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Kissimmee Florida Vacation Rentals - Home
1 / 18

Kissimmee Home
4 BR / 2 BA / Sleeps 10 4 10 4 night min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 2 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
The Pirates Retreat has 4 bedrooms, 2 and bathrooms, Sunny Pool, and it is on the WATER with a beautiful view. It has a Game Room with a Pool Table, Ping Pong Table, Foose Ball Table & Dart Board and other games. Th...
(53) Excellent (53 reviews)
Family Room
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Kissimmee Villa
4 BR / 3 BA / Sleeps 8 4 8 Min stay varies
Villa / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
This four bedroom luxury villa is specifically set up for vacationing guests. The house, just 3 miles from Disney, is located in the 24/7 manned gated, prestigious Emerald Island Resort. So close to Disney you can hea...
(1) Excellent (1 review)
Kissimmee Florida Vacation Rentals - Townhouse
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Kissimmee Townhouse
3 BR / 3 BA / Sleeps 8 3 8 Min stay varies
Townhouse / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
BEST LOCATION! Only 1. 5 miles from Disney World, we are in the 2nd closest resort in entire Disney Vacation Home Rental Area! ! Close to everywhere - Supermarket, Restaurant, Golf Course, Shopping Center, etc. W...
(32) Excellent (32 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 65

Kissimmee Villa
9 BR / 6 BA / Sleeps 20 9 20 Min stay varies
Villa / 9 Bedrooms / Sleeps 20
9 bedrooms 6 bathrooms Sleeps 20
High Speed Internet • Dishwasher • Microwave
Windsor at Westside Resort is one of the newest and most luxurious resort communities in the Orlando/Kissimmee, Developed by one of the nation's largest developer , the Pulte Homes. Just 8 miles from Disney, and withi...
(4) Excellent (4 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 48

Kissimmee Home
8 BR / 5 BA / Sleeps 25 8 25 Min stay varies
Home / 8 Bedrooms / Sleeps 25
8 bedrooms 5 bathrooms Sleeps 25
High Speed Internet • Dishwasher • Microwave
As a recent guest described it, we "have the best homes for kids in all of Orlando"! ! ! (Yes, your many hours of hunting down the perfect vacation property are finally over! Our guests prefer our property over the D...
(8) Excellent (8 reviews)
Kissimmee Florida Vacation Rentals - Condo
1 / 15

Kissimmee Condo
3 BR / 3 BA / Sleeps 8 3 8 Min stay varies
Condo / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Reunion is a world class golf resort community located in Central Florida. Less than 10 minutes from Walt Disney World and 25 minutes from the Orlando Intl Airport. Just fifteen minutes to Universal and Sea World and clo...
Kissimmee Florida Vacation Rentals - Home
1 / 34

Kissimmee Home
7 BR / 4.5 BA / Sleeps 16 7 16 Min stay varies
Home / 7 Bedrooms / Sleeps 16
7 bedrooms 4.5 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
Excecutive 7 bedroom pool home in the prestigious guard gated Emerald Island Resort community! Oversized covered lanai overlooks the screen enclosed pool and whirlpool Game room with a pool table and airhocky table ...
(2) Excellent (2 reviews)
Front view with a Palm Tree at the front door
1 / 22

Kissimmee Home
4 BR / 3 BA / Sleeps 10 4 10 Min stay varies
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Within the most desired gated community of Windsor Palms this fantastic 4 bedroom 3 bathroom vacation home with private pool is furnished with two master suites and is nicely decorated with comfort and relaxation in mind...
(9) Excellent (9 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 31

Kissimmee Home
5 BR / 5.5 BA / Sleeps 12 5 12 Min stay varies
Home / 5 Bedrooms / Sleeps 12
5 bedrooms 5.5 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
Property Ref: RVH_088 This custom home, elegantly decorated to a French Country Style features a private pool and spa, separate guest suite, 4, 400 sq ft of spacious living areas, a Cinema room and stunning golf ...
Kissimmee Florida Vacation Rentals - Home
1 / 16

Kissimmee Home
3 BR / 3 BA / Sleeps 8 3 8 2 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
DVD Player • TV (Antenna) • Private Pool
Spacious 2 Story Towne Home idealy located in the upscale Compass Bay community just off of US- 192 in Kissimmee. This 3 bed / 3 bath home has Wifi and is a fully equipped home that sleeps 8 people in comfort and is perf...
Kissimmee Florida Vacation Rentals - Villa
1 / 22

Kissimmee Villa
7 BR / 4.5 BA / Sleeps 16 7 16 Min stay varies
Villa / 7 Bedrooms / Sleeps 16
7 bedrooms 4.5 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
The villa, an exquisitely furnished property offers 2881 s. f. of air- conditioned flexible living & play space for up to 16 people, is located in the prestigious Emerald Island Resort, the closest gated vacation comm...
Kissimmee Florida Vacation Rentals - Home
1 / 22

