Drop Anchor in Islamorada is a charming oceanfront hideaway that captures the laid-back spirit of the Florida Keys. With colorful, island-inspired accommodations and lush tropical landscaping, this boutique hotel offers guests a peaceful and scenic retreat. Its prime location provides direct access to a private beach and breathtaking views of the Atlantic Ocean. Perfect for relaxation or adventure, Drop Anchor is an ideal escape for couples, families, and solo travelers alike. Private beach and swimming pool Colorful, island-themed guest rooms and suites Lush tropical gardens and outdoor lounging areas Close to fishing, diving, and local attractions
Drop Anchor offers Beach Access, Dock, Outdoor pool, Walk to shops and restaurants, Bar/lounge, Kitchen/Kitchenette, Restaurant, Free WiFi, Parking onsite, Accessible property, Free toiletries, Sleep sofa/futon, Air conditioning, Iron/ironing board, Patio, Porch, Private bathroom, Coffeemaker, Mini-fridge, Cable TV service, Ceiling fan, Flat-panel TV.
Drop Anchor is located at 84959 Overseas Highway, Islamorada.
Drop Anchor has an average rating of 4.1 out of 5 based on 588 guest reviews. It holds a 3-star Stars rating.
1 Queen Bed
Oceanfront Trailer
2 Queen Beds and 2 Twin Beds
Resort View Family Suite w/ Kitchen
1 Queen Bed
Oceanfront Queen Room
1 Queen Bed
Resort View Queen Room w/ Kitchen & Private Porch
1 King Bed
Oceanfront King Suite w/ Kitchen & Private Balcony
1 King Bed
Oceanfront King Suite w/ Beach Walkout & Kitchen
1 Queen Bed, 1 Double Bed and 1 Queen Sofa Bed
Resort View Queen Family Suite w/ Kitchen
1 King Bed, 2 Twin Beds and 1 Queen Futon
Oceanfront Family Suite w/ Kitchen
1 King Bed
Resort View ADA King Room
2 Queen Beds
Ocean View Double Queen w/ Kitchen & Private Balcony
2 Queen Beds
Ocean View Double Queen Room




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Drop Anchor in Islamorada is a charming oceanfront hideaway that captures the laid-back spirit of the Florida Keys. With colorful, island-inspired accommodations and lush tropical landscaping, this boutique hotel offers guests a peaceful and scenic retreat. Its prime location provides direct access to a private beach and breathtaking views of the Atlantic Ocean. Perfect for relaxation or adventure, Drop Anchor is an ideal escape for couples, families, and solo travelers alike.
This property offers mixed experiences, balancing affordable oceanfront appeal and renovated rooms with significant concerns regarding cleanliness and maintenance. Guests frequently disagree with the advertised room setup, while services and amenities are described inconsistently.
Very clean and well managed establishment. Quite Reasonably priced. Clean private pool. Nice view of ocean. Access via service road, little difficult to spot north bound on US1/A1A, just know @ 85 MM to get on service road.
BEWARE: THEY DO NOT HAVE HOT WATER AND THEIR PHOTOS DO NOT MATCH WHAT IT ACTUALLY LOOKS LIKE Deceptive marketing. Do not book here. They will say and show one thing online and give you something different and not let you cancel. Had to fight to get the advertised room. Upon ariving we found that there are few amenities and what is available is only available until 6 when the owners leave. Parking sucks. Air conditioners dont work well. You get a really ugly view of the top of a run down camper. Place is not well kept. Maintenance is not kept up with. Broken tiles building is damaged all over. Tvs are super small. Beds not comfortable. Not worth the price paid. Not very happy with my stay. You can also only use resort amenities until 5pm.
Beautiful location but the rooms are very tired. No headboards on beds mean your pillows fall between the mattress and wall. No curtains mean no privacy. No battery in my ac unit meant no heat on a 34 degree night. No pressure in shower and 20 minute hot water warmup time. No thanks, too many other great choices
I give the Drop Anchor and 4.8 stars. The rooms advertised as suites are really studios. That being said location is awesome; beautiful pool, beach plenty of games on the beach and kayaks and hammocks. If you’re looking for a 5 ?? resort this isn’t it, but it’s a well priced hotel on a beach ?? Book directly through their website, you’ll save more $$$ than with a third party!
Some friends and I stayed here while on a fishing trip. It was a great location near some good restaurants. We were able to catch some fish right by the hotel after a slow day in the boat. The staff was consistently friendly and helpful. They found an expensive set of headphones I left behind while cleaning the room. They notified us immediately, dropped them off at UPS for me, and shipped them to my home. 10/10 for service and location.
My experience at Drop Anchor Resort was the least welcoming I encountered anywhere in the Keys. After days of travel, I expected basic hospitality, but instead felt judged and uncomfortable from the moment I arrived. Staff interactions came across as cold and dismissive, and there was a noticeable lack of courtesy or flexibility that made the stay unpleasant. Whether intentional or not, the atmosphere felt uninviting and unaccommodating compared to other places in the area. If you’re looking for warmth, openness, or genuine hospitality, this may not be the right stop for you.
We've stayed here a few times now and it was great before but this time around there were rats in the room. Very disappointed. I saw one outside right in front of our sliding door and was told to just remove it myself.. luckily my husband did that. Then upon waking in the middle of the night I saw two scurrying across the room. As a woman I am very scared of these kinds of pests, which I did let the front desk know and honestly I was very surprised that it was our job to remove the first one, and then to see that they were also in the room. Seems very unsanitary... this was our favorite spot though so it is not easy for me to write this but I just want to hopefully help someone else if pests are a deciding factor for hotel stay.
We had a nice stay at the Drop Anchor Resort. The suites are a little older and ours was an odd layout but it lends to the charm. We showed up after a long bike ride then enjoyed the ocean and the pool. In the morning before we left we went to sit by the water again to find manatees swimming by. We accidentally left something in our room and the staff held it until we swung back by. It's not an exquisite resort but it is lovely for what we needed.
Room was very clean, bed was comfortable, AC was cool and quiet. Donna checked us in and she was super helpful and kind. You can hear traffic from the Us 1 highway but that’s kinda unavoidable with how the keys are. The pool was nice and there was even a very thoughtful scrub in the bathroom for us which was wonderful! The grounds were clean, there were hammocks and places to lounge. It was a simple and nice hotel. I’d stay here again for sure!
The hotel and grounds were clean and manicured. The hotel staff were so pleasant and genuinely happy to be there. My room was just as described and steps away from the beach…. It was a great stay and I appreciate the great customer service… book direct!!!