Kissimmee (827) Filter Cancel
Loading...
Kissimmee Florida Vacation Rentals - Condo
1 / 44

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
"HEMINGWAY'S ANIMAL KINGDOM! " WOW! ! ! ! Imagine you and your family staying in this NEW, spacious home for your Disney World vacation at nightly rates that are typically LESS than those of a small local Disney ...
(3) Excellent (3 reviews)
Kissimmee Florida Vacation Rentals - Townhouse
1 / 33

Kissimmee Townhouse
3 BR / 2.5 BA / Sleeps 7 3 7 3 night min stay
Townhouse / 3 Bedrooms / Sleeps 7
3 bedrooms 2.5 bathrooms Sleeps 7
High Speed Internet • Dishwasher • Microwave
Only 4 miles to Mickey's front door! 3 Bedrooms, 3 Bathrooms, Sleep 8, Free Wifi, Nintendo Wii, Baby Ready! You will say "this place is amazing" the moment you arrive at your Paradise Cay vacation townh...
(26) Excellent (26 reviews)
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...
(15) Excellent (15 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 24

Kissimmee Home
6 BR / 5.5 BA / Sleeps 12 6 12 Min stay varies
Home / 6 Bedrooms / Sleeps 12
6 bedrooms 5.5 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
Villa, 6 Bedrooms, 6 Baths, (sleeps 12- 14) Brand New High End Furniture And Bedding Through Out. All Photos Are Up To Date And Personally Taken In October 2014. Our 5 Star Orlando Vacation Villa Is Centrally L...
(2) Excellent (2 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)
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 - Home
1 / 67

Kissimmee Home
7 BR / 7.5 BA / Sleeps 18 7 18 Min stay varies
Home / 7 Bedrooms / Sleeps 18
7 bedrooms 7.5 bathrooms Sleeps 18
High Speed Internet • Dishwasher • Microwave
Property Ref: RVH_080 One of the most sought after homes in the exclusive Reunion Resort! Enjoy the benefits of the stunning main home and added privacy of a guest home. The dream location for both small and large gr...
Kissimmee Florida Vacation Rentals - Home
1 / 25

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_081 This beautiful home has everything you need to create your dream stay in Reunion Resort. A large pool and spa, luxurious decor that creates a homely ambiance, over 5, 000 sq. ft of spacious li...
(1) Excellent (1 review)
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 / 16

Kissimmee Home
4 BR / 3 BA / Sleeps 8 4 8 Min stay varies
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
Washer/Dryer • Air Conditioning • DVD Player
This lovely Pool home is situated in the prestigious The Manor at West Haven community in Davenport, Florida, with only a short 15 minute drive to the gates of the Disney theme parks. This is the perfect villa for conv...
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)
1 / 41

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
Luxurious and Beautiful Villa is ideally located at exclusive Seasons Community , about 5. 5 miles short distance from Disney World & about minutes distance from the best restaurants and shops of the Central FL. Close t...
(27) Excellent (27 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...
(9) Excellent (9 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 16

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 • Private Pool • Hot Tub
Nicely tucked away in the secure community of Emerald Island Resort lies our Manchester 5- Star luxury vacation home. Guests will enjoy over 2, 800 square feet of breathtaking vacation space across 2 floors. Rich leath...
Kissimmee Florida Vacation Rentals - Home
1 / 24

Kissimmee Home
4 BR / 3 BA / Sleeps 8 4 8 Min stay varies
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
TV (Antenna) • Washer/Dryer • Air Conditioning
Enjoy your next vacation in this lovely, bright and open space end unit Town Home located in Bella Vida, just moments from everywhere! Boasting 4 large Bedrooms and 3 Full Baths, there will be plenty of room to sprea...
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...
(5) Excellent (5 reviews)
Kissimmee Florida Vacation Rentals - Apartment
1 / 6

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
Dishwasher • Microwave • Air Conditioning
The very cozy Key West- style gated resort offers a great lakeside setting in the heart of Kissimmee. The air- conditioned establishment has 40 guest rooms, children's playground and Internet access. The luxurious condo...
Kissimmee Florida Vacation Rentals - Home
1 / 26

Kissimmee Home
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
TV (Antenna) • Washer/Dryer • Air Conditioning
Cozy Condo with Customized Furniture & Accessories. Vacation has a new meaning when you stay at Bella Piazza. Book this pool view unit today and enjoy what this community and Orlando has to offer you! The unit features ...
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 - Villa
1 / 26

Kissimmee Villa
10 BR / 10 BA / Sleeps 24 10 24 1 night min stay
Villa / 10 Bedrooms / Sleeps 24
10 bedrooms 10 bathrooms Sleeps 24
High Speed Internet • Dishwasher • Microwave
This 4800sq/ft villa includes the following amenities: - 10 Luxurious Bedrooms (7 King Rooms suites and 3 Twins Room) - 10 Full Bathrooms - 9 Bedrooms With Private En- Suite Bath - Loft with Big Screen TV and g...
Kissimmee Florida Vacation Rentals - Condo
1 / 26

Kissimmee Condo
3 BR / 2 BA / Sleeps 8 3 8 3 night min stay
Condo / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
We Have 3 Condos In The Same Resort So Our Calendar Will Show Dates As Available Unless The Same Dates For All 3 Condos Are Booked. You Can Rely On Our Availability Information As Our Calendar Is Always Up- To- Date ...
(81) Excellent (81 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
7 BR / 4 BA / Sleeps 20 7 20 Min stay varies
Home / 7 Bedrooms / Sleeps 20
7 bedrooms 4 bathrooms Sleeps 20
High Speed Internet • Dishwasher • Microwave
As a recent guest stated, we have the "BEST HOUSES FOR KIDS IN ALL OF ORLANDO"! ! ! After all your hours of searching properties for the perfect stay by Disney, this is it! You can stop looking; even our guests who ...
(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 - Apartment
1 / 17

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 • Dishwasher • Microwave
These Mediterranean- style houses offer comfort and luxury in an extravagant experience, within a short driving distance from a wide range of bars, and Orlando's main attractions and theme parks, like Walt Disney Worl...
Legacy Park
1 / 16

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
Two Luxury Private Villas: within 5 minutes walking distance to each other, each house 3500 s. f - 7 Bedrooms - 4. 5 Bathrooms - Oversized private Heated Pool/Spa - Game Room - 10 min. to Disney World; can be rent...
(1) Excellent (1 review)
Kissimmee Florida Vacation Rentals - Condo
1 / 47

Kissimmee Condo
3 BR / 1 BA / Sleeps 8 3 8 3 night min stay
Condo / 3 Bedrooms / Sleeps 8
3 bedrooms 1 bathroom Sleeps 8
High Speed Internet • Dishwasher • Microwave
3 Bedrooms, 3 Bathrooms, Sleep 8, Free Wifi, Nintendo Wii, Baby Ready! Welcome to Sun Lake condo, just 1 of 3 identical units that we have available in this wonderful resort, is the perfect place for your nex...
(4) Excellent (4 reviews)
1 / 24

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 • Dishwasher • Microwave
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 - 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 • Dishwasher • Microwave
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)
1  2  3  4  5 
12345
page 1 of 28
LoadingLoading...

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.


----

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.