Kissimmee Vacation Rentals

(325 rentals)
Summer Savings!! 8 bedroom Luxury Pool Villa!!

$409

avg/night

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Key Amenities

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

About this property

Come and enjoy our home away from home that offers peace & relaxation while only being 6 miles from all the action at Disney. Our home is furnished with the most luxurious items for your comfort & enjoyment and we have tried to think of every possible thing you would need to have the most relaxing ...

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Property Type

Kissimmee Villa

"Beautiful Villa"
Reviewed January 19, 2019

Thank you for letting us stay at your beautiful villa. My four children and their families and myself enjoyed everything from the great stocked kitchen to the comfy mattresses. Plenty of room for all of ...

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Solara Luxury | Amazing Pirate Ship & Surf Van Custom Bunk Beds,

$380

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

If You're Looking For One Of The Best 5 Bedroom Vacation Homes In Solara Resort, Or Central Florida, Look No Further!Located just minutes from Orlando’s theme parks, shopping, dining and other area attractions, this luxury villa is located in Solara Resort. Solara Resort is jusStay close to ...

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Property Type

Kissimmee House

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Amazing pool home, Hardwood Floors, Game room, SAFETY POOL FENCE. Has It All!!!

$125

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

POOL SAFETY FENCE!!!! - Florida law requires that doors leading out to the pool have an alarm. THAT IS NOT ENOUGH!. If you are traveling with children please make sure the house you are renting has a pool safety fence.This Beautiful home is well situated, close to all major attractions and amenities, ...

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Property Type

Kissimmee House

"Great Villa for my needs"
Reviewed November 16, 2019

I volunteer each year at GKTW in Kissimmee so Mark's villa for perfect for my needs. Used 3 of the 4 bedrooms with guests so we all had bathrooms as well - important for our early starts! A few things cropped ...

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

$201

avg/night

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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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Hidden Oasis | 4 Bedroom 3 Bath Private Pool Villa

$317

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Are you looking for something exceptional for your vacation home in Orlando? Look no further - this beautiful home will be your Hidden Oasis providing you a chance to leave the 'everyday' behind. This home offers 3,600 square feet of tastefully appointed and light filled interiors, a secluded pool long ...

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Property Type

Kissimmee House

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Lakeview Retreat, luxury villa, large pool, game room and cookout area

6 BR | 5 BA | Sleeps 14 | Quick View

Distance to park: 4 miles to Disney Animal kingdom

$264

avg/night

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Key Amenities

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

About this property

Luxury 6 bed 5 bath Villa with large south west facing pool, just 4 miles from Disney! Our wonderful villa can sleep up to 14 guests. Situated in the prestigious gated upscale community of Formossa Gardens, where properties enjoy spacious garden plots giving privacy, your wonderful pool home has a ...

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Property Type

Kissimmee House

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The Lake House at Sunset Lakes - Upscale Lakeside Villa Near Disney

4 BR | 2 BA | Sleeps 8 | Quick View

Distance to park: 7 miles to Walt Disney World

$193

avg/night

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Key Amenities

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

About this property

WE NOW HAVE AVAILABILITY FOR FAMILIES OVER CHRISTMAS 2020 (18-27 DECEMBER, MINIMUM 7 DAY STAY). FAMILY GROUPS ONLY (2 ADULTS 2 CHILDREN), DON'T HESITATE. THIS WONT LAST LONG!!Welcome to our Florida villa, the Lake House at Sunset Lakes. The Lake House at Sunset Lakes is an upscale rental villa in ...

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Property Type

Kissimmee Villa

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3BR 1st Floor Condo Near Disney, Steps from Pool, Loaded with Amenities

$82

avg/night

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Key Amenities

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

About this property

Built in 2002, Windsor Palms Resort is a gated community approximately five miles from Disney. This luxury complex has a 7500 square foot clubhouse, basket ball courts, volleyball courts, children's play area, olympic-size swimming pool, toddler pool, hot tub, picnic and barbecue area, outdoor bar, convenience ...

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Property Type

Kissimmee Condo

"Disney trip"
Reviewed January 5, 2020

Our stay was wonderful! Clean, close to Disney, beautiful pool! Loved it!! Check-in was easy and quick. Everyone was very polite and helpful.

