Specialists in Orlando villa holidays
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Villas in Kissimmee

Renting a vacation home in Kissimmee is one of the most exciting things you can do for you and your family and will help you get the most out of your time in Orlando.

Our comprehensive list of privately owned Florida villas, town homes and apartments have been visited and checked by our full-time inspectors who live and work in Orlando, so you will have complete peace of mind that what you see online is what you will find when you arrive.

Resort-Style Communities in Kissimmee

The properties on the resort-style communities will allow you and your family to have access to a variety of facilities during your stay, helping you to fully enjoy your ‘relaxing villa days’ when you decide not to venture too far out or if you want to just take things easy.

The resort facilities at many of our Orlando properties include:

  • Heated swimming pools
  • Lazy river or water parks
  • Separate heated spas
  • Fully-equipped gyms and fitness centres
  • Outdoor sports courts for tennis, volleyball and basketball
  • Tiki bars serving cold drinks and snacks every day
  • Games rooms
  • Kids play areas with swings and slides
  • BBQ and picnic areas
  • Clubhouse with TV lounge and wi-fi

Peace of Mind for Your Orlando Holiday

Many of the Kissimmee communities we have properties on are gated, helping to give you extra peace of mind when deciding which community to stay on. These are often manned with security guards who can also help answer any questions about local restaurants, shops and other places to visit; extremely useful if this is your first time in Orlando.

Holiday Homes Close to Disney World

Even if you choose a holiday home on a community in Kissimmee that is not gated or does not have resort facilities, then you are still going to be in a fantastic location to enjoy everything in the area. All our Kissimmee communities are close to Disney World, with some of them around a 5 to 10 minute drive away from the magic and excitement. This means of course that you can spend all day with your family enjoying the rides, parades and character meets before heading back home for a dinner, followed by a second visit of the day to see the amazing firework displays later in the evening; without spending another penny on admission fees or car parking charges.

Conveniently Located to Reach Florida’s Many Attractions

Kissimmee is also conveniently close to Orlando’s other major theme parks and popular tourist attractions, including SeaWorld and Discovery Cove, and of course, The Wizarding World of Harry Potter, Volcano Bay water park and the other attractions at Universal Orlando Resorts.

The I-4 Highway is easy to reach from all the Kissimmee communities. This will take you to Tampa, Busch Gardens and LEGOLAND when travelling west, or Daytona and Kennedy Space Center when driving east, not forgetting Florida’s award-winning beaches on both coastlines, which can easily be reached in less than 2 hours.

Our guides to each community can be found here. Each of the properties we list has been regularly inspected by our experienced representatives who live and work in the area, so if there is anything you still want to know, please feel free to contact us.

Choose from 222 properties matching your criteria

Lindfields, 3 Bedroom villa

Property: LNDFW-31874

This three bedroom villa with a good sized pool deck and ample privacy sits on the Lindfields community located just off the US192. Disney theme parks are just a ten minute drive away via the secret shortcut from the community.

  • 1 x Double Bed (1 x King)
  • 4 x Single Beds
  • 2 x Bathrooms (1 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Wi-Fi
  • Baby accessories

Liberty Village, 4 Bedroom villa

Property: LVIQS-42518

This large 4 bedroom private villa is on the Kissimmee community of Liberty Village, close to Disney World. With a southeast-facing pool with conservation view this rental villa is perfect for you to rest and recover. A wide range of shops and restaurants are located within a few miles of here.

  • 2 x Double Beds (1 x King, 1 x Queen)
  • 4 x Single Beds
  • 2.5 x Bathrooms (1 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Spa
  • Wi-Fi
  • Scenic View
  • South or West Facing

Indian Point, 4 Bedroom villa

Property: IPOBK-41622

A few miles south of the US192 is this four bedroom villa on the Indian Point community. From here the Disney parks are only 15 minutes away by car, with SeaWorld and Universal studios slightly further, requiring 25 minutes on the road.

  • 2 x Double Beds (1 x King, 1 x Queen)
  • 4 x Single Beds
  • 2 x Bathrooms (1 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Wi-Fi
  • Games Room
  • Community Facilities
  • Baby accessories

Indian Point, 3 Bedroom villa

Property: IPOBK-31623

This southwest-facing three bedroom villa with private pool is on the Indian Point community a few miles south of the US192. From here the Disney parks are only 15 minutes away by car, with Universal Studios and SeaWorld about a 25-minute drive.

