Kissimmee Vacation Rentals

(374 rentals)
ELEGANT TOWNHOME IN A QUIET, KID FRIENDLY COMPLEX

$65

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Spacious 2 storey, 3 bedrooms, 2 ½ bath town home is conveniently located in the gated community of Fiesta Key. It sits off a tranquil lake and is steps away from communal pool, clubhouse with gym and tennis court. Fantastic location in Kissimmee, only 8 miles from Disney and minutes away from ...

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Property Type

Kissimmee House

"Would stay here again!!!!"
Reviewed January 9, 2019

We rented for two months and had an amazing time! The townhouse was clean, spacious and we loved the layout and location. Close to tons of shopping and restaurants. We can’t say enough good things about ...

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Your private oasis a step away from Disney is awaiting for your arrival !!!

$209

per night

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Key Amenities

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

About this property

Disney on your Doorstep is just a charming, relaxing, and feel at home, kind of home... you know when you're sitting by the pool and the kids are having a ball, that you've picked the right spot.... our, wonderful 5 bedroom, 4 bathroom vacation home with private pool, spa & Game room in the exclusive ...

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Property Type

Kissimmee House

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Westside Charm | 7 Bed Private Pool Home

$205

per 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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Mickeys Getaway - 1 1/2 Miles to Disney! 4BR, 4bath villa with private pool

$155

per night

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Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Mickey's Getaway is a Luxury 4 bedroom/4 bath Villa located in upscale Windsor Hills resort, just 1.5 miles to Disney gates, with many upgrades, including spa and gameroom! And, there are no rear neighbors allowing for more privacy and a great view.Mickeys' Getaway is beautifully decorated and furnished ...

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Property Type

Kissimmee Villa

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15 minutes from all major parks in Orlando/ Kissimmee Area CUMBRIAN LAKES VILLA

5 BR | 3.5 BA | Sleeps 10 | Quick View

Distance to park: 10 miles to Downtown Disney

$121

per night

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Key Amenities

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

About this property

Under new Ownership and management!!!!! Property owner has 2 rentals listed on others sites with Premier 5 star ratings. We decided to try this site to afford our guests the best possible rental experience while paying the least amount of fees. Securely located in a gated community, the home features ...

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Property Type

Kissimmee Villa

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Enjoy this Disney Villa, in Emerald Island with Heated community Pool

$90

per night

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Key Amenities

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

About this property

***NO PETS***3 Bedroom /2 Bathroom (1,168 sqft) Single Story Guarded Community West Facing Private Pool with additional cost for Electric Pool Heat.Living Room: TV / VCR / DVD Playroom in Garage with TV and furniture Dining Area - Seats 6 Breakfast Table - Seats 4Master Bedroom 1 : ...

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Property Type

Kissimmee Villa

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

5 BR | 4 BA | Sleeps 12 | Quick View

3

Distance to park: 6 miles to Disney Animal Kingdom

$146

per 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 oldAs you enter our lovely home, you will be impressed with the soaring 17ft high ceilings in the ...

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Property Type

Kissimmee House

"Amazing stay, no need to look anywhere else"
Reviewed July 8, 2019

We’ve stayed at this villa twice. The communication from Pam was always excellent, answering our queries but also providing really useful hints and tips for days out, places to eat and shop and so on. ...

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

$143

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

4 BR | 3 BA | Sleeps 8 | Quick View

7

Distance to park: 4 miles to Disney

$115

per night

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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

"Nice place, quiet street,"
Reviewed January 23, 2020

House was clean, beds comfortable, pool was too cool to use even with the heater. Close to Disney, walmart and restaurants.

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Disney Vacation Rental/heated pool - call for Nov/Dec. Specials now

4 BR | 3 BA | Sleeps 8 | Quick View

Distance to park: 3 miles to Mgm

$119

per night

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Key Amenities

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

About this property

Beautiful 4 bedroom /3 bath private villa only 3 miles to Disney and other parks. Including heated pool/jacuzzi and game room. Free wifi and phone use in USA and Canada and PR. Fully furnished with all kitchen needs . Greatest location to shopping , all major restaurants and stores including supermarkets ...

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Property Type

Kissimmee Villa

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MAGICAL 5* LAKE VIEW VILLA, HEATED POOL & SPA, DISNEY, LAKE BERKLEY RESORT

$179

per night

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Key Amenities

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

About this property

‘The Magic Lake View' is just 7.8 miles to Disney! Majestic, totally private (no neighbors looking in either side) off the pristine pool deck with spa overlooking a 14 acre natural fishing lake on a prestigious select gated community. The Magic View villa has everything and more that you could ...

