Kissimmee Vacation Rentals

(201 rentals)
Completely Renovated 3 Bed/3 Bath Town home - Only 2 miles from Disney World!!

$125

per night

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Villa Yvette, good value 3 Bedroom Villa at the Venetian BaY Villages

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Riva del Lago 4 bedroom villa with Lake View

$130

per night

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LUXURY VILLA ( Sunset Boulevard Community )

$150

per night

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Up-to-date calendar-Quick response-Easy to reserve-Near Disney-Clean-Low cost!

Up-to-date calendar-Quick response-Easy to reserve-Near Disney-Clean-Low cost!

4 BR | 3 BA | Sleeps 8 | Quick View

4

$129

per night

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Formosa Gardens home is the perfect getaway for your Orlando Disney vacation

$210

per night

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

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

6 BR | 4 BA | Sleeps 13 | Quick View

$284

per night

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Affordable Home Near Disney World

$99

per night

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Luxury villa with theater room, lake view and south-facing pool

Luxury villa with theater room, lake view and south-facing pool

7 BR | 5.5 BA | Sleeps 16 | Quick View

$225

per night

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Villa Cosy - Kissimmee

Villa Cosy - Kissimmee

3 BR | 2 BA | Sleeps 6 | Quick View

1

$95

per night

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DISNEY AREA LUXURY TOWN HOUSE/ LAKE BERKLEY RESORT

DISNEY AREA LUXURY TOWN HOUSE/ LAKE BERKLEY RESORT

4 BR | 3.5 BA | Sleeps 8 | Quick View

$93

per night

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South facing heated pool and spa

South facing heated pool and spa

6 BR | 4 BA | Sleeps 12 | Quick View

$145

per night

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

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

5 BR | 3.5 BA | Sleeps 8 | Quick View

$160

per night

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Enjoy resort style living in this outstanding brand new lakeside home

$139

per night

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Robson's Retreat

Robson's Retreat

5 BR | 3.5 BA | Sleeps 10 | Quick View

$150

per night

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The Emerald Villa

The Emerald Villa

7 BR | 5 BA | Sleeps 16 | Quick View

$293

per night

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Sunshine Days! June dates open! $885.92 for 7 nights!

$120

per night

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Gino's Vacation Home

Gino's Vacation Home

5 BR | 5 BA | Sleeps 10 | Quick View

1
Owner special: Check in on May 10 and check out on May 13 and pay only $900 all fees and tourist tax included.

$171

per night

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Stylishly Florida Design Southfacing Villa Near Disney

Stylishly Florida Design Southfacing Villa Near Disney

4 BR | 3 BA | Sleeps 8 | Quick View

$105

per night

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Disney by, Celabration, Kissimmee, family condo, gated, Free WI-FI

$85

per night

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The Princess Villa in Emerald Island Close to Disney World

$200

per night

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4987 Trafalgar Village

4987 Trafalgar Village

4 BR | 4 BA | Sleeps 8 | Quick View

$125

per night

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Minutes From Mickey - 3Bed 3Bath Townhome with South Facing Pool

Minutes From Mickey - 3Bed 3Bath Townhome with South Facing Pool

3 BR | 3 BA | Sleeps 6 | Quick View

1

$99

per night

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***At Disney's Door*** Just 5 minutes to Animal Kingdom!

***At Disney's Door*** Just 5 minutes to Animal Kingdom!

4 BR | 1 BA | Sleeps 10 | Quick View

1

$193

per night

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Emerald Island Resort is 3 Miles from Walt Disney World - 7 Br Pool Home with Sp

Emerald Island Resort is 3 Miles from Walt Disney World - 7 Br Pool Home with Sp

7 BR | 4.5 BA | Sleeps 14 | Quick View

Owner special: Pay for 5 nights and get 1 FREE. Valid April 16 - May 25.

$200

per night

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Snow White Villa Close to Disney World

Snow White Villa Close to Disney World

6 BR | 4 BA | Sleeps 14 | Quick View

$200

per night

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Mickey's Magical Palace

Mickey's Magical Palace

6 BR | 3.5 BA | Sleeps 14 | Quick View

$250

per night

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Vacation Rental near Disney

Vacation Rental near Disney

3 BR | 2 BA | Sleeps 8 | Quick View

$70

per night

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"The Waters Edge" This Really is The Classiest of Them All - Award Winning Home.

"The Waters Edge" This Really is The Classiest of Them All - Award Winning Home.

7 BR | 6 BA | Sleeps 22 | Quick View

$450

per night

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Serenity Vacation Villa

Serenity Vacation Villa

3 BR | 2 BA | Sleeps 6 | Quick View

$95

per night

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Updated 2018 photos! Four Bedroom Family Vacation Home Close to Disney World!

Updated 2018 photos! Four Bedroom Family Vacation Home Close to Disney World!

4 BR | 2.5 BA | Sleeps 8 | Quick View

$130

per night

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Fun for all Villa south facing pool

$150

per night

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Perfect Paradise

Perfect Paradise

7 BR | 4.5 BA | Sleeps 16 | Quick View

$225

per night

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Enjoy our 3000 square foot, custom luxury pool home

$239

per night

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Just Reduced - Hurry! Peaceful & Private - NO Rear Neighbors! Games Room, Pool!

$155

per night

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

$85

per night

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Luxury Windsor Hills 3/2 Condo

Luxury Windsor Hills 3/2 Condo

3 BR | 2 BA | Sleeps 6 | Quick View

$65

per night

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Hundred Acre Wood

Hundred Acre Wood

6 BR | 4 BA | Sleeps 14 | Quick View

Beautiful family friendly villa in quiet location. Very private pool area.
Holiday Rest

Holiday Rest

3 BR | 2 BA | Sleeps 7 | Quick View

1

$98

per night

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The Five Star Villa (Near Disney)

The Five Star Villa (Near Disney)

5 BR | 4 BA | Sleeps 10 | Quick View

10

$139

per night

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Orlando condo with Pool View

Orlando condo with Pool View

2 BR | 2 BA | Sleeps 6 | Quick View

1

$714

per night

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Tiger Lake Villa

Tiger Lake Villa

7 BR | 5 BA | Sleeps 16 | Quick View

$396

per night

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Fairway Elegance

Fairway Elegance

6 BR | 5 BA | Sleeps 12 | Quick View

$279

per night

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Over $1 Million Worth of Luxury

$545

per night

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Fairway Ridge Paradise

Fairway Ridge Paradise

5 BR | 4 BA | Sleeps 10 | Quick View

$240

per night

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Sensational 3 Bedroom with everything Upgraded Low Weekly Rates

$100

per night

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8 Bedroom Luxury Pool Villa with Outdoor Kitchen, Themed Rooms & Game Room!

$345

per night

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Westside Holiday

Westside Holiday

7 BR | 5 BA | Sleeps 14 | Quick View

$225

per night

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Steps to Disney Top Rated Gated Resort, 3BR Luxury Condo, Free Wifi, Great Rates

$79

per night

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Local Weather

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JANUARY
73°  49°
FEBRUARY
77°  53°
MARCH
82°  58°
APRIL
87°  64°
MAY
90°  70°
JUNE
92°  72°
JULY
92°  72°
AUGUST
90°  71°
SEPTEMBER
84°  65°
OCTOBER
79°  57°
NOVEMBER
73°  50°
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!