We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Island City House or Southernmost Hotel

Which Key West hotels are on sale?
mm/dd/yyyy mm/dd/yyyy
See hotels
posts: 44
reviews: 1
Island City House or Southernmost Hotel


I have never been to Key West and have been planning a surprise weekend for my husband's birthday this august. Which hotel do you prefer-Southernmost Hotel or Island City? Why?

I want to be able to lay by the pool or walk to the beach(I know they stink but I still want to go at least once!) and we want to be close to the action on Duval.

Thanks for your help....this site is great!

Western MA
posts: 12
1. Re: Island City House or Southernmost Hotel

I can only tell you about the Island City House. It is a cross between a hotel and B&B. There are 3 buildings surrounding a lush garden and pool area. We stay in the Island City House, the 3 story building. It has 1 and 2 bedroom suites. We've stayed in the one bedrooms which have a living room area, full kitchen, king or queen bedroom and full bath. They are furnished in Victorian era antiques. The 2 bedroom units give you a sitting area on the porch in front of the room, but people will be walking by as they climb the stairs. Their is a "Widows Walk" rooftop deck that is a nice place to take the continental breakfast in the morning, sunbath or have a nightcap.The other buildings are the Cigar House which is very nice and has balconies that over look the pool, and the Arch House which fronts on Eaton St. The only negatives I've heard are from people with rooms in the Arch House that are on the road side (noise).

Very nice pool and only a quick walk to the heart of Duval and even closer to the Bight. The staff is very helpful and will arrange any outing or reservation. The office does close at 8pm. We like it because it is like an oasis, just far enough from Duval.

The Southermost will put you right on a beach, and the pool looked nice, but you'll be at the opposite end of Duval from Sloppy Joe's etc. Not a bad way to build an appetite or burn off some alcohol though :-)

Others will have to provide more details about SM.

Destination Expert
for Key West
posts: 3,770
reviews: 3
2. Re: Island City House or Southernmost Hotel


Here's a good one for you the cheapest store for Cabo we found is just off Duval behind the Bull and Whistle called cheapest.

We are in Key West now with a couple staying at the Island City House. IMO stay at Island city the day you want to go to the beach rent bikes. We rented a tandom so we talk too each other without taking our life in our hands, at Paradise rentals (look in phone book and call when you get here).

The short stumble back to Island City from Duval is much easier. Both places you picked are great.


Benton, Arkansas
posts: 616
reviews: 4
3. Re: Island City House or Southernmost Hotel

How much are you looking to spend? We stayed last week the Dewey House which is part of the Southernmost Resorts complex. It was GORGEOUS! We did not pay for the primo ocean view room, but, for a deluxe garden view. We were in 417. When you sat on the balcony you had a lovely view of the fountain and the beach! This place is too nice. They provide breakfast and a nice "tea time" afternoon snack. This sits right on the beach and I did not find the beach stinky at all! We enjoyed relaxing on it sipping some drinks under a palm tree!

If this is too pricey you may want to look at the Southermost on the Beach. This place looked very nice and their pool is the one we used. I don't think they provide any food services but they still have the beach front location.

As far as the walk goes, we walked from one end to the other of Duval at least two times every day... sometimes back and forth more! The only thing bad about it was when you needed to go to the bathroom and you were on the wrong end of Duval. We would just head to another bar, order another drink, and use their bathroom! My husband and I loved the walk really, it was not a problem at all.

westbrook, maine
posts: 75
reviews: 1
4. Re: Island City House or Southernmost Hotel

We stayed at ICH in March - It was superb!! We stayed on the third floor of the Cigar house and had a private balcony that overlooked the pool. Full kitchen facilities and very comfortable beds!

We loved it so much we have already booked for next March. This time we decided to go budget and we booked a room in the ICH on the third floor. This is a one bedroom suite with full kitchen facilities WITH a semi-private balcony. I just CANNOT wait to get there!

It is such a beautiful and convenient location. You will be really happy there!

Cape Coral, Florida
Destination Expert
for San Pedro
posts: 11,604
reviews: 9
5. Re: Island City House or Southernmost Hotel

The third floor unit in the back of the 'main' house is a one bedroom and has a huge veranda, right at coconut level. Great place to stay, it's the only place in Key West that we've stayed more than once.