Kissimmee Vacation Rentals

(243 rentals)
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Four Bedroom Family Vacation Home Close to Disney!

4 BR | 2.5 BA | Sleeps 8 | Quick View

4

Distance to park: 4 miles to Disney World

$200

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

"Nice home, horrible host"
Reviewed June 24, 2021

My family and I stayed in this home for 2 weeks. The home was overall nice. WiFi was horribly slow. Big issue when you have a teenager and 10y/o twin boys. Game room was extremely hot, it only had fans ...

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Perfect Paradise

7 BR | 4.5 BA | Sleeps 16 | Quick View

$348

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

LOCATED IN GUARD GATED RESORT COMMUNITY of Emerald Island 3 MILES TO DISNEY 4 KING MASTER BEDROOMS (7 TOTAL BEDROOMS) 4 FULL BATHROOMS plus a half bath downstairs HUGE PATIO AREA so you always have sun on the pool PLUSH PORCH FURNITURE SPA AIR-CONDITIONED MOVIE THEATRE ROOM/GAME ROOM (POOL ...

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Property Type

Kissimmee Villa

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SOUTH FACING POOL/ COME AND RELAX

$117

avg/night

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Key Amenities

  • Air Conditioning
  • Full 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

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Stunning 5 Bed 4 Bath Villa with own private pool. Gated Resort close to Disney.

$130

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Welcome to our stunning, larger than average, 5 Bed 4 Bathroom villa with a beautiful view of the conservation area at the rear as background of our private pool. All rooms in the villa are spacious. The villa is furnished and maintained to a very high standard.The villa is located just off US 192 ...

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Property Type

Kissimmee Villa

"Very Nice Villa"
Reviewed May 19, 2021

This villa was very spacious and was more than capable of accommodating my family during our stay. I loved the location. It isn’t far from the theme parks. It is securely located in a gated community ...

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The perfect Disney vacation home rental property! ATTENTION-ONLY WEEKLY RENTALS

3 BR | 2 BA | Sleeps 8 | Quick View

6

Distance to park: 12 miles to All Disney Theme Park

$104

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

"We loved our stay in this lovely peaceful home"
Reviewed December 28, 2020

We rented this house from Dec 8 to 14, 2020 for our vacation to Disney and Universal Studios, and was truly impressed by all it offered. The location was perfect as it is close to the Florida Turnpike, ...

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West Reunion Estate | Games Room, Theater and South Facing Pool!

$364

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Situated within the West-side of the exclusive Reunion Resort and Just 6 miles from the gates of Disney World!Pull up to your home away from home, and prepare to indulge in luxury. This home has been furnished with no expense spared. This beautiful home boasts a rare combination of characteristics ...

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Property Type

Kissimmee House

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Modern Serenity Vacation Home | Private and Screened Pool | Home Theater |

$322

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

THIS HOME IS LOCATED IN THE RETREAT AT CHAMPIONS GATE, WHICH IS 6 MILES FROM REUNION RESORTThis home has everything you need for your next vacation. This brand new home with 8 beds and 5 baths can accommodate up to 16 guests with a spacious living area, fully equipped kitchen, private and screened ...

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Property Type

Kissimmee House

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Milazzo Florida Villa - 3 Miles from Disney / Orlando - Indian Creek / Kissimmee

4 BR | 3 BA | Sleeps 8 | Quick View

Distance to park: 2 miles to Disney's Animal Kingdom

$160

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

4 Bedroom /3 Bath / Pool & Spa Vacation HomeCONTACT US AND REQUEST A DETAILED QUOTE !! No Booking Fees - Book Direct with the HomeownerCheck our Reviews on VRBO - Property #284051

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Property Type

Kissimmee House

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The Floridian : Ultra Luxuary 5BR Pool Home, 2 Master Suites, Sleeps 12!

$250

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Enjoy our three-thousand square foot, custom luxury pool home, less than four miles from Disney World. We offer two master suites with king-size beds (one with Jacuzzi), two queen-bedrooms, one twin-bedroom, and queen size pullout-couch, all on one floor. This is not your typical Rolling Hills house. ...

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Property Type

Kissimmee House

"Our Dream Vacation"
Reviewed July 30, 2018

This home was PERFECT for my family! It was very spacious and had everything we needed to make us comfortable. Very close to Disney and close to a lot of nice eating places we could not have chosen a ...

