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Kissimmee Florida Vacation Rentals - Home
1 / 16

Kissimmee Home
8 BR / 5.5 BA / Sleeps 18 8 18 Min stay varies
Home / 8 Bedrooms / Sleeps 18
8 bedrooms 5.5 bathrooms Sleeps 18
High Speed Internet • Dishwasher • Microwave
Our emerald island villa with luxury furnished 8 bedrooms / 5. 5 baths 4 Master bedrooms ( 3 master suite, 2 family suite ) and private pool/spa is situated in the magnificent 24- hour gated security resort, just 3 mil...
(6) Excellent (6 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 - 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 - Home
1 / 46

Kissimmee Home
6 BR / 4 BA / Sleeps 16 6 16 Min stay varies
Home / 6 Bedrooms / Sleeps 16
6 bedrooms 4 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
Our spacious family villa features 3500 square feet of luxury living space with 6 bedrooms and 4 bathrooms which can accommodate 16 comfortably. Our South facing screened in swimming pool with hot tub and a covered patio...
Kissimmee Florida Vacation Rentals - Townhouse
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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 - Apartment
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Kissimmee Apartment
Studio / 1 BA / Sleeps 4 0 4 1 night min stay
Apartment / Studio / Sleeps 4
Studio 1 bathroom Sleeps 4
Dishwasher • Microwave • Washer/Dryer
Situated just 5 miles from Walt Disney World's massive theme park complex, this comfortable holiday resort provides the perfect base for a fun- filled family holiday. Epcot, Hollywood Studios, the Typhoon Lagoon water...
Kissimmee Florida Vacation Rentals - Home
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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)
1 / 25

Kissimmee Villa
6 BR / 5 BA / Sleeps 14 6 14 Min stay varies
Villa / 6 Bedrooms / Sleeps 14
6 bedrooms 5 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
The brand new 6- bedroom, 5- bathroom villa is professionally designed and decorated and has an amazing conservation view. It has three king sized master bedrooms, a loft, kitchen, dining room, living room, private...
Kissimmee Florida Vacation Rentals - Villa
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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...
(30) Excellent (30 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 / 12

Kissimmee Villa
4 BR / 2.5 BA / Sleeps 9 4 9 No min stay
Villa / 4 Bedrooms / Sleeps 9
4 bedrooms 2.5 bathrooms Sleeps 9
High Speed Internet • Dishwasher • Microwave
Take a "Palm" Escape and still be close to everything. Located behind the Super Walmart... in Popular Indian Point Subdivision that features - tennis - a play ground - community pool and recreation center. Relax at th...
(21) Excellent (21 reviews)
Kissimmee Florida Vacation Rentals - Villa
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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 - Home
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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 - Townhouse
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Kissimmee Townhouse
5 BR / 4.5 BA / Sleeps 12 5 12 Min stay varies
Townhouse / 5 Bedrooms / Sleeps 12
5 bedrooms 4.5 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
The 5- bedroom, 4. 5- bathroom Town House is professionally designed and decorated. It has two king sized master bedrooms, a queen sized master suite, a loft, kitchen, dining room, living room, private lanai, and...
Kissimmee Florida Vacation Rentals - Villa
1 / 14

Kissimmee Villa
3 BR / 2 BA / Sleeps 8 3 8 7 night min stay
Villa / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Rent a Vacation Home Near Disney with it's heated Pool for the same price of a standard hotel room Located near Disney, this modern 1400 square foot bungalow holds all the amenities that you would expect to have a wo...
(4) Excellent (4 reviews)
Kissimmee Florida Vacation Rentals - Villa
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Kissimmee Villa
8 BR / 5 BA / Sleeps 18 8 18 Min stay varies
Villa / 8 Bedrooms / Sleeps 18
8 bedrooms 5 bathrooms Sleeps 18
High Speed Internet • Dishwasher • Microwave
Welcome to our brand new luxury finished 3600 Sqft pool home at beautiful Crystal Cove Resort. It is conveniently located close to shopping and dining (less than 1 mile away). Disney is only 6 miles away. Just minutes fr...
(13) Excellent (13 reviews)
Kissimmee Florida Vacation Rentals - Villa
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Kissimmee Villa
6 BR / 4 BA / Sleeps 14 6 14 Min stay varies
Villa / 6 Bedrooms / Sleeps 14
6 bedrooms 4 bathrooms Sleeps 14
Dishwasher • Microwave • Washer/Dryer
[We also have another beautiful 5 bed, 3. 5 bath villa on Sunset Lakes ~ Please enquire about availabiliy if Sunset Lakes is booked ] Superior 6 bed, 4 bath Vacation Home ~ Sleeps 14 Guests Affordable Luxury ~ ...
(28) Excellent (28 reviews)
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
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Kissimmee Home
4 BR / 4 BA / Sleeps 11 4 11 Min stay varies
Home / 4 Bedrooms / Sleeps 11
4 bedrooms 4 bathrooms Sleeps 11
Washer/Dryer • Air Conditioning • Private Pool
Exciting Lakeview 4 Bedroom 3 Bath Town Home in Festival Orlando! Enjoy a family vacation or a family reunion in the community of Festival. Your immediate family will enjoy the luxury and style of this brand new home. Y...
Kissimmee Florida Vacation Rentals - Townhouse
1 / 26

Kissimmee Townhouse
3 BR / 2 BA / Sleeps 6 3 6 No 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 - Villa
1 / 25

Kissimmee Villa
6 BR / 4 BA / Sleeps 12 6 12 No min stay
Villa / 6 Bedrooms / Sleeps 12
6 bedrooms 4 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
Pool, Spa, Extended Deck, Luxury Poolside Furniture 2 King Master Suites, 1 Queen Master Suite, 3 Twin Bedded Rooms, 4 Bathrooms Double Sofa Bed In Family Room, Bed Linen, Towels, Hairdryers High Speed In...
(4) Excellent (4 reviews)
Kissimmee Florida Vacation Rentals - Home
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)
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 - Villa
1 / 31

Kissimmee Villa
7 BR / 6 BA / Sleeps 22 7 22 Min stay varies
Villa / 7 Bedrooms / Sleeps 22
7 bedrooms 6 bathrooms Sleeps 22
High Speed Internet • Dishwasher • Microwave
This Home Has 56 - Up To Date, 5 Star, Trip Advisor Reviews, A Lot More, Than Just The One That Is Shown On The Photo. The Site Cannot Move Them Across, So I Have Placed Them In The Testimonials Page, Please View ...
(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 - 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 • Dishwasher • Microwave
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)
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 • Dishwasher • Microwave
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...
(9) Excellent (9 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 41

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
101 Dalmatians Den FL090 Designed for the child in all of us - clean, beautiful and comfortable this private villa makes it easy to soak up the fun for which Orlando is known. Your “pups” will thank you for all the...
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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.