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Property Type

Kissimmee Villa

"Best place to stay on your vacation"
Reviewed November 25, 2019

The house is gorgeous, the lake view is fantastic, exactly like on the pictures, very close to Disney, the gated territory is very convenient. We definitely will come back!

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

$310

per 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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My Disney Townhouse

4 BR | 3.5 BA | Sleeps 10 | Quick View

3

Distance to park: 5 miles to Animal Kingdom

$100

per night

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Key Amenities

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

About this property

Enjoy Orlando, Florida, home to Disney World, Sea World, Universal Studios, and Islands of Adventure, in style. Our home is within minutes of all the Orlando attractions, golf courses, shopping, and exciting night life. Our richly appointed vacation Townhouse will give you luxurious living and a vacation ...

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Property Type

Kissimmee Townhome

"Excellent place to stay."
Reviewed December 3, 2019

The location is amazing-everything was close every one was friendly pool was great hot tub was amazing. I love it so much that I will like to buy a property there.Can some one tell me how I can buy ...

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

$571

per 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

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Stunning 5 Bed 3 Bath villa on secure gated Lake Berkley Resort. Close to Disney

$128

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

A stunning, larger than average, 5 Bed 3 Bathroom villa with a fantastic private pool. All rooms in the villa are spacious. The villa is furnished and maintained to a very high standard. Fully air conditioned throughout and free WiFi.The villa is split over two floors which makes it ideally beneficial ...

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Property Type

Kissimmee Villa

"Amazing Villa"
Reviewed August 15, 2019

We stayed in this spacious, well equipped villa last two week in July. We all had an amazing time by the really large pool. Plenty sun loungers/chairs for sunbathing . Pictures don't do it justice you ...

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MAKING HAPPY MEMORIES

4 BR | 2 BA | Sleeps 6 | Quick View

$90

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

LARGEST POOL IN THE COMMUNITY! HUGE POOL AND DECK. ENJOY BREAKFAST AND MEALS IN THE SUNSHINE . TERRIFIC SOUTH FACING POOL AND BACKS TO CONSERVATION SO YOU ARE NOT OVERLOOKED. SPLIT PLAN BEDROOMS, KING AND 2TWINS IN BACK BY THE POOL, AND QUEEN AND 2TWINS IN FRONT. EAT-IN KITCHEN, BREAKFAST BAR, Q-LED ...

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Property Type

Kissimmee House

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Mickey's Villa -- New home now available! Wide-open calendar! Low rates!

5 BR | 4 BA | Sleeps 11 | Quick View

11

Distance to park: 4 miles to Disney World

$134

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

Florida State License DWE5910390 (Near Disney) COME SWIM WITH MICKEY! This beautiful 5-Bed 4-Bath home located in the very popular community of Indian Creek is one of only three homes in the development with a Mickey Pool. Featuring two en-suites with private baths and three other bedrooms and two ...

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Property Type

Kissimmee House

"familia est sempiternum"
Reviewed March 26, 2020

Our family was able to be together for a week, just before the COVID-19 Pandemica rolled in to epic proportions. Though we were unable to go to any of the parks, or typical tourist destinations, we did ...

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Luxury Tennyson Villa- close to Disney -Pool-WiFi-Gamesroom

5 BR | 3.5 BA | Sleeps 8 | Quick View

5

Distance to park: 10 miles to Disney

$184

per night

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Key Amenities

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

About this property

Luxury Disney-themed Villa - spacious accommodation over 2 floors. PRIVATE HEATED POOL AND AIRCONDITIONED GAMES ROOMNEW for 2019 SALT WATER POOL Gentler on skin and eyes, soft water feel.Tennyson has 5 bedrooms ALL with TV and Net Flix 3 Bathrooms with 2 walk in showers and a guest toilet. Three ...

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Property Type

Kissimmee Villa

"A real hone from home"
Reviewed March 9, 2020

We had a wonderful time at this Villa. You will not need anything as it is fully equipped. It is clean and tidy and the beds are very comfortable. It is very spacious which meant plenty of room as their ...

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Enjoy resort style living in this outstanding brand new lakeside home

$139

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

This two story 2 bedroom 2 & 1/2 bathroom townhome is located in Regal Oaks: the perfect location for your next Orlando getaway. Situated right behind Old Town with Fun Spot right next door, entertainment abounds. Take a stroll down the brick lined street of Old Town and wander into one of the specialty ...