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Free Pool Heat -3 Miles to Disney Private Pool Themed Villa

$142

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Newly decorated villa in November 2019 contains new laminate floor in all bed rooms and family room and two theme rooms for the kids: Minions for the boys and Princesses for the girls. Your Vacation Villa is nestled on the exclusive Emerald Island Resort, one of the nearest top resorts to Walt Disney ...

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Property Type

Kissimmee Villa

"Family trip"
Reviewed June 14, 2020

The house was so beautiful and me and my kids loved the house i would tell everyone i know to rent from u all.the house was clean the beds was soft and my family love it the pool was big it just wat i want

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South facing heated pool and spa

6 BR | 4 BA | Sleeps 12 | Quick View

6

Distance to park: 3 miles to Disney World

$232

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

"Girls Trip 2020"
Reviewed July 24, 2020

My friends and I absolutely loved this home ...it was perfect for the 8 of us. I WOULD DEFINITELY RENT AGAIN!!

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Windsor Hills resort Private Pool Home (FREE WATER PARK USE DURING STAY!)

6 BR | 3.5 BA | Sleeps 14 | Quick View

Distance to park: 2 miles to Disney World

$350

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

COVID 19 INFO UPDATED ON OUR WEBSITE, CANCEL FOR ANY REASON TRAVEL PROTECTION COVERAGE OFFERED, FLEXIBLE CHANGES.PLEASE SEE RATE NOTES FOR RATES FOR VARIOUS SEASONS AND SIZE HOMES 4-6BR Private pool homes in Windsor Hills resort and other resorts available. All homes this size include private pool, ...

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Property Type

Kissimmee House

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Gigantic Pool 6 BR 4 BA, Two Themed Bedrooms, Games room

6 BR | 4 BA | Sleeps 13 | Quick View

2

Distance to park: 3 miles to Disney World Animal Kingdom

$243

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Welcome to BigPoolVilla!Our 6 bed (3 en-suite masters) 4 full bathrooms (with a spectacular pool) is where you want to be - as close to Disney as it gets, only at 2 miles from Disney in the prestigious Rolling Hills at Formosa Gardens Estate on a QUIET street.The Pool is Gigantic it's in the top ...

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Property Type

Kissimmee Villa

"Awesome"
Reviewed May 7, 2021

This house was located just a short driving distance from Walt Disney World. It was very easy to get to the parks. This was the first time we have ever rented a vacation home and we were not disappointed! ...

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Mansion with Outside Kitchen, Theatre, Games RM. Huge House with Outside

$780

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Welcome to Mickey's Atlantis. All the amenities of a 5-star luxury resort in a mansion house.• Amazing 8 bed mansion • Sleeps 16 • Just 5 mins from Walt Disney World • All bedrooms have boutique-style ensuite bathrooms • Large swimming pool and hot tub • Cinema room ...

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Property Type

Kissimmee House

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Stunning Lake Front Villa, 3.5 miles to Disney!

6 BR | 5 BA | Sleeps 12 | Quick View

4

Distance to park: 4 miles to Disney

$429

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

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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Property Type

Kissimmee Villa

"Our dreamhome"
Reviewed May 22, 2020

Our house was beautiful with a large heated pool and jacuzzi overlooking the lake and gorgeous sunsets every night. Great eat in kitchen and lots of bedrooms and bathrooms all wonderful. TV’s in every ...

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2021 Labor Day Holiday Week Rental ( Dates: 09/04 through 09/11)

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

We shall reach some sort of life normalization by then! Perhaps, you want celebrate your Labor Day Holiday with a week rental (09/04-09/11; Sat-Sat) at Vacation Village at Parkway Resort, 2975 Arabian Nights Boulevard, Celebration, Orlando, FL 34747. The 1,500 square feet apartment will contractually ...

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Property Type

Kissimmee Apartment

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6BR/5.5Bath/4Miles to DisneyAK/$129 Specials/FreeSpa/Lanai

6 BR | 5.5 BA | Sleeps 18 | Quick View

45

Distance to park: 4 miles to Animal Kingdom

$147

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

The daily rate for all open dates in June 2021 is just $129. ********************************************************** Summary of this House’s best features (from 200+ Guest Reviews) • Less than a 4-mile drive to Disney World’s Animal Kingdom • Two leather couches and a recliner ...

