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Kissimmee Florida Vacation Rentals - Home
1 / 19

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 / 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 • Dishwasher • Microwave
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 / 22

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
A Beautiful 5 bedroom 3 bathroom villa, 3 Main Living areas, Large Master Bedroom on suites with A King size Bed. Second King Bedroom with King Size Bed. First Floor Bedroom with Queen size Bed. 2 Twin Bedrooms...
(2) Excellent (2 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 - 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 / 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 / 34

Kissimmee Villa
8 BR / 4.5 BA / Sleeps 19 8 19 No min stay
Villa / 8 Bedrooms / Sleeps 19
8 bedrooms 4.5 bathrooms Sleeps 19
High Speed Internet • Dishwasher • Microwave
Located in the guarded resort community of Terra Verde, our home is only 8 miles from Disney and offers over 3200 sq. feet of fully air conditioned flexible living & play space.  Terra Verde Resort is one of ...
(9) Excellent (9 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 20

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
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 - Apartment
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Kissimmee Apartment
7 BR / 5.5 BA / Sleeps 16 7 16 3 night min stay
Apartment / 7 Bedrooms / Sleeps 16
7 bedrooms 5.5 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
Our vacation home is a perfect example of a Luxury rental which is beautifully furnished with ceramic tile and quality bedding with very spacious living rooms. 3123 S/F Please call or email us for availability. SP...
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Kissimmee Villa
6 BR / 5.5 BA / Sleeps 14 6 14 3 night min stay
Villa / 6 Bedrooms / Sleeps 14
6 bedrooms 5.5 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
Welcome to Disney Sunshine Villa! The gorgeous and luxury villa has distinguished privacy and unbeatable views! This gated resort community is only 15 minutes from Disney, 20 minutes south of Sea World and Universal S...
(6) Excellent (6 reviews)
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)
Dinning Area
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Kissimmee Villa
7 BR / 5.5 BA / Sleeps 20 7 20 Min stay varies
Villa / 7 Bedrooms / Sleeps 20
7 bedrooms 5.5 bathrooms Sleeps 20
Dishwasher • Microwave • Washer/Dryer
First class furnished house is waiting for you! It's newly renovated keeping your class, comfort, privacy, fashion, modernization in mind. Best floor plans for the best five star community resort which is very s...
(30) Excellent (30 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 32

Kissimmee Home
4 BR / 4 BA / Sleeps 8 4 8 Min stay varies
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 4 bathrooms Sleeps 8
Washer/Dryer • DVD Player • Air Conditioning
Located on the Regal Palms resort in Davenport this is a pretty end of terrace 2 storey town home with 4 bedrooms and 3. 5 bathrooms. The downstairs has been newly tiled and the whole villa is tastefully decorated and fu...
Front View
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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 - Townhouse
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Kissimmee Townhouse
4 BR / 3 BA / Sleeps 8 4 8 No min stay
Townhouse / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Fully furnished 4 bedroom, 3- bath townhouse that sleeps eight, and includes 2 pack and play cribs and a stroller for your little ones. Home is located within the premiere resort community of Paradise Palms; home is l...
(3) Excellent (3 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 38

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
Welcome to Villa by the Castle! If you are looking for vacation getaway, a family reunion, a golf retreat or shopping with the girls - you'll find this Villa will more than meet your needs. It's comfortable, ample...
(1) Excellent (1 review)
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 / 28

Kissimmee Villa
7 BR / 4.5 BA / Sleeps 16 7 16 5 night min stay
Villa / 7 Bedrooms / Sleeps 16
7 bedrooms 4.5 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
For those looking for the ultimate vacation rental experience, this is the right villa! Located in the tropical grounds of Emerald Island Resort near Disney World, this huge 7 bed villa offers outstanding amenities at...
(1) Excellent (1 review)
Fully Loaded Game Room with air conditioning
1 / 15

