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84959 Overseas Hwy, Islamorada, FL 33036
COVID-19 update: See the added health and safety measures this property is taking.Read more
Lowest prices for your stay
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Free cancellation until 23/06/22
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Free cancellation until 23/06/22
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Free cancellation until 23/06/22
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Prices are provided by our partners, and reflect average nightly room rates, including taxes and fees that are fixed, known to our partners, and due at time of booking. Other miscellaneous taxes and hotel fees which are not fixed or due at time of booking may be payable at the property at time of stay. Please see our partners for more details.
Traveller (862)
Panoramas (7)
Room & Suite (298)
Travel safe during COVID-19
Visit our Travel Safe hub to see how we're helping you make more informed travel decisions during COVID-19.
What you can expect during your stay
  • All linens sanitised in high-temperature wash
  • Face masks required for guests in public areas
  • Face masks required for staff in public areas
  • Floors marked for social distancing
  • Hand sanitiser available to guests & staff
  • Regularly sanitised high-traffic areas
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Updated 22/06/20 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.
A note from Drop Anchor
Updated 22/06/20 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.


#4 of 19 hotels in Islamorada
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
Free High Speed Internet (WiFi)
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
Private balcony
Flatscreen TV
Complimentary toiletries
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Room types
Ocean view
Non-smoking rooms
Good to know
Ocean View
Great View
Languages Spoken
929Reviews30Q+A100Room tips
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Popular mentions
Dayamis H wrote a review Dec 2021
Coral Gables, Florida66 contributions18 helpful votes
I loved this hotel style with it’s vintage vibe, bright colors and old style. The room could have been perfect for us three. My daughter positioned herself very eagerly in the sofa bed in front of the tv. Linens are provided. The was also a large terrace with a bbq just outside the living/dining room, it was very, very spacious and the layout surprised me in a positive way. The kitchen was big and even though we didn’t cooked, I noticed it had everything for cooking and cleaning afterwards. The refrigerator was big enough. This room has two doors with independent numbers. The bedroom was like a regular hotel room and it can be separated of the living space. Is the closest room to the boat ramp. The only downside was the humidity smell that punched us in the face, just by opening the door, and the poodle in the middle of the bedroom’s floor, it had been raining a lot and there was still water dropping from the ceiling. The check in/ check out process was made easier by the box outside the office stating you can drop your keys there, before leaving.
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Date of stay: November 2021Trip type: Travelled with family
Darren Simonson wrote a review Oct 2021
West Palm Beach, Florida6 contributions1 helpful vote
My wife & I stayed at Drop anchor over the weekend. The room + pool were very clean. The grounds were well-kept & the twinkle lights in the back were a very nice touch. We chose to stay in a smaller room, as it was just my wife & I. We, personally, didn't feel as thought the size of the room mattered since the whole point of Islamorada is to spend as much time outside as possible (which, we did!) Shout out to Cliff for being an amazing individual, who I believe is the manager of the property. He took GREAT care of us. The hotel is in close proximity to everything you could possibly want to do in Islamorada. We will 100% be back in the very near future.
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Date of stay: October 2021
Sleep Quality
Room Tip: Rooms with Queen beds tend to be smaller. Simply call ahead and ask for a king bed along with the...
