About Drop Anchor

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

Amenities at Drop Anchor

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.

Location

Drop Anchor is located at 84959 Overseas Highway, Islamorada.

Reviews and ratings

Drop Anchor has an average rating of 4.1 out of 5 based on 599 guest reviews. It holds a 3-star Stars rating.

Rooms and accommodations at Drop Anchor

  • Oceanfront Trailer

    1 Queen Bed

    Oceanfront Trailer

  • Resort View Family Suite w/ Kitchen

    2 Queen Beds and 2 Twin Beds

    Resort View Family Suite w/ Kitchen

  • Oceanfront Queen Room

    1 Queen Bed

    Oceanfront Queen Room

  • Resort View Queen Room w/ Kitchen & Private Porch

    1 Queen Bed

    Resort View Queen Room w/ Kitchen & Private Porch

  • Oceanfront King Suite w/ Kitchen & Private Balcony

    1 King Bed

    Oceanfront King Suite w/ Kitchen & Private Balcony

  • Oceanfront King Suite w/ Beach Walkout & Kitchen

    1 King Bed

    Oceanfront King Suite w/ Beach Walkout & Kitchen

  • Resort View Queen Family Suite w/ Kitchen

    1 Queen Bed, 1 Double Bed and 1 Queen Sofa Bed

    Resort View Queen Family Suite w/ Kitchen

  • Oceanfront Family Suite w/ Kitchen

    1 King Bed, 2 Twin Beds and 1 Queen Futon

    Oceanfront Family Suite w/ Kitchen

  • Resort View ADA King Room

    1 King Bed

    Resort View ADA King Room

  • Ocean View Double Queen w/ Kitchen & Private Balcony

    2 Queen Beds

    Ocean View Double Queen w/ Kitchen & Private Balcony

  • Ocean View Double Queen Room

    2 Queen Beds

    Ocean View Double Queen Room

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Image of Drop Anchor
Image of Drop Anchor
Image of Drop Anchor

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Image of Drop Anchor

Rooms

Property Overview

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

Amenities

Activities

  • Beach Access
  • Dock
  • Outdoor pool
  • Walk to shops and restaurants

Food and drink

  • Bar/lounge
  • Kitchen/Kitchenette
  • Restaurant
  • Coffeemaker
  • Mini-fridge

Internet access in public areas

  • Free WiFi

Parking

  • Parking onsite

Property services

  • Accessible property

Bathroom

  • Free toiletries

Bedding and linens

  • Sleep sofa/futon

Features

  • Air conditioning
  • Iron/ironing board
  • Patio
  • Porch
  • Private bathroom

Media and electronics

  • Cable TV service
  • Ceiling fan
  • Flat-panel TV

Reviews

4.1
599
Reviews

Drop Anchor Resort receives mixed reviews, highlighting both positive aspects like location and friendly staff, alongside significant concerns regarding cleanliness, room issues, and deceptive practices. Recent feedback indicates recurring problems with shower backups, clogged sinks, inaccurate room descriptions, and unexpected fees, while some guests appreciate the location and basic amenities.

Beautiful LocationFriendly StaffClean GroundsConvenient Pool AccessOcean View
cleanliness2
location4
value2.5
service3.5
amenities3
N
N Stelling
21 days ago

Booked a family suite for my family of five and was very disappointed with our stay. The shower repeatedly backed up with dirty water, and the kitchen sink was clogged for our entire stay. The shower would sometimes drain but then fill back up on its own, with debris, food particles, and a foul odor. As a result, we were unable to properly shower or use the kitchen facilities we paid for. We reported the issue to staff, but it was never resolved. We were not offered a room change, and at checkout management said they would look into compensation. After following up, we were told no refund would be provided and were only offered a discount on a future stay. For our stay all we expected was clean, functional accommodations. I’m sharing our experience so other travelers, especially families, can make an informed decision before booking. Side note: Office staff is only there until 6pm so I would recommend checking the room out thoroughly upon check-in just in case there are any issues that arise.

R
Robb W.
3 months ago

While the water front location is well positioned, the grounds clean and well laid out, and the pool nice enough (warmed but not that warm), I couldn't recommend this place due to our check in experience. We reserved an ocean view room but didn't receive it, and were then told by manager (who did not admit to being so) that our room had a view. 'If you go outside (exit) the room and look to your left, the ocean is there, so we offer it as a view room.' I guess I drive a convertible then, because if I roll down my window and stick out my head, it's the same? When my wife went back to enquire once she confirmed we'd reserved (and paid for) one, he admitted he had given away our nicer room to the people who checked in before us. So it's our fault we didn't get the room we reserved because we arrived at 5 pm, between the check-in hours of 4 to 6 pm? What?! Nonsensical. What topped it off was that he implied that, because we booked through Expedia, we shouldn't expect him to accommodate the room that we paid for. WTH? The room itself was pleasant enough, although for the appliances to function you need to swap plugs in the nest of cords. We sacrificed the coffee machine so we could use the microwave (a nice plus to have). Do be aware, should you sign in to any of the services on the TV, the property doesn't sign you out. On any service I tried on the RokuTV (YouTube, Netflix, etc.), there were previous visitor accounts still logged in. Should you choose to book with them, keep these caveats in mind.

V
Victor Archilla
3 months ago

First time here, the place is nice and quiet, nice pool but not heated like it says. The front window room 6 blind not working correctly, you can see into the room. Told manager but never fixed it. Bathroom tiny and toilet very small like for children. Don't think we'll book here again. That's why gave 2 stars only.

D
Dan Shaeffer
4 months ago

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.

D
DS
5 months ago

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.

J
Jake Jones
5 months ago

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

M
Mary MD
5 months ago

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!

W
Wes Walker
6 months ago

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.

A
Alexander Pierce
6 months ago

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.

L
Layla Menke
7 months ago

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.

Map

Property Address
84959 Overseas Highway
Islamorada
Property Contact
305-664-4863