statues and sculptures was a bit of a task but we definitely enjoyed.

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6 BR | 5.5 BA | Sleeps 18 | Quick View

50

Distance to park: 4 miles to Animal Kingdom

$211

avg/night

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Key Amenities

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

About this property

Some of the best features of this house from Guest Reviews • Beautiful Vinyl Plank Flooring in all bedrooms, halls and on the steps • Less than a 4-mile drive to Disney World’s Animal Kingdom Theme Park • Two leather couches and a recliner with a total of 5 power reclining seats • ...

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Property Type

Kissimmee House

"BEST EXPERIENCE EVER!"

I had booked this rental 10 months in advance. Paid promptly, and received all the information promised and so much more! John is an attentive, welcoming, and helpful owner that is very appreciated. The ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

This stunning 4 Bed 2 Bath Villa enjoys one of the premier positions on Lake Berkley Resort with an unspoilt beautiful view over the lake. Enjoy breakfast, lunch or dinner on the pool patio whilst watching the wildlife on the lake. If you enjoy fishing then you only need to walk a few yards to fish in ...

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Property Type

Kissimmee Villa

"Amazing place"

I stayed here with my family. We had a really wonderful stay! The house had everything we needed, more than we expected. Tons of towels which were really handy. We had hours of fun in the pool which was ...

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4 BR | 3 BA | Sleeps 8 | Quick View

17

$151

avg/night

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Key Amenities

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

About this property

Indian Creek Disney Retreat is a beautiful 1800SF, well maintained home in the Indian Creek subdivision which is literally on Disney's doorstep and your home away from home. Indian Creek is not a gated community but has a lot of community amenities.COVID-19 Precaution Implementations: We have installed ...

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Property Type

Kissimmee Villa

"Family vacation"

Nice quiet area. Pool was very nice. Easy to get to places. Had plenty of items we needed to cook. Grill was included. Owner responds very fast. Mattresses and carpets need updating.

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Key Amenities

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

About this property

Large townhouse sleeps 8 people very large space screened in patio, furnished with patio furniture by lake can feed the ducks. One bedroom is the king room with shower and bathroom ,second bedroom has 2 double beds with bathtub an bathroom. also with full kitchen appliances blender, toaster, coffee maker, ...

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Property Type

Kissimmee Townhome

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5 BR | 4 BA | Sleeps 12 | Quick View

5

Distance to park: 6 miles to Disney Animal Kingdom

$204

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** ***FREE NATIONAL AND INTERNATIONAL LANDLINE PHONE CALLS***Sleeps a maximum 12 guests, with a maximum of 8 guests over the age of 14 years oldIn these strange times we are doing all we can to ensure our home is safe for your stay. We ...

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Property Type

Kissimmee House

"Lovely home"

Lovely home will definitely recommend to others wish the pool and jacuzzi was heated though. Bring tissue and your own dish liquid and own laundry detergent if staying full week

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5 BR | 3 BA | Sleeps 10 | Quick View

$199

avg/night

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Key Amenities

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

About this property

This is a NON SMOKING HOME * Community: Calabay ParcFloors: 2 Floors, 5 Bedrooms, master downstairs and 4 bedrooms up. Pets: NO pets allowed Minimum stay: 4 nightsRooms: 5 Bedrooms, 3.5 Bath rooms.Bed Configuration: Bedroom 1: King size bed with En-suite Bedroom 2: Queen size bed with ...

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Property Type

Kissimmee Estate

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4 BR | 3 BA | Sleeps 10 | Quick View

2

Distance to park: 3 miles to Disney

$156

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

This spacious four bedroom, three bath executive home with optionally heated private pool, spa and Games Room with pool table, air hockey and foosball table, is situated on the exclusive Emerald Island Resort (the nearest to Disney). It is located just 3 miles and less than five minutes drive from Disney ...

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Property Type

Kissimmee House

"Flawless rental!"

We had a fantastic stay! Home is clean and comfortable. Excellent communication with owner, Gillian. Would highly recommend and will be a future guest!

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Key Amenities

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

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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Property Type

Kissimmee Villa

"Spacious and convenient"

We really enjoyed our stay in this villa. There were 5 bedrooms and 3 full bathrooms which allowed us plenty of space, a great pool and a washer and dryer is always a plus. Convenient to shops and not far ...

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Key Amenities

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

About this property

Sunset Vista Shores is a vacation home located in the gated Sunset Lakes community, just a few miles from Walt Disney World and convenient to Universal and Sea World. This lakeside retreat offers stunning water and sunset views. With the lake on one side of the home and acres of natural conservation ...