Kissimmee Home
6 BR / 4 BA / Sleeps 14 6 14 No min stay
Home / 6 Bedrooms / Sleeps 14
6 bedrooms 4 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
This luxury home is situated in the 5 star resort community of Windsor Hills in Kissimmee, Florida. It is located only 2 miles from Disney World! Closer to Disney and other Orlando attractions than most hotels! This h...
(2) Excellent (2 reviews)
Poolside Dining - Patio with BBQ Grill
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Kissimmee Home
4 BR / 2 BA / Sleeps 10 4 10 4 night min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 2 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
The Pirates Retreat has 4 bedrooms, 2 and bathrooms, Sunny Pool, and it is on the WATER with a beautiful view. It has a Game Room with a Pool Table, Ping Pong Table, Foose Ball Table & Dart Board and other games. Th...
(53) Excellent (53 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 61

Kissimmee Home
7 BR / 6 BA / Sleeps 14 7 14 Min stay varies
Home / 7 Bedrooms / Sleeps 14
7 bedrooms 6 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
As the owners of this beautiful 7- bedroom, 6- bath villa, we invite you to stay in The Enchanted Retreat! Located in the beautiful gated community of Formosa Gardens Estates, you will enjoy a large lot in a priv...
Kissimmee Florida Vacation Rentals - Villa
1 / 13

Kissimmee Villa
4 BR / 3.5 BA / Sleeps 8 4 8 Min stay varies
Villa / 4 Bedrooms / Sleeps 8
4 bedrooms 3.5 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Fairways at Remington luxury holiday accommodation has a spacious and open- plan family room with ceiling fan, 2 over- stuffed sofas, plus occasional and coffee tables with lamps, a LCD flat screen HDTV, Digital HD V...
(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 - Villa
1 / 23

Kissimmee Villa
8 BR / 6 BA / Sleeps 20 8 20 Min stay varies
Villa / 8 Bedrooms / Sleeps 20
8 bedrooms 6 bathrooms Sleeps 20
High Speed Internet • Dishwasher • Microwave
Rent Directly From The Owners And Save! No Booking Fees, No Admin Fees, No Per- Person Fees. Welcome To Our Luxurious 8 Br/6 Ba Home In The New Windsor At Westside Gated Community (sister Community To Windsor Hill...
Kissimmee Florida Vacation Rentals - Villa
1 / 25

Kissimmee Villa
4 BR / 3 BA / Sleeps 10 4 10 Min stay varies
Villa / 4 Bedrooms / Sleeps 10
4 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Only 7. 5 miles from Disney's main gate. Featured with 2 master suites, 4 bedrooms and 3 bath rooms. 2 living areas, plus private screen enclosed swimming pool and spa. Comfortably sleeps 8 to 10 people. Ga...
(3) Very Good (3 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 24

Kissimmee Home
5 BR / 2 BA / Sleeps 10 5 10 Min stay varies
Home / 5 Bedrooms / Sleeps 10
5 bedrooms 2 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Beautiful 5 bedroom 2 bath Disney Movie Castle Completely refurnished and Redecorated: Both bathrooms have been upgraded to include new bath tub, new overhead rain showers, wood floors and new vanity and hardware. The ...
Family Room
1 / 17

Kissimmee Home
7 BR / 4.5 BA / Sleeps 16 7 16 3 night min stay
Home / 7 Bedrooms / Sleeps 16
7 bedrooms 4.5 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
Kirk Manor is a beautiful 7 bed/4. 5 bath home situated at the most prestigious vacation spot- Emerald Island Resort. Kirk Manor vacation home has a private pool and screen lanai with lots of patio furniture and is clos...
(6) Excellent (6 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 19

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
DVD Player • TV (Antenna) • Private Pool
Located just 3. 5 miles to Disney. The Private Pool two story town home has 3 Bedrooms / 3 Baths. The home has a King bedroom with ensuite and Twin bedroom with ensuite on the second floor as well as a Queen bedroom with...
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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.