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Champions Escape | 2 Kids Bedrooms and Games Room with Pool Table, Screened Pool

$281

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

airs you will find the master suite featuring a king bed with large en-suite bathroom with walk in showers and large counter space. There is a second bedroom downstairs with king bed and attached shared bathroom.Upstairs you will find the additional 6 bedrooms, 2 of which are kids themed rooms, a ...

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Property Type

Kissimmee House

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♥Disney Area♥☆24hrs gated☆CornerTownHouse PrvtPool

4 BR | 3 BA | Sleeps 8 | Quick View

1

Distance to park: 18 miles to Magic Kingdom

$131

avg/night

View Details

Key Amenities

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

About this property

☆ Bella Vida Resort ☆ Walmart Walk-in distance ☆ All Lines/Towels Provided ☆ 24hrs Gated Community ☆ Private Pool ☆ Cable TV ☆ Free UNLIMITED Wireless Internet ☆ Easy Self Checkin-Personalized door coded ☆ Smart NEST Thermostat ☆ Complete Kitchen ☆ In Unit Washer&Dryer ☆ ...

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Property Type

Kissimmee Townhome

"Excellent location, amazing pool!"
Reviewed February 24, 2019

Everything was perfect!!! Righlights: reception, furniture, cleaning, accommodations, location, pool.. I´m definitively coming back!

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Golden Villa | 6 Bed 4 Bath Pool Home with Golf Course Views in Reunion Resort

$272

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Enjoy comfort during your next vacation in this gorgeous 6 bedroom 4.5 bath, the perfect home for you and your family to stay in. Located in the Reunion Resort allows for you to easily access world-famous theme parks and attractions.As soon as you pull into the driveway of your new vacation home you’ll ...

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Property Type

Kissimmee Villa

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

$401

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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LUXURY 5 Bed 3 Bath - South facing pool vacation rental Villa near Disneyworld

$135

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Planning to visit Disney during 2020/21How would you like to rent our 5 bed 3 bath rental villa.It has its own south facing screened private swimming pool that is located on the exclusive Lake Berkley gated Resort in Kissimmee, Orlando, Florida.We are just minutes from the theme parks like ...

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Property Type

Kissimmee Villa

"Great weather and the pool was wonderful!"
Reviewed March 19, 2020

Gated community was wonderful and secure. Walking in neighbourhood around the lake was very peaceful. House size was nice, updated furniture was one suggestion in living room and beds in general. ...

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Palmilla Oasis | Fantastic 8 Bedroom Pool Villa with Two Kids Theme Rooms

$805

avg/night

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Key Amenities

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

About this property

This beautiful 8 bedroom 8 bath private estate home is simply amazing! Situated within the luxurious Legends Corner neighborhood of the 5 star Reunion Resort on the greens of the Jack Nicklaus Tradition golf course. Sure to delight and please everyone in your group as no expense was spared when this home ...

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Property Type

Kissimmee House

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Golden Sunrise | Great Low Price, Air hockey, PS3 and Breathtaking Views!

$251

avg/night

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Key Amenities

  • Pet Friendly
  • Private Pool

About this property

Situated in the Legends Corner community, this beautiful 5 bedroom 5.5 bath is the perfect home for your Orlando getaway. Located within the world-renowned Reunion Resort just minutes from the heart of the theme parks and local area attractions.Pull into the driveway of your new home away from home, ...

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Property Type

Kissimmee House

"Great house super pool"
Reviewed July 5, 2019

We loved staying in this property the location was great for Disney took only 10 mins to Animal Kingdom and 15 mins to the other Disney parks depending on Traffic. Easy to get to Universal and Sea World ...

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New 6 Bedrooms, Special lighting ,4 miles - Disneys, CHECK THIS OUT!!

$259

avg/night

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Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Private Pool

About this property

THANK YOU FOR LOOKING MY VILLA * Please note: If you do an Instant booking online.. there rate not include Pool and Spa to be heated ... additional cost is $25/ day.This is the second villa of mind, please visit my first villa for Reference of Reviewed + Service and Product I provided.This ...