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Property Type

Kissimmee House

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3 BR | 2 BA | Sleeps 8 | Quick View

3

Distance to park: 12 miles to All Disney Theme Park

$108

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

If you will be visiting Orlando Florida for all of the great attractions including Walt Disney World, Universal Studios, Sea World theme parks, and all of the other major attractions? You can stay in our beautifully decorated 3 bedroom private villa, which boasts it's own private pool for less than it ...

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Property Type

Kissimmee Villa

"2021 vacation"

A well kept nice home. Everything as shown in the pictures. Excellent communication from owner and the property manager.

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Key Amenities

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

About this property

About this spaceWhat makes this listing special? This New Vacation Home is perfect for family gatherings and for creating lasting memories. You will have access to your own movie theater, private pool, spa and game room. The kids will absolutely love their very own Toy Story Land, Harry Potter room ...

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Property Type

Kissimmee House

"The house has enough entertainment for a week."

OMG! The house is amazing! You don’t even need to go to Disney. The house has enough entertainment for a week. Tim was also amazing and very responsive. Our kids had so much fun and it was an unforgettable ...

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8 BR | 4.5 BA | Sleeps 16 | Quick View

Distance to park: 4 miles to Disney

$236

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Property Description With a sunny pool and spa, games room, access to the amazing resort facilities and plenty of space for everybody, this is a perfect home for your family Orlando vacation. Situated in Kissimmee, on the popular Emerald Island gated resort, close to Disney theme parks, shops and restaurants. ...

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Property Type

Kissimmee Villa

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4 BR | 3 BA | Sleeps 8 | Quick View

3

Distance to park: 4 miles to Disney World

$154

avg/night

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Key Amenities

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

About this property

Enjoy Orlando, Florida, home to Disney World, Sea World, Universal Studios, and Islands of Adventure, in style. Conveniently located on the Exclusive Emerald Island Resort. The house is spacious where family can enjoy being together and also have some alone time. Our home is within minutes of all the ...

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Property Type

Kissimmee House

"Magnificent Place"

We enjoyed this place so much, truly amazing all that you need for your completely stay is there, if you are traveling with kids. Pictures and description are as described. We spent one week there. Very ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Less than 2 miles and only 5 minutes to Disney! Located in the new and most upscale location, the Emerald Island Resort, just 3 traffic signals from Disney off of Hwy 192 in Kissimmee. We feature concierge service, so you are never "on your own" unless you want to be! Tennis and basketball, ...

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Property Type

Kissimmee Villa

"46 Nights Feb thru March 2022"

Nice Home close to Disney - Enjoyed our stay there. Had plenty of room and everything worked well. Quick response when we needed pool heat turned on - Main King on 1st floor all other rooms on 2nd floor

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4 BR | 3 BA | Sleeps 8 | Quick View

5

$161

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • 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 Townhome

"Love this home"

This home was very convenient spacious and clean we loved our stay here and the person in charge I was able to contact with no issues

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$131

avg/night

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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

"Great if going to the Parks!"

If you want to be about 15 minutes from the parks this is it. The house is very well decorated. We enjoyed using the pool and the view of the lake.

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$164

avg/night

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About this property

Emerald Island Resort - Kissimmee, Florida is a resort paradise located 2.5 miles from the area's main attraction, Walt Disney World. During your stay, you will enjoy this well-appointed townhome that has been designed and decorated to provide you and your family an abundance of luxury amenities and leaves ...

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Property Type

Kissimmee House

"Very enjoyable"

We had a wonderful time vacationing in this home! There was eight of us and the house was well set up for eight people.

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6 BR | 5.5 BA | Sleeps 18 | Quick View

Distance to park: 4 miles to Animal Kingdom

$433

avg/night

View Details

Key Amenities

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

About this property

Pack your bags for an unforgettable trip to the happiest place on Earth at 'Minnie's Maingate Manor'! Minnie’s Maingate Manor is a 6-bedroom, 5.5-bathroom vacation rental home with themed bedrooms, sleeping accommodations for 16, and a private screened-in pool and spa. This Florida escape is perfect ...

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Property Type

Kissimmee House

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5 BR | 4 BA | Sleeps 12 | Quick View

2

Distance to park: 5 miles to Disney's Animal Kingdom

$387

avg/night

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Key Amenities

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

About this property

Imagine coming home at the end of an exhilarating day at the theme parks...You grab a refreshing drink from the fridge, flake out on the sofa in the outdoor living area right by the pool and reminisce about all the amazing things you did that day.The kids are splashing around in the pool, you ...

