Kissimmee (827) Filter Cancel
Loading...
Kissimmee Florida Vacation Rentals - Condo
1 / 8

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
Beautiful Kissimmee vacation condo with three bedrooms and two full bathrooms. It can sleep up to eight guests comfortably. The Kissimmee vacation rental features a fully equipped kitchen with all the necessities to make...
(7) Excellent (7 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 19

Kissimmee Home
4 BR / 3 BA / Sleeps 8 4 8 5 night min stay
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
Dishwasher • TV (Antenna) • Air Conditioning
This wonderful Orlando Florida vacation home, features a nautical theme through out the home. It has a game room with pool table with a ping pong top and a private screened in pool and patio. You will not want to miss t...
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 / 35

Kissimmee Home
4 BR / 3 BA / Sleeps 10 4 10 3 night min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
This luxurious 4 bedroom, 3 bath resort pool home has it all: A game room with a pool table, air hockey table and foosball table, a private screen enclosed swimming pool with build in whirlpool overlooking a conservat...
Kissimmee Florida Vacation Rentals - Home
1 / 35

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 • Washer/Dryer • Air Conditioning
Located in the Solana development which has a wealth of on site facilities including beach volleyball court, an intriguing outdoor kids play area, table tennis, crazy golf course, fitness center, TV room, shop, vi...
Kissimmee Florida Vacation Rentals - Home
1 / 15

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
Spacious 4bedrooms home, perfectly located in subdivision on Crescent Lakes. Rental is fully furnished and offers hardwood and ceramic floorings, Fully equipped kitchen, air condition, whole house sound system are pa...
(4) Excellent (4 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 59

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)
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 / 21

Kissimmee Home
4 BR / 3.5 BA / Sleeps 10 4 10 No min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 3.5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
$1200 Per Week In Month Of February , March, April ( Ask About May & June Specials ) (cleaning & Taxes Included ) Optional Pool Heat Is $140 Per Week No Animals & No Smoking No Animals & No Smoking This Luxuriously...
Kissimmee Florida Vacation Rentals - Townhouse
1 / 24

Kissimmee Townhouse
3 BR / 2 BA / Sleeps 8 3 8 Min stay varies
Townhouse / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Encantada Resort - Kissimmee, Florida is an upscale gated community located just 4 miles from Walt Disney World. This luxury resort sits nestled just off Hwy 192 in Kissimmee, Florida and is one of the most desired re...
Kissimmee Florida Vacation Rentals - Villa
1 / 13

Kissimmee Villa
4 BR / 3 BA / Sleeps 10 4 10 No min stay
Villa / 4 Bedrooms / Sleeps 10
4 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Gorgious private Disney vacation villa only 3 miles from disney and close to all other attractions. Including 4 Bedrooms/3 full baths/ south facing private enclosed pool and jacuzzi/ game room/ and all the comforts of ho...
(2) Excellent (2 reviews)
Kissimmee Florida Vacation Rentals - Villa
1 / 31

Kissimmee Villa
6 BR / 4 BA / Sleeps 12 6 12 Min stay varies
Villa / 6 Bedrooms / Sleeps 12
6 bedrooms 4 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
Windsor Hills villa description Located in the 24/7 guarded and gated community of Windsor Hills, the Disney area's #1 Vacation Resort! Only 2 Miles from Disney. South facing pool/SPA for all day Sun exposure AND Ex...
(7) Excellent (7 reviews)
Kissimmee Florida Vacation Rentals - Home
1 / 26

Kissimmee Home
7 BR / 4.5 BA / Sleeps 14 7 14 Min stay varies
Home / 7 Bedrooms / Sleeps 14
7 bedrooms 4.5 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
Welcome to this spacious seven bedroom luxurious home. Just 3 miles from Walt Disney World at the gated Emerald Island resort. This beautifully furnished and professionally decorated villa has 7 bedrooms (one master ...
(9) Excellent (9 reviews)
Kissimmee Florida Vacation Rentals - Condo
1 / 30

Kissimmee Condo
3 BR / 3 BA / Sleeps 8 3 8 Min stay varies
Condo / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
It's called "The Lion Kings! " and WOW, will you and your family absolutely fall in love with this Disney World area home, This spectacular, newly re- designed and newly furnished Disney World area home has TWO k...
Kissimmee Florida Vacation Rentals - Villa
1 / 42

Kissimmee Villa
5 BR / 3 BA / Sleeps 10 5 10 Min stay varies
Villa / 5 Bedrooms / Sleeps 10
5 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Florida and County licensed newly renovated and furnished villa has 5 bedrooms and 3 baths with two kings, (one downstairs ( master suite) and one upstairs), two queens, (one downstairs and one upstairs), and one twi...
(2) Excellent (2 reviews)
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 / 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 - 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 / 28

Kissimmee Villa
6 BR / 5 BA / Sleeps 16 6 16 Min stay varies
Villa / 6 Bedrooms / Sleeps 16
6 bedrooms 5 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
Brand new luxury 3, 300 sqft, two- story single family home located on an exclusive gated resort. It is only 10 minutes away from Disney theme parks. 6 bedrooms, 5 bath, loft, and game room. Spacious kitchen...
(3) Excellent (3 reviews)
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 - 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)
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 - 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 - 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 ...
Kissimmee Florida Vacation Rentals - Townhouse
1 / 21

Kissimmee Townhouse
4 BR / 3 BA / Sleeps 10 4 10 Min stay varies
Townhouse / 4 Bedrooms / Sleeps 10
4 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
'Every Day with Rachael Ray' Magazine recommended vacation home, on page 162, Dec. 2010/Jan. 2011 issue! ! ! Minutes to parks. Affordable luxury. Free Wireless Internet. Charming four- bedroom villas in the heart ...
(49) Excellent (49 reviews)
Kissimmee Florida Vacation Rentals - Apartment
1 / 9

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
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 - 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 - Townhouse
1 / 22

Kissimmee Townhouse
3 BR / 3 BA / Sleeps 6 3 6 Min stay varies
Townhouse / 3 Bedrooms / Sleeps 6
3 bedrooms 3 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
By renting our home, you will be renting DIRECT with the property owners - not an agent or management company acting on behalf of many owners at Regal Oaks. The photos on this page are your accommodation. We take pride...
(3) Excellent (3 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...
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.