Kissimmee Vacation Rentals

(287 rentals)
Westside Charm | 7 Bed Private Pool Home

$273

avg/night

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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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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

$233

avg/night

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Key Amenities

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

About this property

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 thought of the details to make your vacation a wonderful ...

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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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Modern 5BD 5BA Windsor at Westside Sleeps 14 Pool/Spa Games Room TV Loft

$218

avg/night

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Key Amenities

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

About this property

5 Bedrooms 5 Bathrooms SLEEPS UP TO 14 Family Room with large HD Cable TV Upstairs TV Loft/Den is a great kids hang out space All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 8 plus breakfast bar ...

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Property Type

Kissimmee House

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Amazing 7BD 5BA Windsor at Westside. Game Room. Cinema Room. Pool & Spa

$357

avg/night

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Key Amenities

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

About this property

7 Bedrooms 5 Bathrooms Family Room with large HD Cable TV Upstairs Loft with Cinema Screen All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 10 plus breakfast bar and outdoor dining Private screened ...

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Property Type

Kissimmee House

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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

$156

avg/night

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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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JEWEL OF DISNEY 6BR POOL HOME

6 BR | 3.5 BA | Sleeps 12 | Quick View

$292

avg/night

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Key Amenities

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

About this property

Step into sheer Luxury and experience gated resort style vacationing at its finest. at our Windsor Palms, 6 bedroom pool home, the special touches will leave every family member with a smile. This gorgeous home has two king bedrooms, two queen bedrooms and two rooms with 2 twin beds. With 4 bathrooms ...

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Property Type

Kissimmee House

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Luxury 5BD 4.5BA Solara Sleeps 12. Private Pool Spa Games Room Resort Facilities

$197

avg/night

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Key Amenities

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

About this property

5 Bedrooms 4.5 Bathrooms Family Room with large HD Cable TV Upstairs TV Loft/Den with HD Cable TV All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 8 plus breakfast bar and outdoor dining Private ...

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Property Type

Kissimmee House

"Beautiful home!!"
Reviewed December 24, 2019

This is an amazing home! We have no complaints at all. Everyone loved the pool and hot tub. The beds were comfortable and those of our group that exercise enjoyed the convenience of the gym facility. Very ...

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Beautiful 3BD 2BA Condo Storey Lake Resort

$138

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

3 Bedrooms 2 Bathrooms Family Room with large HD Cable TV All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room plus breakfast bar Patio with Outdoor Furniture Washer/DryerCentral Air Towels and Bed ...

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Property Type

Kissimmee Condo

"Beautiful villa"
Reviewed October 7, 2019

We enjoyed our stay in the beautiful storey lake resort, everything new, clean and spacious. We will be back.

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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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Goofy’s Getaway

5 BR | 5 BA | Sleeps 10 | Quick View

$247

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

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Westside Extravaganza

8 BR | 6 BA | Sleeps 16 | Quick View

$353

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

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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10 Bed 6 Bath Windsor at Westside. Private Pool Spa. Cinema Room. Game Room.

$382

avg/night

View Details

Key Amenities

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

About this property

10 Bedrooms 6 Bathrooms Family Room with large HD Cable TV Upstairs TV Loft/Den with HD Cable TV Cinema / Movie Theater Room All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 14 plus breakfast ...

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Property Type

Kissimmee Villa

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Amazing Brand New 2/2, Storey Lake Resort, 4 miles Disney

$97

avg/night

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Key Amenities

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

About this property

Amazing 2BD / 2BA in the beautiful community of Storey Lake Resort Style, perfect stay to relax, have a good time with family/friends, and of course, enjoy the parks and many attractions that Orlando offers.Two comfortable rooms accommodate 6 guests: one king bed in Master Suite with smartTV and private ...

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Property Type

Kissimmee Apartment

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Refinished/Painted S. Facing Pool/Spa, Updated Decor, Near Disney, Sleeps 8

4 BR | 3 BA | Sleeps 8 | Quick View

9

Distance to park: 4 miles to Disney

$135

avg/night

View Details

Key Amenities

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

About this property

Magical Dreams come true in our elegant private 4 bedroom villa, 3 bathroom, all located on one floor, Quiet upgraded comforts of home and luxuries of an exceptionally rated vacation resort/hotel. Newly resurfaced and freshly painted pool and spa is sure to impress. There will be no waiting in line ...

