[raney3099]

Stay in Key West. Our friend told us to stay in Marathon to be in the middle of Key Largo and Key West. Didn’t work for us. We had an hour drive every day to Key West. Parking was horrendous. Better to stay in Key West walking distance to everything or rent mopeds or bikes to get around. To be honest next time I would fly there cause the drive from Miami to Key West was horrible as well. One lane bumper to bumper 3 hrs of traffic

[Juliebythesea]

Pier House at the business end of Duval. Quiet but in the middle of everything 😎

[Barbscats]

Key West is an 8 1/2 hr drive from here and a nice ride once you hit the Keys. If you want to stay in the heart of town, Crowne Plaza-La Concha. Hyatt, Pier House and Opal Key Resort are on the water…tiny beach area. Southernmost is at the far end of Duval-Havana Cabana, Double Tree are on Roosevelt just out of town. Parking can be a problem in town…
Fantasy Fest is a huge week long celebration the last week in Oct and hotel rates skyrocket and the Offshore boat races also bring in large crowds. There are many B&B’s…you can google them. Take the Conch Train ride…you’ll see pretty much everything of interest.

[Kathryn Putt]

The Curry House B&B on Caroline St is awesome. Walking distance to all the Duval St. fun AND they have parking.

[LuvNH]

We love Key West, but not for too long. We stay at the Crowne in the middle of the action. Enjoy your visit. Rent a golf cart to get around.

[Marywhite630]

We have been to Key West a few times as an extension to other stays we had while vacationing in Florida. If you don’t mind boat rides, I highly recommend driving to Fort Myers and taking The Key West Express to Key West. It is a FABULOUS way to travel that far south. We stayed at The Banyan Resort which is a block or so off Duval. Close to museum and several restaurants. They have a pool. There is a tiki bar and bartender will also make you breakfast. We never missed having a car there.

[Gsfraga]

Truman Annex.
Blue Marlin
Any of the Key West Inns

I have stayed at all three and was never disappointed.
They are all getting very expensive
The Casa Marina will be closing later this year for renovations

[G.R.I.T.S.]

Originally Posted by Kenswing

Now that we’ve been here for over a year and are settled in it’s time to explore. The better half wants to take a drive down to Key West.

Where is your favorite place to stay? I’m looking for replies from people who have actually been there.

Courtney’s Place b&b.

[DianeKellerWilliams]

Originally Posted by Kenswing

Now that we’ve been here for over a year and are settled in it’s time to explore. The better half wants to take a drive down to Key West.

Where is your favorite place to stay? I’m looking for replies from people who have actually been there.

Been there for work and play dozens of times. Casa Marina is the place to stay! Second choice is Hawks Cay in Duck's Key (middle keys). For a long vaca I would recommend staying mid-keys then you can drive up to Key Largo for the great tourist spots and restaurants or down to Key West for day trips.

[larrycrilley@gmail.com]

Originally Posted by Kenswing

Now that we’ve been here for over a year and are settled in it’s time to explore. The better half wants to take a drive down to Key West.

Where is your favorite place to stay? I’m looking for replies from people who have actually been there.

Been there twice and the one thing I learned from my first trip was to research and book hotels before getting there. And consider staying on another key where its just a short car or Uber ride. If money is not an issue staying right in the middle of the action comes with great convenience.

This trip was 11 years ago. Every hotel we went to were sold out except the Marriott Courtyard where we got the last room for $350 for one night.The the property was quite night nice with lots of amenities but with an 11am checkout we did not get to use any of the facilities. We basically paid $350 for a nights sleep. My mistake for just ‘winging it’.

Great idea of asking for advice and planning well in advance.

P.S. - The second trip we stayed in my sisters time share in Marathon. It was quite nice but still was a looong drive to Key West. Good luck and you will enjoy your trip!

[Dodenh]

Originally Posted by Kenswing

Now that we’ve been here for over a year and are settled in it’s time to explore. The better half wants to take a drive down to Key West.

Where is your favorite place to stay? I’m looking for replies from people who have actually been there.

FYI, locations that list adults only, means bathing suits are optional in the pools.

[OhioBuckeye]

Stayed there several times, nothing is very cheap in Key West but very interesting to see how they live there.

[mkjelenbaas]

Originally Posted by Kenswing

Now that we’ve been here for over a year and are settled in it’s time to explore. The better half wants to take a drive down to Key West.

Where is your favorite place to stay? I’m looking for replies from people who have actually been there.