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CC wrote a review Jul 2021
Miami, Florida7 contributions
I've stayed in hotels, motels, and hostels all over the world and this by far was the worst place I've ever stayed in. The place was booked 2 weeks prior and I did not know it was a trailer at time of booking. The pictures on the travel site were not the same as the room I stayed in. From the outside the place looks clean and amenities were nice. We couldn't find the room because the numbers were gone but realized it was the trailer. First, as you walk into the room the smell of old cigarettes and musty air is overwhelming. As you look to your left at eye level there were loose electrical wires just hanging next to an outlet. The floors were uneven, rotten, and in some places it felt like we were going to step through the floor. The ceilings were low, but I guess expected out of a trailer, what was not expected was the holes and metal pins from an a device that must have existed there before. There were random holes on the walls as well. The shower was broken and the floor was rotten and had holes, we definitely could not shower there We checked in later in the afternoon and left for dinner, by the time we returned there was no parking and by looking at the pictures it looks like it's by locals who may live there. There was also no one in the front desk to relay our concerns. The worst part that was trying to sleep in the bed and futon. I had to put the covers back on the bed and lay on towels because of what I noticed after getting in it, human hair that was clearly not mine. I was not sure what was also itchy about the sheets but I did not want to check. My friend opted to sleep in the car than on the futon as well, the floor was so uneven the futon could not be supported. Luckily we only spent 10 hours there as we had to leave at 6am, but the day was ruined by the lack of sleep. For $300 a night this was a ripoff, I hope that trailer gets retired
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Date of stay: July 2021
Room Tip: Do not stay in a trailer
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Response from Drop Anchor, General Manager at Drop Anchor
Responded 21 Jul 2021
We are sorry your stay did not meet your expectations. Our travel trailer is categorized by itself on all booking sites, so I'm not sure how it was booked without your knowledge. I inspected the travel trailer based on your review and found the following: The room number is attached securely to the front of the trailer, this must have just been an oversite. Additionally, you should have received a property map at the time of your check-in. I found no smell (other than cleaner) inside the room, all of our rooms are non-smoking. The inside was re-constructed less than 3 years ago and we do our best to assure no one smokes in our rooms. I was unable to find any loose electrical wiring. I did see the uneven section of the floor, where the extension goes out on the side of the camper, but as it is a camper trailer this is somewhat to be expected. I found no areas on the floor that was rotting. I looked thoroughly at the walls and found no random holes. I did find a crack in the shower bottom, which has now been addressed. As far as hair, all of our linens are removed and cleaned after each guest checks out. Our cleaning staff replaces clean sheets and bedding prior to arrival. We also staff our office from 9 AM until 9 PM. If we need to leave the office (we do property checks throughout the day and also assist any guest with their needs) we leave a sign in the window that we are on the property and will return in 15 minutes. I am sorry you did not enjoy your stay. We take pride in our place and work very hard to ensure our guests are well taken care of. I wish you the best in your future travels, Regards, Cliff - GM
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Jennifer L wrote a review Jun 2021
12 contributions1 helpful vote
We stayed for 2 nights and we were very pleased! It’s definitely an older property, but our room was clean, roomy, cool and met our needs. It was nice to have a mini fridge and access to ice. We had a couple of hiccups but both Cliff and Tina were most helpful! The property is very quiet which was nice and relaxing. It is a man made beach area because boats dog there, but I still enjoyed the scenery and the accommodations every day! The pool was clean and not busy at all. We felt it was a great location. It would be a great place to stay with a group of families and feel like you have the place to yourself. Everyone we met there was lovely!
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Date of stay: June 2021Trip type: Travelled with friends
Response from Drop Anchor, General Manager at Drop Anchor
Responded 29 Jun 2021
Dear Valued Guest, Thank you for your positive feedback. We are delighted that you enjoyed yourself and were able to find some relaxation during your stay. We hope to see you again soon. Best, Drop Anchor Staff
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vincent p wrote a review May 2021
Bethlehem, Pennsylvania68 contributions19 helpful votes
Imagine being invited to your friends house for the weekend, and they put you up in the shed in the back yard. Room 14B really shouldn't be advertised as a room at all. There are no closets, no shelves, no hangers, the bathroom toilet rocks back and forth, the bathroom is for skinny people only. I must say that the property is in very new condition. The buildings are freshly painted, the pool is excellent, the kayaks are brand new (10 dollars an hour) there is one paddle board, but someone stole the paddle. Also there were two bicycles, but someone stole them too.
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Date of stay: May 2021
Sleep Quality
Room Tip: do not stay in room 14B
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$134 - $304 (Based on Average Rates for a Standard Room)
drop anchor hotel islamorada
United StatesFloridaFlorida KeysIslamorada
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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.
Is parking available at Drop Anchor?
Yes, free parking is available to guests.
What are some restaurants close to Drop Anchor?
Conveniently located restaurants include Bayside Gourmet, Twisted shrimp, and Mangrove Mike's Cafe.
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.