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Property Type

Kissimmee House

"Family Vacay 2020"
Reviewed July 7, 2020

We enjoyed our family vacay 2020. A great getaway family was able to relax and enjoy themselves on the beach

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6BR/5.5Bath/4Miles to DisneyAK/$99 Specials/FreeSpa/Lanai

6 BR | 5.5 BA | Sleeps 18 | Quick View

37

Distance to park: 4 miles to Animal Kingdom

$123

avg/night

View Details

Key Amenities

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

About this property

We adjusted our prices for our 6 bedroom house just 4 miles to Disney’s Animal Kingdom. All open nights in Jan and Feb 2021 are just $99. Open nights in March 2021 are just $119. ********************************************************** Summary of this House’s best features (from 200+ Guest ...

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Property Type

Kissimmee House

"Beautiful home!! Close to everything!!"
Reviewed January 11, 2021

Absolutely loved this house!! Super spacious and well kept! Great furniture! Our 3 sons loved having their own King bedroom en suites! Great appliances and everything you need in the kitchen. The private ...

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

$130

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

"Beautiful island home away from home feeling❤️"
Reviewed December 2, 2020

My family and I stayed at 314 Alison Ave in Davenport. It was a beautiful ambiance in the home whick made me sleep well each night. The lounging area out back is where we spent most of our time, but everything ...

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

$150

avg/night

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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

"Covit-19"
Reviewed May 31, 2020

Unfortunately due to the current pandemic we were in lockdown in the U.K for the period we should have been in beautiful Florida.The owners of this villa were extremely helpful all through the period ...

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Paradise Breeze - Brand New 5 Bed Pool Villa

$269

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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Gorgeous Modern Luxurious W/ pool, hot tub, fitness centre mins away from Disney

$151

avg/night

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Key Amenities

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

About this property

Welcome to 7558 Sunville Avenue, your home away from home. This luxurious townhome at Summerville Resort features 3-bedroom, (plus a bonus room) and 3.5 bathrooms easily accommodating up to 8 guests comfortably. This brand new luxury townhome is perfect for a family or a big group who are coming to enjoy ...

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Property Type

Kissimmee Townhome

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Stylish 9BD 6BA Solara Pool/Spa. Games Room. Free use of Resort Facilities.

$329

avg/night

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Key Amenities

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

About this property

9 Bedrooms 6 Bathrooms Family Room with large HD Cable TV Upstairs Loft HD Cable TV All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 10 plus breakfast bar for 12 and outdoor dining Private screened ...

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Property Type

Kissimmee Villa

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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

$230

avg/night

View Details

Key Amenities

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

About this property

COVID 19 INFO UPDATED ON OUR WEBSITE, INCLUDES PAYMENT PLANS, 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 like this one. All homes this size include ...

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Property Type

Kissimmee House

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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

$97

avg/night

View Details

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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Modern 10BD 8BA Sonoma. Pool/Spa. Cinema Room. Free use of Resort Facilities.

$399

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

10 Bedrooms 8 Bathrooms Family Room with large HD Cable TV Upstairs Cinema Loft with Cinema Screen All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 16 plus breakfast bar and outdoor dining Private ...

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Property Type

Kissimmee Villa

"Beautiful & Roomy"
Reviewed March 10, 2019

We were attending a tournament at Silver Spur Arena and the location of the house was perfect. We were the first to rent the house and everything wasn't quite ready as far as furniture in position and ...

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

$940

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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Westside Deluxe | New in Windsor at Westside

$365

avg/night

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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

"Amazing Property"
Reviewed December 16, 2020

The owner Ann is amazing I love their property it was amazing. The home which includes 8 bedrooms a game room spa and swimming pool all at the home. There was also an additional pool at the community club ...

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LUXURIOUS 14B 11BA PRIVATE POOL/PATIO Solterra Resort-7013- Property 4831

14 BR | 11 BA | Sleeps 28 | Quick View

1
Owner special: SAVE $310/night in LOW season! (1/3-2/11) & (4/11-6/10); SAVE $235/night in MID season! (2/12-3/11)!

$663

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Be sure to visit our website to check availability on all our homes!Visit us at lostinthemagic . comSolterra Resort - Davenport, Florida is a paradise located only 15 minutes from the area's main attraction... Walt Disney World. This luxury resort sits nestled just outside of Orlando, Florida ...

