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Kissimmee Florida Vacation Rentals - Villa
1 / 41

Kissimmee Villa
4 BR / 2 BA / Sleeps 10 4 10 3 night min stay
Villa / 4 Bedrooms / Sleeps 10
4 bedrooms 2 bathrooms Sleeps 10
High Speed Internet • Microwave • Dishwasher
Welcome to Indian Point Villa, our Villa is fully air- conditioned has four bedrooms two bath rooms a dinning area, kitchen and breakfast area, a double garage/games room its own very large private pool with toddlers ...
(19) Excellent (19 reviews)
Kissimmee Florida Vacation Rentals - Condo
1 / 32

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 • Microwave • Dishwasher
Condominium: It is a professionally decorated and furnished and spacious 3- bedroom/2- bathroom condominium offering space, style, luxury and privacy. It is nestled in Villas at Island Club Resort. This beautiful, gat...
(8) Excellent (8 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 15

Kissimmee Home
6 BR / 4 BA / Sleeps 14 6 14 No min stay
Home / 6 Bedrooms / Sleeps 14
6 bedrooms 4 bathrooms Sleeps 14
High Speed Internet • Microwave • Dishwasher
This luxury home is situated in the 5 star resort community of Windsor Hills in Kissimmee, Florida. It is located only 2 miles from Disney World! Closer to Disney and other Orlando attractions than most hotels! This h...
(2) Excellent (2 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 13

Kissimmee Home
5 BR / 3.5 BA / Sleeps 10 5 10 Min stay varies
Home / 5 Bedrooms / Sleeps 10
5 bedrooms 3.5 bathrooms Sleeps 10
High Speed Internet • Microwave • Dishwasher
5 Bedroom / 3. 5 Bath luxury vacation home in Orlando close to Disney. Private swimming pool, outdoor hot tub, and free wireless internet included on all reservations. This villa has two master bedrooms, each with a p...
(1) Excellent (1 review)
Kissimmee Florida Vacation Rentals - Villa
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 • Microwave • Dishwasher
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 / 19

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 • Microwave • Dishwasher
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...
(56) Excellent (56 reviews)
Kissimmee Florida Vacation Rentals - Townhouse
1 / 35

Kissimmee Townhouse
4 BR / 3 BA / Sleeps 10 4 10 3 night min stay
Townhouse / 4 Bedrooms / Sleeps 10
4 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Microwave • Dishwasher
Welcome to your "home away from home! " You'll be greeted by a spacious and inviting interior when you step inside your vacation townhome at Coral Cay Resort . You will enjoy watching your favorite shows and DVD movies ...
(36) Excellent (36 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 16

Kissimmee Villa
7 BR / 4.5 BA / Sleeps 16 7 16 No min stay
Villa / 7 Bedrooms / Sleeps 16
7 bedrooms 4.5 bathrooms Sleeps 16
High Speed Internet • Microwave • Dishwasher
Two Luxury Private Villas: within 5 minutes walking distance to each other, each house 3500 s. f - 7 Bedrooms - 4. 5 Bathrooms - Oversized private Heated Pool/Spa - Game Room - 10 min. to Disney World; can be rent...
(1) Excellent (1 review)
Kissimmee Florida Vacation Rentals - Condo
1 / 30

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 • Microwave • Dishwasher
It's called "The Lion Kings! " and WOW, will you and your family absolutely fall in love with this Disney World area home, This spectacular, newly re- designed and newly furnished Disney World area home has TWO k...
Kissimmee Florida Vacation Rentals - Villa
1 / 27

Kissimmee Villa
4 BR / 3 BA / Sleeps 8 4 8 4 night min stay
Villa / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Microwave • Dishwasher
Lovely, fully furnished home is one of the best kept turnkey properties you will find in Indian Creek ! Has an airy open floor plan, lots of light. Enjoy the crystal clear South facing pool and the covered lanai on yo...
(15) Excellent (15 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 10

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
High Speed Internet • Microwave • Dishwasher
This is a nice three bedroom homes personally decorated, furnished and maintained well. It is located in Crestwynd Bay a gated community which is peaceful and safe as well as closest to shopping, Disney and restaurants...
Kissimmee Florida Vacation Rentals - Villa
1 / 32

Kissimmee Villa
4 BR / 3 BA / Sleeps 10 4 10 Min stay varies
Villa / 4 Bedrooms / Sleeps 10
4 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Microwave • Dishwasher
This new 4br/3br/2 Masters 4- bedroom/3- bathroom villa has a large pool and Jacuzzi, TV in every room and GameCube, pool table and air- hockey, and is conveniently located in "Hamlet at Westhaven" community, a gated...
(7) Excellent (7 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 41

Kissimmee Home
4 BR / 3 BA / Sleeps 8 4 8 4 night min stay
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Microwave • Dishwasher
Ideally located just minutes from Disney many great golf courses near by. Why stay in a cramped hotel room when you can stay at Debbie's Florida Retreat a beautifully decorated, Luxury Pool Home with 4 bedrooms, 3 ...
(50) Excellent (50 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 29