Kissimmee Home
4 BR / 3 BA / Sleeps 8 4 8 2 night min stay
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • DVD Player • TV (Antenna)
A unique gated vacation community developed and built for the Florida lifestyle! This 4 Bedroom Town Home has all the comforts. There is a King Ensuite on the first floor, a Queen Ensuite and two Twin Bedrooms on the s...
Kissimmee Florida Vacation Rentals - Villa
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Kissimmee Villa
10 BR / 10 BA / Sleeps 24 10 24 1 night min stay
Villa / 10 Bedrooms / Sleeps 24
10 bedrooms 10 bathrooms Sleeps 24
High Speed Internet • Dishwasher • Microwave
This 4800sq/ft villa includes the following amenities: - 10 Luxurious Bedrooms (7 King Rooms suites and 3 Twins Room) - 10 Full Bathrooms - 9 Bedrooms With Private En- Suite Bath - Loft with Big Screen TV and g...
Kissimmee Florida Vacation Rentals - Villa
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Kissimmee Villa
7 BR / 4.5 BA / Sleeps 16 7 16 7 night min stay
Villa / 7 Bedrooms / Sleeps 16
7 bedrooms 4.5 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
An extremely popular vacation home Located less than three miles from Walt Disney World, 3000+ sq ft spacious living space, 7 bedrooms & 4. 5 bathrooms, fully equipped kitchen & laundry, beautifully decorated living...
(15) Excellent (15 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 24

Kissimmee Villa
6 BR / 4 BA / Sleeps 14 6 14 7 night min stay
Villa / 6 Bedrooms / Sleeps 14
6 bedrooms 4 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
Windsor Hills villa description 3 Miles to Disney - Windsor Hills Resort is the nearest gated community to Disney property. Our home has 6 bedrooms, and 4 bathrooms. There are 2 rolling twin beds in the closet, ...
(12) Excellent (12 reviews)
Kissimmee Florida Vacation Rentals - Apartment
1 / 11

Kissimmee Apartment
Studio / 1 BA / Sleeps 4 0 4 No min stay
Apartment / Studio / Sleeps 4
Studio 1 bathroom Sleeps 4
High Speed Internet • Microwave • TV (Cable/Satellite)
Enter into the tropical environment of Magical Dreams, mystical Adventures and Family Fun while staying at this amazing Hotel. As the closest resort to Walt Disney World and the Wide World of Sports, the Resort offers ...
(1) Excellent (1 review)
Kissimmee Florida Vacation Rentals - Home
1 / 37

Kissimmee Home
4 BR / 3 BA / Sleeps 10 4 10 Min stay varies
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
This beautiful 4 bedroom home backs up to the serenity of Star Lake! The views are spectacular, and the house is a comfortable retreat from a long hard day of having fun in Florida! You'll love relaxing by the pool af...
Kissimmee Florida Vacation Rentals - Villa
1 / 22

Kissimmee Villa
5 BR / 3 BA / Sleeps 12 5 12 No min stay
Villa / 5 Bedrooms / Sleeps 12
5 bedrooms 3 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
A Beautiful 5 bedroom 3 bathroom villa, 3 Main Living areas, Large Master Bedroom on suites with A King size Bed. Second King Bedroom with King Size Bed. First Floor Bedroom with Queen size Bed. 2 Twin Bedrooms...
(2) Excellent (2 reviews)
Kissimmee Florida Vacation Rentals - Apartment
1 / 6

Kissimmee Apartment
Studio / 1 BA / Sleeps 4 0 4 No min stay
Apartment / Studio / Sleeps 4
Studio 1 bathroom Sleeps 4
TV (Cable/Satellite) • Air Conditioning • Refrigerator (Mini)
Modest cottages come with decks, cable TV, and WiFi. Individual features depending on the cottage include kitchens, extra bedrooms and pull- out sofas. There are themed events every weekend, and fishing and mini-...
1 / 24

Kissimmee Home
5 BR / 3 BA / Sleeps 12 5 12 Min stay varies
Home / 5 Bedrooms / Sleeps 12
5 bedrooms 3 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
This Luxuriously appointed home is presented with upgraded furniture and fittings throughout, and fully air conditioned to create a comfortable indoor climate. With1 bedroom and bathroom located on the ground floo...
(11) Excellent (11 reviews)
Kissimmee Florida Vacation Rentals - Condo
1 / 30

Kissimmee Condo
2 BR / 2 BA / Sleeps 8 2 8 7 night min stay
Condo / 2 Bedrooms / Sleeps 8
2 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
3 Bedroom 2 Bath Condo For Rent At Windsor Hills! Best Price Guarantee. Closest To Disney - Be On Property In Two Minutes. Full Use Of All Windsor Hills Amenities - king Master Bed - free Wireless Intern...
(15) Excellent (15 reviews)
amazing views from pool deck
1 / 40