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Property Type

Kissimmee House

"Beautiful House"
Reviewed June 23, 2021

The house was better then I pictured! It was huge every room was perfect had the most comfiest beds & came with everything we needed crib, playpen, baby gate & more! The best part was the beautiful pool ...

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The Formosa Grand Mansion! Lakefront! Infinity Pool & Spa! Cinema! Pure Luxury!

$858

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

"Mothers Day out"
Reviewed May 19, 2021

Nothing’s perfect but this was soooo close! Spacious bedrooms everyone enjoyed their private baths. Dishes were not clean and one guest had old, stained linens and the floors hadn’t been mopped. Otherwise, ...

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Sunshine Memories Villa. ☀️❤️ Magical Family Retreat near Disney w/Waterpark

$296

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Welcome to Sunshine Memories Villa, where you will have an amazing vacation enjoying all that the Orlando area has to offer. Our 5-bedroom 5-bathroom villa is located less than 10 minutes away from Disney in the beautiful gated resort of Windsor Hills. As you step inside the foyer of your vacation home ...

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Property Type

Kissimmee Villa

"Don’t worry, be happy"
Reviewed August 7, 2020

Even with all that’s going on, this was a blessing in disguise. Really needed this and everything was perfect. You can’t live your life in fear, just be cautious in all you do. No complaints whatsoever. ...

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Our Goal:- Make your stay Enjoyable! Sleeps 20 - Heated Saltwater Pool & Spa

8 BR | 6 BA | Sleeps 20 | Quick View

2

Distance to park: 11 miles to Disney Theme Parks & Water Parks

$324

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Guest can check availability and book direct at Enjoy your vacation in this lovely and spacious home with large screened in patio which flows into Heated Saltwater Pool & Spa. You will love your stay in this 8 bedroom x 6 bath home as we understand the value of a stress-free vacation and we've ...

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Property Type

Kissimmee House

"Very Nice Villa"
Reviewed December 29, 2020

This Villa was beautiful. The property managers were very helpful in clarifying any doubts that I had. They were quick and super nice. The pool was nice and heated. The spa was my favorite part.

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Holiday villa with pool and entertainment, 10 min to Disneyworld, Orlando, etc.

4 BR | 2.5 BA | Sleeps 9 | Quick View

5

Distance to park: 10 miles to Disneyworld

$120

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Our villa is modern style furnished, has everything you would expect in a holiday home, 4 bedrooms, 2 with king-size beds, 1 with single bed´s, 1 with triple bunk bed all with private TV. 2 bathrooms, 1 guest toilet, fully equipped kitchen, etc. with ceran stove, fridge, oven, microwave, coffee ...

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Property Type

Kissimmee House

"Great place"
Reviewed April 7, 2021

Lots of space out of the Hustle and bustle but close enough for a small drive to get to everything needed kids love the pool

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LAKESIDE POOL AND SPA AHHHH!

4 BR | 2 BA | Sleeps 6 | Quick View

1

$124

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full 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 location- well appointed"
Reviewed May 20, 2021

House was clean, master bedroom bed was comfortable. Water pressure was great! Plenty of tv's, pool & hottub were sure to order the heat. Check-in/ check- out was easy. Houses are very close together ...

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Westside Deluxe | New in Windsor at Westside

$339

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Westside Deluxe. You and your family will immediately love this wonderful vacation home from the moment you take a step inside. The great room has a large plush sofa and chairs for everyone to gather around and watch TV together. The decor is modern and accented with glass coffee and end tables. ...

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Property Type

Kissimmee House

"Wish we stayed in this home"
Reviewed April 27, 2021

and not the pit we Encountered in Emerald Island on siesta key to drive Right now I’m waiting to see if they return the deposit per the contract and the additional fee is a falsely charged us before ...

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Family Disney villa pool/spa 5 bds 15 Mins to Disney

5 BR | 4 BA | Sleeps 12 | Quick View

4

Distance to park: 6 miles to Disney Animal Kingdom

$188

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full 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

"Great Family Vacation"
Reviewed June 18, 2020

We had a wonderful stay at the Windsor Hill Resort in Kissimmee Florida. The home was located near all of the attractions and places to eat. The play house in the home gave us plenty of opportunities to ...

