Specialists in Orlando villa holidays
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Orlando Holiday Villas with Five Bedrooms

Our five-bedroom Orlando villas are close to Disney, Universal and all other theme parks and attractions that you chose Florida to see.

Typically comprising of two or three bedrooms with either a King-size or Queen-size bed and en-suite bathrooms, as well as two or three Twin-bed rooms. Staying in a villa in Orlando is a fantastic opportunity for you and your family to spend some quality time together away from the normal challenges of day-to-day living.

If you have chosen Orlando as a holiday destination to top up your tan, then you might also want to select the South or West facing option in our filter bar. Or if you’re looking for extra privacy, choose the Scenic View option. If you are travelling with active youngsters, then consider selecting the Games Room option too, so that they are kept entertained while you relax outside.

Our five-bedroom villas in Orlando have a private swimming pool, and many of them have a spa attached too, keeping all the family happy, young and old! If you plan to spend a lot of time away from the parks, then why not consider one of our villas located on a community with resort-style facilities? Again, select the option in our filter bar to see what is available for your dates.

Browse through our list of five-bedroom Orlando villas to find the perfect one for your family holiday, but feel free to give our dedicated staff a call if you can’t find exactly what you’re looking for.

Choose from 174 properties matching your criteria

Storey Lake, 5 Bedroom villa

Property: STLFH-51668

A beautifully decorated 5 bedroom private rental villa with a games room, southeast-facing pool and spa and some great themed bedrooms for kids. Sitting on the luxury resort community of Storey Lake in Kissimmee, close to Disney, Universal and other popular Orlando attractions and theme parks.

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

Watersong, 5 Bedroom villa

Property: WATBK-52717

This large 5 bedroom privately owned villa is on the gated community of Watersong, one of the most popular communities in Davenport. The villa has a private pool and spa, games room and an air-conditioned home cinema. Close to Disney World, Universal and all other famous Orlando and theme parks.

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

Windsor Hills, 5 Bedroom villa

Property: WHIFF-51495

This 5 bedroom private villa on the gated Kissimmee resort of Windsor Hills is very close to Disney World and offers a private pool and spa, an air-conditioned cinema and games room, a free BBQ grill and access to the amazing community facilities including heated pool, water park and modern gym.

  • 3 x Double Beds (2 x King, 1 x Queen)
  • 6 x Single Beds
  • 5 x Bathrooms (5 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Spa
  • Wi-Fi
  • Scenic View
  • Games Room
  • Gated Community
  • Community Facilities

Tuscan Hills, 5 Bedroom villa

Property: THIBP-5835

This 5 bedroom rental villa is on the peaceful community of Tuscan Hills, a gated development on the US27 in Davenport. The villa has a southeast-facing pool and spa with no overlooking neighbours and a family games room, it is close to Disney World and many other popular Orlando attractions.

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

Windsor Hills, 5 Bedroom villa

Property: WHIFF-52840

This beautiful 5 bedroom villa is on the luxury Windsor Hills community, a very popular gated resort in Kissimmee, close to Disney World and other Orlando attractions. Features include a fantastic, air-conditioned games room, amazing themed kids bedrooms and a west-facing private pool and spa.

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

Windsor Hills, 5 Bedroom villa

Property: WHIRG-52581

This 5 bedroom private villa is on the luxury gated community of Windsor Hills, close to Disney and offering some of the best resort facilities in Kissimmee. The villa has a well-equipped air-conditioned games room, a west-facing private pool and spa, lake views and space for the whole family.

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

Windsor Hills, 5 Bedroom villa

Property: WHIRG-52805

This 5 bedroom vacation villa is on the luxury gated resort of Windsor Hills, a highly recommended community in Kissimmee. The villa has a south-facing private pool and spa, an air-conditioned games room and tasteful décor throughout. The resort is close to Walt Disney World and other attractions.

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

Windsor Island Resort, 5 Bedroom villa

Property: WIRFH-52778

This amazing vacation villa has 5 bedrooms, each with its own en-suite bathroom, and is on the luxury gated resort of Windsor Island in Kissimmee. It has a games room, west-facing private pool and access to resort facilities. Situated close to Disney, this villa is perfect for your Orlando holiday.

  • 5 x Double Beds (2 x King, 3 x Double)
  • 3 x Single Beds
  • 5.5 x Bathrooms (5 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Wi-Fi
  • Games Room
  • South or West Facing

Windsor Hills, 5 Bedroom villa

Property: WHIFF-51733

With an air-conditioned Star Wars-themed games room, themed bedrooms for the kids and a private pool and spa with no overlooking neighbours, this privately owned 5 bedroom rental villa on the gated Kissimmee resort of Windsor Hills, close to Disney World, is perfect for your Orlando holiday.

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

Westside - Windsor, 5 Bedroom villa

Property: WEWTF-52994

Soak up the sun on the west-facing private pool deck or spend time in the air-conditioned games room at this lovely 5 bedroom rental villa. Situated on the gated resort of Windsor at Westside, one of the nicest communities in Kissimmee, it is close to Disney World and many other Orlando attractions.

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

Windsor Hills, 5 Bedroom villa

Property: WHIFB-51325

A privately owned rental villa with 5 bedrooms, each with an en-suite bathroom, a south-facing private pool and spa with a gorgeous lake view and a family games room. Situated on Windsor Hills, a luxury gated resort in Kissimmee, close to Disney World and all other major Orlando theme parks.

  • 3 x Double Beds (2 x King, 1 x Queen)
  • 4 x Single Beds
  • 5 x Bathrooms (5 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Spa
  • Wi-Fi
  • Scenic View
  • Games Room
  • Gated Community
  • South or West Facing
  • Community Facilities
  • Baby accessories

Reunion - Fairway Ridge, 5 Bedroom villa

Property: REFVV-52843

This 5 bedroom vacation villa is on the exclusive Kissimmee gated community of Reunion close to Disney World and other Orlando attractions and tourist hotspots. The villa has a separate annex with 2 of the bedrooms in, an air-conditioned cinema room and a private pool and spa with scenic views.

  • 3 x Double Beds (3 x King)
  • 4 x Single Beds
  • 4.5 x Bathrooms (4 x En-Suite)
  • Air Conditioning
  • Private Pool
  • Spa
  • Wi-Fi
  • Scenic View
  • Games Room
  • Gated Community
  • Community Facilities
  • Baby accessories

Windsor Hills, 5 Bedroom villa

Property: WHIFF-51537

This 5 bedroom villa with a great games room and a west-facing private pool and spa is on the luxury gated resort of Windsor Hills in Kissimmee. It is close to Disney World and all other Orlando attractions. Resort facilities include a heated swimming pool, water park, clubhouse, gym and cinema.

  • 3 x Double Beds (1 x King, 2 x Queen)
  • 4 x Single Beds
  • 5 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

Solara, 5 Bedroom villa

Property: SLACV-51711

Experience the wow-factor at this amazing five bedroom villa on the new gated resort of Solara in Kissimmee. With the Disney parks practically on your doorstep and plenty to do in the villa and on the resort you won’t ever want your holiday to end!

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