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Kissimmee Vacation Homes for Sale

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1062 Jack Nicklaus Ct, Kissimmee

7 Beds, 9 Baths, 7,142 SqFt
Under Construction. This remarkable 7 bedroom, 7 full baths & 3 half baths custom home will feature a master and secondary bedroom downstairs, an expansive kitchen with a super island with seating for 12, two refrigerators, wine refrigerator, separate dining room as well as a movie room, game room and 2 laundry rooms. You will find ample outdoor areas to relax in, some of which will be a covered upstairs balcony in the front of the home, as

1051 Jack Nicklaus Ct, Kissimmee

7 Beds, 8 Baths, 5,410 SqFt
Under Construction. Luxurious custom home behind the gates of Bear’s Den at Reunion. World class destination 10 minutes from Walt Disney World with access to 3 golf courses, a tennis complex, water park, restaurants and community events. The impressive Clubhouse at Bear’s Den now under construction will feature a club restaurant, patio seating, fully stocked pro shop, men’s and women’s locker rooms, and a well-equipped exercise room. Custom

9054 Paolos Pl, Kissimmee

5 Beds, 7 Baths, 6,312 SqFt
This is THE HOME OF YOUR DREAMS! Enjoy the private luxuries of skiing, boating & living on almost 2 acres of private land nestled on beautiful Lake Davenport. This custom architectural estate home boasts beautiful landscaping, a bright & open floor plan, the finest ARCHITECTURAL DETAILS & finishes, and is a state-of-the-art SMART HOME. Control everything w/ a touch of a finger! The open floor plan boasts a formal living room, family

1081 Jack Nicklaus Ct, Kissimmee

8 Beds, 10 Baths, 5,785 SqFt
Under Construction. Luxurious custom home behind the gates of Bear’s Den at Reunion. World class destination only 10 minutes from Walt Disney World. Luxury custom home built by Encore offers exceptional detail and outstanding craftsmanship. This contemporary home will have 8 bedrooms with a master suite downstairs, 8 full baths and 2 half baths, gourmet kitchen featuring 2 islands, open concept kitchen/dining/family room, and a substantial game

991 Jack Nicklaus Ct, Kissimmee

6 Beds, 7 Baths, 4,582 SqFt
Under Construction. Contemporary and Modern with custom details in every room, this home is featured in the exclusive gated community of Bears Den, “a Jack Nicklaus licensed community in Reunion.” Cool porcelain plank floors lead you into an expansive kitchen with quartz counter tops, dining and family room complete with a stunning stone feature wall warmed by a modern fireplace. This six bedroom, 6.5 bath home has four master suites with

404 S Vernon Ave, Kissimmee

1 Bed, 2 Baths, 2,442 SqFt
1.66 acre site, which includes a 2,442 square foot original wood framed home built in 1894. Directly across the street from Big Toho Marina with approximately 238' fronting Lakeshore Blvd. Walking distance to restaurants, entertainment, the courthouse, etc.... The home could be renovated, however, the highest and best use of the property would likely be consistent with the City of Kissimmee's future land use designation of Mixed-Use Downtown

1087 Jack Nicklaus Ct, Kissimmee

5 Beds, 6 Baths, 3,850 SqFt
Under Construction. Beautiful Modern Classic home located in the exclusive gated community of Bears Den, “a Jack Nicklaus licensed community in Reunion.” Bright and welcoming with lots of natural light, this five bedroom, 5.5 bath home is accented with a coastal color palette. Full of custom features inside and out to include three master suites, two with private balconies, secluded theater, game room with engineered wood floors, apron

2595 Michigan Ave, Kissimmee

3 Beds, 2 Baths, 1,656 SqFt
Incredible Opportunity! This property is zoned Institutional app. 5 acres with app. 220 Ft frontage on Michigan Ave. Easy access to shopping mall, FL Turnpike and Osceola Pkwy and Orlando International Airport. Seller is very motivated and may be willing to do Seller Financing. Can be used for Educational Facilities (Private), Hospital/Health Institute, Houses of Worship, Park and Playgrounds, Pet Rescue/Veterinary, endless possibilities.

241 Falls Dr, Kissimmee

11 Beds, 13 Baths, 5,436 SqFt
The most beautiful and well located home at Encore. This pristine 11 bedrooms, 10.3 bathrooms single family home is nested on the perfect lot that provides a stunning view and easy access to the WATER PARK. This TURNKEY home features many great leisure and social seating areas and includes a fully equipped and well decorated home theater. Its Kitchen is fully equipped with a beautiful granite countertop breakfast bar style. Two double door

491 Burma St, Kissimmee

11 Beds, 13 Baths, 5,436 SqFt
This is the home you have been waiting for, no need to wait to build or get set up in a rental program. This home is turnkey in a fully marketed and managed Jeeves management program. Professionally decorated this vacation home is in mint condition and is sold fully furnished and rental ready. All stainless steel appliances, luxury bedroom suits, two large sitting / media areas, large flat screen Samsung HD televisions in all rooms, a

3620 Reaves Rd, Kissimmee

4 Beds, 3 Baths, 3,296 SqFt
Great location in growing area and with 4 bedrooms and 3 baths it's ready for your family to move in and the Florida lifestyle. Near shopping, restaurants, and schools.

7616 Brookhurst Ln, Kissimmee

11 Beds, 13 Baths, 5,496 SqFt
Fantastic fully furnished 11 bedrooms, 10.3 bathrooms pool home in Encore Resort. The Biltomore floor plan is one of the best in the resort. This TURNKEY home features many great leisure and social seating areas . Its Kitchen is fully equipped with a beautiful granite countertop breakfast bar style. Two double door stainless steel refrigerator, double built in ovens and 2 dishwashers. Family style dining table that seats up to 12 family members


Kissimmee has a relatively small historic Downtown are, which is quaint and full of exciting restaurants and a beautiful lake front park. In fact Kissimmee covers a very large area and houses around 69,000 residents, that number is dramatically increased every year by the millions of people from all around the world who come to visit Kissimmee, where a large portion of Vacation Homes and Villas are located to support the Orlando Vacation Market.

Historic Downtown KissimmeeKissimmee also includes townships such as Celebration, as master planned community and luxury Golf Resorts, Country Clubs and Vacation Home Communities such as Reunion Resort and Champions Gate. These are Close to Disney Orlando, withing 15 minutes drive and perfect locations to spend your leisure time while not working or enjoying the theme parks.

The list of activities to enjoy in Kissimmee is endless, take an air boat ride and enjoy viewing Alligators in their natural habitat or paddle around the "jungle" in a Kayak. Try your hand at Crazy Golf or even the real thing at the many world class golf facilities that Kissimmee has to offer. There are just simply too many restaurants to ever visit them all and a good selection of Dinner Shows.

Old Town, is unique, wander around and see a slice of Americana in action or visit the neighboring Fun Spot where you can dare yourself to take the Sky Ride or keep your feet on the ground and pick up those Florida Disney Souvenirs that you need to bring back to your home to help you remember this in this funky and fun town.

Owning a property here could be a good decision, either a vacation home, villa or condo in Kissimmee with it's close proximity to Disney Orlando makes it almost an unbeatable choice. There are also many opportunities to live the dream here in Kissimmee  where employment is generally better than the national average due to the demands of the service industry and tech companies.  Kissimmee is of course well located to support Lake Nona and it's rapid growth in Health and Science related jobs at places such as Nemours.

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS.

Listing information last updated on July 19th, 2018 at 6:30pm EDT.