Drop Anchor
84959 Overseas Hwy, Islamorada, FL 33036
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About
#5 of 21 hotels in Islamorada
Location
Cleanliness
Service
Value
Drop Anchor is a unique oceanfront nestled in the heart of the fabulous "purple isle" of Islamorada. Private accommodations range from Standard rooms to Suites, in most cases with private balconies. Each room is individually designed with a tropical flair befitting the unique island spirit of the fabulous Florida Keys. Our history is rich; we have been a landmark in for more than 50 years. We aspire to keep the "Old FL Keys" spirit alive while offering just 18 fresh, updated rooms with charming amenities for our guests' comfort is one of our top priorities. Lush palm trees sway over our beautiful pool and private beach. Our grounds feature tropical flora, relaxing sitting areas and hammocks under tall palms. The property also boasts an Oceanside dock and private boat ramp to our guests. Located in the "Fishing Capital of the World", we are within a few miles of the best dining and water sports in the Florida Keys and just over 1 hour from Miami
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Property amenities
Free parking
Parking
Free High Speed Internet (WiFi)
Wifi
Pool
Pool / beach towels
BBQ facilities
Non-smoking hotel
Pool with view
Outdoor pool
Heated pool
Fence around pool
Outdoor furniture
Picnic area
Sun loungers / beach chairs
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Room features
Air conditioning
Housekeeping
Private balcony
Iron
Kitchenette
Microwave
Flatscreen TV
Complimentary toiletries
Refrigerator
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Room types
Ocean view
Non-smoking rooms
Good to know
HOTEL CLASS
HOTEL STYLE
Ocean View
Great View
Languages Spoken
English
Location
46Car recommended
Grade: 46 out of 100
92Restaurantswithin 10 km
61Attractionswithin 10 km
952Reviews31Q+A100Room tips
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Arrived at Drop Anchor at 7 pm after a 3 hour drive. The front office was locked up and dark. After checking the mailbox mounted on the wall next to the front door labeled "Late Arrivals" and not finding an envelope with my room key, I called the "emergency" phone number posted on the front door. Jeff, who actually took my reservation back on Feb 16, answered the phone and after confirming my info, informed me that my reservation was cancelled for some reason on Feb 22 and there were no rooms available that evening. He had no explanation for why they would cancel a reservation made on Feb 16 (screen shot attached) 6 days later without any notice to the guest. No email, no call, nothing. After making the reservation on Feb 16, I did not request a cancellation. In fact, I had no correspondence with Drop Anchor what-so-ever after the 16th. There I stood in front of a locked up office 3 hours from home in amazement. Jeff was kind enough to offer up the suggestion that I call the motel next door to see if they had any rooms. What a prince... Icing on the cake was that they ended up holding back $46 out of the $430 they charged my card for the room THEY cancelled. I called the next day and Jeff said he'd "circle back" to me about making things right. Never heard from him again. Ended up having to dispute the charge with Amex just to get a full refund for a room cancelled by the motel. My advice would be to call them and confirm that your reservation is still in place before making the trip down.…
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Date of stay: March 2023Trip type: Travelled as a couple
Value
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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+1
Do NOT let them put you in room 16B. The mattresses look and feel like they were picked up off the side of the road. They are completely broke down. My daughter fell off of hers because the sides are so broke down. The other bed has a giant crater in the middle that you roll in to. The bedding was dirty as well. I ended up sleeping on the tile floor., and we used our own pillows and blankets. The coffee maker is on a counter with no outlet. It has to be placed on the floor by the door to reach an outlet. Several outlets don’t even work. We asked for clean towels on day 3 and were given pool towels instead. The only beverage machine on the property is out of order, and they do not sell anything in the office. We asked for a room change and were told it wasn’t possible. I then ordered a mattress topper from Amazon to try to make it work, but it was shipped to the wrong address. We ended up leaving early. I asked for a refund, only for the day we left and received no response. The lady at the front desk is very sweet and the property is beautiful, but the rooms are very outdated. I don’t know when the photos on the website were taken, or what photoshop program they used, but I doubt it was in the last 10 years. Our room was absolutely nothing like the pictures, nor were the ones on both sides of us. If there’s no other options open in Islamorada, bring your own mattress and bedding. …
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Date of stay: March 2023
Value
Location
Service
Room Tip: Stay somewhere else if you can.
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Jeff at the front desk was helpful. They have kayaks that you can use. Hammocks to relax in and soak up the sunshine. The property has beautiful views overlooking the water. There are grills and picnic tables. Our room had a comfortable bed. It was on the smaller side but we weren’t in the room for long.
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Date of stay: March 2023Trip type: Travelled as a couple
Value
Location
Service
Room Tip: Pool on site. Hammocks to lay in. Kayaks on site to use.
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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We stayed there for a week. While we enjoyed the historical nature of the place, we were disappointed that the pool was heated the first night yet not after. It was a chilly week and the heated pool was the one amenity we could enjoy. The manager agreed there was a problem with the pool yet refused to accommodate us for the loss of a key amenity. The walls are thin. There was a group of workers staying next door and they were up early by 6 making breakfast and we heard every clink in the kitchen and smell of their food. It also sits right off of Hwy 1 and it is quite loud. If you're in a room that doesn't offer a kitchenette, it is very bare bones. Not even a drawer to put any belongings. We will not be going back.
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Date of stay: February 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Pathfinder381558 wrote a review Feb 2023
The plumbing in our room did not work.. Sewage backup into shower. Toilet never worked. Disgusting. Not $1 of credit. This is the worst place in Islamorada. No admission of a problem. No responsibility. DO NOT STAY HERE.
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Date of stay: February 2023Trip type: Travelled as a couple
Value
Location
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Room Tip: DO NOT STAY HERE!