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Property Type

Kissimmee Townhome

"Great place for a family getaway"
Reviewed March 2, 2020

Our stay at the Regal Oaks resort was a great experience. Overall, it was our favorite resort we've stayed at in the Orlando, FL area (we've stayed at two others). The one area we would have changed was ...

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

$239

per 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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Large spacious home/Private pool/Close 2 Disney

4 BR | 2 BA | Sleeps 8 | Quick View

3

Distance to park: 14 miles to Walt Disney Parks

$139

per night

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Key Amenities

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

About this property

Spacious, Clean family-sized home with a fantastic open concept setting. Located within a gated resort community only 7 miles to Disney, and minutes to shops/restaurants makes the location ideal. The home has been freshly painted, decorated with brand new living room furniture. Perfect for social settings, ...

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Property Type

Kissimmee House

"Great family home"
Reviewed March 2, 2020

We stayed at the house for 10 days in August. The house is in a safe, gated community with a nice big pool in the backyard. The kitchen is fully stocked with everything you need to make a meal. The house ...

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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

$69

per night

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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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LUXURIOUS 14B 13BA PRIVATE POOL/PATIO Sonoma Resort-2613CYA - Property 4831

$515

per night

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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 . comSonoma Resort - Kissimmee, Florida is only 15 minutes to the area's main attraction... Walt Disney World. This brand new resort community sits nestled just outside of Orlando, between W. Osceola ...

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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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South facing heated pool and spa

6 BR | 4 BA | Sleeps 12 | Quick View

5

Distance to park: 3 miles to Disney World

$175

per 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

"Family vacation"
Reviewed February 23, 2020

The house was perfect for us. The two masters were a big plus. Kids rooms were great and the addition of a crib helped a lot. We appreciatedhigh chair but had brought our own booster. The house was clean ...

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HUGE POOL AND SPA

4 BR | 2 BA | Sleeps 7 | Quick View

$90

per night

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Key Amenities

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

About this property

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

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Property Type

Kissimmee House

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Patriots Landing at Reunion | 5 Bedroom Pool Villa

$225

per night

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Key Amenities

  • Air Conditioning
  • Private Pool

About this property

This lovely home in the Patriots Landing neighborhood of the Reunion Resort is perfect for a family vacation. Cool by the pool or let loose in the game/arcade room, the kids will love their themed bedrooms. The whole family can get together in the common living area which opens up to both the kitchen ...

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Property Type

Kissimmee Villa

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Westside Deluxe | New in Windsor at Westside

$269

per 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

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6 Bed 5.5 Bath Disney Dream Home In The Emerald Island Resort

$219

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

A Truly Luxurious Executive Retreat, Main Level Features: Quality Ceramic Tile Flooring throughout. Spacious Family Room with Vaulted Ceiling and Corner Leather Sofa.70″ TV with 5.1 surround sound with blue tooth capabilities. Formal Dining Room/ Sitting Area with table for six, Fabulous Kitchen ...

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Property Type

Kissimmee House

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Solterra Breeze | 6 Bedroom, 5.5 Bath | Themed Kids' Rooms

$195

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Property SummaryGeneral 3,137 sq/ft of luxury accommodation Fully equipped kitchen and formal dining area Smoke-free and pet-free for your comfort Towels and linens are provided Complimentary wireless internet Outside SeatingBedroom/Bed Sizes King Master with Ensuite - First Floor King ...

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Property Type

Kissimmee House

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Toy Story Tower

6 BR | 4 BA | Sleeps 14 | Quick View

Distance to park: 5 miles to Disney World

$243

per 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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Highest Ranked Home Newly Renovated Lowest Weekly Rate Price includes all Fees

$85

per night

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Key Amenities

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

About this property

New Flooring New Air Conditioning ,New Mattresses, Gel Toppers , Keurig ,Our prices include everything! No hidden maid service fee or security fee or taxesOUR PRICES INCLUDE ALL TAXES AND FEESOur resort, is a Gated community  it is a 5 star resort only 5 minutes from the Disney Parks ...

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Property Type

Kissimmee Condo

"honest owner"
Reviewed March 7, 2019

unfortunately had to cancel last minute because of health to both my wife and I. owner was more than reasonable about problem. not everyone would have been more helpful as he was.

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Fable Haven | New in Storey Lake! 9 Bedroom Pool Home with Amazing Games Room!

$325

per night

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Key Amenities

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

About this property

The Storey Lake clubhouse features a fitness center, sauna, game room, internet cafe, and a 50-seat movie theater. Additional amenities include Tennis, basketball, volleyball courts, and a golfing area at this fabulous vacation rental resort community.You're sure to enjoy your time at this vacation ...