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Property Type

Kissimmee House

"Family Birthday Vacation"

Everything was great! The house was very spacious. The back area a bit small but still great! We had a blast!

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6 BR | 5 BA | Sleeps 12 | Quick View

3

$260

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • 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

"Family vacation"

This is a wonderful house to stay in. It is just beautiful inside and out. The property manager was just great. You want a no worry place to stay choose yhis rental.

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7 BR | 5.5 BA | Sleeps 14 | Quick View

1

Distance to park: 5 miles to Disney World

$279

avg/night

View Details

Key Amenities

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

About this property

Excellent Private Detached Family Vacation home/Villa located in prestigious man gated Vacation Resort of EMERALD ISLAND RESORTS. This outstanding villa has 7 BDRs/5.5 WRs will sleep up to 16 .Upgraded interior – all wood- NO CARPETS- designed with good furnishing home caters for the whole ...

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Property Type

Kissimmee House

"An amazing villa"

Our Family had a wonderful time at the Villa in Emerald Island resorts. The villa is superb in every respect. Excellent Big House with lots of room for everybody. Extra Large pool for a good swim. ...

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Key Amenities

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

About this property

Palm Tree Villa Florida, is tucked away in the much sought after location of Doral Woods. This large 4 Bedroom, 3 Bathroom villa, is ideal for making the perfect vacation.This is our own holiday home, so the furnishings are to a high standard, as you can see from the pictures and video. Fully Air ...

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Property Type

Kissimmee Villa

"Great home to stay for a vacation. The home met our expectations, clean and family ready."

Located in Doral Woods, only a few miles from Disney and the other attractions.Fully updated and rooms adequately furnished and beautifully decorated.Large family and living room and large TV.The ...

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Key Amenities

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

About this property

Modern architecture, state-of-the-art furnishings, and hip-to-the-minute décor make this 5 bedroom, 5 bath getaway in Storey Lake a bonafide safe haven for luxury and comfort. This home is brimming with amenities, from an action-packed game room, Star Wars themed bedrooms, your very own private ...

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Property Type

Kissimmee House

"Comfortable vacation home"

Great location and very nice property. Close to Disney Parks and restaurants. I recommend pay the extra fee for the pool heater because the pool was cold even in March. My young daughters enjoy the resorts ...

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6 BR | 4 BA | Sleeps 16 | Quick View

2

Distance to park: 2 miles to Disney World

$300

avg/night

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Key Amenities

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

About this property

**Special Available due to last minute cancellation the only home open Christmas/New Year's week (other than a few small gaps) 8BR Champions Gate Private Pool Home open 12/27-1/7 please ask!!! $7100 per week with tax, pool heat and fees!**COVID 19 INFO UPDATED ON OUR WEBSITE, CANCEL FOR ANY REASON ...

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Property Type

Kissimmee House

"Great family friendly get away"

Not sure where the the water park was. There was a good pool and splash pad on site. The home was clean and well furnished. Some items didn't work, like the Playstation for games, but the Televisions worked ...

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4 BR | 3 BA | Sleeps 10 | Quick View

$181

avg/night

View Details

Key Amenities

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

About this property

Beautifully renovated, decorated corner Townhome. Perfect size for a family to have a getaway. Terra verde Resort has many amenities to enjoy and relax.

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Property Type

Kissimmee Townhome

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Key Amenities

  • Air conditioning
  • Private pool

About this property

Location, Location, Location, situated just 3 miles from Disneys Animal Kingdom and less than a mile from Margaritaville and the Formosa gardens shopping area and restaurants on the US192 you are perfectly placed to hit the parks before the rush, come home to cool down by the pool for dinner and hit the ...

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Property Type

Kissimmee Villa

"Lovely Villa, Great Location"

Really nice villa. Plenty of living space. Sleeps up to 12 but there were 7 of us so it was really roomy.Pool area is so nice, with a view over a lake with lots of wildlife to see. Pool also has a colour ...

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7 BR | 5.5 BA | Sleeps 15 | Quick View

Distance to park: 8 miles to Disney World

$489

avg/night

View Details

Key Amenities

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

About this property

Special Promotion! 44% off nightly rates through June 15th!Waiting to welcome you is this luxurious large 7 bedroom, 5.5 bathroom single family home, perfect for large families or multigenerational gathering with all the comforts of your own home and more! Featuring Star wars, Spiderverse, and Minion ...

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Property Type

Kissimmee House

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4 BR | 2.5 BA | Sleeps 8 | Quick View

5

Distance to park: 4 miles to Disney World

$200

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"

This property had everything we needed. Within a few minutes of Disney. Great central location as well to Universal and within reasonable distance to the beach. Definitely will be coming back!