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Property Type

Kissimmee Villa

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Tranquil Sunshine | Walk to the Solara Resort Clubhouse!

$280

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Located just minutes from Orlando’s theme parks, shopping, dining, and other area attractions, this luxury villa is located in Solara Resort. Solara Resort isEnjoy unlimited access to all the 8 acre resort has plenty to offer with a state of the art 13,000 sq.ft clubhouse, resort pool, FlowRider® ...

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Property Type

Kissimmee House

"Amazing!!!"
Reviewed March 17, 2020

This was our first family trip and we could not be happier with this house!!! We loved the resort too!

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Sandy Ridge Paradise - Top Floor Luxury Condo with Updated Furniture Package!

$127

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Located in the upscale Reunion Resort community, this wonderful top floor (4th) 3 bedroom 3 bathroom condo is in The Villas North at Sandy Ridge Drive and overlooking the Independence golf course by Tom Watson.This truly is a luxurious three-bedroom condominium. The spacious living room and dining ...

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Property Type

Kissimmee Condo

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Popular Luxury Resort Home, Private Pool, 10 Minutes From Disney!☀️

$192

avg/night

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Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pool
  • Private Pool

About this property

6 Bed-4.5 Bath, 2 Masters, Disney Themed Kid's Rooms, Game Room, Private PoolWelcome to Fab Five Villa! We are offering wholesale daily rates. These are our lowest rates ever! These sale rates apply to any open dates on our calendar. Book now. We are pleased to announce that resort amenities are open. ...

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Property Type

Kissimmee House

"Beautiful home great location"
Reviewed March 18, 2020

We were a family of 12 visiting from Michigan. We did not know what to expect as this was my first ever Airbnb booking. The reviews were hit and miss. This home did NOT disappoint. It was beautiful, clean, ...

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Heritage Charm - 3 Bedroom Luxury Condo | Top Floor with Amazing Views

$101

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

This spectacular third floor 3 bed, 2 bath 1,352 sq ft. condo in Heritage Crossing has amazing views over 5 different holes on the Reunion Palmer golf course. Enjoy beautiful sunsets from your own private balcony with the magnificent heritage crossing pool and hot tub just a few steps away. The living ...

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Property Type

Kissimmee Condo

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Paradise Breeze - Brand New 5 Bed Pool Villa

$222

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

Paradise Breeze - Brand New 5 Bed VillaThis large 3,045 sq.ft pool home is located within the Patriots Landing neighborhood of the exclusive Reunion Resort.Patriot's Landing offers Key West-style luxury homes with pastel color schemes. This very distinctive neighborhood is surrounded on three ...

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Property Type

Kissimmee House

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Holiday Rest

3 BR | 2 BA | Sleeps 8 | Quick View

1

$100

avg/night

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Key Amenities

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

About this property

Thinking about taking a Florida Vacation? Why not stay at our wonderful 1950 Sq ft property with three spacious bedrooms two bathrooms. Feature a fantastic floor plan with ceramic Tiles throughout. Master bedroom has a King sized bed, TV, Jacuzzi, stand up shower, his /her sink and a walk in closet. ...

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Property Type

Kissimmee House

"Our vacation house"
Reviewed February 19, 2018

Found the property very nice, close to all our vacation needs, owner and property manager attentive and friendly, on a personal note the pool did not get warm enough for my taste, good experience

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Special price for February, dont miss it !

$140

avg/night

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Key Amenities

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

About this property

MAGIC HOUSE, is a beautifully furnished 4 bedrooms, 3 bathrooms home with a 26ft x 14ft swimming pool and Spa,. covered lanai. It is only a 3 mile drive to Walt Disney World Resort. It's in easy reach of all other major attractions.MAGIC HOUSE is a luxury villa located in the quiet friendly neighborhood ...

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Property Type

Kissimmee House

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Homestead Vista - Arcade Room, Amazing Custom Bunk Beds & Golf Course Views

$461

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

This luxury custom home is located right on the stunning Reunion Resort golf course and just 6 miles to the gates of Disney.Enjoy one of the best outlooks in Reunion from the southeast facing pool deck, unobstructed views of holes #7 and #8 of the beautiful Tom Watson golf course. The private pool ...