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Classic Condo | 3 Bed 3 Bath for 6 in Reunion Resort

$129

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

This condo is located in the neighborhood Villas South in Reunion Resort near the many world-class entertainments and theme parks Orlando is notorious for. It has everything you need for an Orlando vacation, including a fully equipped kitchen with stainless steel appliances and a beautiful granite countertop. ...

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Property Type

Kissimmee Condo

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Fairway Joy | 5 Bedroom Pool Home with Extended Pool Deck and Conservation Views

$285

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

This luxurious and comfortable home is located in Reunion Resort and has 3,203 square feet of living space, complete with a pool and balcony. The location of this property allows you to enjoy the resort’s many amenities and attractions that central Florida has to offer.This vacation home is ...

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Property Type

Kissimmee Villa

"WOW! YOUR HOUSE IS JUST WHAT I,VE BEEN LOOKING FOR WOW!"
Reviewed May 22, 2021

I LOVE THE WAY YOUR HOUSE LOOKS FROM THE OUTSIDE ITS BEAUTIFUL AND IT SEEMS VERY SPACEOUS ALSO AND I LOVE THE WAY YOUR HOUSE LOOKS VERY CLEAN AND VERY SPACEOUS ,I SURE HOPE MY FAMILY WILL ENJOY THEIR STAY.THANK ...

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Lake View, south facing pool, straight road to the Mouse House Covid sanitized

3 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to park: 20 miles to Disney

$85

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

From the hallway you enter the Dining Room & Lounge with patio doors out to the pool deck and breath taking lake view. Off to the right is our Master Bedroom with en-suite shower room, to the left our second & third Bedrooms, with the main bath in-between, giving a private split floor plan. To ...

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Property Type

Kissimmee Villa

"Family Vacation Villa"
Reviewed November 30, 2020

This villa was a good size and had the accommodations that was needed for my family. I would only suggest that they upgrade to bigger televisions in the villa. This villa was convenient to stores & restaurants.

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Palm Tree Villa Florida, 5 Star Review Rating with Pool Lift & Wheel in Shower

$175

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

"Seemed like home! How soon can we stay again?!!"
Reviewed March 22, 2021

The location is quiet neighborhood. The pool is great - large and inviting. The combination of the shaded patio area, the screened pool area, and the sun deck made it possible to be comfortable as the temperature ...

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Luxury 8bd/4.5ba, Pool with SPA, WiFi, Man-Guarded resort, 3 Miles To Disney

$159

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

One of the closest communities to Walt Disney World (less than 3 miles away), Emerald Island Resort is a quiet oasis in which to spend your vacation. Emerald Island is an exclusive man gated resort community less than a mile from the world famous US Highway 192 where you will find shops, restaurants, ...

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Property Type

Kissimmee Villa

"Perfect!"
Reviewed May 19, 2021

The home was beautiful and very close to Disney! The kids loved the pool and loved that the kids park was right across the street from the house. Ann and Gary were very easy to work with and responded back ...

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Goofy’s Getaway

5 BR | 5 BA | Sleeps 10 | Quick View

1

$244

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Goofy’s Getaway is a stunning five bedroom vacation home located at Windsor Hills Resort in sunny Central Florida. Here, you and your family can enjoy the very best in luxurious and stylish living combined with the convenience of being located just minutes from Walt Disney World Resort and many ...

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Property Type

Kissimmee Villa

"Outstanding rental"
Reviewed April 29, 2021

We rented this home as our first vacation home rental. I can definitely say we will return. Ray and Eileen have an amazing home that they offered to us for 10 days. Nothing was wrong and if it was I am ...

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Private Pool/6TVs/GasBBQ/Wifi, Man-guarded resort, 3 miles to Disney

$119

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

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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Property Type

Kissimmee Villa

"Awesome"
Reviewed September 17, 2020

I will definitely be going back..Location was great!! The house is beautiful and The property management was very efficient and their response was fast.

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Enchanted Crystal Castle at Windsor Hills Resort

5 BR | 5 BA | Sleeps 12 | Quick View

1

Distance to park: 5 miles to Disney World/Animal Kingdom

$222

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Our Disney vacation villa is furnished to the highest standard and offers your family the luxury of a Five star hotel combined with the relaxed atmosphere of a family vacation home. Soak up the Florida sun on our extended deck where you can relax in the pool and spa, or simply enjoy the shade of the lanai ...