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$125

avg/night

View Details

Key Amenities

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

About this property

Close to the Attractions but away from the crowds. 4 bedroom/3 bath single story home on "lake". Ducks, Sandhill Cranes, sometimes a falcon, turtles. King, king, and 4 twin beds, TV in all bedrooms, WiFi, FREE US, Canada and US Territory phone calls. Fully furnished. Not suitable for ...

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Property Type

Kissimmee House

"Our favourite place"

Two years we have not been able to get there we have rebooked for next May the couple that own the Villa have been so kind and patient with us and we really appreciate them we just can’t wait to get there

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7 BR | 7 BA | Sleeps 14 | Quick View

$437

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Reunion Resort -Kissimmee, Florida is only 15 minutes to the area's main attraction... Walt Disney World. This gated luxury resort sits nestled just outside of Orlando, Florida and has quickly become one of the most desired resorts in the Orlando area. This home will provide you and your family with an ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

This Disney Villa is a fully furnished home and is one of the best kept turnkey properties you will find in Indian Creek ! Has an airy open floor plan, lots of light. Enjoy the crystal clear South facing pool and the covered lanai on your sunny and warm Florida holidays.This luxurious private home ...

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Property Type

Kissimmee Villa

"Fantastic vacation home"

This home is beautiful and in a wonderful community in Kissimmee. Kim (the homeowner) made everything very easy, booking and paying was a breeze with absolutely no stress!! The home was spotless when ...

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4 BR | 3 BA | Sleeps 8 | Quick View

2

$161

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • 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 Townhome

"The Dimech’s Family Vacation!!"

My Family and I have travelled A lot these past 4 months and have used this property owner twice. His place has all the things necessary for large families to stay. Place was very clean with a washroom ...

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5 BR | 5 BA | Sleeps 10 | Quick View

1

$262

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Reunion Resort -Kissimmee, Florida is only 15 minutes to the area's main attraction... Walt Disney World. This gated luxury resort sits nestled just outside of Orlando, Florida and has quickly become one of the most desired resorts in the Orlando area. This home will provide you and your family with an ...

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Property Type

Kissimmee House

"Open space, perfect for entertaining and gathering."

Property is very nice and well maintained. Space is very accommodating for large families. Well enjoyed!

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4 BR | 3 BA | Sleeps 8 | Quick View

1

Distance to park: 12 miles to Disney World

$161

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

The Retreat at Champions Gate - Kissimmee, Florida is a new upscale gated resort community located just 12 miles from Walt Disney World. This luxury home sits nestled just outside of Orlando, Florida and will quickly become one of the most desired locations in the Orlando area. During your stay, you will ...

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Property Type

Kissimmee House

"It was Awesome! Everything was in order and to my standards.. Love to come back"

Awesome.. Everything was in order and I'm most definitely coming back. Things were great. My family and I shall return

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9 BR | 8 BA | Sleeps 18 | Quick View

Distance to park: 3 miles to Disney Animal Kingdom

$800

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

We’ve fallen in love with our new vacation villa, and we think you will too. Located just minutes from Disney (Animal kingdom is a 6 minute drive!) plus Margaritaville with its Water Park and many restaurants, Hartley House is the perfect home for your next family vacation. You’ll be so close ...

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Property Type

Kissimmee Villa

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3 BR | 2 BA | Sleeps 8 | Quick View

8

Distance to park: 12 miles to All Disney Theme Park

$110

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

If you will be visiting Orlando Florida for all of the great attractions including Walt Disney World, Universal Studios, Sea World theme parks, and all of the other major attractions? You can stay in our beautifully decorated 3 bedroom private villa, which boasts it's own private pool for less than it ...

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Property Type

Kissimmee Villa

"Vacation"

our stay her was nice. It had all our basic needs and a nice private pool. We plan to return to this home on our next trip. The only thing we haven't received our deposit yet. But I'm sure it will be soon.

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4 BR | 3 BA | Sleeps 8 | Quick View

Distance to park: 3 miles to Disney Animal Kingdom

$149

avg/night

View Details

Key Amenities

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

About this property

Great location - fabulous pool area

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Property Type

Kissimmee Villa

Show less

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Our villa is situated on the safe and secure gated Terra Verde Resort.Our villa is a beautifully built 4 bedroom home with a very high spec of furnishings. The villa has 2 ensuite bathrooms, making it ideal for single or two family use. Free air con and WiFi throughout the villa.The large ...