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Property Type

Kissimmee House

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Solara Sanctuary - 7 Bedroom Home in Solara Resort

$284

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Located just minutes from Orlando’s theme parks, shopping, dining, and other area attractions, this luxury villa is located in Solara Resort. Solara Resort is just a 5 mEnjoy unlimited access to all the 8-acre resort has plenty to offer with a state of the art 13,000 sq.ft clubhouse, resort pool, ...

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Property Type

Kissimmee House

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Livin' the Life❤️NEW Clean 9BR/5 King/FREE Resort/WDW/ESPN

9 BR | 6 BA | Sleeps 24 | Quick View

2

Distance to park: 8 miles to Disney

$326

avg/night

View Details

Key Amenities

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

About this property

This is truly one of the best 9 BR homes close to Disney/ESPN!It's just been completely repainted and deep cleaned top to bottom. Our cleaners are top notch - always 5 STAR REVIEW - kitchen, baths and linens are bleached every clean.* We have a second 9 BR 2 doors down! * Private Heated Pool ...

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Property Type

Kissimmee House

"Nice place to stay"
Reviewed September 16, 2020

Very clean place, close to restaurants and stores Short drive to attractions. Close to Orlando international airport.

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SWEET MEMORIES, 7 bd & 7 ba, south facing pool with lake view,sleeps 16

$216

avg/night

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Key Amenities

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

About this property

This is a beautiful 7 bedrooms / 5 full and 2 half bathrooms. The home is perfectly located in the quiet gated community of Cumbrian Lakes. The home has a fabulous view of one of the lakes in the community which is south facing. This house has just been upgraded with all new furniture and has plenty ...

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Property Type

Kissimmee Villa

"Fabulous house"
Reviewed March 24, 2018

Great home, great comfort, great owner. Everything ever expected and more. Clean home, quiet neighborhood, close to shopping and Disney. The pool area was excellent with heater on. it was truly a very enjoyable ...

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Orlando Condo at Legacy Dunes Suitable for a family staycation and remote work

2 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to park: 5 miles to Disney World

$85

avg/night

View Details

Key Amenities

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

About this property

Our lakeside condo is on the ground floor and has a screened lanai seating area for your enjoyment. The living room is quite spacious and has a flat screen television, a DVD player, a queen sleeper sofa bed, and has seating for up to six guests. The dining area also has seating for six. Save money by ...

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Property Type

Kissimmee Condo

"Great condo!"
Reviewed April 2, 2020

This is a beautiful condo. Well furnished and equipped. New appliances and a great location, close to everything! Gated community for security and owner very pleasant to deal with.

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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

$266

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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9025 PP at Calabria at Westside. Calabria 5BDR/4.5BATH pool home close to Disney

$182

avg/night

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Key Amenities

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

About this property

This luxury home sits in the prestigious Calabria community. During your stay you will enjoy this well appointed home that has been designed and decorated to provide you and your family an abundance of luxury amenities and leaves you well equipped to vacation with all the usual items you would expect ...

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Property Type

Kissimmee Villa

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Windsor Palms Resort-2334CISPDITHP

3 BR | 3 BA | Sleeps 6 | Quick View

Owner special: SAVE 20% OFF NOW THROUGH NOV 19TH! Rates have been updated to reflect the discount

$98

avg/night

View Details

Key Amenities

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

About this property

Windsor Palms Resort- Kissimmee, Florida is an upscale gated community located just 2 miles from Walt Disney World. This luxury resort sits nestled just off Hwy 192 in Kissimmee, Florida and is one of the most desired resorts in the Orlando area. During your stay, you will enjoy this well-appointed home ...

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Property Type

Kissimmee Townhome

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Stylishly Florida Design Southfacing Villa Near Disney

4 BR | 3 BA | Sleeps 8 | Quick View

7

Distance to park: 10 miles to Disney Theme Parks

$103

avg/night

View Details

Key Amenities

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

About this property

A brilliant family home for a Florida holidayQuiet and peaceful, Stylishly furnished with granite countertops in kitchen and bathrooms, the open-plan accommodation offers both formal and informal dining inside, as well as al fresco dining in the lanai by the sparkling, South-facing private pool. The ...

