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Kissimmee Florida Vacation Rentals - Villa
1 / 17

Kissimmee Villa
5 BR / 3.5 BA / Sleeps 10 5 10 Min stay varies
Villa / 5 Bedrooms / Sleeps 10
5 bedrooms 3.5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
5 bdrm, 3. 5 baths, sleeps 10 - 2600+ sq ft. This luxurious and well appointed 5 bedroom villa features: On the main floor, 1 master bedroom with a King bed, a private sitting room with direct access to the poo...
Front of Condo
1 / 7

Kissimmee Townhouse
3 BR / 2.5 BA / Sleeps 8 3 8 Min stay varies
Townhouse / 3 Bedrooms / Sleeps 8
3 bedrooms 2.5 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Back overlooks woodland with a southerly aspect. Master bedroom has it's own balcony overlooking same woodland. All the homes are painted in vibrant Mediterranean colors. The home has fully equipped kitchen and seperate ...
(3) Excellent (3 reviews)
Kissimmee Florida Vacation Rentals - Apartment
1 / 41

Kissimmee Apartment
3 BR / 2 BA / Sleeps 8 3 8 7 night min stay
Apartment / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Ada
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)
Kissimmee Florida Vacation Rentals - Condo
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Kissimmee Condo
2 BR / 2 BA / Sleeps 6 2 6 7 night min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Our modern spacious two- bedroom, two bathroom villa will give you the best in comfort and convenience during your vacation. Sleeping four adults in comfort and equipped with an additional double sofa- bed, our villa p...
(9) Excellent (9 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 52

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
Please be our Guest at the amazing “Disney Lillian House”, newly updated just for you! GRANITE KITCHEN not pictured (pics coming first week of May) Perfect for large families and groups, accommodating up to 10 gue...
Day Time pool view
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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
Our main page at our site My Orlando Stay has more details and pictures. Vacation Home features Sleeps Easily sleep up to 8 people Bedrooms 3 bedrooms, master with King, King/Queen in Guest and 2 twins in Kids ...
(24) Excellent (24 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 20

Kissimmee Home
4 BR / 2 BA / Sleeps 8 4 8 Min stay varies
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Tucked away in a quiet, family neighborhood, this 4 bedroom home is a perfect place for families looking for some peace and quiet. Located in a safe cul- de- sac, this home sees very little traffic, making it a great...
Kissimmee Florida Vacation Rentals - Condo
1 / 30

Kissimmee Condo
3 BR / 2 BA / Sleeps 8 3 8 Min stay varies
Condo / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Condominium: It is a reasonably priced, professionally decorated and furnished 3- bedroom/2- bathroom condominium offering comfort, space, style, luxury and privacy. It is located at a luxurious and upscale gated Can...
(5) Excellent (5 reviews)
Exclusive Two Story Home
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Kissimmee Home
6 BR / 3 BA / Sleeps 13 6 13 5 night min stay
Home / 6 Bedrooms / Sleeps 13
6 bedrooms 3 bathrooms Sleeps 13
High Speed Internet • Dishwasher • Microwave
Pooh's Villa is a newer home with the most luxurious "top of the line" furnishings including "high tech" extras yet is has all the comforts of home. Pooh's Villa sits on a huge yard with lot's of privacy that backs up to...
(55) Excellent (55 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 33

Kissimmee Villa
5 BR / 4 BA / Sleeps 12 5 12 Min stay varies
Villa / 5 Bedrooms / Sleeps 12
5 bedrooms 4 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
For those looking for the ultimate vacation rental experience, this is the right villa! Located in the tropical grounds of Emerald Island Resort near Disney World, this huge 5 bed villa offers outstanding amenities at...
Kissimmee Florida Vacation Rentals - Home
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Kissimmee Home
8 BR / 5.5 BA / Sleeps 18 8 18 Min stay varies
Home / 8 Bedrooms / Sleeps 18
8 bedrooms 5.5 bathrooms Sleeps 18
High Speed Internet • Dishwasher • Microwave
Our emerald island villa with luxury furnished 8 bedrooms / 5. 5 baths 4 Master bedrooms ( 3 master suite, 2 family suite ) and private pool/spa is situated in the magnificent 24- hour gated security resort, just 3 mil...
(6) Excellent (6 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 58

