Key West, Florida
Enjoy feeling like you are at a far corner and southernmost outpost of the USA- it feels like a mini New Orleans on the beach!
- More about your Oliver Guide: Sabrina Eliasoph
- Trip type: Family, Beach
- Activity level: easy
- Ideal length of trip: 4 nights is perfect
to & from
Easiest to fly directly in Key West (EYW); but many people start their trip in Miami and drive the four hours down the Keys. I heard there can be a lot of traffic on the many bridges down so we chose to fly directly into Key West.
Where to Stay
Parrot Key Resort– This resort is in center of island, so only drawbacks are that you are an Uber ride (10 minutes) or 1/2 hour bike ride away from downtown. We actually enjoyed being removed from the hustle bustle of downtown. This resort has the most terrific set up of rooms for family with 3 kids; one main master bedroom/ bath, a living room w/ couch that our son slept on; and an upstairs room with twin beds and its own bathroom, for our daughters and balconies on both sides of the suite. There are 4 pools– they are small, not huge, but the grounds are lovely and very lush and landscaped with lots of tropical greenery. The resort runs shuttles to Smathers Beach and also to downtown a few times a day. The concierge help was fantastic; they helped us book our tours and itineraries and are very friendly. The hotel has a small beachfront w/ hammocks and lounge chairs. Looks out on to a Bay, not open water, but it’s pretty enough and you can catch a great sunset, with cocktail in hand. The restaurant at the main pool has a great bar–not the best food, but perfect for breakfast or lite lunch or a snack.
Sunset Key Cottages– We actually initially tried booking this but it was sold out. It is definitely very upscale and probably more luxurious than Parrot Key, but also pricey.