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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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Prices are the average nightly price provided by our partners and may not include all taxes and fees. Taxes and fees that are shown are estimates only. Please see our partners for more details.
Traveler (826)
Panoramas (7)
Videos (1)
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 06/22/20 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.
A note from Drop Anchor
Updated 06/22/20 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.


#4 of 19 hotels in Islamorada
Travelers' 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
Good to know
Ocean View
Great View
Languages Spoken
916Reviews28Q+A100Room tips
Traveler rating
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Time of year
Traveler type
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Selected filters
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  • English
Popular mentions
trn81 wrote a review Feb 9
Montana436 contributions139 helpful votes
We stopped by here on a whim and asked the manager if they had any rooms. Who even does that anymore. I am glad we did. We got a room beachfront with a full kitchen. The rooms are very nice and we loved our stay. We will definitely be coming back.
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Date of stay: February 2021Trip type: Traveled as a couple
2 Helpful votes
Response from Drop Anchor, General Manager at Drop Anchor
Responded 2 weeks ago
Dear Valued Guest, We are so happy you stopped in on a whim and enjoyed yourselves at Drop Anchor. It was a pleasure having you as our guest and we hope we exceeded your expectations. We look forward to seeing you again in the near future.
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StefJax wrote a review Jan 2020
Tampa, Florida2,377 contributions236 helpful votes
Hotel's Favorite
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: Traveled with friends
2 Helpful votes
Response from ZacTranten, General Manager at Drop Anchor
Responded Jan 31, 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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Robin Gelotti wrote a review Jan 2021
1 contribution1 helpful vote
This little gem was great. Very clean. Nice little beach with amenities. Quiet. Cliff at the front desk was great. Very welcoming. And he even gave me a baby coconut tree as we dont have them on the west coast. Well worth it.
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Date of stay: January 2021Trip type: Traveled with friends
1 Helpful vote
Response from Drop Anchor, General Manager at Drop Anchor
Responded 2 weeks ago
Dear Valued Guest, Thank you for choosing Drop Anchor to vacation with. We are delighted that you were able to enjoy our hidden gem in Islamorada. We hope your baby coconut tree is flourishing and you can soon enjoy it. Come back and see us again soon.
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Tim C wrote a review Jan 2021
2 contributions2 helpful votes
Hello, I am an airline pilot and I stay in hotels an average 18 nights per month, so the prospect of staying in a hotel really doesn't float my boat. That is, until my wife and I stayed here... What a fantastic, breathtakingly beautiful place! We barbecued on the beach every night. The room had a fully stocked kitchen, so my wife and I were able to source some great local ingredients and she cooked some stunning meals- there is a fish monger just down the road where we bought a gorgeous steak of grouper which was wonderful on the BBQ and which made beautiful stock with which she made fish soup the next day. Cliff, Zach and the rest of the team are genuinely welcoming, kind people who made us really feel at home. It was SO fantastic that we actually changed our ticket back to the UK so that we could stay a few extra days. We have never done that before. I can not recommend the Drop Anchor highly enough. We will be back.
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Date of stay: January 2021
Sleep Quality
1 Helpful vote
Response from Drop Anchor, General Manager at Drop Anchor
Responded 2 weeks ago
Dear Valued Guest, Thank you for your positive feedback on Drop Anchor. We are glad you were able to take advantage of the BBQ grills on the property. We hope you are able to come back and visit again soon.
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Mike & Cara wrote a review Jan 2021
2 contributions2 helpful votes
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: Traveled as a couple
1 Helpful vote
Response from Drop Anchor, General Manager at Drop Anchor
Responded 2 weeks ago
Dear Valued Guest, We are delighted that you enjoyed your stay with us at Drop Anchor. Thank you for your kind review and we hope to see you again soon.
Read more
$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 (3.8 miles), History of Diving Museum (2.0 miles), and Lobster Trap Art Gift Shop and Gallery (2.8 miles).
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 travelers enjoy visiting Indian Key State Historic Site (3.9 miles) and Pasta Pantaleo Signature Gallery (3.5 miles).
Does Drop Anchor have any great views?
Yes, guests often enjoy the harbor view available here.
Is Drop Anchor accessible?
Yes, it offers wheelchair access and facilities for disabled guests. For specific inquiries, we recommend calling ahead to confirm.