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Property Type

Kissimmee House

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6 BR | 4 BA | Sleeps 12 | Quick View

7

Distance to park: 3 miles to Disney World

$344

avg/night

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Key Amenities

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

About this property

Situated in the Window Hills resort community about 2 miles from Disney, this 6-bedroom, 4-bath vacation rental home specializes in providing fantastic Florida vacations! With 2,812 square feet and accommodations for 14, guests can enjoy not only the private pool and spa in the enclosed lanai but also ...

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Property Type

Kissimmee House

"The house is perfect."

The house is just as you see it in the pictures. EVERYTHING you need is there. The house made us all feel as though we were home. Henry was so nice on the phone, Any question I had he answered right ...

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4 BR | 2 BA | Sleeps 7 | Quick View

1

$128

avg/night

View Details

Key Amenities

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

About this property

WELL CARED FOR HOME IN LOVELY COMMUNITY. HOME BACKS TO CONSERVATION SO YOU ARE NOT OVERLOOKED AND IS A FEW STEPS FROM RETENTION POND WITH POND VIEWS FROM THE POOL DECK. SHADED PATIO WITH TABLE AND CHAIRS .KING, KING AND 4 TWIN BEDS WITH THEMED TWIN BEDROOMS - LITTLE MERMAID AND DORY. TV IN ALL ...

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Property Type

Kissimmee House

"Amazing time"

This is one of the most beautiful homes I've ever stayed in. Plenty of space with private pool cant get any better. Very good location and neighborhood. Will be going back very soon.

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Key Amenities

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

About this property

Luxury villa right on lake edge. Free fishing on 3 lakes. gated Resort.Our 4 Bed, 2 Bath villa is furnished to a very high standard and benefits from a perfect lake view position.Free fishing on 3 well stocked lakes. The villa backs on to one of the lakes. The other 2 lakes are 3/4 minutes walk ...

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Property Type

Kissimmee Villa

"Safe peaceful comfortable villa"

We have stayed at one of Stephens villas before at Lake Berkely and we would always look to book one of the villas again.The location is superb set in a gated safe community close to all amenities, ...

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$130

avg/night

View Details

Key Amenities

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

About this property

Come relax in this 4 bedroom, 3 bathroom home. Sit on the screened in pool deck and just watch the wildlife , eat meals, have a cup of coffee and just relax. You are on vacation. Two king beds, queen and 2 twin beds .

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Property Type

Kissimmee House

"Disney Bound 2021"

The location was perfect with easy access. The house was very nice with a great view overlooking the pond. Had everything we needed. About 15 to 20 minutes away from Disney. Ms. Diane is a great host. Will ...

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7 BR | 4.5 BA | Sleeps 14 | Quick View

3

Distance to park: 4 miles to Animal Kingdom

$250

avg/night

View Details

Key Amenities

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

About this property

Conveniently located on the Exclusive Emerald Island Resort. With 7 Bedrooms and 4.5 bathrooms, Berni’s Home from Home can easily accommodate two families travelling together or will give one family plenty of space.Enjoy relaxing by your very own private extended south facing pool or spend some ...

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Property Type

Kissimmee Villa

"Very well maintained home"

This home was lovely and very well kept. Would rent again if the occasion arose that we needed a home this big again.

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Key Amenities

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

About this property

Beautiful 4 bedroom/3 bathroom Villa in the luxurious Emerald Island Resort - Only ~ 4 miles from Disney & close to other major attractions! This home includes a private pool, spa & game room. There is a large SMART tv in the living room & flat screens in each bedroom. There are queen beds ...

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Property Type

Kissimmee House

"Wonderful Vacation Home"

Thank you so much for allowing us to spend our winter vacation at your beautiful home. Everything was perfect when we arrived. It was very clean, the pool was a special place for us to gather, and the home ...

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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 288 Kissimmee vacation rentals available on FloridaRentals.com. From house rentals to cottage rentals to beach condos 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 $85 per night with an average price per night of $206.

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 241 vacation rentals in Kissimmee with a pool on FloridaRentals.com. Search using our filters and book one for your next vacation!

What are the best vacation rentals in Kissimmee?

Visitors give great reviews to these top-rated Kissimmee vacation rentals available on FloridaRentals.com:
Indian Creek Retreat: Well maintained home in the Indian Creek subdivision which is literally on Disney's doorstep and your home away from home.
Casa Bonita: 'Casa Bonita' which means 'Beautiful Home' is a beautifully furnished four bedroom, three bathroom home with a 26 ft x 14 ft swimming pool.
Mickey's Villa: This beautiful 5-Bed 4-Bath home located in the very popular community of Indian Creek is one of only three homes in the development with a Mickey Pool.