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Hotel

Drop Anchor

Monroe, Florida

The Fun Awaits

Perfect for nature lovers
Perfect for nature loversOnly 6 m to Windley Key Fossil Reef Geological State Park and 3.4 km to Founders Park

Reviews

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4.2/5
GoodFrom 100 reviews
5.0/526 Apr 2026
ronald • Family Trip
Our room was comfortable and clean. The grounds and pool were really nice. The entire staff were awesome. It was really cool having the kayaks on the property. We had a great stay.
5.0/520 Apr 2026
Anna Marie • Couple Trip
What a wonderfully kitschy Florida Keys hotel! The property was beautifully manicured and well taken care of. Our room was clean and very comfortable. We can’t wait to book another stay!
5.0/515 Apr 2026
Amy • Family Trip
Great room. Staff was very helpful and kind. Enjoyed the beachfront
5.0/59 Apr 2026
Godfrey T
Quiet, great staff, plenty to do.
5.0/529 Mar 2026
Ana • Solo Trip
Everything was clean and in good conditions
5.0/528 Mar 2026
vanessa • Family Trip
We loved our stay and definitely will be back . Staff was great, hotel was clean and comfortable, the view amazing, great location. The only thing to improve is the water pressure when taking showers but everything else was fantastic .
5.0/518 Mar 2026
Maria • Couple Trip
Daniel (office staff) was amazing. This is our second time back and won't be our last. Our room was just what we needed for 3 nights. Spacious and clean We loved being able to use the complimentary bikes. There are kayaks to use also but was too windy this trip. Pool was great The views from this resort are AMAZING.
5.0/514 Mar 2026
Wendy • Couple Trip
Very pleasantly surprised with the location and quality of this resort. The water view is available throughout the property and this resort is well taken care of. The pool was exceptionally clean and refreshing.
5.0/513 Mar 2026
dennis
Not our room.
5.0/512 Mar 2026
Cassie
We could see the ocean from the bed so we'd wake up, open the curtains and watch the sunrise from the bed! Amazing!
5.0/58 Mar 2026
Shaney E • Couple Trip
We had a great room with a beautiful view of the beach in front of the ocean. Loved it!
5.0/56 Mar 2026
Jill
Great location! Super cute every room is close to the water. Would stay here again for sure.
5.0/55 Mar 2026
Linda
The ocean was right outside our door. The unit was very clean, very kept up and the quietness was amazing.
5.0/524 Feb 2026
Tony • Couple Trip
My stay at Drop Harbor was excellent. The room was spotless and the location couldn’t have been better. I opened my door and the water was right there — absolutely beautiful. The front desk staff was very friendly and welcoming. Overall, a fantastic experience!
5.0/521 Feb 2026
Miguel • Others
Friendly staff, we checked in early to have access to the kayaks and pool, and they prioritized the room and contacted us early to pick up the keys. Great location and close to our beach destination, Islamorada Sandbar. Highly recommended stay.
5.0/519 Feb 2026
Chris
We were so lucky to find this little hidden gem in Islamorada. We needed a room for 1 night on our way back to Miami, but didn’t need all the frills. Drop Anchor was the perfect place for us.
5.0/517 Feb 2026
MaryBeth • Trip with Friends
Great staff
5.0/517 Feb 2026
James • Family Trip
So clean. Great room. Near everything and so so clean. I would stay here again. The people at the drop anchor are super nice.
5.0/516 Feb 2026
Markee • Couple Trip
The View was amazing!
5.0/52 Feb 2026
Amber • Couple Trip
Loved this place

Location

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84959 Overseas Highway, 222, Islamorada, Florida, US
All distances are measured in straight lines. The actual travel distance may be different.

Accommodation Rules

Announcement

You must show a valid photo ID and credit card upon check-in. Please note that all special requests cannot be guaranteed and are subject to availability upon check-in. Additional charges may apply.Please inform hotel in advance of your expected arrival time. You can use the Special Requests box when booking, or contact the property directly with the contact details provided in your confirmation Guests are required to show a photo identification and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply.
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Check-in Procedure
Check-in3:00 PM-6:00 PM
Check-out11:00

  • Extra-person charges may apply and vary depending on property policy
  • Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
  • Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
  • This property accepts credit cards, debit cards, and cash
  • Safety features at this property include a carbon monoxide detector, a fire extinguisher, and a smoke detector
  • This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

The front desk is open daily from 8:00 AM - 8:00 PM. The front desk is staffed during limited hours. Information provided by the property may be translated using automated translation tools.

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Want to check in early? Fill out the Special Requests form on the booking page.

More Policies
  • 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.

About Drop Anchor

Drop Anchor Location
With a stay at Drop Anchor in Islamorada, you'll be on the waterfront, just a 4-minute walk from Windley Key Fossil Reef Geological State Park and 7 minutes by foot from Hog Heaven. This hotel is 1.7 mi (2.8 km) from Rain Barrel Village and 1.9 mi (3 km) from Founders Park.

Drop Anchor Facility and Service
Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities, which include an outdoor pool. This Art Deco hotel also features complimentary wireless internet access, wedding services, and a picnic area.

Drop Anchor Rooms
Make yourself at home in one of the 18 air-conditioned rooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with showers feature complimentary toiletries and hair dryers. Conveniences include coffee/tea makers and ceiling fans, and housekeeping is provided daily.

Room Type and Price

Sun, 09 Aug 2026 - Mon, 10 Aug 2026 (1 night)
1 Room, 1 Adult, 0 Children