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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 - 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 • Air Conditioning
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 / 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 - Villa
1 / 32

Kissimmee Villa
7 BR / 4.5 BA / Sleeps 18 7 18 Min stay varies
Villa / 7 Bedrooms / Sleeps 18
7 bedrooms 4.5 bathrooms Sleeps 18
High Speed Internet • Dishwasher • Microwave
The spacious 2900 square ft highly furnished and fully air conditioned villa has been tastefully renovated & decorated to feature your all vacation needs . Brand new & high standard beddings & linens to ensure you comfor...
(8) Excellent (8 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 37

Kissimmee Villa
6 BR / 4 BA / Sleeps 14 6 14 Min stay varies
Villa / 6 Bedrooms / Sleeps 14
6 bedrooms 4 bathrooms Sleeps 14
Dishwasher • Microwave • Washer/Dryer
[We also have another beautiful 5 bed, 3. 5 bath villa on Sunset Lakes ~ Please enquire about availabiliy if Sunset Lakes is booked ] Superior 6 bed, 4 bath Vacation Home ~ Sleeps 14 Guests Affordable Luxury ~ ...
(27) Excellent (27 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
Dishwasher • Microwave • Washer/Dryer
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...
(14) Excellent (14 reviews)
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 / 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 - Townhouse
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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 - 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 - Home
1 / 37

Kissimmee Home
3 BR / 3 BA / Sleeps 6 3 6 Min stay varies
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 3 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Thanks for considering our properties. We would be happy to call you or receive your call to discuss any aspect of the rental. Choice of a Splash Pool home or an identical Spa/jacuzzi home on the same street. Or book...
(13) Excellent (13 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 - Villa
1 / 70

Kissimmee Villa
6 BR / 5 BA / Sleeps 14 6 14 3 night min stay
Villa / 6 Bedrooms / Sleeps 14
6 bedrooms 5 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
Welcome to our brand new luxurious villa located at the Paradise Palm Resort. If you are looking for an amazing vacation to enjoy the sun shine, this is the perfect place for you. This resort has one of the best ameniti...
(1) Excellent (1 review)
Kissimmee Florida Vacation Rentals - Home
1 / 9

Kissimmee Home
3 BR / 2 BA / Sleeps 6 3 6 Min stay varies
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Lovely 3 bedroom 2 bathroom villa with private screened in pool, only minutes to Disney and all other major attractions located in Kissimmee, Florida in the most sought out community of Chatham Park. Our Beautiful ho...
(15) Excellent (15 reviews)
Kissimmee Florida Vacation Rentals - Condo
1 / 44

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
"HEMINGWAY'S ANIMAL KINGDOM! " WOW! ! ! ! Imagine you and your family staying in this NEW, spacious home for your Disney World vacation at nightly rates that are typically LESS than those of a small local Disney ...
(2) Excellent (2 reviews)
Kissimmee Florida Vacation Rentals - Condo
1 / 33

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
Our most requested and repeated home! "Simba's Pride" has spectacular framed wildlife and African wildlife photography everywhere that you and the children will adore. You'll enjoy an incredible family room featurin...
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)
1 / 28

Kissimmee Villa
8 BR / 4.5 BA / Sleeps 18 8 18 Min stay varies
Villa / 8 Bedrooms / Sleeps 18
8 bedrooms 4.5 bathrooms Sleeps 18
High Speed Internet • Dishwasher • Microwave
Luxury 8 bedroom villa accommodates up to 18. Upgraded 8- Bedroom Villa, whole home tastefully decorated by designer. On- site property manager just a phone call away. 2 Spacious KING rooms both Ensuite 3 QUEEN...
(10) Excellent (10 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 25

Kissimmee Villa
6 BR / 4.5 BA / Sleeps 13 6 13 3 night min stay
Villa / 6 Bedrooms / Sleeps 13
6 bedrooms 4.5 bathrooms Sleeps 13
High Speed Internet • Dishwasher • Microwave
'Penny Lane' is perfectly located on the exclusive Emerald Island gated resort community, less than 3 miles from Walt Disney World in Kissimmee, Florida. With 6 bedrooms and 4. 5 bathrooms, this fully air- conditioned...
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 - 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 - Villa
1 / 12

Kissimmee Villa
4 BR / 2.5 BA / Sleeps 9 4 9 No min stay
Villa / 4 Bedrooms / Sleeps 9
4 bedrooms 2.5 bathrooms Sleeps 9
High Speed Internet • Dishwasher • Microwave
Take a "Palm" Escape and still be close to everything. Located behind the Super Walmart... in Popular Indian Point Subdivision that features - tennis - a play ground - community pool and recreation center. Relax at th...
(21) Excellent (21 reviews)
Kissimmee Florida Vacation Rentals - Condo
1 / 10

Kissimmee Condo
2 BR / 2 BA / Sleeps 4 2 4 1 night min stay
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
Legacy Dunes, Two bedrooms, Master Suite with King bed with walk in closet with private bathroom, T. V, second bedroom with Queen bed walk in closet T. V. Family room with T. V. and balcony, dishwasher Wi- Fi, 250 ...
Royal Palm Bay entrance
1 / 14

Kissimmee Condo
3 BR / 2 BA / Sleeps 8 3 8 5 night min stay
Condo / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
My Condo Sweet Condo is a great place to vacation. It has 3 bedrooms (master bedroom has queen sized bed, second bedroom has double bed, and third bedroom has 2 twin beds and the king sized sleeper sofa in the living r...
(6) Excellent (6 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 23

Kissimmee Villa
6 BR / 4 BA / Sleeps 14 6 14 Min stay varies
Villa / 6 Bedrooms / Sleeps 14
6 bedrooms 4 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
Located just 3 miles from the gates of Walt Disney, this fully air conditioned home away from home offers comfort and style throughout. To make your stay an extra special one, spread out, relax and enjoy a great night...
Kissimmee Florida Vacation Rentals - Condo
1 / 23

Kissimmee Condo
3 BR / 2 BA / Sleeps 8 3 8 4 night min stay
Condo / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Our Condo is totally new and completely refurnished. Our Kitchen has been totally gutted and completed redone. We have all brand new custom kitchen cabinets. And we have all new beautiful granite kitchen counter tops...
Front View
1 / 15

Kissimmee Home
3 BR / 2 BA / Sleeps 8 3 8 No min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Enjoy this 3 bedroom, 2 bath vacation home, which easily accommodates 1 or 2 families, with a maximum sleeping capacity of 8. For your enjoyment the home has its own private screened in pool, and is located in the ga...
(3) Excellent (3 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 / 23

Kissimmee Villa
8 BR / 4.5 BA / Sleeps 19 8 19 Min stay varies
Villa / 8 Bedrooms / Sleeps 19
8 bedrooms 4.5 bathrooms Sleeps 19
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 / 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)
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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.