Kissimmee Vacation Rentals

(109 rentals)
Heavenly Retreat-3BR-Pool, WiFi, BBQ, TVs in all Rooms, Disney/Orlando

Heavenly Retreat-3BR-Pool, WiFi, BBQ, TVs in all Rooms, Disney/Orlando

3 BR | 2 BA | Sleeps 7 | Quick View

Distance to park: 12 miles to Disney

$100

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

$120

per night

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8 bedroom home with waterview

8 bedroom home with waterview

8 BR | 4.5 BA | Sleeps 18 | Quick View

$171

per night

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117ADC- Bells Palace

117ADC- Bells Palace

5 BR | 4.5 BA | Sleeps 10 | Quick View

$159

per night

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

$138

per night

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Windsor Hills Large 6 Bedroom Executive Vacation pool house

$185

per night

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6 BEDROOM POOL HOME AT ENCORE CLUB near DISNEY!

$280

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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Davenport Angel with Private Pool

$89

per night

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BELLEAIR

BELLEAIR

6 BR | 5.5 BA | Sleeps 13 | Quick View

$195

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

$99

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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Disney area, Lake view south facing pool 7 bedroom 4 and half bath, 3 king bed

$143

per night

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Perfect Paradise

Perfect Paradise

7 BR | 4.5 BA | Sleeps 16 | Quick View

Inquire for rates

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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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5 STAR RESORT NEAR DISNEY!

5 STAR RESORT NEAR DISNEY!

3 BR | 2 BA | Sleeps 8 | Quick View

Any Closer to Disney and You'll Need a Park Pass!  Southfacing Pool

$185

per night

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3BR 1st Floor Condo Near Disney, Steps from Pool, Loaded with Amenities

$75

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

Distance to park: 10 miles to Disneyworld

$127

per night

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Roughtallys Villa

Roughtallys Villa

7 BR | 4 BA | Sleeps 14 | Quick View

Distance to park: 9 miles to magic kingdom

$201

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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3 bedroom, 3 bathroom home

3 bedroom, 3 bathroom home

3 BR | 3 BA | Sleeps 8 | Quick View

$130

per night

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New Opening 9 Br/6 Ba luxurious Pool House

$300

per night

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DEAL
From $75/nt,4br/3ba TownHome /Hot Tub/lake View,Near Disney,Convention Center

From $75/nt,4br/3ba TownHome /Hot Tub/lake View,Near Disney,Convention Center

4 BR | 3 BA | Sleeps 8 | Quick View

Distance to park: 6 miles to Disney,Seworld

$75

per night

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DEAL
6br/4ba pool house from $120,Near Disney,SeaWorld,Convention Center

6br/4ba pool house from $120,Near Disney,SeaWorld,Convention Center

6 BR | 4 BA | Sleeps 12 | Quick View

Distance to park: 6 miles to Disney kingdom

$120

per night

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DEAL
CONFORT AND PRIVACE NEAR DISNEY INSIDE A RESORT

CONFORT AND PRIVACE NEAR DISNEY INSIDE A RESORT

4 BR | 3 BA | Sleeps 8 | Quick View

Distance to park: 3 miles to Animal Kingdon

$114

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

1

Distance to park: 6 miles to Disney,Seworld

$90

per night

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DEAL
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

1

Distance to park: 3 miles to Disney Animal Kingdom

$75

per night

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Disney Vacation Home Orlando - Paradise Palms Gated Resort

$160

per night

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2 Miles to Disney,4BR/3BA Condo,ALL 1ST FLOOR

2 Miles to Disney,4BR/3BA Condo,ALL 1ST FLOOR

4 BR | 3 BA | Sleeps 10 | Quick View

Distance to park: 2 miles to Disney’s Animal Kingdom Park

$102

per night

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DEAL
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

Distance to park: 6 miles to Disney,Seaworld

$75

per night

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DEAL
ST GEORGES MANOR. STUNNING HOME CLOSE TO THEME PARKS

ST GEORGES MANOR. STUNNING HOME CLOSE TO THEME PARKS

8 BR | 8 BA | Sleeps 18 | Quick View

Distance to park: 2 miles to Disney Animal Kingdom

$800

per night

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5 Bed 3.5 Bath 2802LK Pool/Spa/Gameroom Home  in Emerald Island Resort

$170

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

Distance to park: 2 miles to Disney Animal Kingdom

$620

per night

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Amazing 5 Star; 4/3, 2 en suite; A/C Games Room; +++

$129

per night

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Luxury 3 bedroom villa with generous pool overlooking lake.

Luxury 3 bedroom villa with generous pool overlooking lake.

3 BR | 2 BA | Sleeps 8 | Quick View

Distance to park: 17 miles to Disney 17 miles Universal Studios 18 miles

$82

per night

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2 miles to Disney,1650 sqft 4BR/3BA big Condo from $75/nt

2 miles to Disney,1650 sqft 4BR/3BA big Condo from $75/nt

4 BR | 3 BA | Sleeps 8 | Quick View

Distance to park: 2 miles to Disney’s Animal Kingdom Park

$75

per night

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DEAL
Beautiful & Luxurious 6 Bedroom/5 Bathroom Paradise Palms Pool Home

Beautiful & Luxurious 6 Bedroom/5 Bathroom Paradise Palms Pool Home

6 BR | 5 BA | Sleeps 12 | Quick View

Distance to park: 5 miles to Disney

$170

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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The Retreat by the Lake - Upscale Executive Lakeside Villa near Disney

The Retreat by the Lake - Upscale Executive Lakeside Villa near Disney

4 BR | 2 BA | Sleeps 8 | Quick View

Distance to park: 7 miles to Walt Disney World

$150

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

Distance to park: 3 miles to Disney parks

$143

per night

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Orlando Condo at Legacy Dunes

Orlando Condo at Legacy Dunes

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to park: 5 miles to Disney World

$57

per night

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Brand new 8br/6ba pool villa , Close to Disney

Brand new 8br/6ba pool villa , Close to Disney

8 BR | 6 BA | Sleeps 18 | Quick View

Distance to park: 8 miles to Disney World

$289

per night

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DEAL
1.5 M to Disney,1600 sqft 3BR/3BA Townhome

$65

per night

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DEAL
Villa located just 2 miles from Disney World

$269

per night

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Compass Bay

Compass Bay

3 BR | 2.5 BA | Sleeps 8 | Quick View

$79

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

Distance to park: 3 miles to Disney World

$225

per night

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4 Bed 2659 EIB Pool/Spa/Gameroom Home in the Emerald Island Resort!

$140

per night

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Luxury Legacy Dunes condo close to Disney, Golf and Orlando Fun!

Luxury Legacy Dunes condo close to Disney, Golf and Orlando Fun!

4 BR | 2 BA | Sleeps 10 | Quick View

Distance to park: 5 miles to Disney World

$64

per night

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Local Weather

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DECEMBER

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!