Kissimmee Villa
8 BR / 6 BA / Sleeps 20 8 20 Min stay varies
Villa / 8 Bedrooms / Sleeps 20
8 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...
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 - Home
1 / 33

Kissimmee Home
6 BR / 4 BA / Sleeps 15 6 15 Min stay varies
Home / 6 Bedrooms / Sleeps 15
6 bedrooms 4 bathrooms Sleeps 15
High Speed Internet • Dishwasher • Microwave
Located In Rolling Hills (which Is Near Emerald Island, Windsor Hills) 3 Miles To Disney 4 King Bedrooms (6 Total Bedrooms) 1 Queen Bedroom Kids Room Has 2 Queen Beds 4 Full Bathrooms Huge Gigantic Pool And...
(5) Excellent (5 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 14

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 • Washer/Dryer • DVD Player
This villa is all on one level, so makes it perfect if you are traveling with elderly or disabled guests. There are 5 bedrooms and 3 full bathrooms, two separate seating areas both with TVs and a games room, so plenty...
Kissimmee Florida Vacation Rentals - Villa
1 / 49

Kissimmee Villa
6 BR / 4 BA / Sleeps 12 6 12 Min stay varies
Villa / 6 Bedrooms / Sleeps 12
6 bedrooms 4 bathrooms Sleeps 12
Dishwasher • Microwave • Washer/Dryer
1. 'RATED EXCELLENT' by Tripadvisor 2. 'Top Rental Property - Winner 2011, ' awarded by Flipkey Congratulations ! Based at exceptional guests reviews and impressive listings . Kissimmee Vacation Rentals Wit...
(30) Excellent (30 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 68

Kissimmee Villa
7 BR / 5.5 BA / Sleeps 16 7 16 3 night min stay
Villa / 7 Bedrooms / Sleeps 16
7 bedrooms 5.5 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
This 3500sq/ft villa includes the following amenities: - 7 Luxurious Bedrooms (2 King, 3 Queen, 2 kids room) - Loft with Queen Sleeper sofa - 5 Bathrooms - Fully equipped kitchen - Spacious sitting and dini...
(2) Excellent (2 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 25

Kissimmee Villa
5 BR / 5.5 BA / Sleeps 10 5 10 4 night min stay
Villa / 5 Bedrooms / Sleeps 10
5 bedrooms 5.5 bathrooms Sleeps 10
Property Reference # RVH_198 This large 3, 045 sq. ft pool home is located within the Patriots Landing neighborhood of the exclusive Reunion Resort. Patriot`s Landing offers Key West- style luxury homes with past...
Kissimmee Florida Vacation Rentals - Home
1 / 49

Kissimmee Home
5 BR / 5 BA / Sleeps 12 5 12 7 night min stay
Home / 5 Bedrooms / Sleeps 12
5 bedrooms 5 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
Welcome to The Windsor Dream - The Ultimate Villa at Windsor Hills - A luxurious south- facing home with private pool and hot- tub, with no rear neighbors. The most important feature of our family retreat is that ...
(1) Excellent (1 review)
Kissimmee Florida Vacation Rentals - Home
1 / 25

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_081 This beautiful home has everything you need to create your dream stay in Reunion Resort. A large pool and spa, luxurious decor that creates a homely ambiance, over 5, 000 sq. ft of spacious li...
(1) Excellent (1 review)
Kissimmee Florida Vacation Rentals - Villa
1 / 37

