Name: Drop Anchor
Address: 84959 Overseas Highway 222, Islamorada, 33036, US

10/10

Exceptional

25 Jul 2026

Scott

It was a great location on the Keys. The staff was friendly and helpful. The view from our room was amazing.

8/10

Excellent

24 Jul 2026

Diana

I did not like that. The room had windows with no coverings. It woke me up too early and I needed to be able to sleep late. Other than that the room was beautiful in the shower was awesome.

10/10

Exceptional

24 Jul 2026

Lance

Friendly Staff, relaxing pool, and great view. The wife and I would absolutely stay there again. Center all everything you would need.

The downside, the room we booked (ocean walkout room with kitchen) was double booked. We were placed in a regular room with no kitchen, they offered to move us Saturday but it was not feasible as we had our dog and were on the water all day. They did give us a small refund and waive pet fee, it was just disappointing as we specifically booked the hotel for the walkout room with Kitchen. I would recommend calling to confirm the room booked will actually be your room.

8/10

Excellent

23 Jul 2026

dea

This place was set in a beautiful location but you could not swim in the water - the swimming pool was a great substitute and well maintained. There were plenty of places to grill and enjoy the views on the property, and I loved that free bike rentals were included. The staff was very friendly and helpful - really satisfied there, but the standard of the rooms was average. Things were functional but there were several conveniences missing, like a towel rod in the bathroom, or unfinished walls in different parts of the villa. It was nice to be in walking distance to a couple of restaurants, an ice cream place, a pizza place, and a Starbucks.

10/10

Exceptional

22 Jul 2026

Melissa

Great place to stay for a few night fishing trip! I loved the outdoor area, felt like we were in the tropics. Our room was super spacious, we had the king walkout ocean view room. More of a studio apartment I’d say. This isn’t the four seasons, but perfect for what we were there for. If you’re looking for luxury- this isn’t it, but a great value and location for fishing!

10/10

Exceptional

21 Jul 2026

Noel

We really enjoyed the laid back vibe, matched with the amenities and the location. We had a great stay!

Family_with_children

6/10

Pleasant

19 Jul 2026

tara

The air conditioning unit was leaking under the flooring. The entire floor squished when you walked on it. The staff just gave us extra towels to put down on the floor. The room was humid because of the moisture under flooring. Not good for asthmatic people

Partner

10/10

Exceptional

11 Jul 2026

Denis

A very cozy, small hotel in a quiet location by the sea. Perfect for a holiday with children. Highly recommended!

Friends_and_family Family

6/10

Pleasant

07 Jul 2026

Bradley

The entry doors locks make me nervous very outdated. Also, requesting room service should be easier. Finally, I called the number I was given six times and never got a response even when I was calling, because of illegal activity on the property. Housekeeper was very nice and rooms were very clean.

10/10

Exceptional

06 Jul 2026

James

Fun place to stay - clean rooms , well maintained property with pool and sitting areas over looking the water.

8/10

Excellent

06 Jul 2026

Bret

Drop Anchor has been around forever and the floors and couch must be original. I can say I have never sat on a more uncomfortable couch and the pull out bed was utterly useless as it felt like it was a prison camp mattress. That being said, the staff was so exceptional and the room was clean, cool, and uniquely they can sleep more than 4 people.
If they would just burn or throw away the couch that has been overused since what seems like the late 1970's this would have been a 5 star stay.
Don't need the couch? Don't mind floors that almost cave in under your feet? 5 stars. Spending even 10 minutes on that couch however takes away the comfort.
Again, a super-friendly staff and welcoming environment make us want to come back. We likely will - Just praying they replace the antique couch so that the kids can actually sleep. They're light and the springs still poked them pretty bad. Pool was great, fishing off the back seawall is possible too.

Family_with_children

2/10

Poor

05 Jul 2026

Juan Alberto

I reserved this hotel from June 27–July 5 but had to check out early. On June 29 around 10:30 p.m., I found multiple roaches in my room. I immediately packed my belongings and checked into another hotel. Since the front desk was closed, I returned the next morning with my husband, showed Donna photos and videos of the roaches, and officially checked out. Donna at the front desk apologized, said the property is fumigated every three months, and told us a manager would contact me about the unused nights. Despite contacting Expedia, neither Expedia nor I have heard from management.

This ruined our vacation. The new hotel didn't have availability for the rest of our trip, so we had to end our vacation early. We lost money on prepaid restaurant reservations, a Bahamas day trip, missed our Fourth of July plans, and had to pay to change our flight home.