Kissimmee Home
4 BR / 3 BA / Sleeps 8 4 8 Min stay varies
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Outstanding 4 Bedroom, 3 Bathroom Private Pool Home with stunning views over a forested conservation area - newly decorated to appeal to all the family with two gorgeous Master Bedrooms, a Princess bedroom and a Super...
Kissimmee Florida Vacation Rentals - Villa
1 / 32

Kissimmee Villa
5 BR / 5.5 BA / Sleeps 10 5 10 Min stay varies
Villa / 5 Bedrooms / Sleeps 10
5 bedrooms 5.5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Property Ref: RVH_107 Situated in the highly sought after Liberty Bluff neighborhood of the Reunion Resort this luxurious 5 bedroom 5. 5 bath sits atop of the signature Legacy course, and boasts panoramic views of th...
Kissimmee Florida Vacation Rentals - Villa
1 / 31

Kissimmee Villa
7 BR / 6 BA / Sleeps 19 7 19 Min stay varies
Villa / 7 Bedrooms / Sleeps 19
7 bedrooms 6 bathrooms Sleeps 19
High Speed Internet • Dishwasher • Microwave
This Home Has 56 - Up To Date, 5 Star, Trip Advisor Reviews, A Lot More, Than Just The One That Is Shown On The Photo. The Site Cannot Move Them Across, So I Have Placed Them In The Testimonials Page, Please View ...
(1) Excellent (1 review)
Kissimmee Florida Vacation Rentals - Villa
1 / 36

Kissimmee Villa
8 BR / 4.5 BA / Sleeps 20 8 20 Min stay varies
Villa / 8 Bedrooms / Sleeps 20
8 bedrooms 4.5 bathrooms Sleeps 20
High Speed Internet • Dishwasher • Microwave
(Please also check out my similar 8 bedroom in Emerald Island Resort, property 77602, property 77717 and property 154310) This Executive vacation home near Disney located in Emerald Island Resort is tastefully decor...
1 / 27

Kissimmee Villa
5 BR / 3 BA / Sleeps 12 5 12 5 night min stay
Villa / 5 Bedrooms / Sleeps 12
5 bedrooms 3 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
Fully Furnished with Two Master Size Sites bedrooms, Pool/Spa, High Speed Wi Fi, 6 TV, Games Area and Gated Resort . Villa Beaulieu, the luxurious house in top rated Solana Resort features 5BR (2 Masters) includ...
(29) Excellent (29 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 25

Kissimmee Villa
6 BR / 5 BA / Sleeps 14 6 14 Min stay varies
Villa / 6 Bedrooms / Sleeps 14
6 bedrooms 5 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
The brand new 6- bedroom, 5- bathroom villa is professionally designed and decorated and has an amazing conservation view. It has three king sized master bedrooms, a loft, kitchen, dining room, living room, private...
Sunset across the Lake
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Kissimmee Villa
5 BR / 3.5 BA / Sleeps 12 5 12 7 night min stay
Villa / 5 Bedrooms / Sleeps 12
5 bedrooms 3.5 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
A WARM & INVITING WELCOME awaits you at our idyllic LAKESIDE family home ... THE PRESIDENTIAL LODGE. As the name suggests, we've spared no expense in creating a luxurious yet comfortable home where you and your fami...
(8) Excellent (8 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 19

Kissimmee Home
4 BR / 3 BA / Sleeps 8 4 8 Min stay varies
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Luxurious house at Rolling Hills. 3 miles to Disney. Excellent location next to Disney. Bedding arrangements are TWO King master suites. Two twin beds in bedrooms three and four. TV's in Family Room and ALL bedro...
(45) Excellent (45 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 78

Kissimmee Home
5 BR / 5 BA / Sleeps 10 5 10 Min stay varies
Home / 5 Bedrooms / Sleeps 10
5 bedrooms 5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Attention shoppers ! If your inquiry to this listing or any listing results in an email response that does not provide a contact name and phone number or if they are asking for payment by wire transfer your inquiry has ...
(1) Poor (1 review)
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About Kissimmee

Whether you want to visit theme parks or nature preserves, Kissimmee is the place to be in Central Florida. Take your pick from dozens of luxurious Kissimmee villas, and enjoy a dip in the pool and plenty of fun in the Florida sun.

Introduction to Kissimmee

Located just a short hop away from Orlando, Kissimmee is a small city that offers quick and convenient access to a whole range of family friendly activities. When you want to take the kids on a trip to Central Florida but don’t want the stress or expense of vacationing at the theme parks, consider staying at one of the affordable Kissimmee villas. Vacation properties in Kissimmee give you the space to have a good time without breaking the bank.

