Kissimmee Vacation Rentals

(221 rentals)
Villa Cosy Kissimmee - Disney

Villa Cosy Kissimmee - Disney

3 BR | 2 BA | Sleeps 6 | Quick View

2

$95

per night

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3 Miles To Disney, Free WiFi No Extra Fee, Gated Live Guard

3 Miles To Disney, Free WiFi No Extra Fee, Gated Live Guard

3 BR | 3 BA | Sleeps 6 | Quick View

5

$100

per night

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5 Bed 8590 SKD Pool/Spa/Gameroom Home Emerald Island Resort

$130

per night

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The Princess Villa in Emerald Island Close to Disney World

$200

per night

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4 Miles From Disney, Quiet Magical Sanctuary, 4 Beds/3Baths, Sleeps up to 8

4 Miles From Disney, Quiet Magical Sanctuary, 4 Beds/3Baths, Sleeps up to 8

4 BR | 3 BA | Sleeps 8 | Quick View

2

$115

per night

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From $70/nt,Close to Disney.4br/3ba townhome

From $70/nt,Close to Disney.4br/3ba townhome

4 BR | 3 BA | Sleeps 10 | Quick View

$70

per night

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

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

7 BR | 4.5 BA | Sleeps 14 | Quick View

$199

per night

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New Opening 5Br/3Ba Hot Tub/Lake View,Close Disney,Seaworld

New Opening 5Br/3Ba Hot Tub/Lake View,Close Disney,Seaworld

5 BR | 3 BA | Sleeps 12 | Quick View

2

$90

per night

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Tropical Oasis - Windsor at Westside

Tropical Oasis - Windsor at Westside

7 BR | 5.5 BA | Sleeps 18 | Quick View

$226

per night

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

$164

per night

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From $80/nt,4br/3ba TownHome /Hot Tub/lake View,Near Disney,Convention Center

From $80/nt,4br/3ba TownHome /Hot Tub/lake View,Near Disney,Convention Center

4 BR | 3 BA | Sleeps 8 | Quick View

$80

per night

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7BR(4 KING)/5.5BA - SLEEPS 20

7BR(4 KING)/5.5BA - SLEEPS 20

7 BR | 5.5 BA | Sleeps 20 | Quick View

$143

per night

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Sunset View

Sunset View

4 BR | 2.5 BA | Sleeps 8 | Quick View

1

$120

per night

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Sept and Oct dates open save 25% per week!

$120

per night

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Disney Vacation Home Orlando - Bella Vida Gated Resort

$160

per night

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Southwest Facing Pool with a Lake View 6 Bed 5.5 Bath Lady Bug Villa

$225

per night

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6br/4ba pool house from $130/nt,Near Disney,SeaWorld,Convention Center

6br/4ba pool house from $130/nt,Near Disney,SeaWorld,Convention Center

6 BR | 4 BA | Sleeps 12 | Quick View

$129

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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Indian Creek Villa-5 mins to Disney

$114

per night

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

$85

per night

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South Facing Pool home with 5 Bed 2716LKD Pool/Spa/Gameroom

$139

per night

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The Turquoise Palms - Coastal Glam! 4 bedrooms with 5* Mattresses! Harry Potter!

$96

per night

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

$220

per night

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South Facing Pool Home with 4 Bed 3 Bath 2253WP Windsor Palms

$165

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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Perfect Paradise

Perfect Paradise

7 BR | 4.5 BA | Sleeps 16 | Quick View

$225

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

$155

per night

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Lovely Windsor Hills Resort POOL # Bed 2.5 Bath Townhome!

$85

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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Enjoy resort style living in this outstanding brand new lakeside home

$139

per night

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Disney World Area Vacation Townhouse

Disney World Area Vacation Townhouse

2 BR | 2 BA | Sleeps 6 | Quick View

$93

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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7 Bed 4.5 Bath 8509SKC Pool/Spa/Gameroom Emerald Island

$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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Splendid 6 bedroom 4 bathroom home

$220

per night

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Emerald Gem Prime Location In Secure Safe 24/7 manned Gatehouse Community with

Emerald Gem Prime Location In Secure Safe 24/7 manned Gatehouse Community with

4 BR | 3 BA | Sleeps 10 | Quick View

$99

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

$79

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

$199

per night

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2 Miles to Disney,1808 sqft 4BR/3BA Townhome

2 Miles to Disney,1808 sqft 4BR/3BA Townhome

4 BR | 3 BA | Sleeps 8 | Quick View

$80

per night

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Villa located just 2 miles from Disney World

$269

per night

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Close to Disney,Seaworld,Convention Center,4br/3ba Townhome with hot tub

Close to Disney,Seaworld,Convention Center,4br/3ba Townhome with hot tub

4 BR | 3 BA | Sleeps 10 | Quick View

2

$80

per night

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Affordable Home Near Disney World

$99

per night

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2 miles to Disney,1650 sqft 4BR/3BA big Condo from $80/nt

2 miles to Disney,1650 sqft 4BR/3BA big Condo from $80/nt

4 BR | 3 BA | Sleeps 8 | Quick View

1

$80

per night

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From $90/nt,5BR/3BA with hot tub,Near Disney,Seaworld and Convention Center

From $90/nt,5BR/3BA with hot tub,Near Disney,Seaworld and Convention Center

5 BR | 3 BA | Sleeps 12 | Quick View

2

$90

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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New 9Br/6Ba Pool Villa from $300/nt, Close To Disney

New 9Br/6Ba Pool Villa from $300/nt, Close To Disney

9 BR | 6 BA | Sleeps 20 | Quick View

1

$300

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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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

1

$200

per night

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LUXURY VILLA ( Sunset Boulevard Community )

$150

per night

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Local Weather

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MARCH
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92°  72°
JULY
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AUGUST
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SEPTEMBER
84°  65°
OCTOBER
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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!