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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 07/27/21
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SAVE $20
Free cancellation until 07/27/21
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SAVE $20
Free cancellation until 07/27/21
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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 (848)
Panoramas (7)
Room & Suite (287)
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 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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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
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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
925Reviews30Q+A100Room tips
Traveler rating
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Popular mentions
vincent p wrote a review May 2021
Bethlehem, Pennsylvania68 contributions17 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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Joseph H wrote a review May 2021
53 contributions7 helpful votes
We stayed at Drop Anchor for 3 nights in a double queen room. Although we enjoyed the grounds, there were too many issues with the room to want to go back. The room was one of the smallest hotel rooms we’ve ever stayed in. The sink in the bathroom leaked all over the bedroom one of the days we were there. Small bugs would crawl out of the sink each day. The shower drain cover wasn’t attached (which drove us crazy) and it took 3-4 minutes to get any kind of hot water in the shower. Great location, but lacking attention to detail in the rooms. We love Islamorada, but will stay elsewhere next time.
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Date of stay: March 2021Trip type: Traveled with family
Response from Drop Anchor, General Manager at Drop Anchor
Responded May 10, 2021
Dear guest, With each one of your issues you brought forth, we tried to remedy each one to your satisfaction. We are proud to be a small 18 room old school Florida motel, and the majority of our guests love it here. We wish you the best in your future travels.
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prnpr wrote a review Apr 2021
Georgetown, Kentucky263 contributions12 helpful votes
We had a very nice time at this resort. Our room had a beautiful view which was very peaceful in the early mornings and evenings. Loved watching a variety birds from the balcony each day. Great way to unwind IMO. We had the beach area to ourselves much of the time. Good restaurants nearby. Housekeeping was very good. Cliff was a pleasure to chat with and is an asset to the owners. Would return again. Would give a 5 star but Steve was odd.
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Date of stay: April 2021
1 Helpful vote
Response from Drop Anchor, General Manager at Drop Anchor
Responded May 10, 2021
So glad you had a great stay! Hope to see you again soon!! Cliff
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KSLJ1995 wrote a review Apr 2021
Streetsboro, Ohio170 contributions35 helpful votes
Don’t let the initial pictures posted by this place deceive you. This is nothing more than an overpriced, dive motel. There is no sandy beach as described because there’s no beach...it’s a fake beach with a wall that drops off into dirty shallow and rocky water, the pool is also dirty, the room was subpar for the price and the bathroom...well, it’s tiny with only 2 ft of space in front of the sink. There are bugs that get into the rooms and the floors and shower stall were dirty. But wait! There’s more! Plumbing in the bathroom is loose, there are no window coverings in the bathroom, no vent, hot water takes forever to show up, there are no headboards (as pictured by them), sheets are mid-sized, mattresses are old & uncomfortable and some electric outlets in the room didn’t work. Don’t take my word for it, look at my pictures to see for yourself. If this place is priced at more than $99 (and that’s being generous) stay somewhere else. The GM will try to tell you that other hotels with a beach are going for $600+ a night. That’s false and WE wasted $300! Thank goodness we only reserved one night. They did have good lighting on the walkways. Yea, it shined into the room straight through the blinds, which also contributed to our loss of sleep. This place was the epitome of disappointment. Pictures and descriptions were well crafted to lure us in. Take our advice friends and choose a better place to spend your vacation. Obviously...NOT RECOMMENDED.
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Date of stay: April 2021
Sleep Quality
Nicholas K wrote a review Apr 2021
Arlington, Virginia103 contributions41 helpful votes
This is one of the best hotels I’ve stayed at. The rooms are incredibly modern, amenities are nice (our room included a full oven, microwave, and sink), and the staff is helpful and friendly. There’s a lovely artificial beach on the property that’s right on the coastline; a great place to relax and take in the views. Great location accessible to the rest of Islamorada, as well as Key Largo.
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Date of stay: April 2021Trip type: Traveled with family
1 Helpful vote
Response from Drop Anchor, General Manager at Drop Anchor
Responded Apr 13, 2021
We are glad you had a great stay. Thank you for taking the time to review us as well. We are working hard to continue improvements to the property so all our guests have an amazing stay. Cliff - GM
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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 (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, Bayside Gourmet, 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 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.