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Property Type

Kissimmee House

"Vacation Home"
Reviewed September 25, 2019

For starters this home was absolutely beautiful!! The pictures shown here do not do it any justice. The neighborhood was really quiet, the tv’s were already set up to watch Netflix, Hulu, and Amazon Prime. ...

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Beautiful Reunion. 5 BD 4.5BA. Balcony Views. Private Pool. Tiki Bar Game Room.

$263

avg/night

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Key Amenities

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

About this property

This beautiful 5 bedroom golf view pool home has been constructed by one of Reunion's leading builders and boasts many upgrades throughout. Located on the west side of the resort which is becoming the most prestigious location for rental homes in Central Orlando. No other resort can compare to Reunion ...

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Property Type

Kissimmee House

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Fairway Family Getaway - Amazing Games Room and Kids Bedrooms!

$411

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to your Family Getaway! This beautiful 6 bedrooms 5.5 Bath is located in the Fairway Ridge community inside of the prestigious Reunion Resort with expansive, and breathtaking views of the sunset over the signature Jack Nicklaus course.Walk into your home away from home, and set your worries ...

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Property Type

Kissimmee House

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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

$257

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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HUGE POOL AND SPA

4 BR | 2 BA | Sleeps 7 | Quick View

1

$113

avg/night

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Key Amenities

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

About this property

4/15/20 ----PLEASE CALL FOR SPECIAL DEALS DURING THIS TIME. SPECIALS FOR 2 ADULTS. $70/night . 80/night max 4. personal check.WELL CARED FOR HOME IN LOVELY COMMUNITY. HOME BACKS TO CONSERVATION SO YOU ARE NOT OVERLOOKED AND IS A FEW STEPS FROM RETENTION POND WITH POND VIEWS FROM THE POOL DECK. ...

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Property Type

Kissimmee House

"Amazing time"
Reviewed June 14, 2020

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

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

$249

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

$431

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

$563

avg/night

View Details

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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SOUTH FACING POOL/ COME AND RELAX

$110

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

$659

avg/night

View Details

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

"Wedding"
Reviewed December 23, 2020

We had a great time and will definitely be back. Being by the pool grilling was a great time before going in the movie room.

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Fantastic 9BD 6BA Sleeps 20 Home Cinema, Game Room, Pool Spa Free use of Resort

$329

avg/night

View Details

Key Amenities

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

About this property

9 Bedrooms 6 Bathrooms Sleeps 20 Family Room with large HD Cable TV Upstairs Movie Loft with Projection Cinema Screen All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 18 plus breakfast bar and ...

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Property Type

Kissimmee House

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Fairway Comfort | 6 Bedroom 6.5 Bath Pool Villa with Movie Room!

$424

avg/night

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About this property

Welcome to Fairway Comfort. Located on the Westside of the incredible Reunion Resort within the Fairway Ridge community, and situated on the Jack Nicklaus-designed Tradition Golf Course. Fairway Elegance will fulfill all your vacation wants and needs. The home is located close to all the attractions of ...

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Property Type

Kissimmee House

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

$119

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

$479

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, Stylish, Affordable. 3BD 3.5BA Solara Resort. Private Pool.

$150

avg/night

View Details

Key Amenities

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

About this property

Former Model/Show Home 3 Bedrooms 3.5 Bathrooms Family Room with large HD Cable TV Upstairs TV Loft with HD Cable TV Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 6 plus breakfast bar seating 5 and outdoor dining Private screened ...

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Property Type

Kissimmee Townhome

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Florida Family Vacation Rental Home In Disney Area!!!

$120

avg/night

View Details

Key Amenities

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

About this property

We really appreciate your interest in our property, and we are working to re-open it for rental according to guidelines given by the state of Florida and the county of Osceola. We support the precaution of leaving one full day between the departure day of one guest and the arrival day of the next. We ...

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Property Type

Kissimmee Bungalow

"Perfect Disney Vacation House"
Reviewed October 25, 2019

The house was well equipped and stocked with plenty of towels and blankets. Seemed to be updated . LVT flooring throughout. Very clean and comfortable. Pool was a little cold..I recommend adding pool heat ...