  • 2 x Double Beds (1 x King, 1 x Queen)
  • 3 x Single Beds
  • 2 x Bathrooms (1 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Wi-Fi
  • South or West Facing
  • Community Facilities

Lindfields, 4 Bedroom villa

Property: LNDJK-41414

Sitting on the Lindfields community is this spacious four bedroom villa with a private west facing pool deck with a grassed area outside of the pool screen. Situated just off the US192 means the Disney area is just ten minutes drive away.

  • 3 x Double Beds (1 x King, 2 x Queen)
  • 2 x Single Beds
  • 2 x Bathrooms (1 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Wi-Fi
  • Games Room
  • South or West Facing
  • Baby accessories

Windward Cay, 3 Bedroom villa

Property: WCAKB-31144

This lovely three bedroom Windward Cay villa with a good-sized pool and completely private south facing pool deck has views of a lake and woodland to the rear of the property. Situated just off the US192 this villa is ideal for your family holiday.

  • 2 x Double Beds (1 x King, 1 x Queen)
  • 2 x Single Beds
  • 2 x Bathrooms (1 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Spa
  • Wi-Fi
  • Scenic View
  • Games Room
  • South or West Facing

Indian Ridge Oaks, 3 Bedroom villa

Property: IROOJ-32513

This tastefully furnished 3 bedroom vacation villa is on the peaceful Kissimmee community of Indian Ridge Oaks, close to Disney World and other Orlando attractions. The villa has an air-conditioned family games room, a kid’s play area in the garden, a fire pit and a freestanding hot tub.

  • 2 x Double Beds (1 x King, 1 x Queen)
  • 2 x Single Beds
  • 2 x Bathrooms (1 x En-Suite)
  • Air Conditioning
  • Spa
  • Wi-Fi
  • Games Room
  • Baby accessories

Windsor Palms, 3 Bedroom villa

Property: WPACV-32599

This large 3 bedroom villa is on the gated Kissimmee resort of Windsor Palms, just a few minutes from Orlando's famous Disney World theme parks and the ever-popular US192 with it’s abundance of shops and restaurants. The villa offers plenty of space for everybody, a private pool and a games room.

  • 2 x Double Beds (1 x King, 1 x Queen)
  • 3 x Single Beds
  • 3 x Bathrooms (2 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Wi-Fi
  • Games Room
  • Gated Community
  • Community Facilities
  • Baby accessories

Emerald Island, 4 Bedroom villa

Property: EISKS-41306

With a secluded south-facing pool and spa deck, games room and plenty of space for everybody, this 4 bedroom villa on the gated community of Emerald Island in Kissimmee is perfect for your Orlando holiday. Situated close to Disney and with access to resort facilities are two additional benefits.

  • 2 x Double Beds (2 x Queen)
  • 4 x Single Beds
  • 3 x Bathrooms (2 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Spa
  • Wi-Fi
  • Games Room
  • Gated Community
  • South or West Facing
  • Community Facilities
  • Baby accessories

Rolling Hills, 4 Bedroom villa

Property: RHIBG-42011

This 4 bedroom villa is on the Kissimmee community of Rolling Hills, close to Disney World theme parks and Orlando’s famous US192, lined on both sides with restaurants, bars and shops. The villa has a games room and a large private pool deck with no overlooking neighbours and natural lake views.

  • 3 x Double Beds (2 x King, 1 x Queen)
  • 2 x Single Beds
  • 3 x Bathrooms (2 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Wi-Fi
  • Scenic View
  • Games Room

Lindfields Reserve, 3 Bedroom villa

Property: LNRLV-31632

Along the US192 is this quirky three bedroom villa including separate annexe on the gated community of Lindfields Reserve. The Disney parks and SeaWorld are reachable in under 20 minutes by car, with Universal Studios around 30 minutes away.

  • 2 x Double Beds (1 x King, 1 x Queen)
  • 4 x Single Beds
  • 3 x Bathrooms (3 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Spa
  • Wi-Fi
  • Games Room
  • Gated Community
  • South or West Facing

Oak Island Cove, 4 Bedroom villa

Property: OICCK-41563

Around a mile from the US192 is this south-facing four bedroom villa on Oak Island Cove. From here a trip to the Disney area will take you around 10 minutes in a car, or 25 minutes if you wish to pay a visit to SeaWorld and Universal Studios.