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Property Type

Kissimmee Villa

"Nice home"
Reviewed April 8, 2020

Stayed 90 days had a few hiccups at the beginning, no mailbox, shower broken, microwave needed replaced but over the first few weeks got all the things fixed. The carpets are not in great shape and at some ...

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Executive Beautifully furnished South facing villa

5 BR | 3.5 BA | Sleeps 10 | Quick View

4

Distance to park: 7 miles to Disney

$145

avg/night

View Details

Key Amenities

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

About this property

An article on our luxurious villa was featured in a holiday magazine. Luxury and location are the key words for both the villa and Cumbrian Lakes. Surrounded by fountains and lakes the tranquility it presents is a welcome haven from the hustle and bustle of the theme parks. Ample luxury furniture is ...

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Property Type

Kissimmee Villa

"Truly, everything you'd want a home to be."
Reviewed April 3, 2020

What a wonderful way to start our vacation! Such a beautiful, clean villa with plenty of room for everyone. There was everything that you could possibly need here.The pool and lanai were absolutely wonderful ...

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The Floridian Oasis - Relaxing 5 bedroom, 5 bath pool home

5 BR | 5 BA | Sleeps 12 | Quick View

Distance to park: 2 miles to Walt Disney World

$202

avg/night

View Details

Key Amenities

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

About this property

Terrific 5-bedroom/5-bathroom rental home located in Windsor Hills Resort. This beautiful villa includes upstairs and downstairs King Bedroom suites. It also has a Queen Bedroom, Twin Bedroom and sleeper sofa on the first floor. And there is an another Twin Bedroom on second floor making this home ideal ...

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Property Type

Kissimmee House

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Disney Villa - Large 5bdr w/Private Pool/Spa/Game with A/C

$182

avg/night

View Details

Key Amenities

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

About this property

Dreamy Disney Destination at Lake Berkley Resort with Private Pool/ Spa, Game Room w/ AC and Xbox - minutes away from Orlando's main attractions!Welcome to the Longhi Story Orlando! Our beautiful vacation home in Kissimmee, Orlando, FL is located in the prestigious gated community Lake Berkley Resort ...

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Property Type

Kissimmee Villa

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Entire Home with Private Pool Minutes to Disney

4 BR | 3 BA | Sleeps 8 | Quick View

Distance to park: 6 miles to Disney

$199

avg/night

View Details

Key Amenities

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

About this property

Welcome to Peaceful Emerald Island Gated Resort, nestled upon a tropical Oasis, minutes to Disney Parks and tons of nearby amenities. Fantastic open concept layout with formal seating and dining areas. Enjoy your own private pool or take advantage of the community pools and recreation. Large kitchen with ...

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Property Type

Kissimmee House

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Storey Lake-4953CIWAILTHP

4 BR | 3 BA | Sleeps 8 | Quick View

1
Owner special: SAVE 20% OFF NOW THROUGH NOV 19TH! Rates have been updated to reflect the discount

$124

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full 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

"Great town home with wonderful amenities"
Reviewed July 14, 2020

The location was a short trip from the airport. Large town home to accommodate space for all. Loved having our own pool and we all loved the community pool area. We will be back.

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CLOSE TO DISNEY *LUXURY LAKESIDE VILLA * PET FRIENDLY

4 BR | 2 BA | Sleeps 10 | Quick View

Distance to park: 12 miles to Disney World

$127

avg/night

View Details

Key Amenities

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

About this property

To ensure your comfort level we want you to know we have always and continue to use a professional cleaning company to clean and disinfect the Villa after every guest.04/20 New King bed/mattress in master bedroom 03/20 New Weber gas BBQ grill 08/19- New dinette table and chairsBeautiful lakeside ...