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DISNEY OASIS WITH PRIVATE POOL AND GAME ROOM

4 BR | 3 BA | Sleeps 8 | Quick View

Distance to park: 12 miles to Disney World

$130

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Beautiful lakeside home with a private south facing pool in a gated community 12 miles from Disney. Enjoy fishing in the lake behind the house. Game room with pool table, skeet ball, foosball table and a gaming system with hundreds of old favorites like Pac Man and Mario Brothers. 4 bedrooms and 3 bathrooms. ...

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Property Type

Kissimmee House

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Blue Travel (VP4H2633)

4 BR | 3 BA | Sleeps 8 | Quick View

Inquire for rates

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Key Amenities

  • Air Conditioning
  • Kid Friendly

About this property

Situated in this beautiful gated community, centrally located for all the major attractions, Veranda Palms offers first class accommodation for your holiday. Beautifully furnished contemporary 4 bedrooms home is very spacious and features your own private pool. It is ideally located for quick access to ...

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Property Type

Kissimmee House

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

$209

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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❤️ Make Your Memories Magical ❤️ Family Friendly ❤️ 4 Miles to Disney

5 BR | 4 BA | Sleeps 12 | Quick View

2
LAST MINUTE DEAL 1/11 - 2/22: Free Disney Planning Guide with all reservations booked by February 22nd 2021.

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

$380

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee House

"Family Birthday Vacation"
Reviewed August 25, 2020

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

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DEAL
Beautiful 8BD 5BA Windsor at Westside. Private Pool/Spa. Games Room. Cinema Loft

$329

avg/night

View Details

Key Amenities

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

About this property

8 Bedrooms 5 Bathrooms Family Room with large HD Cable TV Upstairs Loft with Cinema Projection Screen All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 14 plus breakfast bar and outdoor dining Private ...

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Property Type

Kissimmee Villa

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Gorgeous Villa w/ Private Pool in Indian Creek, Kissimmee 4BR / 3BA

$120

avg/night

View Details

Key Amenities

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

About this property

***NO PETS***4 Bedroom / 3 Bathroom (1,791 sqft) Single Story East Facing Private Pool and SPA Gas Pool Heat is an additional cost.Living Room: TV / DVD / VCR Dining Area - Seats 6 Breakfast Table - Seats 4Master Bedroom 1: Queen / TV / Garden Tub / Pool Access Master Bedroom 2 : Full Bedroom ...

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Property Type

Kissimmee Villa

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Designer Furnished. 6BD 5BA Free use of Solara Resort. Games Room. Pool/Spa.

$220

avg/night

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Key Amenities

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

About this property

6 Bedrooms 5 Bathrooms Family Room with large HD Cable TV Upstairs Loft /Games Room with HD Cable TV, including Foosball, Air Hockey and Games Console. All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating ...

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Property Type

Kissimmee House

"Modern clean home"
Reviewed May 23, 2020

This home is very open, modern, clean and comfortable. The outdoor space has nice seating as well. It is situated in a pretty community. The home does lack basic amenities, like dishwasher tabs, dish ...

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Private South Facing Pool w/ Jacuzzi & Kiddy pool - 4 bed, 3 bath

$164

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Private Pool

About this property

RECENTLY REFURBISHEDLuxurious Windsor Palms with an extra wide cul de sac lot and with a pool that is not overlooked. Our guests enjoy terrific privacy in one of the premier resorts in the Disney vicinity. We have a south facing pool with kiddy pool and stand alone hot tub. Numerous child friendly ...

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Property Type

Kissimmee Villa

"Relaxing vacation"
Reviewed February 22, 2020

We just spent a week at this house. There were 5 adults and plenty of room for all of us. It was great having a full kitchen to cook our meals and Walmart was very close for groceries. The house was ...

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Fantastic 5BD 4BA Solara. Private Pool/Spa. TV Den/Loft. Games Room. Great Value

$168

avg/night

View Details

Key Amenities

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

About this property

5 Bedrooms 5 Bathrooms Family Room with large HD Cable TV Upstairs Loft/Den with HD Cable TV All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 8 plus breakfast bar and outdoor dining Private screened ...

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Property Type

Kissimmee House

"Perfect multi family home"
Reviewed January 21, 2020

Beautiful place to rest after a long day at the Disney parks. Very clean and accommodating. Great layout with each bedroom having their own access to a bathroom. Basic linens and kitchen supplies. Limited ...

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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 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Book today!