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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 / 31

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
In our house, fell like you are at home, with the comfort of a King bedroom suite and an attached bathroom with a deep soaker tub and 3 more bedrooms : one queen bedroom suite with its own bathroom and kids twins rooms...
(1) Excellent (1 review)
Kissimmee Florida Vacation Rentals - Apartment
1 / 9

Kissimmee Apartment
1 BR / 1 BA / Sleeps 4 1 4 1 night min stay
Apartment / 1 Bedroom / Sleeps 4
1 bedrooms 1 bathroom Sleeps 4
Air Conditioning • TV (Cable/Satellite) • Telephone
Situated in Kissimmee, this hotel is less than 800 meters from a range of bars and restaurants, and 1. 5 km from a plethora of shops. A prime location, 2. 5 km from Walt Disney World, 8 km from Orlando, and 25 km fr...
Kissimmee Florida Vacation Rentals - Condo
1 / 30

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
Condominium: It is a reasonably priced, professionally decorated and furnished 3- bedroom/2- bathroom condominium offering comfort, space, style, luxury and privacy. It is located at a luxurious and upscale gated Can...
(5) Excellent (5 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 30

Kissimmee Villa
4 BR / 2 BA / Sleeps 8 4 8 4 night min stay
Villa / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Located in the 5 star gated (guarded) resort of Windsor Palms, this 4 bedroom home is minutes away from Disney World, Universal Studios, and other major attractions. Keyless entry for easy access. You'll find all ...
(24) Excellent (24 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 32

Kissimmee Home
8 BR / 7 BA / Sleeps 18 8 18 Min stay varies
Home / 8 Bedrooms / Sleeps 18
8 bedrooms 7 bathrooms Sleeps 18
High Speed Internet • Dishwasher • Microwave
This BRAND NEW 8 bedroom 7 bath encore reunion luxury home is 6 miles away from Disney World. Situated in a highly sought after Liberty Bluff neighborhood and it is perfect for families wanting a comfortable and relaxing...
Kissimmee Florida Vacation Rentals - Home
1 / 25

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
Come and enjoy the family vacation of life time when guests stay on fantastic 6bedrooms resorts home in 5 Star Windsor Palm Resorts in Kissimmee, most sought after luxurious gates communities. About 3 miles distance for...
(15) Excellent (15 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 / 22

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
Dishwasher • Microwave • Washer/Dryer
Fantastic vacation rental with 3 bedroom 2. 5 bath luxury townhouse is located in an attractive community in Reunion. Unlike anywhere else this home is just 8 minutes from Disney World and three of golf's greatest legend...
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 - Townhouse
1 / 28

Kissimmee Townhouse
3 BR / 3 BA / Sleeps 8 3 8 2 night min stay
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 ...
(25) Excellent (25 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...
(1) Excellent (1 review)
Kissimmee Florida Vacation Rentals - Villa
1 / 24

Kissimmee Villa
7 BR / 4.5 BA / Sleeps 16 7 16 No min stay
Villa / 7 Bedrooms / Sleeps 16
7 bedrooms 4.5 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
This is your dream vacation home! Back on beautiful sunny reserved forest in the Resort - Our villa has the unique private location! - Swim in the joyful private pool/spa (optional heated) or simply relax on luxury p...
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)
Kissimmee Florida Vacation Rentals - Villa
1 / 8

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
This 4 bedroom 3. 5 bathroom vacation villa is the perfect location for your family vacation - whether you are visiting Florida for the golf, shopping or the theme parks! The villa is within the gates of Remington Gol...
(4) Excellent (4 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 43

Kissimmee Home
7 BR / 5 BA / Sleeps 16 7 16 Min stay varies
Home / 7 Bedrooms / Sleeps 16
7 bedrooms 5 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
Simba's Sunset is a 7 Bedroom, 5 Bathroom, 3354 sqft, 2 Story Pool and Spa Home in the executive gated community of Formosa Gardens. Famous for it's large lots, this home is no different, plants and a fence keep thi...
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 / 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 • Dishwasher • Microwave
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 - Villa
1 / 64

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
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 ...
(3) Excellent (3 reviews)
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 - 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 • Dishwasher • Microwave
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 - 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...
Comfortable 4 Bedroom 2 1/2 bath Villa near Disney World
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 - Home
1 / 21

Kissimmee Home
5 BR / 3.5 BA / Sleeps 10 5 10 5 night min stay
Home / 5 Bedrooms / Sleeps 10
5 bedrooms 3.5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Rolling Hills at Formosa Gardens villa description This magnificent and tastefully furnished villa is located in Rolling Hills Estates at Formosa Gardens, a prestigious community just three minutes away from Walt Dis...
(1) Excellent (1 review)
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 / 16

Kissimmee Villa
6 BR / 3.5 BA / Sleeps 14 6 14 Min stay varies
Villa / 6 Bedrooms / Sleeps 14
6 bedrooms 3.5 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
Come to Enjoy this cal- de- sac villa in famous Windsor Palm. Walking distance to clubhouse house and tennis courts. Only 4. 5 Miles to Disney in a luxurious guard gated community. This turnkey investment home provid...
(1) Excellent (1 review)
Kissimmee Florida Vacation Rentals - Villa
1 / 9

Kissimmee Villa
6 BR / 5 BA / Sleeps 14 6 14 2 night min stay
Villa / 6 Bedrooms / Sleeps 14
6 bedrooms 5 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
Luxury 6Br/5Bt Villa with Pool/Spa, Games, Wireless High Speed Internet, Gas BBQ Grill. Beautiful Villa in breathtaking, highly maintained resort community. Professionally decorated 6 bedrooms, 5 full bathrooms with...
(1) Excellent (1 review)
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 • Dishwasher • Microwave
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)
Kissimmee Florida Vacation Rentals - Apartment
1 / 12

Kissimmee Apartment
Studio / 1 BA / Sleeps 4 0 4 1 night min stay
Apartment / Studio / Sleeps 4
Studio 1 bathroom Sleeps 4
High Speed Internet • Microwave • Washer/Dryer
This hotel is located just moments from Walt Disney World and a variety of other exciting attractions, offering comfortable guestrooms, relaxing amenities, and convenient dining options. The hotel is close to Old Town...
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...
(16) Excellent (16 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.