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84959 Overseas Hwy, Islamorada, FL 33036
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Traveler (913)
360
Panoramas (7)
Room & Suite (309)

About

#4 of 21 hotels in Islamorada
Location
4.5
Cleanliness
4.5
Service
4.3
Value
4.2
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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Property amenities
Free parking
Parking
Free High Speed Internet (WiFi)
Wifi
Pool
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
Housekeeping
Private balcony
Iron
Kitchenette
Microwave
Flatscreen TV
Complimentary toiletries
Refrigerator
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Room types
Ocean view
Non-smoking rooms
Good to know
HOTEL CLASS
HOTEL STYLE
Great View
Ocean View
Languages Spoken
English
947Reviews31Q+A100Room tips
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Blake421 wrote a review Jan 2023
3 contributions
The hotel had great amenities and was set up perfectly on the Atlantic to view the sunset in the evenings. We were torn between Fisher Inn and Drop Anchor, so glad we picked Drop Anchor. It was easier to get the boat in and out when docking and we wouldn’t have been able to enjoy the great sunset from FI. A manatee even swam right up and greeted us on our first night there while viewing sunset! Hotel was within walking distance to several great restaurants or a short Uber ride/drive to many other attractions that Islamorada has to offer. Also in a great location to get out to the Sandbar, Alligator Reef Light or those famous great Islamorada fishing holes when boating! Staff was very friendly and helpful! If you’re looking for fancy smancy pay the full price at a resort; if you’re looking for a good room with all you need to experience a great stay in the Keys, Drop Anchor is your place! You’re actually only in the room just to sleep, anyways!
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Date of stay: January 2023Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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dturner-24 wrote a review Nov 2022
Pearl, Mississippi48 contributions31 helpful votes
+1
Looking for luxury accommodates where you'll be pampered? This isn't it. Looking for cheap -- both price and quality? This isn't it, either. If you're going to the Keys, ask yourself: "Am I going for the room, or the experience of the Keys?" If your answer is the latter, take a good look at the Drop Anchor as a place to sleep, park your clothes, bathe, etc. They handle that and a lot more. First, you'll notice the 50's style look of the place. Second, you'll fine each room has a unique flare. Some are pretty sizable; others are quite cozy. At the Drop Anchor, the room serves as your base of operations. There's a large, sandy waterfront with huts, chairs, picnic tables and chairs. There's a pool (yes, it's clean), and you have access to kayaks, paddle boards, a boat launch. We initially booked a room with a queen bed, but we upgraded to a little larger room will a full 'fridge and oven, which came in nicely when we grilled shrimp, salmon and stakes on the grill. Which brings me back to location... about two miles south, there's a Publix. (If you've lived in Florida, you know that's nice.) Also, there's more than a handful of interesting drinking/dining options in the Islamorada area. The overall vibe of the Drop Anchor is relaxing. Again, if you need to be the center of attention or if there's a Karen in your group, stay away. They don't need the headache, and the other inhabitants probably won't put up with it. That's not to say there is a lack of basic services. The housekeeping staff is pretty stealthy. We'd venture out to explore/shop/eat/etc., and when we returned, there were fresh towels, there'd been some general straightening, and the dishes we meant to wash before we left had been cleaned and left to dry. This place suits all age ranges. By the way, from the water-facing rooms, the sun rises and sunsets are outstanding.
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Date of stay: October 2022
Value
Location
Service
Trip type: Traveled as a couple
Room Tip: Book early. Ideally, book directly, not through a third party.
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Harvy T wrote a review Nov 2022
Apopka, Florida43 contributions8 helpful votes
It was clean, spacious, great ocean view, staff was excellent and very relaxing. Would definitely go back and plan to do so. Many good restaurants close and of course the Bass Pro Shop is close. They have a boat slip on property and alligator reef as we; and is sand bar where many boats hang out are close..
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Date of stay: October 2022
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Location
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MaxB wrote a review Aug 2022
Wayland, Massachusetts35 contributions1 helpful vote
+1
Photos of 14B - I don't think I need to say more. We rented this property in May. We were looking for something with a local flare that could accommodate our adult family of 4 ( needing three beds). We were excited to find an "ocean view" family suite. I even called and was assured there was a nice outdoor space. I don't like to post negative reviews but hope to save someone else from being disappointed. They charged a lot for this "resort" room. I begged them to move us or refund a portion of our money. I reached out to the owners, the manager - no help at all. It really put a damper on our short get away. It was our first time being disappointed in Islamorada. Shame on them for false advertising.