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Property Type

Kissimmee House

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"Livin' Large"♦️9 BR Free Windsor Resort - 8 mi Disney/ESPN-Great Family/Corp

$328

avg/night

View Details

Key Amenities

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

About this property

Come to Livin' Large at Windsor Westside with 100% Free Resort amenities!* Private Heated Pool & Spa * FREE Arcade! Yes, play all you want for Free! * Poolside Tiki Bar & Grill * FREE Resort w/ Heated Lazy River * Kids water playground & slides * FREE 400MB Wifi * Roku: 11 tvs ...

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Property Type

Kissimmee House

"Exceeded our expectations"
Reviewed January 17, 2020

What a beautiful home!!! Our family spent the Thanksgiving holiday at this home. Laura is a great host. Very responsive and accommodating our needs and last minute request. Everything you need is there! ...

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OUR LUXURY HOME IN THE SUN WITH LARGE SOUTH FACING 34ft x 18ft POOL

4 BR | 3 BA | Sleeps 8 | Quick View

10

Distance to park: 12 miles to Disney

$119

avg/night

View Details

Key Amenities

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

About this property

PLEASE NOTE Due to the Covid-19 pandemicThe Governor of Florida is currently not allowing people from numerous US States to rent a vacation rental property in Osceola County or Orange County unless guests stay a minimum 14 nights or more and follow CDC self-quarantine guidelines.Since Covid-19 ...

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Property Type

Kissimmee Villa

"Amazing Holiday Villa"
Reviewed December 10, 2019

I cannot put in to words how amazing the communication was with Sue in the preparation of my families trip to Florida. She was prompt at answering all our questions and was always there to check in with ...

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Bonjour

7 BR | 5.5 BA | Sleeps 15 | Quick View

3

$302

avg/night

View Details

Key Amenities

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

About this property

Located in the guarded resort community of Emerald Island, our home is only 3 miles from Disney and offers over 3200 sq. feet of fully dual air conditioned flexible living & play space. It is so close to Disney that you can come back for a nap at noon time every day and go back to the Disney parks ...

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Property Type

Kissimmee Villa

"Perfect Golf Get Away"
Reviewed March 17, 2020

This home was the perfect spot for an eight person golf trip. Plenty of space and close to dining, shopping, and golf courses. We had an issue initially with the spa which they handed right away. Might ...

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Berni's Home from Home on the Gated Development of Emerald Island Resort

7 BR | 4.5 BA | Sleeps 14 | Quick View

1

Distance to park: 4 miles to Animal Kingdom

$251

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

"Fantastic. Everything we needed and more !"
Reviewed February 5, 2019

We stayed at Berni's home from home in July 2018 and had a fantastic time. There were 7 of us (five adults and 2 teenagers). There was loads of room for us all in the villa and some of the bedrooms we didn't ...

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Camellia Villa. Gated Community. Less than 2 miles to Disney.

$340

avg/night

View Details

Key Amenities

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

About this property

Camellia Villa will appeal to the most discerning guest who requires the most luxurious villa available. It is most impressive and is situated on one-third acre of magnificent landscaped gardens, with 21 palm trees and 12 assorted citrus fruit trees - orange, lemon, lime, grapefruit. The enormous 40ft ...

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Property Type

Kissimmee Villa

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NEW! 4/3 Townhome w/Private Pool at Storey Lake Resort

$175

avg/night

View Details

Key Amenities

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

About this property

Private 2 story home with 4 Bedroom/3 Bathroom with heated pool has all of the spacious and convenient accommodations for your entire family vacation. Storey Lake is very close to all of the major attractions of Disney World, Epcot, Animal Kingdom, Disney Water Parks, Universal Studios and Sea-World.The ...

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Property Type

Kissimmee Townhome

"Lovely, clean home"
Reviewed March 29, 2020

We stayed here for 7 weeks and really enjoyed it. We found the home to be a bit dark throughout the day because it’s a townhouse without windows on side walls, but there’s lots of lighting available ...

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Lakeside Villa -10 min to Disney-Lakefront -South Facing Pool-Gameroom-Free WiFi

3 BR | 2 BA | Sleeps 8 | Quick View

9
LAST MINUTE DEAL 9/15 - 10/26: *** $15 OFF Per night *** inquiry about extended stay specials ~ Stay - Work - Study - Play ***

$92

avg/night

View Details

Key Amenities

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

About this property

The Lakeside Villa has 3 bedrooms, 2 baths and a south facing pool with lots of privacy that backs to a beautiful lake. The pool get's plenty of sun but also has a shaded area for dining & relaxing. The home features a game room with a Pool Table & Dart Board. Free High Speed Wireless Internet. ...

