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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 - 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)
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 - 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...
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 - Condo
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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 / 27

Kissimmee Villa
5 BR / 3 BA / Sleeps 12 5 12 5 night min stay
Villa / 5 Bedrooms / Sleeps 12
5 bedrooms 3 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
Fully Furnished with Two Master Size Sites bedrooms, Pool/Spa, High Speed Wi Fi, 6 TV, Games Area and Gated Resort . Villa Beaulieu, the luxurious house in top rated Solana Resort features 5BR (2 Masters) includ...
(29) Excellent (29 reviews)
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 - 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 • Dishwasher • Microwave
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)
Private Home Cinema
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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
This is an exquisite home which will leave you, your family or guests with warm memories in a home styled, furnished and decorated with no expense spared! This home was purchased in August 2012 and has been compl...
(5) Excellent (5 reviews)
Very Safe and Peaceful Family Property
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Kissimmee Townhouse
3 BR / 2 BA / Sleeps 6 3 6 3 night min stay
Townhouse / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
Dishwasher • Microwave • Washer/Dryer
3Bedroom & 2 Bath Townhouse in gated community. The house is very well kept & clean. The house and complex offer a great place for families to stay and enjoy your vacation. LOCATION, LOCATION, LOCATION! The ho...
(24) Excellent (24 reviews)
Kissimmee Florida Vacation Rentals - Townhouse
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Kissimmee Townhouse
3 BR / 2.5 BA / Sleeps 6 3 6 Min stay varies
Townhouse / 3 Bedrooms / Sleeps 6
3 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Beautiful 3 bed townhouse on Regal Oaks resort at Old Town Kissimmee. Regal Oaks resort is ideally located 3 minutes from Disney and very close to the I4 for easy access to Universal and Sea World which are about 15 ...
(46) Excellent (46 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 30

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
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)
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 - Apartment
1 / 41

Kissimmee Apartment
3 BR / 2 BA / Sleeps 8 3 8 7 night min stay
Apartment / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Ada
Kissimmee Florida Vacation Rentals - Home
1 / 42

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 • Dishwasher • Microwave
2 Story Luxury 6 Bedroom 3. 5 Bath, Private Pool&spa, BBQ Grill, Game room with Billiard Pool Table, pingpang table, Highchair, Baby playpen and Stroller Gated community with Playground, Tennis Court, 10 Minut...
(15) Excellent (15 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 20

Kissimmee Home
3 BR / 2 BA / Sleeps 8 3 8 4 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
The Pocahontas Villa Retreat is a beautiful 3 bedroom 2 bath modern home with all tile. It has a sparkling private pool - under umbrella table & chairs and BBQ Grill. Enjoy the modern eat in Kitchen that overlooks The f...
(8) Excellent (8 reviews)
Exclusive Two Story Home
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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 • Dishwasher • Microwave
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...
(55) Excellent (55 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 • Dishwasher • Microwave
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 / 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 / 24

Kissimmee Home
5 BR / 3 BA / Sleeps 12 5 12 Min stay varies
Home / 5 Bedrooms / Sleeps 12
5 bedrooms 3 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
This Luxuriously appointed home is presented with upgraded furniture and fittings throughout, and fully air conditioned to create a comfortable indoor climate. With1 bedroom and bathroom located on the ground floo...
(11) Excellent (11 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 - Home
1 / 21

Kissimmee Home
4 BR / 2 BA / Sleeps 10 4 10 No min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 2 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Welcome to Sunset Vista Court enjoy this 4 bedroom, 2 bath vacation home, which easily accommodates 1 or 2 families, with a maximum sleeping capacity of 10. For your enjoyment the home has its own private screened in ...
(7) Excellent (7 reviews)
Day Time pool view
1 / 28

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
Our main page at our site My Orlando Stay has more details and pictures. Vacation Home features Sleeps Easily sleep up to 8 people Bedrooms 3 bedrooms, master with King, King/Queen in Guest and 2 twins in Kids ...
(24) Excellent (24 reviews)
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 • Air Conditioning
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 / 41

Kissimmee Villa
5 BR / 3 BA / Sleeps 12 5 12 Min stay varies
Villa / 5 Bedrooms / Sleeps 12
5 bedrooms 3 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
Brand New! Beautiful 5 bed- room, 3 full bath villa in Emerald Island Resort, nestled within an area of protected wetland! Three miles to Walt Disney World and near a myriad of other attractions in Central Florida! ...
(19) Excellent (19 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 - 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 • Dishwasher • Microwave
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 - Villa
1 / 14

Kissimmee Villa
4 BR / 3 BA / Sleeps 8 4 8 No min stay
Villa / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Gated community, private screened pool, 4 BR, 3 BA, living room, dining room, kitchen, washer/dryer. Living Room- This spacious, comfortable room is beautifully furnished and looks directly out onto the swi...
(17) Excellent (17 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 20

Kissimmee Home
4 BR / 2 BA / Sleeps 8 4 8 6 night min stay
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Large, private backyard with NO rear neighbors! NOT a condo! Game Room, WIFI, Private Pool, Four bedrooms, Two baths, More! Private backyard. Unlike most homes in the developments near Disney, there is NO walki...
(5) Excellent (5 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.