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Property Type

Kissimmee Villa

"Wonderful home and resort"
Reviewed December 6, 2019

This home was super clean and there was so much room. The two kids rooms upstairs are amazing. My kids were in heaven. The game room was so much fun. Always nice to be able to come back after a day at ...

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Champions Estate

8 BR | 5 BA | Sleeps 16 | Quick View

$371

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Located in one of the most sought-after resorts in the Orlando area, welcome to Champions Estate. The newly built 8 bedroom, 5 bath pool home is the perfect destination for your family getaway. The home was designed to fit every need that you could have when visiting the area. This villa accommodates ...

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Property Type

Kissimmee Villa

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Outstanding villa with pool on gated Resort near Disney.

$121

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Our home is what you needed: ☆ TWO Master Bedrooms ☆ No Carpet/PetSmoke free ☆ All Lines/Towels Provided ☆ 24hrs Gated Community ☆ Private Heated* Pool ☆ Cable TV ☆ Free UNLIMITED High Speed Wireless Internet ☆ One Story ☆ Easy Self Checkin ☆ Smart NEST Thermostat ☆ Complete ...

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Property Type

Kissimmee Villa

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Toy Story Tower

6 BR | 4 BA | Sleeps 14 | Quick View

Distance to park: 5 miles to Disney World

$244

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Toy Story Tower is an imposing, six bedroom vacation home located within the prestigious gated community of Windsor Hills Resort. Here, you can enjoy the very best in luxurious accommodation all while being located just minutes from Walt Disney World Resort as well as many other great attractions. As ...

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Property Type

Kissimmee House

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LUXURY 6 BED 6 BATH ENCORE RESORT VILLA

$281

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

This 6 bedroom 6 bath home is located at the Encore Resort, less than a 10 minute drive to Walt Disney World and their 4 incredible theme parks! Conveniently located for you and your loved ones to experience and enjoy, Walt Disney World's proximity from this vacation home is an added bonus while staying ...

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Property Type

Kissimmee Villa

"This House Is Great"
Reviewed October 12, 2020

We loved this house! Everything was clean, the decor is beautiful, the owner was very responsive to any concerns. Would definitely look to rent it again.

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Exquisite Villa with Private Pool/Spa. Gated Resort near Disney

$175

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Vacation in style with this luxurious family-friendly villa with your very own south facing pool, spa and private conservation view. The villa is located on the 5 Star safe gated Bella Vida Resort in the heart of Kissimmee, close to shops, restaurants and bars, and is only 15 minutes from Disney. Offering ...

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Property Type

Kissimmee Villa

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Gated Resort, Spacious Town-home with pool and fancy club Paradise Palms Resort

$99

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Welcome to this beautiful vacation townhouse located in most desired Paradise Palms Gated Resort community, built in 2012. It is internationally known for its close to Walt Disney World (5 miles) and its paradise fancy clubhouse. It is also close to plenty of restaurants, shopping, and other recreational ...

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Property Type

Kissimmee Townhome

"Beautiful home"
Reviewed September 13, 2019

My family & I stayed in this amazing house & the service was good. We had no issues and everything was set up nicely to make payments convenient & easy. The hood vent stopped working & they came out to ...

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Any Closer to Disney and You'll Need a Park Pass! Southfacing Pool

$175

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

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 & shuttle service, so you are never "on your own" unless you want to be! Tennis and ...

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Property Type

Kissimmee Villa

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Resort living while visiting the theme parks and next door to Margaritaville

$161

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full 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

"Last min vaca"
Reviewed May 30, 2021

We booked this house very last min everything went smooth the house was very clean had everything we needed the area does have quiet time which we found out after being in pool laughing and listening to ...

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Enchanted Emerald Oasis (At the gates of Disney World)!

7 BR | 4.5 BA | Sleeps 16 | Quick View

1

Distance to park: 3 miles to Disney World Resort

$284

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Welcome to the Enchanted Emerald Oasis! The perfect vacation rental home for you, your family and friends! Located in the upscale Emerald Island Resort, just outside of the gates of Disney World theme parks, minutes to Universal Studios Orlando, Sea World and so much more in the Orlando area! Also, ...

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Property Type

Kissimmee Villa

"Can’t wait to go back!"
Reviewed January 18, 2020

Awesome property that was simply perfect for our extended family trip to Disney. Over half of our group flew in from Ireland and the remainder of us are Irish living here in the states. Comfortable, clean, ...