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Property Type

Kissimmee House

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Stunning lake view villa with own South facing pool. On gated Resort near Disney

4 BR | 2 BA | Sleeps 8 | Quick View

3

Distance to park: 8 miles to Disney

$114

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Stunning 4 Bedroom Villa, private pool, 5 Star gated Lake Berkley Resort, Kissimmee, near Disney The villa is located in Lake Berkley Resort, a safe secure gated Resort.Our 4 Bed, 2 Bath villa is furnished to a very high standard and benefits from a perfect lake view position.As well as a large ...

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Property Type

Kissimmee Villa

"Great villa to visit florida"
Reviewed October 29, 2019

Lovely villa in a great location and with all the facilities you could possibly need. Lots of space and good beds. Minor change would be to drop the ACsetting a couple of degrees as 77 degrees is a bit ...

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Disney Villa

4 BR | 3 BA | Sleeps 8 | Quick View

1

$95

per night

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Key Amenities

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

About this property

4BR Vacation Rental Kissimmee, Florida. This is luxury villa for only $650/$950 week. A pool room is located in a quiet neighborhood and is perfect for all of family to stay in during their Orlando visit. The spacious home have a very comfortable atmosphere with their own private screened porch ...

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Property Type

Kissimmee Villa

"Family vacation 2018"
Reviewed August 27, 2018

This was a very clean, open and spacious inviting house with a pool that my family of 4 really enjoyed. We would consider renting again from the owner . Great central location to shopping and Disney. We ...

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

$89

per 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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Gino's Vacation Home

5 BR | 5 BA | Sleeps 10 | Quick View

1

$143

per night

View Details

Key Amenities

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

About this property

Vacation Home 5.6 miles from Disney.This beautiful fully furnished with open floor plan, mediterranean style 5 bedroom 5.5 bathroom house is located just 5 miles from Walt Disney World and is only a 30 minute drive from Orlando International Airport. Not only is this home open and spacious, but private ...

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Property Type

Kissimmee Villa

"Excellent Orlando Villa"
Reviewed April 15, 2018

Hi Gino & Eva Just wanted you to know we had a fantastic time in your fabulous Villa/Home We all enjoyed every part of it Ideally positioned Large double bedrooms with comfy beds Excellent pool ...

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Encantada Resort Townhouse with pool 3 bedrooms

$99

per night

View Details

Key Amenities

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

About this property

This amazing townhouse located at Encantada Resort has been recently upgraded. The fully equipped kitchen has new granite countertops and everything you need to eat at home or prepare some snacks for the parks. There is a dining set for 6 that shares the open plan with the living room where there is a ...

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Property Type

Kissimmee Townhome

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Newly Renovated-Incredible Game Room-South Facing Pool and Spa

$175

per night

View Details

Key Amenities

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

About this property

**To check on availability and to get an up to date quote please go to our website listed below under owner info**Are you looking for a vacation home with an incredible game room, a very private south facing heated pool, children's wading pool and Jacuzzi, and a new modern kitchen, in Formosa Gardens ...

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Property Type

Kissimmee House

"Wonderful Vacation Rental!!!"
Reviewed December 1, 2019

We had a wonderful extended family vacation in this lovely home! It really made our vacation! The location/neighborhood was beautiful, well maintained, secure & peacefully quiet. We didn’t have any “issues”, ...

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Beautiful 3 Bedroom 2 Bathroom Townhouse. Amazing Resort. Minutes to Disney.

3 BR | 2 BA | Sleeps 6 | Quick View

4

Distance to park: 5 miles to Walt Disney World

$99

per night

View Details

Key Amenities

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

About this property

Beautiful 3 Bedroom 2 Bathroom Townhouse just off of 192 in Kissimmee, Fl. Minutes to Walt Disney World, Universal Studios, Sea World, Outlet shopping. You can walk to great restaurants and shopping. One of the best locations in the community. Only one building back from the Clubhouse and Pool, and ...

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Property Type

Kissimmee Condo

"Amazing!"
Reviewed January 2, 2020

We booked this online, had never done anything like this before. The owner was very responsive to my emails and questions. When we arrived at the gate we were greeted by security who reviewed our info ...

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

3 BR | 2 BA | Sleeps 8 | Quick View

5

Distance to park: 12 miles to All Disney Theme Park

$89

per 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

"Perfect Family Vacation Home"
Reviewed March 18, 2019

We rented this home for a week in early February. Everything was perfect. All of the amenities need for our stay were there. The pool was great. All of the restaurants and Theme parks were just a short ...

