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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 - 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 / 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 / 29

Kissimmee Villa
6 BR / 4 BA / Sleeps 14 6 14 2 night min stay
Villa / 6 Bedrooms / Sleeps 14
6 bedrooms 4 bathrooms Sleeps 14
High Speed Internet • Microwave • Washer/Dryer
Welcome to our luxury villa, which is just 2 miles from Disney Orlando. Luxury villa has 6 bedrooms, 4 baths with Private Pool & Spa, and sleeps up to 14 people. It covers more than 3000 square feet of living spac...
(2) Excellent (2 reviews)
Kissimmee Florida Vacation Rentals - Condo
1 / 40

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
Watch Walt Disney World Fireworks EVERY NIGHT off of your Screened Balcony. See Magic Kingdom, EPCOT, Hollywood Studios, and Sea World / Universal Studios Fireworks too! This is an AMAZING Windsor Hills 2 Bedroom...
(4) Excellent (4 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 34

Kissimmee Villa
4 BR / 2.5 BA / Sleeps 8 4 8 Min stay varies
Villa / 4 Bedrooms / Sleeps 8
4 bedrooms 2.5 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
This beautiful villa offers executive living at affordable prices. Just 2 miles from Disney yet within walking distance of numerous restaurants, shops and a 24 hr supermarket which can be reached without crossing a main...
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 - 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 - 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 / 20

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 - Condo
1 / 25

Kissimmee Condo
3 BR / 2 BA / Sleeps 8 3 8 7 night min stay
Condo / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Best Priced 3 Bedroom Condo For Rent At Windsor Hills. Disney Fireworks View Building - Watch Disney Fireworks, Never Leave Building. Closest To Disney - Be On Property In Two Minutes. - king Master Bed ...
(67) Excellent (67 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 35

Kissimmee Home
6 BR / 6 BA / Sleeps 12 6 12 Min stay varies
Home / 6 Bedrooms / Sleeps 12
6 bedrooms 6 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
Spend your vacation relaxing in this stunning 6 bedroom 6 bath vacation villa, located in the beautiful Retreat at Champions Gate. Minutes from Walt Disney World Orlando, this remarkable home features a coastal inspire...
Kissimmee Florida Vacation Rentals - Villa
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 - Townhouse
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...
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 • Dishwasher • Microwave
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 / 21

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
Please note that we don't maintain the availability calendar on this site because we have 14 other spectacular homes as well. Therefore, in the event this home is sold out we may have others available, so just send the...
(7) Excellent (7 reviews)
Kissimmee Florida Vacation Rentals - Condo
1 / 30

Kissimmee Condo
3 BR / 2 BA / Sleeps 10 3 10 Min stay varies
Condo / 3 Bedrooms / Sleeps 10
3 bedrooms 2 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
King in master, queen in 2nd bedroom and 2 twins in the 3rd bedroom Converted den area has additional 2 twin beds. Sleeper in living area. Game room. Free high- speed wireless internet access are provided. With such...
(2) Excellent (2 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...
Screened backyard with heated pool and spa, BBQ, dinning table and lounge chairs
1 / 39

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 • Dishwasher • Microwave
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...
(7) Excellent (7 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 46

Kissimmee Home
6 BR / 4 BA / Sleeps 16 6 16 Min stay varies
Home / 6 Bedrooms / Sleeps 16
6 bedrooms 4 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
Our spacious family villa features 3500 square feet of luxury living space with 6 bedrooms and 4 bathrooms which can accommodate 16 comfortably. Our South facing screened in swimming pool with hot tub and a covered patio...
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 • Dishwasher • Microwave
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)
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 - 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 - 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 • Dishwasher • Microwave
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...
(14) Excellent (14 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 • 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 / 18

Kissimmee Villa
5 BR / 2.5 BA / Sleeps 11 5 11 7 night min stay
Villa / 5 Bedrooms / Sleeps 11
5 bedrooms 2.5 bathrooms Sleeps 11
High Speed Internet • Dishwasher • Microwave
Our home is a gorgeous fully air conditioned, 2 storey, 5 bedroom home ideal for 2 or more families to share and still have plenty of privacy. The master bedroom has a King size bed, tray ceiling, cable tv, dvd ...
(27) Excellent (27 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 16

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 / 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)
Private pool/spa with Lake view
1 / 18

Kissimmee Villa
4 BR / 2 BA / Sleeps 8 4 8 5 night min stay
Villa / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Luxury Lakeside Villa - 10 mins to Disney. 4 Bedrooms, 2 bathrooms, sleeps 8 Weekly rates start from $895 plus tax per week. Peak rates are $1295 plus tax per week. Last minute specials sometimes available. Please ...
(4) Excellent (4 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 27

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
This executive vacation home is located in the prestigious Emerald Island Resort. It is close to Disney and convenient to all amenities. The villa has 4 King master suites and 1 Queen master bedroom so is perfect for lar...
(1) Excellent (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.