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Spacious Vacation Home with Pool & Spa Near Disney

5 BR | 5 BA | Sleeps 11 | Quick View

1

Distance to park: 5 miles to Disney World

$378

avg/night

View Details

Key Amenities

  • Air Conditioning

About this property

This beautifully decorated and spacious single family home sleeps 11 with 5 bedrooms, a well appointed kitchen, private heated pool and spa.Enjoy the convenience of a fitness center, tennis courts, sand volleyball, basketball, game room, movie theater, huge pool, hot tub and tiki bar for hours of ...

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Property Type

Kissimmee Apartment

"Amazing Vacation Home"
Reviewed June 19, 2021

I can’t say enough about this home. It’s modern and updated. My teens absolutely loved the game room and my husband and I enjoyed the spaciousness of it all which gave us the privacy we needed.I ...

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Casa Bonita -- near Disney!

4 BR | 3 BA | Sleeps 8 | Quick View

29

Distance to park: 4 miles to Walt Disney World

$132

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Florida License DWE5916118 (A five day minimum stay is required to reserve this property)'Casa Bonita' which means 'Beautiful Home' is a beautifully furnished four bedroom, three bathroom home with a 26 ft x 14 ft swimming pool and covered lanai and is just a 3.5 mile drive to Walt Disney ...

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Property Type

Kissimmee House

"Great home"
Reviewed May 13, 2021

We stayed a week and loved it! Bob was a great host he called and checked in with is through out our stay ! Even during a pandemic year he made my family and I feel safe and comfortable! Will be returning ...

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Lakeside pool villa, kissimmee 3 miles disney

$194

avg/night

View Details

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 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 parks again for ...

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Property Type

Kissimmee Villa

"Lovely Villa, Great Location"
Reviewed June 14, 2019

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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Luxury Windsor Hills 3/2 Condo

3 BR | 2 BA | Sleeps 6 | Quick View

5

Distance to park: 2 miles to Disney

$106

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Windsor Hills is one of the greatest gated community located within the heart of Orlando’s premier tourist attractions. Windsor Hills boasts the closest proximity to Central Florida's theme parks. Windsor Hills has all the amenities of a Five Star Hotel or Resort.Our 3 bed/2 bath (1 king, 1 ...

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Property Type

Kissimmee Apartment

"Excellent resort facilities"
Reviewed March 24, 2020

Resort was excellent with all the Disney attractions. Plus all the restaurants nearby and the Walmart store just one half mile away. The pool area was very large and accommodated all the guests. Very well ...

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CLOSE TO DISNEY BUT NOT EXPENSIVE

$76

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Nice 3/2 condo. Granite counters, new cupboards, tile floors except for bedrooms. patio with table & chairs. Pool, hot tub, workout area, playground, grills, Close to the Attractions, and less than 10 minutes from 24 hour Walmart, fast food, fine dining, shopping. You can be at Disney Springs or ...

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Property Type

Kissimmee Condo

"EXCELLENT PROPERTY"
Reviewed January 4, 2020

CONDO IS VERY ROOMY AND VERY COMFORTABLE. UP-TO-DATE APPLIANCES AND LARGE SCREEN TV. VERY REASONABLE PRICES,WILL DEFINITELY RECOMMEND TO FRIENDS AND FAMILY

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Affordable Disney Villa - just 5 minutes to Disney

$132

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Our property maintains a gap of 3 days between each booking for health safety measures during this crisis and we also follow stated mandated cleaning procedures and guidelines after each guest checks out.This Disney Villa is a fully furnished home and is one of the best kept turnkey properties you ...

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Property Type

Kissimmee Villa

"Perfection vacation getaway"
Reviewed March 24, 2020

I rented this house for my 1 week vacation to Disney and Universal Studios and was truly impressed by all it offered. To start the location was perfect, as it was close to both theme parks (being minutes ...

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Westside Charm | 7 Bed Private Pool Home

$238

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Windsor at Westside is a gated vacation rental community close to Disney featuring an 8,000 sq.ft. clubhouse with the Tu Casa Bar & lounge, market & deli, video arcade, sundries shop & fitness center. Other fantastic amenities such as a playground, volleyball court & multi-purpose sports ...