I was also charged $301 in resort fees, yet this property felt more like a motel than a resort. There is no beach access, the rooms are outdated, the floors were dirty, the pots and utensils had dirt on them, the shower tiles had mold, and the pool is very small.

This hotel charges premium prices but fails to meet even basic expectations for cleanliness, quality, and value. In my opinion, it is not worth the money. This review reflects my personal experience, and I am extremely disappointed with both the condition of the property and the lack of follow-up from management. I would not stay here again or recommend this hotel.

Family

10/10

Exceptional

30 Jun 2026

Rebecca

Beautiful property right on the beach. Loved that we could just grab kayaks right off the beach and go paddle around. Our room was clean and the AC was cold.

Friends_and_family Friends

4/10

Poor

29 Jun 2026

Kurt

We had a late check in 7:30 pm, Staff left 6:00
Got the key made it to our room
Room was not the oceanside with a balcony that we booked.
Went to desk next day asking about our room, apparently they gave the balcony we reserved and paid for a week prior to someone else.
They had no room with the amenities we reserved. Next day i saw our room on hotels.com that we had reserved was now available. The desk staff would not let me have the vacant room we reserved.

Partner

10/10

Exceptional

29 Jun 2026

Thomas

Best place I ever stayed! It’s was amazing!

8/10

Excellent

29 Jun 2026

Elizabeth

We stayed in room 1 by the office, I loved the little porch in the front and the back area. However, the bed is too small for 2 people to sleep in and the bathroom wasn’t as clean as it should’ve been. We didn’t use the amenities since we only stayed one night but all in all, it was pretty good for an overnight stay. The staff was very nice with check in and check out.

Pet

8/10

Excellent

23 Jun 2026

Sutton

We could walk to hog heaven They had complementary bikes, paddle boards, and kayaks.

Family

2/10

Poor

23 Jun 2026

Henry

Nice ocean view. The smell was horible because of the dead sea weeds. Kayaks and bicycles were available but locked up. Staff was not available in the evening and in the morning to supply the equipment. The shower was pressure was so low that water just dripping out. TV also was not working.

Family

10/10

Exceptional

22 Jun 2026

Joan

Drop Anchor was very clean and quiet, the room was great! There were not any issues with checking in or checking out. They had a full-time maintenance person working that was picking up, raking the sand, and helping maintain a very pleasant stay!

Friends_and_family Friends

10/10

Exceptional

21 Jun 2026

Zorangel

La estancia fue súper , bello paisaje , todo limpio el personal atento y muy agradable brindando un servicio excelente pues yo no sé inglés y enseguida me tradujeron y me explicaron todo, ,un lugar súper para pasar unas vacaciones en familia o como yo un fin de semana de luna de miel 😜.

Friends

10/10

Exceptional

21 Jun 2026

Marisol

We were greeted by Daniel when we checked in. He was kind and very respectful with many recommendations in the area. Our unit was GREAT. Perfect views of the bay and the kitchen had everything we needed for a short stay.

Partner

10/10

Exceptional

10 Jun 2026

Melissa

Great stay for boaters! right on the water and easy to launch. The rooms were clean and had the essentials. The staff was super friendly and helpful.

2/10

Poor

31 May 2026

Braulio

Muy mal trato del personal que te recibe en la propiedad

Family_with_children

10/10

Exceptional

25 May 2026

Jasmine

The room wasn’t the most luxurious and needed work. The pool needs a reface as well, but the location and the boat ramp was great and we were able to get across to the sand bar in no time! The staff was helpful, the location is absolutely amazing, the scenery is amazing, and the convenience of launching there was a great perk! Definitely recommend if you want something laid back, a great view, and convenient. Definitely call before booking and let them know about your plans for launching! They’re a little sticky about this!

Family_with_children

10/10

Exceptional

25 May 2026

Nadya

The staff was phenomenal, any request I may have had it was promptly attended to it. The stay was a very great experience and I will become a regular.

Thank you 🙏

Friends_and_family Family

10/10

Exceptional

10 May 2026

Barbaro

Excellent

Family_with_children

10/10

Exceptional

26 Apr 2026

ronald

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.

Family

6/10

Pleasant

20 Apr 2026

Katherine

The place over charges this is not a resort it’s more like a motel I payed over $1200 for two nights and I feel this place shouldn’t charge more than $250 a night.
Also be aware there was a resort fee the kayaks weren’t working and the office was always closed. Will not be going back.

Family_with_children

10/10

Exceptional

20 Apr 2026

Anna Marie

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!

