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8.8 / 10 Guest Rating

Drop Anchor

84959 Overseas Highway, 222, Islamorada, Florida, 33036, Islamorada, US

Drop Anchor - main view

About the Property

Escape to paradise at Drop Anchor, where stunning waterfront views meet exceptional comfort.

Private Beach & Outdoor Pool
Bask in the sun on our exclusive private beach or take a refreshing dip in the outdoor pool, perfect for a relaxing day under the Florida sun.

Modern Comforts
Our 18 air-conditioned rooms are designed with your comfort in mind, featuring flat-screen televisions, complimentary Wi-Fi, and coffee/tea makers to start your day right.

Business & Leisure Amenities
Take advantage of our convenient business center and enjoy free self-parking. Whether you're here for leisure or work, we cater to all your needs with attentive services and a charming picnic area.

Don’t miss your chance to experience all that Drop Anchor has to offer—book your stay with us today!

Facilities & Amenities

Boat tours nearby
Paddleboard on site
Parasailing nearby
Free bicycles on site
Fish cleaning table
Free WiFi
Garden
Designated smoking area
Wheelchair accessible
Picnic area

Important Information

Check-in & Out

Check-in
Check-out11:00 AM

Property Notes

Pool access available from 7:30 AM to 6:30 PM.The property has connecting/adjoining rooms, which are subject to availability and can be requested by contacting the property using the number on the booking confirmation. Contactless check-out is available.

Check Room Availability

1 night · 2 adults

No rooms available

We couldn't find any available rooms for these dates and guests. Try adjusting your search criteria.

Guest Reviews

8.8
Excellent154 verified reviews
AI Summary

Guests highly rate the beautiful location and frequently praise the friendly staff.

Categories

Cleanliness8.5
Service9.2
Location9.3
Room Quality8.2
Amenities8.8
Value for Money8.7
Food and Beverage8.8
Overall Experience9.0

Select topics to read reviews

C
CarolusUS
Verified booking
couple
Standard Room
Stayed in Mar 21, 2026

"Excellent"

8.0
Helpful?
M
MaricarmenusUS
Verified booking
couple
Standard Room
Stayed in Mar 16, 2026

"Exceptional"

10.0
Helpful?
T
ThomasusUS
Verified booking
solo_traveller
Standard Room
Stayed in Mar 13, 2026

"Paradise"

10.0

Location and waterfront area out back.

No dresser in room, no drawers for clothes! 2 tiny six inch wide drawers in sink vanity, that's it.

Helpful?
A
angelaitIT
Verified booking
couple
Standard Room
Stayed in Mar 13, 2026

"Good"

6.0
Helpful?
J
JenygbGB
Verified booking
couple
Standard Room
Stayed in Mar 3, 2026

"A lovely little gem tucked away, with kind and friendly staff. Nothing was too much trouble for them"

9.0

We love going to the Keys, but noticed how expensive it is now becoming, sadly, so this was a decent price for a decent product. Drop Anchor was just lovely. The sun area to the rear of the property was a huge bonus and beautifully kept. If I stay again, I would like a room at the rear of the property because I like to relax in the sun, whilst my husband goes out fishing a lot. The cooker and fridge/freezer were really good. And there was a container of ice in there already for us to use.

The shower was ok but not brilliant. There needed to be a little unit in the bathroom to put stuff on as the sink area was too small. The towels could be bigger. In the kitchen, perhaps have plastic cups to use outside in the seating area. Plus, a kettle would be good for a cup of tea (British!).

Helpful?
R
ReannecaCA
Verified booking
extended_group
Standard Room
Stayed in Mar 1, 2026

"Exceptional"

9.0

Good location, cute and clean and cheerful service. Walking distance to a couple good spots, good for a midway stop in the keys.

Helpful?
D
DougcaCA
Verified booking
couple
Standard Room
Stayed in Feb 28, 2026

"Great getaway at peaceful clean resort"

8.0

Very clean and well kept older property. Staff very friendly and helpful..room was large and comfortable and good restaurants nearby

The room we booked, oceanfront king suite, did not look like the pictures on Booking.com . We felt we were in the old section (room16) and had expected the newer section based on the pictures and the price paid. Even so, we would recommend the resort

Helpful?
C
caseyusUS
Verified booking
family_with_children
Standard Room
Stayed in Feb 25, 2026

"Good"

5.0

Pool was nice

Bed was very uncomfortable

Helpful?
T
ThijsnlNL
Verified booking
solo_traveller
Standard Room
Stayed in Feb 13, 2026

"Exceptional"

9.0
Helpful?
C
CourtneyusUS
Verified booking
extended_group
Standard Room
Stayed in Feb 9, 2026

"Exceptional"

9.0
Helpful?