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Property Type

Kissimmee House

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Sunny Luxury Legends Villa only 6 miles to Disney

$366

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This beautiful home has everything you need to create your dream stay in Reunion Resort - 6 Miles to Disney!Legends Villa includes a large pool with a spillover spa, luxurious decor that creates an elegant ambiance, over 5,000 sq.ft of spacious living areas & large inviting bedrooms, a cinema, ...

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Property Type

Kissimmee Villa

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Family Fun | Games Room & No Rear Neighbors

$294

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This expansive 3,909sq. ft home can also sleep 18 comfortably, set within a luxury resort. With 9 bedrooms and 5 bathrooms, this is a perfect home for a large family or group vacation. Your family will love relaxing in the Florida sun by the pool!The living area has an open floor plan, you will find ...

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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

Find your ideal Kissimmee vacation rental today
 
Aiming to take an incredible vacation to this year? Ditch the traditional hotel and opt for one of our Kissimmee vacation rentals instead. We have plenty of condos available in Kissimmee on FloridaRentals.com. Whether you’re looking for luxury Kissimmee villa rentals or kid-friendly mansions with an arcade, you can find it on our site.
 
Kissimmee, Florida travel advice
 
A short drive south of Orlando finds you in sunny, friendly Kissimmee. Here you’ll be near all the theme parks, but you’ll be away from the bustling crowds. Rentals will cost less than a stay in Orlando, so you’ll have extra cash to spend on park tickets and meals. This area also offers activities for those who love outdoor exploration, with exotic plants and animals in the local nature preserves.
 
Top attractions
 
The Florida theme parks are the major draw for visitors to the area. Walt Disney World, Universal Studios, SeaWorld, and the Wizarding World of Harry Potter draw millions of families every year. 
 
The fun doesn’t stop as kids and adults alike can mingle with their favorite characters, feel the chills and thrills of amusement rides, and cool off in the area’s water parks. If the theme parks don’t meet your need for speed, spend an afternoon at Fun Spot America. With two unique go-kart tracks and 18 rides you’ll be dizzy with delight. 
 
The Museum of Military History offers exhibits that highlight the bravery and humanity of the men and women who have served in the armed forces. Genuine artifacts, military relics, photographs and memorable accounts by former soldiers are on display here.
 
For some Florida history, stop in to Osceola County Pioneer Village and Museum. This museum features many exhibits depicting life in the 19th century. The Pioneer Village has a general store, blacksmith shop, one room schoolhouse, and nature preserve.
 
Family-friendly activities
 
Strap on your hiking boots and take off on the Shingle Creek Regional Trail. The trail offers a beautiful, natural environment for cyclists, pedestrians, canoeists/kayakers, bird watchers and other nature lovers.  A wide variety of habitats on the trail include Lake Tohopekaliga waterfront and islands, a pristine cypress swamp, an orange grove and wild grasslands.
 
For a more cuddly experience, Green Meadows Petting Farm has over 50 acres of animals to greet and family rides. If you’re visiting during spring training, stop in to see the Houston Astros practice as Osceola County Stadium. 
 
Of course, the options for fun aren’t limited to the parks. For golfers, Central Florida is a veritable paradise. With dozens of award-winning courses within a few square miles, you should definitely pack your clubs when visiting. If your family prefers mini-golf you have plenty of options, too. 
 
Kissimmee Lakefront Park features a playground and splash park for kids, BBQ grills for a cookout, and fishing piers. For more along these lines, nearby St. Cloud Lakefront Park and Beach offers a family picnic area and volleyball court. Located along the breathtaking Lake Tohopekaliga, these parks are great options to spend a relaxing afternoon.
 
Spend your evenings in Old Town Kissimmee, where every Saturday night there is a classic car cruise through the city streets, accompanied by a live band. In Old Town you’ll also find everything from high end retailers to souvenir shops. There is live music playing almost every night, and restaurants offering pizza, Tex-Mex, or anything in between. 
 
Annual events
 
Osceola Heritage Park has a variety of world-class shows and sporting events. You'll find the Silver Spurs Rodeo here, too. It's a real crowd pleaser, offering a taste of the Wild West and reflective of the area's ranching heritage. You can watch bull riding, bronco bucking, barrel racing, steer wrestling, team roping, and even those funny rodeo clowns.
 
Kissimmee vacation home rentals on FloridaRentals.com
 
Booking one of our vacation homes in Kissimmee on FloridaRentals.com can save you 15% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Book today!