Partner

10/10

Exceptional

15 Apr 2026

Amy

Great room. Staff was very helpful and kind. Enjoyed the beachfront

Family

10/10

Exceptional

09 Apr 2026

Godfrey T

Quiet, great staff, plenty to do.

8/10

Excellent

30 Mar 2026

Ben

Great for a two night stay in Islamorada!

10/10

Exceptional

29 Mar 2026

Ana

Everything was clean and in good conditions

Self

10/10

Exceptional

27 Mar 2026

vanessa

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 .

Family_with_children

4/10

Poor

20 Mar 2026

Carol

This place needs an entire makeover. The staff were super nice and the views were beautiful. It’s in a great location but the rooms are run down. The free kayaks and bikes were in terrible condition and the pool was dirty and had many visible concrete holes on the bottom. The WiFi and ice machine were both not working and the water pressure was almost nonexistent.

Partner

10/10

Exceptional

18 Mar 2026

Maria

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.

Partner

10/10

Exceptional

14 Mar 2026

Wendy

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.

Partner

10/10

Exceptional

13 Mar 2026

dennis

Not our room.

10/10

Exceptional

12 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!

10/10

Exceptional

07 Mar 2026

Shaney E

We had a great room with a beautiful view of the beach in front of the ocean. Loved it!

Partner

10/10

Exceptional

06 Mar 2026

Jill

Great location! Super cute every room is close to the water. Would stay here again for sure.

10/10

Exceptional

05 Mar 2026

Linda

The ocean was right outside our door. The unit was very clean, very kept up and the quietness was amazing.

8/10

Excellent

04 Mar 2026

Scott

Water pressure was too low to wash hair

8/10

Excellent

04 Mar 2026

Alexander

Rooms are very small

Family

6/10

Pleasant

02 Mar 2026

Robert

The unit was older but clean. The facility was well maintained. The issue was the noise. The folks in the adjacent unit began arguing loudly around 8:00 pm. There was a lot of bagging on the walls that could be felt in our bed. Chairs were scooted across the floor with a loud screeching sound. The noise finally stopped around midnight

2/10

Poor

26 Feb 2026

anna

The photos of the booking were NOT the room we booked. When I asked about changing rooms, I was told they were sold out. The hotel only had 5 rooms booked, if that. I was happy to pay for an upgrade. Instead he told me to let him know about the incident next time I booked and he could discount me. I was asking for an upgrade at my expense, not a
Discount to a place I would never return.

10/10

Exceptional

24 Feb 2026

Tony

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!

Partner

2/10

Poor

24 Feb 2026

Dzastina

We had some bugs issues, the place was very nice and clean.

Partner

10/10

Exceptional

21 Feb 2026

Miguel

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.

Pet

10/10

Exceptional

19 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.

10/10

Exceptional

17 Feb 2026

MaryBeth

Great staff

Friends

4/10

Poor

17 Feb 2026

Lisa

Pverpriced for dingy interior, musty smelling room

10/10

Exceptional

16 Feb 2026

James

So clean. Great room. Near everything and so so clean. I would stay here again. The people at the drop anchor are super nice.

Friends_and_family Family

10/10

Exceptional

16 Feb 2026

Markee

The View was amazing!

Partner

4/10

Poor

12 Feb 2026

Christopher

There was no Hot water & the maintenance guy tried to say island water didn’t get that warm ! Don’t stay 🙄

Business_and_leisure Friends

6/10

Pleasant

12 Feb 2026

Julie

We had a queen room that was super small and rated as ocean view. No room in the bathroom to put anything around the sink while you are getting ready. Area where the bed is is so tight you have to get on the bed from the foot of the bed. Definitely not the best room we have ever had. The property did seem nice but be aware there is a $35 resort fee and all I saw was about 5 kayaks??? Not worth $35 in my opinion. There is also not enough parking spots for all guests and we had to park on the road next to our tiny room. I would probably not stay there again. At least not in room 14b!!

Leisure Partner

4/10

Poor

01 Feb 2026

Jacob

Hotel manager just isn’t professional had to call twice and leave messages to extend my stay. Only to find Shower pressure is a dribble and won’t get hot. No privacy in room as there are only blinds that you can see through. Remote for the ac unit had dead batteries and wouldn’t operate and it’s 30 degrees out today. Just a tired place and not worth the price for sure. Won’t be back way too many other good options

Business Self

10/10

Exceptional

01 Feb 2026

Amber

Loved this place

Leisure Partner

10/10

Exceptional

01 Feb 2026

Brian

Clean room, beautiful view and loved being able to walk out to the beach.