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Date of stay: May 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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swordfish-miami wrote a review Aug 2022
Fort Myers Beach, Florida223 contributions53 helpful votes
+1
First time at Drop Anchor. We basically needed a room to shower, sleep and regroup during lobster mini season. Note: you can launch directly from Drop Anchor. Bonus! Every hotel was pretty much ridiculously over priced due to mini season. Found room 15 at Drop Anchor for $235/night! Far and away the top deal on the keys. Despite on the small side, the $/sq ft was in line with their larger rooms and much better than what competitors up and down the road were trying to lure. Room 15 is Oceanfront and has a better view and deck than the larger room behind it! If you need more room, you can book the 16 rooms behind 15. They are closer to the road but under the same roof. Our room was super clean and comfortable. Would certainly return again!
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Date of stay: July 2022Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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liatgo wrote a review Jul 2022
1 contribution1 helpful vote
We stayed in room 14B at April 2022. There are many disadvantages in the room, but the thing that bothered us the most was the strong smell of mold. The room is also very tiny, so it is not possible to place things on either side of the bed or in the room in general. There is no closet or a dresser. The bathroom is even worse- it's barely possible to move in it. In the morning we even saw a cockroach there.
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Date of stay: April 2022
Value
Location
Service
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Michael A wrote a review May 2022
1 contribution
Couldn't ask for a better place to relax and enjoy the beautiful Florida Keys. Friendly staff, clean rooms, and quiet private beach area make for a perfect getaway. Stayed in a Walkout Oceanfront room with a nice kitchen.
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Date of stay: May 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Hwy12er wrote a review May 2022
Mechanicsville, Virginia12 contributions1 helpful vote
We are so glad that we picked Drop Anchor for our 2 night stay. This is a rare jewel in the Keys. Property very well maintained with beautiful waterfront views. We enjoyed kayaking, sitting on the balcony relaxing and taking in the views. It was nice to sit by the pool enjoying friendly conversations with the other guests. Cliff and staff very friendly and helpful.
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Date of stay: April 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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dks68 wrote a review Apr 2022
22 contributions11 helpful votes
+1
This is old keys history. The old highway lays right at the front door. We had a family suite that had a full kitchen two queen beds and a fold out futon . The inside has been renovated yet showed its history. gave me memories of visiting the area in my childhood. The outside of resort is breathtaking with the colorful buildings with many palm trees and hammocks for relaxing. Views are amazing. Pool was fresh and clean. Plenty to do with paddle boats , kayaks, and bicycles. The staff was always friendly and helpful. I couldn’t be happier with picking drop anchor to spend my vacation:)
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Date of stay: April 2022Trip type: Traveled with family
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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NickyB120 wrote a review Apr 2022
Rochester, United Kingdom31 contributions10 helpful votes
+1
This is a reluctant review but purely because it’s such a hidden part of heaven that has fallen from the sky. The location is beautiful. Immaculately maintained and completely dreamy. You’d never guess how close to the road you are so don’t be put off. On the beach you could literally be on a desert island. Cliff on reception was so lovely and helpful. I truly cannot fault this small resort. Don’t tell everyone because spaces are limited and I want one of my very own. Thank you guys so very much
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Date of stay: April 2022Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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PRICE RANGE
$315 - $461 (Based on Average Rates for a Standard Room)
ALSO KNOWN AS
drop anchor hotel islamorada
LOCATION
United StatesFloridaFlorida KeysIslamorada
NUMBER OF ROOMS
18
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DROP ANCHOR - Updated 2023 Prices & Motel Reviews (Islamorada, FL)

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 Bayside Gourmet, Wahoo's Bar and Grill, 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.