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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...
Kissimmee Florida Vacation Rentals - Condo
1 / 20

Kissimmee Condo
3 BR / 2 BA / Sleeps 7 3 7 Min stay varies
Condo / 3 Bedrooms / Sleeps 7
3 bedrooms 2 bathrooms Sleeps 7
High Speed Internet • Dishwasher • Microwave
The Absolute Best Location within the Windsor Palms Community! ! The convenience of this location will save you Money and Time. Easy to get around the the Parks, Stores and Restaurants of your choice. Within the ...
Kissimmee Florida Vacation Rentals - Villa
1 / 25

Kissimmee Villa
6 BR / 5.5 BA / Sleeps 14 6 14 Min stay varies
Villa / 6 Bedrooms / Sleeps 14
6 bedrooms 5.5 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
Our Luxury Villas are located in the 5 Star Gated Community at Solana Resort. This HIgh End Villa is very spacious and are ideal for a two party groups or extended families. The nightly rate starts at $175 to $265 pe...
(6) Excellent (6 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 13

Kissimmee Villa
4 BR / 3 BA / Sleeps 10 4 10 No min stay
Villa / 4 Bedrooms / Sleeps 10
4 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Gorgious private Disney vacation villa only 3 miles from disney and close to all other attractions. Including 4 Bedrooms/3 full baths/ south facing private enclosed pool and jacuzzi/ game room/ and all the comforts of ho...
(2) Excellent (2 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 20

Kissimmee Villa
3 BR / 2 BA / Sleeps 8 3 8 Min stay varies
Villa / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Our charming sweet home is conveniently located , in a dead- end and a small, quiet gated community called :Windward cay. The villa is fully furnished in a comtemporay style. This 3 bedrooms 2 bathrooms, can put off 8...
(37) Excellent (37 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 • 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...
Kissimmee Florida Vacation Rentals - Villa
1 / 33

Kissimmee Villa
6 BR / 5.5 BA / Sleeps 15 6 15 Min stay varies
Villa / 6 Bedrooms / Sleeps 15
6 bedrooms 5.5 bathrooms Sleeps 15
High Speed Internet • Dishwasher • Microwave
Emerald Island Resort is one of the most prestigious vacation home communities. It is located less than 3 miles from Walt Disney World. This villa is the most private villa in the resort. It has a private pool and a heat...
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...
Windsor Palms Resort Club House
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Kissimmee Home
6 BR / 3.5 BA / Sleeps 12 6 12 3 night min stay
Home / 6 Bedrooms / Sleeps 12
6 bedrooms 3.5 bathrooms Sleeps 12
Dishwasher • Microwave • DVD Player
This luxury vacation home is located in the top- rated popular Windsor Palms resort, which is a 24x7 securely gated community with just 3 miles (5 mins drive) to Disney. This home was equipped with all solid wood high q...
(4) Excellent (4 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 44

Kissimmee Villa
7 BR / 4.5 BA / Sleeps 14 7 14 3 night min stay
Villa / 7 Bedrooms / Sleeps 14
7 bedrooms 4.5 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
Welcome to the latest additions to our Emerald Island Resort collection, Emerald Island #2 and Emerald Island #3. With its luxurious decor and prime location only 4 miles to Disney, this is our very best of the best! ...
(4) Excellent (4 reviews)
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 / 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 ...
1 / 28

Kissimmee Villa
6 BR / 5 BA / Sleeps 16 6 16 Min stay varies
Villa / 6 Bedrooms / Sleeps 16
6 bedrooms 5 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
Brand new luxury 3, 300 sqft, two- story single family home located on an exclusive gated resort. It is only 10 minutes away from Disney theme parks. 6 bedrooms, 5 bath, loft, and game room. Spacious kitchen...
(3) Excellent (3 reviews)
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)
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)
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 • Dishwasher • Microwave
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 / 29

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_211 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 paste...
Kissimmee Florida Vacation Rentals - Home
1 / 26

Kissimmee Home
7 BR / 4.5 BA / Sleeps 14 7 14 Min stay varies
Home / 7 Bedrooms / Sleeps 14
7 bedrooms 4.5 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
Welcome to this spacious seven bedroom luxurious home. Just 3 miles from Walt Disney World at the gated Emerald Island resort. This beautifully furnished and professionally decorated villa has 7 bedrooms (one master ...
(9) Excellent (9 reviews)
Front
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Kissimmee Home
4 BR / 3 BA / Sleeps 10 4 10 3 night min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
This 4 bedroom vacation house has it ALL. It can fit two families (8- 10 people) This model features a spacious single story open floor plan, and a screened- in private pool With beautiful ceramic tile throughout the ho...
(18) Excellent (18 reviews)
Sunset across the Lake
1 / 48

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 - Villa
1 / 16

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
This beautiful 5- bedroom and 3- full bathroom pool home with a beautiful water view is waiting for you and your family to enjoy your vacation in sunshine Central Florida. This home is located right off Highway 27, Nort...
(28) Excellent (28 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 29

Kissimmee Villa
7 BR / 5.5 BA / Sleeps 16 7 16 Min stay varies
Villa / 7 Bedrooms / Sleeps 16
7 bedrooms 5.5 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
Our 7 Bedroom villa is ideal for the two things you are supposed to do on an Orlando Vacation - REST and PLAY! ! ! It is spectacular because you will be Razzle- Dazzled by the many amenities that abound. Travel the wor...
(26) Excellent (26 reviews)
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)
Kissimmee Florida Vacation Rentals - Home
1 / 37

Kissimmee Home
6 BR / 6 BA / Sleeps 12 6 12 2 night min stay
Home / 6 Bedrooms / Sleeps 12
6 bedrooms 6 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
This home offers luxury with modernity featuring fresh and clean style. The home has been fully upgraded appliances with high end art pieces and decor. The space feels open and airy with a spacious living room, conversa...
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 • Dishwasher • Microwave
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 - Condo
1 / 13

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 - Townhouse
1 / 16

Kissimmee Townhouse
3 BR / 2 BA / Sleeps 8 3 8 4 night min stay
Townhouse / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
Dishwasher • Microwave • Washer/Dryer
Venetian Bay Villages is a community full of white picket fences, friendly sidewalk trails, numerous pools and a clubhouse that rivals any major resort. It is located only minutes away from the restaurants and attracti...
(7) Excellent (7 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 23

Kissimmee Villa
8 BR / 4.5 BA / Sleeps 20 8 20 No min stay
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...
(2) Excellent (2 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 19

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
VERY FRIENDLY, PET FRIENDLY Sunny Oak is a very clean, ALL NEW TILED T/O, except bedrooms, perfect for Pet friendly, very well kept villa located in the peaceful community of Indian Point, only minutes to Disney...
1 / 24

Kissimmee Townhouse
5 BR / 4.5 BA / Sleeps 12 5 12 Min stay varies
Townhouse / 5 Bedrooms / Sleeps 12
5 bedrooms 4.5 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
The 5- bedroom, 4. 5- bathroom Town House is professionally designed and decorated. It has two king sized master bedrooms, a queen sized master suite, a loft, kitchen, dining room, living room, private lanai, and...
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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.