Usually a house or condo from a community like Windsor Hills will be the least expensive (A condo here is probably your least expensive condo option. A house is good if you want your own private pool and will offer the most in terms of bedrooms/bathrooms for the money. With lots of options for five, six bedroom and bigger home, it's the way to go for a very large group staying together.) Also this is very flexible for any length of stay, as you pick your start and end time. Seriously consider paying for pool heat depending on time of year or you may have your own fabulous pool that no one uses because it's freezing cold and end up driving to the community pool. Downside to me is that it doesn't have as much of a resort feel that I really like. Usually these don't feel as upscale as the lovely timeshare resorts either in terms of the decorating and furnishings, although furnishings are perfectly acceptable.
The next least expensive in price will probably be a timeshare resort. This is my personal favorite for a week long stay or longer and with the size of your group, if it were me, this is what I would do. I often rent on sites like TUG2.net and Redweek.com These have the kitchen, washer/dryer, two or three bedrooms, nice common area and usually a fab balcony or patio. I love the balcony/patio for sitting out. Typically too you will have lovely resort amenities -- beautiful pool and hot tubs and depending on the size of resort additional amenities too -- tennis, lake, golf, playground. Furnishings in general seem more upscale than most home rentals. Furnishing have broad based appeal vs. whims of owners trying to do a tacky Mickie or Minnie room some adult in your party gets stuck in. The resorts I have rented most often are Sheraton Vistana Resort (one king bedroom, another double double beds bedroom and hydabed in the common area) and Cypress Pointe (two king suite bedrooms, third bedroom with double bed, and hyde a bed in common area. These have ensuites for each master and a third bathroom too if you rent their three bedroom). There are so many great timeshares in Orlando, and the others people have mentioned in this post would be wonderful also. Downsides: If you want two king suites for adults, kids in a separate bedrooms/beds without any usage of a hydabed and kids not needing to sleep together (houses likely to have twin bed rooms), a house is going to give you that, but not the timeshare resort. The timeshare resort may not give you the sleeping space and privacy that you want. Usually you have to rent a full week and from a Friday to Friday, Saturday to Saturday, or Sunday to Sunday, so if your trip doesn't fit this, that can be a pain to find extra nights, etc. elsewhere (have to move). Usually you only have two bedrooms and two baths. You might need to use the hydabed depending on the size of your group. Also make sure to just say no to the resort tour which is a high pressure timeshare sales presentation. You will be asked to pickup a coupon book which is an opportunity to have someone talk you into a resort tour. Skip picking up the coupons or if you are curious definitely don't sign up for the tour/sales pitch (not worth the freebies and may give a negative vibe to your otherwise wonderful stay).
The most expensive of the options is the hotel suite: Lots of these: Marriott Residence Inn type places and lots of others. These are a favorite of mine for short stays. Pluses: So easy to book and booking from a resort, you have no concerns about an unscrupulous owner or rental company. Breakfast is usually included (nice if you aren't in the area long enough to bother with a larger grocery run). There are very lovely resort amenities -- usually a nice pool and hot tub (not as nice as the timeshare resort amenities typically, though). Downsides: No balcony or patio, less room, fewer bedrooms, considerably more expensive, less upscale than the timeshare resorts. // Very acceptable and I'm doing this on my next trip which is just a four night / three day stay with just me and my son (doing a double queen studio room at Marriott Residence Inn SeaWorld). We will have a kitchen and little sitting area on top of the double queen beds, breakfast included, a nice pool and hot tub area with palm trees. These places often offer a two bedroom/two bath plus kitchen and common area option also, which you would want for your group. There is typically a hyda a bed too, so a two bedroom would in most cases be able to accommodate your group.
Orlando is a wonderful place to book all these options and offers great values for your money in all three categories (good value for your dollar in terms of quality for a good price and better deals than in any other resort area I have been to in all three categories).
