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 212 properties matching your criteria

Lindfields, 3 Bedroom villa

Property: LNDFW-31874

This 3 bedroom vacation villa has a good sized private pool deck with no overlooking neighbours and sits on the Lindfields community in Kissimmee, close to Disney World theme parks and many more Orlando attractions. Shops and restaurants along the US192 can be reached in a couple of minutes.

  • 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

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

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

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

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

Indian Creek, 4 Bedroom villa

Property: ICRQQ-42484

This 4 bedroom villa is on the Kissimmee community of Indian Creek, very close to Disney World. It has an extended deck with great privacy, a private pool and a bonus kiddies pool for toddlers to splash around in. With an air-conditioned games room, this villa is perfect for any holiday to Orlando.

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

Lindfields Reserve, 3 Bedroom villa

Property: LNRLV-31632

This 3 bedroom privately owned Orlando villa, with enough beds to sleep 8 people, has a secluded south and east-facing pool deck and an annexe that is ideal for in-laws or teenagers. Situated on the gated Kissimmee community of Lindfields Reserve, close to Disney and restaurants along the US192.

  • 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
  • BBQ
  • Baby accessories

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

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

Indian Ridge, 4 Bedroom villa

Property: IRICB-41207

Sitting on the Indian Ridge community in Kissimmee is this 4 bedroom rental villa with an extended, completely private pool deck. Situated just 10 minutes from the magic and excitement of Disney World, the location is ideal for visiting everything Orlando has to offer.

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

Emerald Island, 4 Bedroom villa

Property: EISDN-4655

With a west-facing private pool and spa, games room and access to some amazing resort facilities, this 4 bedroom privately owned villa is perfect for your Orlando holiday. Situated on the highly recommended gated community of Emerald Island in Kissimmee means that it is very close to Disney World.

  • 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
  • Gated Community
  • South or West Facing
  • Community Facilities
  • BBQ
  • Baby accessories

Emerald Island, 4 Bedroom villa

Property: EISDN-4656

With a southeast-facing private pool and spa, well-equipped games room and access to some amazing resort facilities, this 4 bedroom villa is perfect for your Orlando holiday. Situated on the highly recommended gated Kissimmee resort of Emerald Island, close to Disney World, shops and restaurants.

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

Emerald Island, 4 Bedroom villa

Property: EISDN-4657

Located close to Disney World is this 4 bedroom private rental villa on the highly recommended Emerald Island gated community in Kissimmee. The villa has a games room and a southeast-facing pool and spa. Guests staying here have full access to all resort facilities including heated pool and gym.

  • 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
  • BBQ
  • Baby accessories

Emerald Island, 4 Bedroom villa

Property: EISDN-4658

This 4 bedroom rental villa has a private pool and spa with no overlooking neighbours to the rear and a great games room for the kids. It is on the highly recommended gated resort of Emerald Island in Kissimmee, close to Disney World and all other popular Orlando attractions and tourist hotspots.

  • 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
  • Spa
  • Wi-Fi
  • Games Room
  • Gated Community
  • Community Facilities
  • Baby accessories

Creekside, 3 Bedroom villa

Property: CRKCQ-31241

Sitting on the Creekside community is this 3 bedroom villa that has a completely private southwest-facing pool deck with a good-sized pool. Situated just a short drive off the US192, the Disney theme parks are a 25 minute drive away.

  • 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
  • Games Room
  • South or West Facing
  • Baby accessories

Indian Creek, 4 Bedroom villa

Property: ICRFW-42629

This 4 bedroom rental villa is on the popular Kissimmee community of Indian Creek, a few minutes from Disney World and even closer to a range of shops and restaurants along the US192. With a games room and a pool with privacy on all sides, this is a great choice for your family holiday to Orlando.

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

Lake Berkley, 3 Bedroom villa

Property: LBELZ-31686

A comfortable 3 bedroom private rental villa with a secluded west-facing pool deck, games room and with access to resort facilities. The villa sits on the gated Kissimmee community of Lake Berkley, close to Disney World and all other popular Orlando attractions and theme parks.

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