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Property Type

Kissimmee House

"Amazing House"
Reviewed July 7, 2020

This house was exactly as described. It was incredibly clean, very safe, and very close to the Orlando attractions. My kids would NOT get out of the pool. There was a super small noise issue that was ...

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DEAL
Tropical Oasis - Windsor at Westside

7 BR | 5.5 BA | Sleeps 18 | Quick View

Distance to park: 8 miles to Disney

$199

avg/night

View Details

Key Amenities

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

About this property

This remarkable seven bedroom pool and spa home located in the popular Windsor Westside Resort - ideally located for a memorable family or pool of friends. It is a beautifully designed Tropical Oasis getaway to the theme parks and attractions of Orlando, including Walt Disney World®,Universal Studios, ...

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Property Type

Kissimmee Villa

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Florida - Sunsations Condo Rental

3 BR | 2 BA | Sleeps 8 | Quick View

Distance to park: 5 miles to Disneyworld and Disney Springs

$94

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool
  • Rentals by Owner

About this property

Finally! You have arrived in the "Vacation Capital of the World" and you're going to love staying in our luxury, three bedroom, two bath, fully equipped vacation condo rental situated near DisneyWorld and all other theme park attractions. The property rental is located within the resort community ...

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Property Type

Kissimmee Condo

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Holiday Travel Home-South Facing Pool-On Water-Natural Conservation-Games Room

6 BR | 4 BA | Sleeps 16 | Quick View

LAST MINUTE DEAL 9/15 - 10/26: *** $15 OFF Per night *** inquiry about extended stay specials ~ Stay - Work - Study - Play ***

Distance to park: 4 miles to Walt Disney World

$138

avg/night

View Details

Key Amenities

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

About this property

The Holiday Travel Home is a beautiful villa on a natural pond with a south facing pool. This two story 6 bedroom 4 bath vacation retreat is perfect for larger familes or just people that want room to relax. With an emphasis on space and comfort, this air-conditioned home easily accommodates up to ...

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Property Type

Kissimmee House

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DEAL
Magicbay Villa,Best Deal 7 Br in Emerald, Beat lowest offer

7 BR | 4.5 BA | Sleeps 16 | Quick View

3

Distance to park: 3 miles to Disney

$160

avg/night

View Details

Key Amenities

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

About this property

Magicbay villa located in the exclusive Emerald Island Resort (EIR), only 2 miles from Disney parks. Best Value, we *beat* the lowest 7 bed villa price in EIR. Fully Loaded over 3000 sq feet, perfect for large family groups, sleeping up to 16 guests. 2 King-bed suites with private bath on each floor, ...

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Property Type

Kissimmee House

"Nice property"
Reviewed November 5, 2018

The house was very niceI rented 2 homes this trip and my son and his friends stayed at this villa they were very pleased!

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Luxury 5 bed villa with south-facing pool

5 BR | 4 BA | Sleeps 12 | Quick View

1

Distance to park: 3 miles to Disney World

$179

avg/night

View Details

Key Amenities

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

About this property

A luxurious 5 bedroom 4 bath villa with south-facing pool situated in luxury Emerald Island Resort Orlando. Located a short distance from the popular destinations such as Disney World, Sea World and Universal Studios and accommodates 10-12 guests.This tastefully-decorated 5 bedroom/4 bath vacation ...

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Property Type

Kissimmee Villa

"Tigger's Magic"
Reviewed January 6, 2019

It was a pleasure renting this house in Emerald Island Resort, Florida. It was exactly what posted on the website and surpassed our expectations once we got there. The house was very spacious, clean, ...

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Kissimmee Vacation Rentals

Kissimmee Weather

 | 

7222°  489°
JANUARY
7323°  499°
FEBRUARY
7725°  5312°
MARCH
8228°  5814°
APRIL
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MAY
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JUNE
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JULY
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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 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Book today!