Kissimmee Climate

Like most of Central Florida, Kissimmee enjoys hot, humid summers followed by mild winters. If you visit in December or January, you’ll find temperatures around 60 degrees, while temperatures top out around 90 in July and August.

How to Get Around Kissimmee

If you’re flying to Kissimmee, Orlando International Airport is an easy 25-minute drive away. Public busses and private shuttles can transport visitors around the Kissimmee area, but if you want to explore on your own, renting a car is your best bet. You can easily get from your vacation home to the theme parks, or to the natural attractions, on your own schedule with a car.

Visit the Parks

The rides and attractions at Disney World are just a short drive away, but Kissimmee also boasts several of its own parks. Right on Lake Tohopekaliga, Kissimmee Lakefront Park features a playground and splash park for kids, BBQ grills for family get togethers, and fishing piers for everyone. If you time your visit right, you can even catch one of the many festivals or events on the park’s outdoor stage.

If you’re looking for something more outdoorsy, visit Shingle Creek Regional Park, which encompasses over 1,000 acres. Canoe along the creek, hike the trails, and enjoy a picnic near the park’s historic pioneer homes. Even more impressive is the Disney Wilderness Preserve, which includes 11,500 acres and over 1,000 plant and animal species. Explore wetlands, swamps, and a freshwater marsh while spotting bats, snakes, and even panthers.

Shop and Dine in Old Town

When you’re ready to do some shopping or grab a bite to eat, head straight for Kissimme’s Old Town neighborhood. Here you’ll find everything from souvenir shops to places to stock up on warm weather gear. To fuel up for more adventures, dig into pizza, Tex-Mex, or pub grub. You can even enjoy a night out at one of the live music venues or nightclubs in Old Town.

Just a few miles from Disney, Kissimmee offers the best of everything. With parks and preserves that will keep everyone entertained, Kissimmee villas that comfortably fit the whole family, and easy access to all the fun at Disney World, Kissimmee is a great vacation destination.


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Kissimmee, Florida Travel Tips

Families looking for vacation rentals in Kissimmee, FL have many accommodations to choose from, but renting a home is the best bang for your buck while on a Kissimmee vacation. Rentals by owner offer much more space and privacy than a hotel room, and ensures that homes are very well maintained and updated. Keep reading to learn more tips about how to have a memorable vacation in Kissimmee.

Beaches and Parks

St. Cloud Lakefront Park and Beach offers a fishing pier, splash pad, family picnic area, volleyball court, and playground. Located along the breathtaking Lake Tohopekaliga, this park is a great place to spend a relaxing afternoon.
Cocoa Beach, located just an hour's drive from Kissimmee, features beautiful weather, whale watching, fine dining, and golf.

Theme Parks

What probably comes to mind when looking for houses for rent in Kissimmee, FL is the town's close proximity to world-famous theme parks. The magic of Disney World, Universal Orlando, and SeaWorld are only a short drive away while staying at this delightful vacation spot.
Walt Disney World needs no introduction. As the most visited entertainment complex in the world, this beloved attraction boasts four theme parks and two water parks.
Universal Orlando consists of Universal Studios, Islands of Adventure, and Wet N' Wild Orlando. Visitors can enjoy a variety of shows, dining, and events right within the borders of the park.
SeaWorld is another favorite of those visiting the Orlando area. With tons of shows, exhibits, dining, and shopping, there is surely to be something for everyone to enjoy. Kids will adore seeing killer whales, dolphins, manatees, sharks, polar bears, flamingoes, and penguins up close.

Outdoor Adventures

Airboat Tours are available via Aquatic Adventures Airboat Tours . Go bird watching, look out for alligators, or take a combination hiking tour/boat ride and learn all about the wildlife of the Florida wetlands.
Golf is a popular sport in Florida because of its year-round sunny weather. If you're a seasoned pro looking for challenging courses or just want to play mini-golf with the kids, Kissimmee has you covered.
Hot Air Balloon Rides are a great way to top off your Kissimmee vacation. Take a sunrise balloon ride over Central Florida's beautiful landscape and check out the wildlife from high above.

Fun With Kids

The kids will have no shortage of things to do while enjoying their time in Kissimmee. Kids and parents will have a blast exploring the nearby attractions. In addition to the great outdoors and amazing theme parks, the Kissimmee area also features lots of relaxing, family-friendly activities.
Medieval Times Dinner & Tournament is guaranteed to always be a fun time. Have dinner while being entertained by a live-action jousting tournament.
Osceola County Pioneer Village and Museum features many exhibits depicting life in the 19th century. Located in northwestern Osceola County, the Pioneer Village has a general store, blacksmith shop, one room schoolhouse, and nature preserve.
Green Meadows Petting Farm , located just minutes from Orlando, teaches kids about a variety of farm animals and even allows them to milk a cow. The farm also has a train ride and offers pony rides.