  • 2 x Double Beds (1 x King, 1 x Queen)
  • 4 x Single Beds
  • 2.5 x Bathrooms (1 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Spa
  • Wi-Fi
  • Scenic View
  • South or West Facing

Eagle Pointe, 3 Bedroom villa

Property: EPOCV-31704

Immerse yourself in the Floridian lifestyle at this three bedroom villa on the quiet community of Eagle Pointe in Kissimmee. With the Disney parks 15 minutes away and the US192’s restaurants and shops close by, this is your perfect holiday villa!

  • 2 x Double Beds (1 x King, 1 x Queen)
  • 2 x Single Beds
  • 2 x Bathrooms (1 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Wi-Fi

Emerald Island, 4 Bedroom villa

Property: EISBZ-4797

This four bedroom villa with a stunning south-west facing pool deck and plenty of space for the whole family is a perfect choice to accommodate the entire family’s needs.

  • 2 x Double Beds (2 x King)
  • 5 x Single Beds
  • 3 x Bathrooms (2 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Wi-Fi
  • Games Room
  • Gated Community
  • South or West Facing
  • Community Facilities
  • Baby accessories

Indian Creek, 4 Bedroom villa

Property: ICRNT-42006

A nicely decorated 4 bedroom vacation villa with a well-equipped games room and a private south-facing pool and spa with privacy fences all round. Situated on the very popular Kissimmee community of Indian Creek, close to Disney World and many other Orlando theme parks and major tourist attractions.

  • 2 x Double Beds (1 x King, 1 x Queen)
  • 4 x Single Beds
  • 3 x Bathrooms (2 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Spa
  • Wi-Fi
  • Games Room
  • South or West Facing
  • Community Facilities
  • Baby accessories

Indian Ridge Oaks, 4 Bedroom villa

Property: IROOS-42075

This 4 bedroom rental villa has a west-facing private pool with no overlooking neighbours, a well-equipped games room and themed bedrooms for the kids. It sits on the peaceful Kissimmee community of Indian Ridge Oaks, close to Disney World theme parks and all other popular Orlando attractions.

  • 2 x Double Beds (1 x King, 1 x Queen)
  • 4 x Single Beds
  • 2 x Bathrooms (1 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Wi-Fi
  • Scenic View
  • Games Room
  • South or West Facing
  • Baby accessories

Lake Berkley, 4 Bedroom villa

Property: LBELZ-41661

This 4 bedroom private rental villa has a games room and a conservation view from the pool area. Sitting on the gated community of Lake Berkley in Kissimmee, close to Disney World and all other Orlando attractions as well as just a couple of miles from shops and restaurants along the popular US192.

  • 2 x Double Beds (1 x King, 1 x Double)
  • 4 x Single Beds
  • 2 x Bathrooms (1 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Wi-Fi
  • Scenic View
  • Games Room
  • Gated Community
  • Community Facilities
  • Baby accessories

Rolling Hills, 4 Bedroom villa

Property: RHIFW-41961

Sitting on the popular Kissimmee community of Rolling Hills, this 4 bedroom vacation villa has a well-equipped games room and a private swimming pool. Located close to shops, restaurants and all major Orlando theme parks including Disney World, SeaWorld and Universal.

  • 3 x Double Beds (2 x King, 1 x Queen)
  • 2 x Single Beds
  • 3 x Bathrooms (2 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Wi-Fi
  • Games Room
  • Baby accessories

Terra Verde, 4 Bedroom villa

Property: TVECK-41876

This 4 bedroom Kissimmee villa has a south-facing private pool and spa with lake views and a great family games room. Situated close to Disney World on the beautiful, gated resort of Terra Verde with amazing facilities including gym, heated swimming pool, sauna and Tiki bar.

  • 2 x Double Beds (2 x Queen)
  • 4 x Single Beds
  • 3 x Bathrooms (2 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Spa
  • Wi-Fi
  • Scenic View
  • Games Room
  • Gated Community
  • South or West Facing
  • Community Facilities
  • Baby accessories

Westside - Tuscany, 4 Bedroom villa

Property: WETCK-41853

Four bedroom villa with west-facing pool deck and conservation views on Tuscany, a subdivision of the Westside community. From here the Disney parks and SeaWorld can all be reached in 20 minutes or less, with Universal Studios a 25-minute drive away.

  • 3 x Double Beds (1 x King, 2 x Queen)
  • 2 x Single Beds
  • 2.5 x Bathrooms (1 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Wi-Fi
  • Scenic View
  • Games Room
  • South or West Facing