1st time to the Keys....where to stay

Question

Hello! We are first timers coming to the Keys July 12-15th. There will be 2 families consisting of 7 adults (ages 19-58) and a 14-year-old. We are unsure what part of the Keys to stay in; but have already ruled out Key West even though plan to visit there for a day. We would prefer all of us in a condo or house together with a pool (if possible). We are considering Key Largo or Islamorada' but confused of the best location. Any suggestions would be greatly appreciated.

And if anyone has must do activities that only locals and frequent Keys visitors know about, please share that as well. Thanks for any and all help as we are running out of time to get this vacay planned.

Answer

For a first-time trip to the Florida Keys with a large group, Key Largo and Islamorada are both excellent options, especially if you want to stay together in a condo or house with a pool. Both areas offer a more relaxed atmosphere compared to Key West, and they are conveniently located for a day trip to Key West.

Key Largo vs Islamorada:

Key Largo: Slightly closer to Miami, making travel from the airport shorter. Offers plenty of waterfront condos and houses, many with private pools. Great for snorkeling, diving, and exploring John Pennekamp Coral Reef State Park. Easier access to marine activities for families and larger groups.
Islamorada: Known as the “Sportfishing Capital of the World,” it has charming boutique accommodations and vacation rentals, many with pools. Excellent for fishing trips, kayaking, and enjoying local seafood. Slightly more central in the Keys, so it provides a nice balance if you want to drive down to Key West for a day trip.

Recommended Areas to Look for Vacation Rentals:

Key Largo: Ocean Reef, Largo Sound, or near the Overseas Highway for easy access to restaurants and shops.
Islamorada: Plantation Key, Tavernier, or areas close to Islamorada Village for restaurants and attractions.

Must-Do Activities Known to Locals:

Snorkeling or diving at John Pennekamp Coral Reef State Park (Key Largo) to see colorful coral and marine life.
Visiting Robbie’s Marina (Islamorada) to feed the tarpon and browse local crafts.
Kayaking or paddleboarding through the mangroves—peaceful and scenic, perfect for families.
Exploring local seafood joints, like Morada Bay or Mrs. Mac’s Kitchen, for a laid-back meal with fresh catches.
Taking a sunset cruise or a glass-bottom boat tour to enjoy the unique Keys waters without going far from your base.

Overall, if your priority is minimizing drive time from Miami and having lots of pool options, Key Largo might be slightly more convenient. If you want a central location with easy access to multiple Keys and a slightly more “Keys vibe,” Islamorada is a fantastic choice. Both will allow you to make a day trip to Key West without having to stay there overnight.