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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+1
The hotel had great amenities and was set up perfectly on the Atlantic to view the sunset in the evenings. We were torn between Fisher Inn and Drop Anchor, so glad we picked Drop Anchor. It was easier to get the boat in and out when docking and we wouldn’t have been able to enjoy the great sunset from FI. A manatee even swam right up and greeted us on our first night there while viewing sunset! Hotel was within walking distance to several great restaurants or a short Uber ride/drive to many other attractions that Islamorada has to offer. Also in a great location to get out to the Sandbar, Alligator Reef Light or those famous great Islamorada fishing holes when boating! Staff was very friendly and helpful! If you’re looking for fancy smancy pay the full price at a resort; if you’re looking for a good room with all you need to experience a great stay in the Keys, Drop Anchor is your place! You’re actually only in the room just to sleep, anyways! …
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Date of stay: January 2023Trip type: Travelled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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+1
Looking for luxury accommodates where you'll be pampered? This isn't it. Looking for cheap -- both price and quality? This isn't it, either. If you're going to the Keys, ask yourself: "Am I going for the room, or the experience of the Keys?" If your answer is the latter, take a good look at the Drop Anchor as a place to sleep, park your clothes, bathe, etc. They handle that and a lot more. First, you'll notice the 50's style look of the place. Second, you'll fine each room has a unique flare. Some are pretty sizable; others are quite cozy. At the Drop Anchor, the room serves as your base of operations. There's a large, sandy waterfront with huts, chairs, picnic tables and chairs. There's a pool (yes, it's clean), and you have access to kayaks, paddle boards, a boat launch. We initially booked a room with a queen bed, but we upgraded to a little larger room will a full 'fridge and oven, which came in nicely when we grilled shrimp, salmon and stakes on the grill. Which brings me back to location... about two miles south, there's a Publix. (If you've lived in Florida, you know that's nice.) Also, there's more than a handful of interesting drinking/dining options in the Islamorada area. The overall vibe of the Drop Anchor is relaxing. Again, if you need to be the center of attention or if there's a Karen in your group, stay away. They don't need the headache, and the other inhabitants probably won't put up with it. That's not to say there is a lack of basic services. The housekeeping staff is pretty stealthy. We'd venture out to explore/shop/eat/etc., and when we returned, there were fresh towels, there'd been some general straightening, and the dishes we meant to wash before we left had been cleaned and left to dry. This place suits all age ranges. By the way, from the water-facing rooms, the sun rises and sunsets are outstanding. …
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Date of stay: October 2022Trip type: Travelled as a couple
Value
Location
Service
Room Tip: Book early. Ideally, book directly, not through a third party.
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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It was clean, spacious, great ocean view, staff was excellent and very relaxing. Would definitely go back and plan to do so. Many good restaurants close and of course the Bass Pro Shop is close. They have a boat slip on property and alligator reef as we; and is sand bar where many boats hang out are close..
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Date of stay: October 2022
Value
Location
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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+1
Photos of 14B - I don't think I need to say more. We rented this property in May. We were looking for something with a local flare that could accommodate our adult family of 4 ( needing three beds). We were excited to find an "ocean view" family suite. I even called and was assured there was a nice outdoor space. I don't like to post negative reviews but hope to save someone else from being disappointed. They charged a lot for this "resort" room. I begged them to move us or refund a portion of our money. I reached out to the owners, the manager - no help at all. It really put a damper on our short get away. It was our first time being disappointed in Islamorada. Shame on them for false advertising.
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Date of stay: May 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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+1
First time at Drop Anchor. We basically needed a room to shower, sleep and regroup during lobster mini season. Note: you can launch directly from Drop Anchor. Bonus! Every hotel was pretty much ridiculously over priced due to mini season. Found room 15 at Drop Anchor for $235/night! Far and away the top deal on the keys. Despite on the small side, the $/sq ft was in line with their larger rooms and much better than what competitors up and down the road were trying to lure. Room 15 is Oceanfront and has a better view and deck than the larger room behind it! If you need more room, you can book the 16 rooms behind 15. They are closer to the road but under the same roof. Our room was super clean and comfortable. Would certainly return again!
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Date of stay: July 2022Trip type: Travelled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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PRICE RANGE
$333 - $445 (Based on Average Rates for a Standard Room)
ALSO KNOWN AS
drop anchor hotel islamorada
LOCATION
United StatesFloridaFlorida KeysIslamorada
NUMBER OF ROOMS
18
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Frequently Asked Questions about Drop Anchor
Which popular attractions are close to Drop Anchor?
Nearby attractions include Old Road Gallery (6.1 km), History of Diving Museum (3.1 km), and Lobster Trap Art Gift Shop and Gallery (4.4 km).
What are some of the property amenities at Drop Anchor?
Some of the more popular amenities offered include free wifi, a pool, and free parking.
Which room amenities are available at Drop Anchor?
Top room amenities include a kitchenette, air conditioning, and a flat screen TV.
What food & drink options are available at Drop Anchor?
Guests can enjoy barbeque facilities during their stay.
What are some restaurants close to Drop Anchor?
Conveniently located restaurants include Bayside Gourmet, Mangrove Mike's Cafe, and Twisted shrimp.
Are there opportunities to exercise at Drop Anchor?
Yes, guests have access to a pool during their stay.
Are there any historical sites close to Drop Anchor?
Many travellers enjoy visiting Indian Key State Historic Site (6.3 km) and Pasta Pantaleo Signature Gallery (5.6 km).
Does Drop Anchor have any great views?
Yes, guests often enjoy the harbour view available here.
Is Drop Anchor accessible?
Yes, it offers wheelchair access and facilities for disabled guests. For specific enquiries, we recommend calling ahead to confirm.