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Executive Beautifully furnished South facing villa

5 BR | 3.5 BA | Sleeps 10 | Quick View

3

Distance to park: 7 miles to Disney

$125

per night

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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

"Highly recommend - beautiful villa"
Reviewed December 16, 2019

We were a family of 8 staying here in November. I can not recommend this beautiful villa highly enough. We have stayed in Cumbrian lakes on multiple occasions but this is the first time I had stayed at ...

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Hidden Oasis | 4 Bedroom 3 Bath Private Pool Villa

$275

per 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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Large 5 Bed villa sleeps 12, with private pool. Games room. Near Disney

$130

per night

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Key Amenities

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

About this property

This villa is a stunning 5 Bed 3 Bath villa that can comfortably sleep 12 guests.A stunning, larger than average, 5 Bed 3 Bathroom villa with a fantastic private pool. All rooms in the villa are spacious. The villa is furnished and maintained to a very high standard.The villa is spaciously arranged ...

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Property Type

Kissimmee Villa

"Awesome Family Rental"
Reviewed July 27, 2019

My entire family was impressed with my choice in rental home. This well appointed rental had comfy beds, a well appointed kitchen and plenty of space for everyone. The kids were torn between the game room ...

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Emerald Pearl

7 BR | 5.5 BA | Sleeps 18 | Quick View

2

$128

per night

View Details

Key Amenities

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

About this property

Welcome To The Emerald Island Resort, Orlando's Premier Gated Community *** ***Fantasmic Location***closest Resort To Disney*** ***free Wireless Internet Just Bring Your Laptop*** Our 7/bedroom 5.5/bath villa (with 4 Master Bedrooms, all King bed with full private bath!) 3 bedroom each have 2 single ...

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Property Type

Kissimmee House

"Emerald Island Resort"
Reviewed January 3, 2020

My family and I highly recommend this home for your vacation rental. It contained everything we needed and much more. Its space, cleanliness, and comfort was exactly what we were looking for. Its location ...

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Fun House with Grande View

7 BR | 7.5 BA | Sleeps 14 | Quick View

$395

per night

View Details

Key Amenities

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

About this property

Situated a short drive away from Disney, this impressive 7-bedroom, 7.5-bathroom mansion has enough space to sleep up to 14 guests. Inside you are spoiled with a home theater, themed game room, spacious living spaces, themed children’s bedrooms. Outside you have a private infinity pool with a spillover ...

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Property Type

Kissimmee House

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Beautiful & Spacious Family Villa in Rolling Hills, Kissimmee 4BR / 2BA

$98

per night

View Details

Key Amenities

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

About this property

***NO PETS***4 Bedroom / 2 Bathroom (1,822 sqft) Single Story South Facing Private Pool Electric Pool Heat is an additional cost.Living Room: TV / DVD Dining Area - Seats 6 Breakfast Table - Seats 4Master Bedroom 1: Queen/ TV / Garden Tub Bedroom 2: Double Bedroom 3: Twins Bedroom ...

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Property Type

Kissimmee Villa

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

$125

per 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

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3 Miles From Disney - Pet Friendly - Free Wifi - Grill - AC - Baby Equipment

$186

per night

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Key Amenities

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

About this property

Sleeps 8-10. Beachy decor. 2 master suites (one king / one queen) both with private bathrooms. 2 twin bedrooms / 2 twin beds each share the 3rd bathroom. Queen sofa sleeper in the living room. Private pool and free standing hot tub. Extra large fenced rear yard. Great for kids and pets (2-3 pet with paid ...

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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

9 BR | 6 BA | Sleeps 25 | Quick View

1
LAST MINUTE DEAL 3/18 - 4/29: Sparkling Clean 9 BR Retreat 60% OFF Spring Break MARCH-MAY!! $239/NT

$259

per 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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DEAL
Affordable Home Near Disney World

$100

per night

View Details

Key Amenities

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

About this property

Indian Creek Disney Retreat is a beautiful 1800SF, well maintained home in the Indian Creek subdivision which is literally on Disney's doorstep and your home away from home. Indian Creek is not a gated community but has a lot of community amenities.In the 1st section of Indian Creek you will find ...

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Property Type

Kissimmee Villa

"Second time staying here"
Reviewed November 18, 2019

Once again this home did not disappoint. Beautiful home, the owners are wonderful and we enjoyed every moment of our stay there. Will for sure stay here again. 100 stars

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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!