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Kissimmee Florida Vacation Rentals - Villa
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Kissimmee Villa
5 BR / 4 BA / Sleeps 12 5 12 7 night min stay
Villa / 5 Bedrooms / Sleeps 12
5 bedrooms 4 bathrooms Sleeps 12
High Speed Internet • Microwave • Dishwasher
Our luxurious 5 bedroom and 4 bathroom vacation home provides spacious accommodation for up to 12 people. It is located on the Hampton Lakes community on Hwy27, with convenient access to I- 4 and just a 15- 20 minute dr...
(5) Excellent (5 reviews)
Resort pool - Free to use for guests
1 / 32

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 • Microwave • Dishwasher
This private, luxurious and spacious home is one of the very few lake view 6 bedrooms Home at Windsor Hills, with no rear neighbors. Less than 5 Minutes walking to Club House, Community Pool and Playground. ...
(5) Excellent (5 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 52

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 • Microwave • Dishwasher
Welcome to Lake Berkley Resort, one of the most popular vacation home resort community just 6 miles to Disney World. This vacation home includes the following amenities: - Total of 7 bedrooms, 4. 5 bathrooms, slee...
(1) Excellent (1 review)
Kissimmee Florida Vacation Rentals - Home
1 / 26

Kissimmee Home
4 BR / 3 BA / Sleeps 8 4 8 Min stay varies
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
Air Conditioning • Washer/Dryer • Private Pool
Lovely 4 Bedroom, 3 bath home in the popular community of Hampton Lakes on Hwy 27. Hampton Lakes is located only 11 Miles to Walt Disney World! This home has two master suites, both with queen sized bed, en suite bat...
House front
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Kissimmee Villa
6 BR / 5.5 BA / Sleeps 14 6 14 7 night min stay
Villa / 6 Bedrooms / Sleeps 14
6 bedrooms 5.5 bathrooms Sleeps 14
High Speed Internet • Microwave • Dishwasher
Pool, Spa, Extended Deck, Luxury Poolside Furniture 2 King Master Suites, 2 Queen Master Suite, 2 Twin Bedded Rooms, 5. 5 Bathrooms Double Sofa Bed In Family Room, Bed Linen, Towels, Hairdryers High Speed...
(8) Excellent (8 reviews)
Front view with a Palm Tree at the front door
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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 - 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 - Home
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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 • Microwave • Dishwasher
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 / 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 • Microwave • Dishwasher
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 - 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 • Microwave • Dishwasher
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)
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Kissimmee Home
6 BR / 5.5 BA / Sleeps 16 6 16 Min stay varies
Home / 6 Bedrooms / Sleeps 16
6 bedrooms 5.5 bathrooms Sleeps 16
High Speed Internet • Microwave • Dishwasher
Located in Emerald Island which is one of the most desirable Resort Communities in the area and it is less than 3 miles to Disney World. This home offers, 6- 7 bedrooms 5 1/2 bathrooms, 4 Master Suites all fit for a Ki...
Beautiful Villa at Emerals Island Resort
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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 • Microwave • Dishwasher
Our lovely 8 bedroom pool/spa home is located on the prestigious Emerald Island Resort, a gated community with 24/7 guard, it's only 3 miles away from World Disney. Emerald Island Resort featured with its own club hous...
(14) Excellent (14 reviews)
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Kissimmee Condo
4 BR / 3 BA / Sleeps 10 4 10 Min stay varies
Condo / 4 Bedrooms / Sleeps 10
4 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Microwave • Dishwasher
This huge 1650 sqft condo has 4 bedrooms and 3 full bathrooms. It is located at Sun Lake Resort, just 2 Miles to Disney world Florida. sleeping accommodations for 10. King- size Master bedroom with bathroom O...
(4) Excellent (4 reviews)
Kissimmee Florida Vacation Rentals - Home
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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 • Microwave • Dishwasher
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 - Villa
1 / 53

Kissimmee Villa
7 BR / 5.5 BA / Sleeps 14 7 14 3 night min stay
Villa / 7 Bedrooms / Sleeps 14
7 bedrooms 5.5 bathrooms Sleeps 14
High Speed Internet • Microwave • Dishwasher
Luxurious 7 Bedroom Vacation Home In Exclusive Resort Community - Just Minutes Away From Disney! Welcome to our Emerald Island Resort. With its luxurious decor and prime location only 4 miles to disney, this is o...
(9) Excellent (9 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 - Villa
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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
Property Ref: RVH_227 Situated in the highly sought after Liberty Bluff neighborhood of Reunion Resort this luxurious BRAND NEW 5 bedroom 5. 5 bath home sits atop of the signature Legacy course. The home has resort me...
Kissimmee Florida Vacation Rentals - Townhouse
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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 • Microwave • Dishwasher
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)
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 • Microwave • Dishwasher
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 - Villa
1 / 16

Kissimmee Villa
4 BR / 2 BA / Sleeps 8 4 8 Min stay varies
Villa / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Microwave • Dishwasher
Come enjoy the peace and serenity of ''Ariels Cove''. Our three bedroom home is located on a quiet cul- de- sac in the popular ''Indian Point'' community. Out the front door you'll find an expanse of grassland that's hom...
(11) Excellent (11 reviews)
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 • Microwave • Dishwasher
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...
(5) Excellent (5 reviews)
front of house
1 / 14

Kissimmee Home
6 BR / 5 BA / Sleeps 14 6 14 5 night min stay
Home / 6 Bedrooms / Sleeps 14
6 bedrooms 5 bathrooms Sleeps 14
High Speed Internet • Microwave • Dishwasher
ONLY 3 Miles to Disney 6br 5ba ranch Special rate Summer Sale $129 nt until- Sep 30 5 night minimum stay required Please look at our floor plan(see pictures). Our home has more square feet than most ...
(7) Excellent (7 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 20

Kissimmee Villa
5 BR / 4.5 BA / Sleeps 10 5 10 5 night min stay
Villa / 5 Bedrooms / Sleeps 10
5 bedrooms 4.5 bathrooms Sleeps 10
High Speed Internet • Microwave • Dishwasher
You will feel it the moment you pass the entry gates to this beautiful new community - Cumbrian Lakes. The sense of peace and harmony with nature. Pleasing streetscapes are lined with ancient oak tree preserves. This ex...
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 • Microwave • Dishwasher
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 - 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 - 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 • Microwave • Dishwasher
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 - 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 • Microwave • Dishwasher
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 / 18

Kissimmee Villa
4 BR / 2 BA / Sleeps 8 4 8 No min stay
Villa / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Microwave • Dishwasher
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)
Private Pool with Lake View and Sunset Watching
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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 • Microwave • Dishwasher
Welcome to Clyde's Cove! This stunning villa is a bright and spacious vacation home with 3000 sq/ft, 7 bedrooms including 4 Master Suites with private full bathrooms. Comfort and convenience are the hallmarks of this h...
(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.