Orlando is Central Florida: It is land-locked. It is hot in the summer. It is not on the beach, and thus does not get afternoon sea breezes. The average winter temperatures are not too cold, but sometimes a cold front blows down and it can be down right cold in Orlando/Kissimmee! If you come in the winter, be prepared for the occasional chill, especially at night. If you travel in winter, it is advantageous to bring layered warm clothes!
Bring a small first aid kit that includes bandages, cold/allergy medicine and Aspirin. It seems someone always gets a headache or a cold. Expect blisters on kids’ feet. Your sinuses are likely to suffer from air travel, dry air conditioning and swimming pools.
Bring hats and sunscreen for the parks/pool. "Flip-flops" and small pool toys (kids love to play with foam footballs and diving rings) are practical at the community pool.
If you're visiting in the summer, bring one of those spray water bottles with a built-in fan. They work! These water bottles are cheap to buy at discount stores, but may cost $20 at the parks.
Bring rain ponchos or trash bags for everyone. In summer it seems to rain many afternoons… generally only for a short time each day.
Bring a good Orlando road map. If you have access, get a map from AAA in your hometown and get the AAA tour book for Orlando. Another possible source are the maps provided in books such as "The Unofficial Guide To Walt Disney World."
On the maps you get in advance, highlight routes to the parks from your vacation rental, and how to get to your vacation rental property prior to arriving in Orlando. You may even want to do Mapquest Driving Directions for each car trip you plan to make in advance of arriving at your vacation rental.
Bring your own stroller. Renting daily is expensive and a logistics hassle. If you don't want to bring your big stroller, consider purchasing an inexpensive "umbrella" stroller.
Expect to walk 3-5 miles each day on the hot/hard pavement of the parks. Comfortable shoes are an absolute must. Have bandages handy in case of blisters.
You will be tired (and maybe stressed out) by the end of an Orlando vacation. Know this going in. You will see and do a lot, but it likely will leave you with the classic feeling of needing a "vacation from your vacation."
Especially for the more crowded times, like summer. Learn the rules for each park's fast pass ticket system. Plan and manage your each day's route and activities by time of day through the parks so you can get and use as many fast passes as possible throughout the day.
Double check every time you use a fast pass machine. It's unbelievable how many people forget their park tickets at these machines!
Be a good neighbor, offer any of your unused fast passes to other people on the way out.
Other than theme parks. It's not uncommon for some to want to do other things than theme parks after a few days, or more than one visit to Orlando/Kissimmee. If you've had your fill with the theme parks, there are numerous other options including heading to a water park, the beach, Kennedy Space Center (60 minutes to the east), Bush Gardens (a bit more than 60 minutes to the west), the everglades (3 hours to the south), or even the Florida Keys (5 hours to the south.) I've provided an extensive list for you. Click Other Activities to go to the page where I list a number of them.
Slow Times Of The Year: Once there were completely predictably slow times of the year for Orlando theme parks. Being good business people, the parks are combating "slow" times by offering large-scale special events. If you are planning your trip for a "slow" time to avoid long lines, double check with the parks. They may have scheduled a special event for the exact time you plan to come, like marathons, concerts, food festivals, golf tournaments, etc., that will attract large crowds for the duration of that event.
The first two weeks of December are traditionally Orlando's slowest. The last week of December and first week of January are typically Orlando's busiest. The Memorial Day Monday and the days immediately following also tend to be very light on attendance. Fall after kids go back to school tend to be slower.
Park attendance can be gauged somewhat by operating hours. If the parks close early (say 7pm), generally that means the owners anticipate light crowds. If the parks are open late (11pm or midnight), they are expecting large crowds, which means long lines. The place to check this is on the website for each specific park you are interested in.
Little Known: Baby Swap: For couples with small children that are too small to go on some of the rides for safety reasons, most theme parks will allow you to do a "baby swap" on rides. This is a real benefit to families with such young children. The entire family can wait in line for a "grown up" ride. Once you are at the boarding station, you can ask the attendant for a "baby swap." One adult will remain in the station with the young child while the other adult and kids ride. When they return from the ride, they wait in the station with the child while the other adult rides. This saves the family from having to wait in line twice. Check out this link for more suggestion from Disney World.
Orlando is not something you can see in one trip. It is simply not possible to enjoy all of the area’s attractions in a week. You will leave without having seen it all. Define what interests you and leave enough time to enjoy it. Don’t get caught in the trap of trying to see it all. Although you will not be able to see it all, if you plan ahead, you can see what's more important to you.
Stay hydrated. Airplanes, air conditioning (cars and your vacation rental property) and the relentless Florida sun in summer will dehydrate you in a couple of hours. Drink lots of water or juice. Avoid diuretics like coffee, cola and beer.
Three months ahead of time get the brochures from any theme parks you plan to visit. You might also consider buying a good book about the theme parks. One example is The Unofficial Guide To Walt Disney World (click here to see more.) This book contains good information about all the Orlando parks, not just Disney. It gives you lots of information you need to create an effective plan for your theme park visits. The author even suggests theme park routes and times that can allow you to see more attractions in the amount of time you have available.
Over the years the unofficial Guide has grown to be quite expansive (so has Orlando!) A thorough book like this will take you several weeks to read, digest and plan your trip. Expect to pay at least $20 at a local bookstore for such books. (It's cheaper at Amazon.com if you have the time.) This is a small fraction of the cost of your trip. Information is power. Books like this give you details not possible to encompass in a travel brochure or web site.
After reading your book, layout a detailed plan highlighting what you want to do each day. Write out your plan and keep it with you.
Buy your tickets in advance. If you have access, consider doing it through your hometown AAA (American Automobile Association) office. AAA functions as an authorized reseller of many entertainment tickets, including Disney World, and generally offers tickets that are a few dollars cheaper than at the gate. At the very least, the discount from AAA for a family will save you money toward covering your AAA membership cost for the year (which in turn means you then also have access to their great travel planning services, including a map of Orlando and their AAA tour book for Orlando.)
Also, you can check via the Internet with the official park web sites for deals on individual tickets. The parks will generally offer a slight discount to you online in advance versus buying at the front gate. Tickets purchased in advance online can be sent directly to your home or picked up at the park's "will call" window. I've provided links to a number of sources on my FAQ page.
Note. The discounts offered through resellers and online are generally small.
The best way to save money is to look for deals on your flight or rental car, and I highly recommend using a vacation rental by owner, such as my Butterfly or Crystal. My resort vacation rentals enable you to save money on food because my vacation rental has a fully furnished kitchen and you can stock up on food at one of Orlando's Publix or Winn Dixie supermarkets. My places also have fully equipped laundries, and are located only 3 miles from the Disney World main gate entrance in Kissimmee. For more details on why these are such great deals, click here to see Advantages of a Vacation Rental.