Kissimmee Vacation Rentals

(211 rentals)
2 Miles to Disney World. 6 BR with Private Pool & Spa. Fireworks Views

2 Miles to Disney World. 6 BR with Private Pool & Spa. Fireworks Views

6 BR | 3.5 BA | Sleeps 14 | Quick View

$165

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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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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Enjoy resort style living in this outstanding brand new lakeside home

$139

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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Disney Adventure Villa at Windsor Hills Resort Sleeps up 16*

Disney Adventure Villa at Windsor Hills Resort Sleeps up 16*

6 BR | 6 BA | Sleeps 16 | Quick View

Owner special: July 18-25 Reduced Rates for this time period. 4 night minimum stay. Free Pool/Spa Heating!!

$219

per night

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Luxury 6 bedroom villa in a gated community

$118

per night

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Luxury 4 bed pool villa, 15 minutes from DisneyWorld

$130

per night

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Villa located just 2 miles from Disney World

$269

per night

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Resort living while visiting many of the entertainment parks near orlando

$150

per night

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Villa Cosy Kissimmee - Disney

Villa Cosy Kissimmee - Disney

3 BR | 2 BA | Sleeps 6 | Quick View

2

$95

per night

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Across From Disney

Across From Disney

4 BR | 3 BA | Sleeps 8 | Quick View

$142

per night

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Stay in this gorgeous 7 BR vacation pool home located in Terra Verde Resort

Stay in this gorgeous 7 BR vacation pool home located in Terra Verde Resort

7 BR | 4.5 BA | Sleeps 16 | Quick View

$199

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

$200

per night

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Lake Berkley Villa

Lake Berkley Villa

4 BR | 3 BA | Sleeps 8 | Quick View

$130

per night

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Family fun dates in July and August!!

$120

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

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

5 BR | 4 BA | Sleeps 11 | Quick View

$139

per night

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LUXURY VILLA ( Sunset Boulevard Community )

$150

per night

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Enjoy our 3000 square foot, custom luxury pool home

$239

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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South Facing Pool Conservation Area Free Wi Fi 3 Mile to Disney

$153

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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Luxury 7 bed Emerald Island Villa

Luxury 7 bed Emerald Island Villa

7 BR | 4.5 BA | Sleeps 16 | Quick View

$150

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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Perfect Paradise

Perfect Paradise

7 BR | 4.5 BA | Sleeps 16 | Quick View

$225

per night

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The Orlando vacation home: 6 Bedrooms, 5 and a half Bathrooms

$220

per night

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

$155

per night

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Affordable Home Near Disney World

Affordable Home Near Disney World

4 BR | 3 BA | Sleeps 10 | Quick View

1

$99

per night

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"VACATION FOR LESS" Welcome to NewHaven Palms and Resorts on Cumbrian Lakes

$170

per night

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

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

3 BR | 2 BA | Sleeps 8 | Quick View

$85

per night

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4BR TOWNHOUSE JUST MINUTES FROM DISNEY

$64

per night

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Emerald Island Best

Emerald Island Best

8 BR | 4.5 BA | Sleeps 20 | Quick View

$170

per night

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

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

4 BR | 2.5 BA | Sleeps 9 | Quick View

$127

per night

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Family Friendly Golf Fronted Home with South Facing Pool & Spa

Family Friendly Golf Fronted Home with South Facing Pool & Spa

5 BR | 4 BA | Sleeps 12 | Quick View

Owner special: Hot Deal Aug 17th - Aug 31st Special - $239 plus tax per night for 7 night Min. July Dates Avail

$199

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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Mickeys Retreat

Mickeys Retreat

4 BR | 2 BA | Sleeps 8 | Quick View

$140

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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5 Bed 3.5 Bath Villa with Pool, Spa, and Conservation View

$114

per night

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The Princess Villa in Emerald Island Close to Disney World

$200

per night

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Nov/Dec Special! Windsor Hills Villa SF Pool, Arcade Game, 2.5 Miles to Disney

$199

per night

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Stay in this 4 Bedroom Pool and Spa Home with game room in Windsor Palms Resort

Stay in this 4 Bedroom Pool and Spa Home with game room in Windsor Palms Resort

4 BR | 3 BA | Sleeps 9 | Quick View

$140

per night

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Gino's Vacation Home

Gino's Vacation Home

5 BR | 5 BA | Sleeps 10 | Quick View

1

$143

per night

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Compass Bay

Compass Bay

3 BR | 2.5 BA | Sleeps 8 | Quick View

1

$79

per night

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Disney Vacation Home Orlando - Paradise Palms Gated Resort

$160

per night

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MULBERRY PARK. SUPERB FAMILY MANSION ON DISNEY'S DOORSTEP

MULBERRY PARK. SUPERB FAMILY MANSION ON DISNEY'S DOORSTEP

9 BR | 8 BA | Sleeps 18 | Quick View

$620

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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3 bedroom, 3 bathroom home

3 bedroom, 3 bathroom home

3 BR | 3 BA | Sleeps 8 | Quick View

$120

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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Emerald Pearl

Emerald Pearl

7 BR | 5.5 BA | Sleeps 18 | Quick View

$143

per night

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Local Weather

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72°  48°
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!