Kissimmee Villa
6 BR / 3.5 BA / Sleeps 12 6 12 Min stay varies
Villa / 6 Bedrooms / Sleeps 12
6 bedrooms 3.5 bathrooms Sleeps 12
High Speed Internet • Microwave • Dishwasher
Luxurious 6 Bedrooms 3. 5 Bathroom Vacation Home w/ Heated Pool, Hot Tub, Surround Sound HD TV and Internet. Situated 10 min. from Disney. Vacation in the comfort and safety of Lake Berkley Resort - a gated resort...
(2) Excellent (2 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 25

Kissimmee Home
6 BR / 3.5 BA / Sleeps 14 6 14 Min stay varies
Home / 6 Bedrooms / Sleeps 14
6 bedrooms 3.5 bathrooms Sleeps 14
High Speed Internet • Microwave • Dishwasher
Come and enjoy the family vacation of life time when guests stay on fantastic 6bedrooms resorts home in 5 Star Windsor Palm Resorts in Kissimmee, most sought after luxurious gates communities. About 3 miles distance for...
(15) Excellent (15 reviews)
Kissimmee Florida Vacation Rentals - Condo
1 / 18

Kissimmee Condo
3 BR / 2 BA / Sleeps 6 3 6 Min stay varies
Condo / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
Microwave • Dishwasher • Air Conditioning
Windsor Hills is one of the newest and greatest gated community located within the heart of Orlando’s premier tourist attractions. Windsor Hills boasts the closest proximity to Central Florida's theme parks. Windsor Hi...
(15) Excellent (15 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 • Microwave • Dishwasher
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 / 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 • Microwave • Dishwasher
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 - Townhouse
1 / 18

Kissimmee Townhouse
3 BR / 2 BA / Sleeps 8 3 8 No min stay
Townhouse / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Microwave • Dishwasher
Gorgeous Newer Townhome With All The Features Of Home In A Private Gated Resort- like Community - You Wont Want To Leave! ! ! 5- star Resort Townhouse Features 3 Bedrooms, 2 Bathrooms, Full Kitchen, Dining And Livin...
(3) Excellent (3 reviews)
Kissimmee Florida Vacation Rentals - Home
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 • Microwave • Dishwasher
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...
(10) Excellent (10 reviews)
Kissimmee Florida Vacation Rentals - Townhouse
1 / 20

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 • Microwave • Dishwasher
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 / 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 • Microwave • Dishwasher
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 - 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 • Microwave • Dishwasher
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...
Kissimmee Florida Vacation Rentals - Townhouse
1 / 16

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 • Microwave • Dishwasher
Just perfect for families who want to be close to the Theme parks but don't want to spend big $$$ on accommodation! This wonderful home is located in the highly popular gated resort community of Terra Verde. This ...
(10) Excellent (10 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 44

Kissimmee Villa
8 BR / 5 BA / Sleeps 18 8 18 Min stay varies
Villa / 8 Bedrooms / Sleeps 18
8 bedrooms 5 bathrooms Sleeps 18
High Speed Internet • Microwave • Dishwasher
Welcome to our brand new luxury finished 3600 Sqft pool home at beautiful Crystal Cove Resort. It is conveniently located close to shopping and dining (less than 1 mile away). Disney is only 6 miles away. Just minutes fr...
(13) Excellent (13 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 16

Kissimmee Villa
6 BR / 3.5 BA / Sleeps 14 6 14 Min stay varies
Villa / 6 Bedrooms / Sleeps 14
6 bedrooms 3.5 bathrooms Sleeps 14
High Speed Internet • Microwave • Dishwasher
Come to Enjoy this cal- de- sac villa in famous Windsor Palm. Walking distance to clubhouse house and tennis courts. Only 4. 5 Miles to Disney in a luxurious guard gated community. This turnkey investment home provid...
(1) Excellent (1 review)
Kissimmee Florida Vacation Rentals - Townhouse
1 / 28

Kissimmee Townhouse
3 BR / 3 BA / Sleeps 8 3 8 7 night min stay
Townhouse / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Microwave • Dishwasher
New End Unit! Our Most Private And Best Priced 3 Bedroom, 3 Bath Townhouse With Private South Facing Pool For Rent At Windsor Hills. It Features A Large Yard Out Back, A Screened In Lanai, And South Facing Pool W...
(17) Excellent (17 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 16

Kissimmee Home
5 BR / 4 BA / Sleeps 12 5 12 No min stay
Home / 5 Bedrooms / Sleeps 12
5 bedrooms 4 bathrooms Sleeps 12
High Speed Internet • Microwave • Dishwasher
Dopey's Delight is a Disney vacation rental that is nestled in the popular Indian Creek community, less than 3 miles from Disney's doorstep in Kissimmee, Florida and is perfectly placed for the shops, restaurants, fu...
(17) Excellent (17 reviews)
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 • Microwave • Dishwasher
(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) Excellent (1 review)
Kissimmee Florida Vacation Rentals - Villa
1 / 52

Kissimmee Villa
7 BR / 7 BA / Sleeps 16 7 16 Min stay varies
Villa / 7 Bedrooms / Sleeps 16
7 bedrooms 7 bathrooms Sleeps 16
High Speed Internet • Microwave • Dishwasher
This is a beautiful 7 bedrooms / 5 full and 2 half bathrooms. The home is perfectly located in the quiet gated community of Cumbrian Lakes. The home has a fabulous view of one of the lakes in the community which is south...
(4) Excellent (4 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

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.