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 248 properties matching your criteria

Indian Ridge Oaks, 2 Bedroom villa (Sleeps up to 4 Guests)

Property: IROFJ-21625

This standard 2 bedroom privately owned villa on the Indian Ridge Oaks community in Kissimmee has a south-facing private pool with no overlooking neighbours and is close to Disney World and other popular Orlando attractions and theme parks as well as a range of restaurants, shops and golf courses.

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

Indian Point, 3 Bedroom villa (Sleeps up to 6 Guests)

Property: IPOBK-31623

This standard 3 bedroom rental villa, with enough beds to sleep 7 guests, is on the Kissimmee community of Indian Point. The villa has a southwest-facing private pool with no overlooking neighbours and is close to Disney World and many other popular Orlando attractions and theme parks.

  • 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
  • Baby accessories

Indian Point, 4 Bedroom villa (Sleeps up to 8 Guests)

Property: IPOBK-41622

Sitting on the well-established Kissimmee community of Indian Point, this traditional 4 bedroom vacation villa has a pool table in the games room, a large sunny pool deck and plenty of space to relax. Situated close to Disney and many other popular Orlando tourist hotspots and theme parks.

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

Seasons, 4 Bedroom villa (Sleeps up to 8 Guests)

Property: SNSBK-4830

With a south-facing private pool and spa area, games room and lots of space for everybody to relax, this 4 bedroom rental villa is ideal for your family holiday to Orlando. Situated on Seasons, a peaceful community in Kissimmee, close to Disney World and other theme parks and 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

Windward Cay, 3 Bedroom villa (Sleeps up to 6 Guests)

Property: WCAKB-31144

This 3 bedroom vacation villa sits on the peaceful Windwood Cay community in Kissimmee. Features include a south-facing private pool and spa with a gorgeous lake view, a games room and spacious bedrooms. Located a few minutes from the US192, close to Disney World and many other Orlando attractions.

  • 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
  • BBQ

Creekside, 3 Bedroom villa (Sleeps up to 6 Guests)

Property: CRKCQ-31241

This traditional 3 bedroom vacation villa has a games room and a secluded southwest-facing solar-heated pool with no overlooking neighbours. It is situated on the peaceful Kissimmee community of Creekside, close to Disney World and many other popular Orlando theme parks and holiday attractions.

  • 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

Rolling Hills, 4 Bedroom villa (Sleeps up to 8 Guests)

Property: RHIBK-42686
Air Con in Games Room

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Games Room

Sitting on the popular Rolling Hills community in Kissimmee, close to Disney World and a few minutes’ drive from shops and restaurants along Orlando's famous US192, is this 4 bedroom rental villa with a secluded south-facing pool deck and an air-conditioned games room for the kids to enjoy.

  • 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
  • Wi-Fi
  • Games Room
  • South or West Facing
  • Baby accessories

Seasons, 4 Bedroom villa (Sleeps up to 8 Guests)

Property: SNSBK-4654

This well-furnished 4 bedroom villa has a great games room and a south-facing private pool and spa with no rear neighbours. The villa is situated on Seasons, a peaceful Kissimmee community close to Disney World and many other popular Orlando theme parks and tourist attractions.

  • 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
  • Spa
  • Wi-Fi
  • Games Room
  • South or West Facing
  • Baby accessories

Westside - Tuscany, 5 Bedroom villa (Sleeps up to 10 Guests)

Property: WETBK-52845

This beautiful 5 bedroom vacation villa is on the Kissimmee community of Tuscany at Westside, close to Disney and many of Orlando’s other top attractions. This villa has a games room and an extended south-facing pool deck with plenty of space for sunbathers to enjoy the glorious Florida sunshine.

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

Storey Lake, 3 Bedroom villa (Sleeps up to 6 Guests)

Property: STLVG-33302

This modern vacation home on the gated resort of Storey Lake in Kissimmee, close to Disney, SeaWorld and Universal has 3 bedrooms, with enough beds to sleep up to 8 guests, and a west-facing patio area with BBQ grill. Guests staying here have access to all nearby resort facilities.

  • 5 x Double Beds (1 x King, 4 x Double)
  • 2.5 x Bathrooms (1 x En-Suite)
  • Air Conditioning
  • Wi-Fi
  • Gated Community
  • South or West Facing
  • Community Facilities
  • Baby accessories

Rolling Hills, 4 Bedroom villa (Sleeps up to 8 Guests)

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

Seasons, 4 Bedroom villa (Sleeps up to 8 Guests)

Property: SNSBK-43350

This tastefully decorated and furnished vacation villa is on Seasons, a peaceful Kissimmee community close to Disney World and other Orlando theme parks and attractions. The villa has 4 bedrooms, a well-equipped games room and a south-facing private pool with a gorgeous lake view to the rear.

  • 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
  • Scenic View
  • Games Room
  • South or West Facing

Eagle Pointe, 3 Bedroom villa (Sleeps up to 6 Guests)

Property: EPOCV-31704

This nicely furnished and decorated 3 bedroom villa is on the Kissimmee community of Eagle Pointe, close to Disney World and many other Orlando attractions. The villa has a private pool with privacy fences all around and plenty of space, inside and out, for you to be able to relax.

  • 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
  • BBQ
  • Baby accessories

Emerald Island, 4 Bedroom villa (Sleeps up to 8 Guests)

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 (Sleeps up to 8 Guests)

Property: EISDN-4656

With a private pool and spa, well-equipped games room and access to some amazing resort facilities, this 4 bedroom villa is a great base 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 (Sleeps up to 8 Guests)

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 (Sleeps up to 8 Guests)

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
  • BBQ
  • Baby accessories

Emerald Island, 4 Bedroom villa (Sleeps up to 8 Guests)

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, 4 Bedroom villa (Sleeps up to 8 Guests)

Property: IROLR-41624

This 4 bedroom privately owned Kissimmee villa has a secluded south-facing private pool with a standalone hot tub and a well-equipped family games room. The villa is on Indian Ridge Oaks, a peaceful community close to Disney World and many other Orlando attractions, restaurants and shopping malls.

  • 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
  • South or West Facing
  • BBQ
  • Baby accessories

Indian Ridge Oaks, 4 Bedroom villa (Sleeps up to 8 Guests)

Property: IRORR-42730

A uniquely furnished and decorated 4 bedroom villa with an air-conditioned home cinema room, a west-facing pool, standalone hot tub and great privacy. Sitting on the Kissimmee community of Indian Ridge Oaks, close to Disney World and other popular Orlando attractions and theme parks.

  • 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
  • Spa
  • Wi-Fi
  • Scenic View
  • South or West Facing
  • Baby accessories