Kissimmee Vacation Rentals

(143 rentals)
Spacious Venetian Bay Townhouse, Sleeps up to 10, Close to Disney

Spacious Venetian Bay Townhouse, Sleeps up to 10, Close to Disney

4 BR | 3.5 BA | Sleeps 10 | Quick View

Distance to park: 8 miles to Walt Disney world

$92

per night

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Disney Executive Villa, private south-facing pool, overlooking lake

$86

per night

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Private Luxury Villa only 10 minutes from Disney World

$98

per night

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Two story, 4 Bedroom / 3 Bathroom townhouse is in Regal Oaks

$125

per night

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BRAND NEW HOME WITH GAME ROOM, JACUZZI

$467

per night

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Disney Vacation Pool Home/Villa In Deluxe Resort

$129

per night

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

$87

per night

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LUXURY VACATION RENTAL POOL VILLA NEAR DISNEY by Owners

$135

per night

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Luxury Modern Villa Near Disney $20,000 of recent upgrades

$119

per night

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Magicbay Villa,Best Deal 7 Br in Emerald, Beat lowest offer

Magicbay Villa,Best Deal 7 Br in Emerald, Beat lowest offer

7 BR | 4.5 BA | Sleeps 16 | Quick View

Distance to park: 3 miles to Disney

$200

per night

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My Magical Homes

My Magical Homes

4 BR | 3 BA | Sleeps 10 | Quick View

$165

per night

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❤️ You'll Love Making the Most of the Wonderful Florida Outdoor Lifestyle - BOOK NOW ❤️

❤️ You'll Love Making the Most of the Wonderful Florida Outdoor Lifestyle - BOOK NOW ❤️

5 BR | 4 BA | Sleeps 12 | Quick View

Distance to park: 4 miles to Disney's Animal Kingdom

$360

per night

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BELLEAIR

BELLEAIR

6 BR | 5.5 BA | Sleeps 13 | Quick View

$195

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

$396

per night

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6 BEDROOM POOL HOME AT ENCORE CLUB near DISNEY!

Inquire for rates

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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

Distance to park: 10 miles to Disney Theme Parks

$101

per night

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Pool Home -Sleeps 6-12 Lake View Located in the Disney Area!

$199

per night

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Lindfields Vacation Home with Private Pool, Mins from Disney

$125

per night

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Enjoy our 3000 square foot, custom luxury pool home

$239

per night

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EMERALD ISLAND RETREAT 1

EMERALD ISLAND RETREAT 1

4 BR | 3 BA | Sleeps 10 | Quick View

$143

per night

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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

Distance to park: 2 miles to Disney World

$185

per night

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Lakefront,gated 4Br,6mi2Disney, free WiFi/Cable TV

Lakefront,gated 4Br,6mi2Disney, free WiFi/Cable TV

4 BR | 3 BA | Sleeps 10 | Quick View

Distance to park: 6 miles to Disney park

$95

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

Distance to park: 3 miles to animal kingdom

$99

per night

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Stunning Lake View House 2mls Disney,free Wi-FI,games room,spa

Stunning Lake View House 2mls Disney,free Wi-FI,games room,spa

4 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to park: 3 miles to Disneys Animal Kingdom

$150

per night

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Newly renovated and equipped with water view

$119

per night

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"A House near the mouse" - BEST LOCATION ATTRACTIVE PRICE !!!

$153

per night

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Stay in this gorgeous 6 BR vacation pool home located in Terra Verde Resort

$169

per night

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Disney Florida vacation rental/3 miles to disney/heated pool/jacuzzi/gameroom/wi

$110

per night

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Lake view, west facing extra large pool deck

$199

per night

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

$99

per night

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Luxury 3/3 Disney Villa( Free pool heat) ( Welcome Pkg close to club house pool

$110

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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Luxurious family friendly private villa in Florida - 3 miles from Disney!

Luxurious family friendly private villa in Florida - 3 miles from Disney!

4 BR | 3 BA | Sleeps 10 | Quick View

Distance to park: 3 miles to Disneys Animal Kingdom

$145

per night

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Royal 132

Royal 132

2 BR | 2 BA | Sleeps 6 | Quick View

$79

per night

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Four Bedroom Family Vacation Home Close to Disney World!

Four Bedroom Family Vacation Home Close to Disney World!

4 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to park: 4 miles to Disney World

$130

per night

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6 Bedroom 5.5 Bath Home in Terra Verde , Private Pool, Wi-Fi, Gameroom, Bbq Gril

$237

per night

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Disney Kids Kingdom Florida Large Villa Rental

$114

per night

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Exclusive Family Home and Pool

$78

per night

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3 Bedroom Home For Rent in Emerald Island Resort

$11

per night

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OUTSTANDING VACATION PROPERTY WITH EVERY POSSIBLE AMENITY FOR A FABULOUS STAY!

$138

per night

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Disney Contemporary 3

Disney Contemporary 3

4 BR | 2.5 BA | Sleeps 16 | Quick View

$199

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

Distance to park: 2 miles to Disney

$65

per night

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Gino's Vacation Home

Gino's Vacation Home

5 BR | 5 BA | Sleeps 10 | Quick View

$193

per night

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

$150

per night

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4 bed 3 bathroom privately owned villa in Kissimmee
Holiday Rest

Holiday Rest

3 BR | 2 BA | Sleeps 7 | Quick View

$98

per night

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Sensational 3 Bedroom with everything Upgraded Low Weekly Rates

$96

per night

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DEAL
My Disney Townhouse

My Disney Townhouse

4 BR | 3.5 BA | Sleeps 10 | Quick View

Distance to park: 5 miles to Animal Kingdom

$100

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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DEAL

Find your ideal Kissimmee vacation rental today
 
Aiming to take an incredible vacation to Kissimmee this year? Ditch the traditional hotel and opt for a vacation rental instead. We have plenty of properties available in Kissimmee on FloridaRentals.com. Whether you’re looking for a luxury retreat or a kid-friendly home 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. Kissimmee also offers activities for those who love outdoor exploration, with exotic plants and animals in the local nature preserves.
 
Top attractions in Kissimmee
 
The Florida theme parks are the major draw for visitors to the Kissimmee 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 in Kissimmee
 
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 Kissimmee. 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 in Kissimmee
 
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 Kissimmee area's ranching heritage. You can watch bull riding, bronco bucking, barrel racing, steer wrestling, team roping, and even those funny rodeo clowns.
 
Why book your Kissimmee house on FloridaRentals.com?
 
And remember - booking a Kissimmee vacation rental 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!