This is for Military/DOD only with base access.
We stayed at two locations over the New Years break. First was
Navy Lodge at Sigsbee point. The lodge does not have many rooms, kind of small. Call ahead for sure. About 98 a night, compared to 800 in town over New Years, no joke!
The Navy Lodge has many pros: the exchange and commissary are right there. MWR is just across the way, the boat slips and rentals are well within walking distance, including the Sunset lounge ( never went there but it looked nice right next to water). The boat house rents out 21 foot fishing boats, not pontoons or family style cruisers, however you could you do it in these boats. They are cheap and available during non busy periods. We rented kayaks and snorkel gear on base, very helpful and friendly enlisted guys there. The only con is you will have to drive into the main area of Key West such as Mallory Square and such. Other than that, I enjoyed the lodge. FYI, the staff leaves at 8pm, you have to use the side entrance to get in and out. I do recommend the lodge without any reservation!
Trumbo Condo: These were great. Right inside the gate and about a 20 minute walk to the main area of Key West (just an estimate, I never walked it). Trumbo point is mostly the Gateway Inn, the condos, and a small mini mart that is open till about 7 pm. The location is nice, but there isn’t much else on this base called Trumbo point.
Driving to Duval street. Most parking is about $4 an hour. I’m from Chicago so that’s not bad. However, I parked inside of Truman Annex (Navy) and it was free.
Lodging overview: If you can get the condos, go for it. If you can’t, not a big deal. I liked the Navy Lodge just as much, and your not going here to sleep or stay in the room. We liked the condo because we had 7 people in our party with us. All of the staff was just fine everywhere we went. If you have a RV or camper, this is heaven for you. They are all over the Navy bases down there.
Commissary and NEX. The main ones are located at Sigsbee, which is about a 5 minute drive from Trumbo point.
Truman annex also has a MWR but was closed for the New Years weekend.
One major point: NAS Boca Chica is about 8 miles out from Key West. If you stay at the Navy INN, you could wind up out here. I think the Navy INN was 70 a night, the condo was 90 a night with a ton of room to move around.
Side notes. I stayed at Trumbo Point, if you take Bertha St. right across the island, you will wind up at Smathers Beach, just off of South Roosevelt BLVD. Is less than a 5 minute drive, and is a public beach. The was plenty of parking and we didn’t have to fight any crowds to find an open beach spot. The sand was real smooth and easy to walk on. We went to Naval Station Truman annex which also has beach but is was way too rocky, I do not recommend going there to swim. Other wise its ok. Smathers beach is also a good place to bring your kayak(from the base), sit in the water and watch the sunset. That’s what my three kids did, about 30 yards out from shore (kids are 14, 11,10).
My recommendations are:
Do Mallory Square for the sunset one night, then all the other nights at Smathers beach. Rent kayaks from one of the bases for the day, 18 dollars I think and you can take them in your car to another location (like we did). Bikes are 18 dollars a day at MWR too. Check out all MWR locations, Boca Chica, Truman annex, and Trumbo point (at the condos). They basically rent the same items, bikes and scuba gear.
Maps. Once you get in town, grab a map. They are free and everywhere. Once you come in town there is a CVS, Walgreens, Food Lion, Winn Dixie, and Public. Dominos Pizza has 5 dollar specials, we got three and ate and ran.
We stayed four nights and 5 days, that was just about enough. We had jet skis, parasailed, and kayaked. We all had a great time. For us, water stuff during the day, Duval Street, Mallory Square, and nightlife at night.
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Alternate lodging: About 2 and half hours out, the Air Force has homestead Air Force Base. 39 a night. This maybe useful for those who can’t make it in or have to leave early. Check it out at dodlodging.net. Its clean and safe.