Kissimmee Villa
4 BR / 2.5 BA / Sleeps 8 4 8 3 night min stay
Villa / 4 Bedrooms / Sleeps 8
4 bedrooms 2.5 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Extremely close to Walt Disney World! Our lovely Lakeside Villa is located in Oak Island Harbour in the Formosa Gardens Area. This two story home is situated on a quiet, tree lined street less than 1/2 mile to Highway ...
Kissimmee Florida Vacation Rentals - Home
1 / 32

Kissimmee Home
4 BR / 4 BA / Sleeps 8 4 8 Min stay varies
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 4 bathrooms Sleeps 8
Washer/Dryer • DVD Player • Air Conditioning
Located on the Regal Palms resort in Davenport this is a pretty end of terrace 2 storey town home with 4 bedrooms and 3. 5 bathrooms. The downstairs has been newly tiled and the whole villa is tastefully decorated and fu...
Kissimmee Florida Vacation Rentals - Home
1 / 17

Kissimmee Home
6 BR / 4 BA / Sleeps 12 6 12 Min stay varies
Home / 6 Bedrooms / Sleeps 12
6 bedrooms 4 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
Veranda Palms Resort- Kissimmee, Florida is an upscale gated community located just 5 miles from Walt Disney World. This luxury resort sits nestled just outside of Orlando, Florida and has quickly become one of the mos...
(1) Excellent (1 review)
Kissimmee Florida Vacation Rentals - Townhouse
1 / 21

Kissimmee Townhouse
4 BR / 3 BA / Sleeps 10 4 10 Min stay varies
Townhouse / 4 Bedrooms / Sleeps 10
4 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
'Every Day with Rachael Ray' Magazine recommended vacation home, on page 162, Dec. 2010/Jan. 2011 issue! ! ! Minutes to parks. Affordable luxury. Free Wireless Internet. Charming four- bedroom villas in the heart ...
(48) Excellent (48 reviews)
1 / 14

Kissimmee Villa
4 BR / 2.5 BA / Sleeps 10 4 10 Min stay varies
Villa / 4 Bedrooms / Sleeps 10
4 bedrooms 2.5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Note: If This House Is Booked For Your Desired Days, Feel Free To Send Us An Inquiry Because We Have Several Vacation Homes In The Disney Area And May Have One Available For Your Desired Days. Hi And Thank You For...
(15) Excellent (15 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 16

Kissimmee Home
3 BR / 3 BA / Sleeps 8 3 8 Min stay varies
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
This is a 3 Bedroom 3 Bath Town House Located In Crestwynd Bay And Just A Mile From Disney Gates. The Home Consists Of 1 KING Bed With Attached Bathroom, 1 QUEEN Bed With Bathroom On The Side, 1 Kids Bedroom With 2 Twi...
Kissimmee Florida Vacation Rentals - Home
1 / 21

Kissimmee Home
4 BR / 3.5 BA / Sleeps 10 4 10 4 night min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 3.5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
$1200 Per Week In Month Of February , March, April ( Ask About May & June Specials ) (cleaning & Taxes Included ) Optional Pool Heat Is $140 Per Week No Animals & No Smoking No Animals & No Smoking This Luxuriously...
Kissimmee Florida Vacation Rentals - Villa
1 / 18

Kissimmee Villa
5 BR / 4 BA / Sleeps 12 5 12 3 night min stay
Villa / 5 Bedrooms / Sleeps 12
5 bedrooms 4 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
Beautiful Vacation Villa by the name Tree House is highly furnished and decorated with up scale furnishings, attractive amenities, new beddings and lot of upgrades. Situated about 3 miles away from the Disney’s e...
(27) Excellent (27 reviews)
Kissimmee Florida Vacation Rentals - Townhouse
1 / 13

Kissimmee Townhouse
3 BR / 3 BA / Sleeps 8 3 8 30 night min stay
Townhouse / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Welcome to 1 of my 2 gorgeous vacation houses located on the same site, couple steps from each other. They are located on the quiet and beautiful Crestwynd Bay in Kissimmee, which has the definition of "convenience"....
(103) Excellent (103 reviews)
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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.