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84959 Overseas Hwy, Islamorada, FL 33036
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COVID-19 update: See the added health and safety measures this property is taking.Read more
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Payments made by partners impact the order of prices displayed. Room types may vary.
Travel safe during COVID-19
What you can expect during your stay
  • All linens sanitized 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 sanitizer available to guests & staff
  • Regularly sanitized 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
Travellers' Choice
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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Room & Suite (296)296
Full view
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
Sun terrace
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Room features
Air conditioning
Private balcony
Flatscreen TV
Complimentary toiletries
Room types
Ocean view
Non-smoking rooms
See more room details
Good to know
Ocean View
Great View
Languages Spoken
913Reviews27Q+A100Room tips
Traveller rating
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Popular mentions
Mike & Cara wrote a review 21 Jan.
2 contributions
We loved everything about Drop Anchor ! One of the few remaining old feel Keys hotels in Islamorada. Centrally located and completely relaxed. Our rooM was #10 and while not ocean front it did have ocean views from balcony, full kitchen and extremely clean. The ground and our room were spotless and pool is open 24hrs and heated. Highly recommend!
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Date of stay: January 2021Trip type: Travelled as a couple
StefJax wrote a review Jan. 2020
Tampa, Florida2,370 contributions214 helpful votes
Hotel's Favourite
I cannot recommend this place enough! I loved all of the fun colors and the retro vibe it had. The pool was perfect for us and loved that they had other activities like kayaks available for rent and a life-size chess board. You can also book tours from here and the boats pull right up to you since they have two docks. Or if you have your own you can bring that. The rooms were great, nothing too fancy but perfectly adequate for your beachy stay! The whole area was so relaxing and fun.
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Date of stay: March 2019Trip type: Travelled with friends
1 Helpful vote
Response from ZacTranten, General Manager at Drop Anchor
Responded 31 Jan. 2020
Dear Valued Guest, Thank you for providing us with your positive feedback. We value your input and are happy to hear that you enjoyed your stay. We are so glad you chose Drop Anchor, we look forward to your future stay with us. Sincerely, Drop Anchor Team
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jawalkerpe . wrote a review Dec. 2020
5 contributions1 helpful vote
Dont choose this place unless you know what you are getting. I got a closet with micro closet moldy bathroom ( I had to sit sideways 9n the toilet). The room was not properly cleaned, there were skid marks in the toilet, mold on the inside and outside of the shower stall, it was gross. Dirty door, broken chairs outside, etc The website looked great. I ended up leaving after the first night and nobody at the front desk would answer to anything until the manager got there which he never showed up. Stay away!
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Date of stay: December 2020Trip type: Travelled as a couple
1 Helpful vote
Laura H wrote a review Dec. 2020
Layton, Utah4 contributions
I was enticed by the cuteness of this motel and its high ratings, but do not be deceived. This place is so close to the highway it is difficult to sleep through the sounds of trucks whizzing by even when wearing earplugs. We stayed in the trailer, which needs to be demolished. It was moderately clean, but the shower was similar to those in RVs. I really wish I had brought my own cleaner and a mop. The lighting was poor. The noise was the biggest issue. The beachfront was wonderful as well as the sandy beach. I am not sure whether the sound issues and state of the rooms is worth the view. In Florida, you need to pay a bit more to get better accomodations.
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Date of stay: December 2020
Margaret R wrote a review Dec. 2020
Hollywood, Alabama23 contributions
King size bed with, large shower, complete kitchen, dining table and chairs, sitting area with futon and tv. Beautiful beach area with hammocks, lounge chairs, tables. Bbq grills. Owners and staff were friendly and helpful.
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Date of stay: December 2020Trip type: Travelled as a couple
Response from Drop Anchor, General Manager at Drop Anchor
Responded 5 weeks ago
Thank you for taking the time to review us. We are happy you enjoyed your stay, and hope to see you again real soon! Cliff, Front Desk
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USD 134 - USD 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 Twisted shrimp, Mangrove Mike's Cafe, and Bayside Gourmet.
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.