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All 20 Islamorada hotels

Drop Anchor Resort

3.0 of 5 Motel   |   84959 Overseas Hwy, Islamorada, FL 33036
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Ranked #5 of 20 hotels in Islamorada
Certificate of Excellence 2014
A recent review
5 of 5 stars reviewed 3 days ago
aefl223 Gainesville, Fl
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318 people have reviewed this hotel

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Rating summary
  • Location
    4.5 of 5 stars
  • Sleep Quality
    4.5 of 5 stars
  • Rooms
    4.5 of 5 stars
  • Service
    4.5 of 5 stars
  • Value
    4 of 5 stars
  • Cleanliness
    4.5 of 5 stars
Traveler tips help you choose the right room.   Room tips (67)
Date | Rating
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English first
Gainesville, Fl
13 reviews 13 reviews
6 hotel reviews
11 helpful votes 11 helpful votes
5 of 5 stars Reviewed 3 days ago NEW

The hotel is a nicely updated slice of Keys charm, right on the Atlantic, on Windley Key in Islamorada. Room 15 faces the ocean and was clean and spacious, with a very comfortable bed. We spent 4 nights here and will return based on our experience. Nice to sit at the waters edge in the morning with a cup of... More

Was this review helpful? Yes 1
Dorlisheim, France
4 reviews 4 reviews
1 helpful vote 1 helpful vote
4 of 5 stars Reviewed 5 days ago NEW

We've stayed at the Drop Anchor Resort for one night, on our way to Key West. The place is very nice : from the outside, the hotel has several colors, a fountain and a lovely view on the ocean. But you cannot swim in this part of the Islamorada. The simming pool is average, but has a oceanfront. We had... More

Was this review helpful? Yes 2
Houston, Texas
Senior Contributor
23 reviews 23 reviews
8 hotel reviews
12 helpful votes 12 helpful votes
5 of 5 stars Reviewed 1 week ago

My wife and I stayed here on the way to Key West. As soon as we checked in my wife said " I could just stay here and not go any farther." I agree. From the outside the rooms have bright colors and charm. Upon entering our room (#8 with an ocean view) we were pleased to find a wonderful... More

Was this review helpful? Yes 1
West Palm Beach, Florida
Senior Contributor
42 reviews 42 reviews
19 hotel reviews
12 helpful votes 12 helpful votes
5 of 5 stars Reviewed 1 week ago

Had a nice one night stay here. We were in room #5 which had it’s own private patio overlooking the Atlantic and steps away from the pool. The room was clean, the bed comfortable. The room was huge for a hotel room. It has a full kitchen, a king bed with a futon which was a comfortable couch to watch... More

Was this review helpful? Yes 1
Hobe Sound, Florida
Senior Contributor
25 reviews 25 reviews
11 hotel reviews
11 helpful votes 11 helpful votes
4 of 5 stars Reviewed 1 week ago

The hotel was ok. We stayed in room 12 which was a two bedroom apartment. There was a full size bed that took up most of the room, but there was a very large closet. The second bedroom was off the first bedroom and had two twin beds. These rooms were very cute and very clean with window AC units... More

Was this review helpful? Yes 1
Englewood, Florida
Senior Contributor
32 reviews 32 reviews
12 hotel reviews
29 helpful votes 29 helpful votes
4 of 5 stars Reviewed 2 weeks ago

We stayed in room 3. It was spacious and the view was fantastic of the ocean. The pool was nice. The room was decorated very tastefully. Comfortable bed and kitchen with bare necessities so you can cook of BBQ. Little tip: The Trading Post just south on 1 has very fair prices, especially for an island market. They were experiencing... More

Was this review helpful? Yes 1
Miami, Florida
Senior Contributor
40 reviews 40 reviews
27 hotel reviews
32 helpful votes 32 helpful votes
4 of 5 stars Reviewed 4 weeks ago

I just returned from a short - too short - trip to Islamorada and this hotel. The fact that it was too short was my own fault, as they only had a vacancy on a Friday and the hotel was full on Saturday. I had planned to stay longer, but weather is a big "if" for a boater and fisherman... More

Was this review helpful? Yes 4
Delray Beach
Top Contributor
62 reviews 62 reviews
4 hotel reviews
20 helpful votes 20 helpful votes
4 of 5 stars Reviewed 4 weeks ago

We stayed here for only one night, wish it could have been more. We stayed in 14B, small room but you really don't need more room. Its on the first floor, it is kind of like having your own private cottage. They have the cutest chairs with their logo on them in front of every room. The grounds are very... More

Was this review helpful? Yes 2
Miami, Florida
14 reviews 14 reviews
8 helpful votes 8 helpful votes
4 of 5 stars Reviewed July 5, 2014

My boyfriend and I needed to get away for a little from work and the craziness of Miami life. We found Key West to be a little pricey for our budget, so we looked into Islamorada. This little place had great reviews and got a great price for 3 nights so I booked it. Loved it!! The location was perfect.... More

Was this review helpful? Yes 2
West Chester, PA
Senior Contributor
38 reviews 38 reviews
16 hotel reviews
21 helpful votes 21 helpful votes
4 of 5 stars Reviewed July 3, 2014

We spent a night here on our way to a wedding in Key West - this place is just what we were looking for -on the water, some character and not a chain resort. 'Resort' may be a misleading term with this place, to me it was just more of an old fashioned motel/cottage spot with a great pool. We... More

Was this review helpful? Yes 2
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Additional Information about Drop Anchor Resort

Address: 84959 Overseas Hwy, Islamorada, FL 33036
Phone Number:
Location: United States > Florida > Florida Keys > Islamorada
Price Range (Based on Average Rates): $$
Hotel Class:3 star — Drop Anchor Resort 3*
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Also Known As:
Drop Anchor Hotel Islamorada

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Hotel & grounds (50)
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Free High Speed Internet ( WiFi ) Free Parking Kitchenette Swimming Pool Wheelchair access
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