Don’t drive - it is terrible - fly down and save the headaches of the SLOW (traffic ridden) trip!!8

[Sharla]

KW has been a favorite vacation spot of mine for decades! This is some of the info I give friends who want to visit:

My first recommendation is to stay in Old Town, staying in new town (on or near Roosevelt Road) looks to be cheaper at first, but there is nothing to do out there, so you will be spending money and valuable vacation time driving into Old Town (20-40 minutes depending on where you are staying), finding and paying for parking or paying cabs/ubers. Just not worth it and not really saving anything. If you stay in Old Town you will not need your car, it's very walkable. I love to stay in the waterfront hotels in Old Town. The Pier House is probably my favorite, Ocean Key, Opal Key, Hyatt Centric and slightly off the water is the Marker, all nice. There is the historic Casa Marina and The Reach on the other end of Duval but there again you'll have a hike to most attractions on the other end of Duval. Other lodging options to consider are the Gardens (romantic) (not to be confused with garden house), Curry Mansion Inn, Ambrosia, Marrero’s Guest House (haunted), Tropical Inn, Island City House, Orchid Key Inn, and Marquesa. That should get you started, TripAdvisor has pretty up-to-date advice in the KW forum. Staying in the guest homes gives you a better feel for the Island while the hotels have more amenities (room service, etc.). Do not rent from airb&b, lots of scams in KW!

You can get a condo if you are Sat to Sat in Truman Annex, a very comfortable option located next to Truman’s Little White House, or try for The Galleon timeshare (check redbook.com), it's nice to have a kitchen if you don’t want to eat out every meal.

One rule we have while there, drink in the bars, eat in the restaurants. With a few exceptions, the food in the bars is sub-par. There are so many great restaurants in Key West, why take a risk on crummy bar food? A couple of exceptions is Jack Flats sports bar (good fish sammies and burgers and killer a/c) and Smokin' Tuna (my favorite place for music). If you aren't in the mood for a full dinner the Happy Hours at the bight (waterfront) are great options with food and drink specials. TripAdvisor had a sticky list of all the HH times and deals.

Here are some restaurants we like, in no particular order:
Blue Heaven (very Key Westy, get the yellowtail snapper at dinner, we crave it) B/L/D, must go here, no reservations, go early
Bagatelle (ask for a balcony seat),
Cafe' Sole',
Santiago's Bodega (tapas)(HH 3-6 pm with half-price menu and sangria), but anytime is good
Garbo's food truck at Hanks (nice setting, great food, self-serve),
Blue Rams Head Southenrmost, B/L/D,
Louie's Backyard (on the water) L/HH/D, nice happy hour food menu
Sarabeths (B/L),
915 for dinner (sit on porch),
Prime for steak,
A&B Lobster at the marina, dinner only (ask for a balcony table) must do,
Banana Cafe' (B/L),
Azur (dinner),
Harpoon Harry’s for hearty basic cheap breakfast,
Moondog Cafe' and bakery (B/L),
Antonia’s, inside seating only, excellent Italian (L/D)
Sunset Pier for casual on the water, beautiful views
Salute’ on the water, Blue Heaven's sister, free parking,
And for a unique dessert-only experience, Better than Sex! is so delicious!
We make reservations everywhere we go, especially during high season. Sometimes we don’t need them, but we don’t like wandering around trying to find a place when we are starving.

I highly recommend Latitudes for lunch or dinner. It’s beautiful and relaxed with great food. You take a little shuttle boat to get to the island (5 minutes) and have dinner on the beach. Get a reservation TODAY! because they book out weeks and sometimes months in advance. If you go for dinner make the reservation so that you arrive before sunset and ask them for a table on the sand. If you can’t get in there for dinner, my other go-to is A&B Lobster, again wonderful food and service, ask to sit on the balcony overlooking the marina, we always go when they open at 6 to make sure we can get on the balcony. If you get there early you see all the boats going out for the sunset and back again afterward.

Make sure to visit Mallory Square one night for sunset. It happens 1 hour before and 1 hour after sunset. Bring lots of singles for tips as this is how the artists make their living (they have to pay the city to perform). The guy with the ‘green thing’ cart has the best mojitos anywhere, he is usually by the Opal Key Resort. (may be different with COVID)

Get out on the water!!! Wind and Wine is a great wine-tasting sunset cruise, highly recommend it.
Commotion on the Ocean for unlimited beer & wine and live music, usually a younger crowd.
We love the tall sail ships, so peaceful. Jolly Rover is a good one. Family-friendly, it’s less $$, and bring your own drinks (they supply ice, cups, and bottled water).
A good snorkeling trip is Island ‘Ting, which combines kayak and snorkel.
We also like the dolphin watch/sunset combo, great fun finding and seeing the dolphin pods. You can’t go to Key West and stay on the land! So many water activities to pick from and most offer the best deals online.
If you are there for a few days, visit the Dry Tortugas National park. It’s a full day trip by boat and a ½ day trip by air, must get reservations in advance.

Have a blast, I'm jealous and wish I could be there!

[HJBeck]

I have allergies and recommend a high rise that has never been flooded by sea water. 3rd floor or above. I've spent some difficult nights in other charming places near sea level and truly regretted it.