8/10

Excellent

30 Jan 2026

Alberto

Great room and amazing view

Leisure Partner

4/10

Poor

30 Jan 2026

Joanne

The property itself was ok (nice view with the beach walk-out unit) however there was no actual beach so their photos were very deceiving; our King suite with kitchen meant for four people was really sub-par. The single bathroom was so tiny your knees hit the wall when going to the bathroom and the sink had a large crack in it; on check-in we asked for extra pillows and was told by the property manager he would “try his best” which I guess was code for “no” because the pillows never came (the six pillows in the unit were smaller than standard pillows and simply not enough for our party). When coming home for dinner we went to close the curtain over the sliding glass door and the entire thing fell off the wall - since there is no manager on site after 5pm we had to rig the curtain to stay up until they could be notified in the morning…The next morning we went to get ice for the room but the ice machine did not work or was empty (the property manager brought some a while later). Seriously disappointing for the price and will definitely not be back…

Leisure Family

10/10

Exceptional

29 Jan 2026

Erin

the staff was wonderful, the room was perfect, the location/view was awesome . the pool was wonderful. i am very very pleased with our stay !

Leisure Partner

10/10

Exceptional

29 Jan 2026

Jeff

Staff member at front desk was friendly and courteous! Room was just what we wanted costal, cozy and clean. Coffee and a pastry or fruit at the office in the am would be a nice touch.

Leisure Partner

8/10

Excellent

28 Jan 2026

Joseph

Very nice

Leisure Family

10/10

Exceptional

21 Jan 2026

Nina

Great stay, better than I even expected from the pictures. Quiet, quaint little place right on the water. The edge is actually a dock, but it looks like it’s right on its own, private, wide beach! The internet was good - I had a half day of doing Zoom work calls and had no problems. It’s quiet, the bed and pillows were comfortable, and the coffee in the room was strong and good. Close to a couple restaurants within walking distance, one of which was dockside with outdoor seating that was so relaxing (Island Grill). Definitely would stay again.

Self

4/10

Poor

19 Jan 2026

Joann

The room was not as discribed. I booked two rooms with balcony and my room did not have a balcony and was smaller that the room i booked for thmy second room. The scond room was larger and had a balcony. sencond room i booked for the cou

Leisure Friends

10/10

Exceptional

19 Jan 2026

Christy

The room walked right out to water. Staff came around to ask if we needed anything. It was amazing!

Leisure Partner

10/10

Exceptional

18 Jan 2026

Elena

Good times staying at the property. Great view out of the window.

Partner

10/10

Exceptional

18 Jan 2026

DeeDee

The room was clean, property is nice, pool is really heated and lovely to get in and out. Most places lie about heating their pool this one is for real! Daniel in the office is super great! They have bikes and kayaks to use, that is included in your resort fee.( which is reasonable). Definitely be back☀️.

Leisure

10/10

Exceptional

14 Jan 2026

Kelly

Great

4/10

Poor

04 Jan 2026

Elena

The staff was very nice, but unfortunately that is not enough. The room was spacious but lacked storage. No dresser or nightstands available.
Housekeeping was available only if requested during a guest's stay. The hot water was at most luke warm and only intermittently. The door of the room could not/lock properly, Ice machine broken;

10/10

Exceptional

01 Jan 2026

Ron

The staff was personable, great location, having the bicycles and kayaks were a great touch

Partner

6/10

Pleasant

26 Dec 2025

Raman

Overpriced! No breakfast available and room was falling apart- needed maintenance. The only thing we liked was the location- beautiful view from balcony.

10/10

Exceptional

25 Dec 2025

Brook

Amazing and peaceful lady at front desk was amazing and friendly

Friends_and_family Family

10/10

Exceptional

25 Dec 2025

Traci

The room was very clean and the staff was great. We didn’t cook. The kitchen was small but it would work if we needed it…full size appliances and a microwave. The place is right on the water. There isn’t a beach but they have sand and they rake it every morning. Pool is small but nice enough. A small place, never crowded while we were there even though it was fully booked. We enjoyed the hotel and Islamorada more than Key West…to crowded to enjoy.

Leisure Pet

10/10

Exceptional

16 Dec 2025

Melissa

Staff was wonderful! Location and amenities were great! Room was clean and comfortable!

Leisure Self

10/10

Exceptional

07 Dec 2025

Laura

Had a wonderful stay at Drop Anchor! Very adorable and super clean. Loved the amenities and the hotel staff were amazing!

8/10

Excellent

23 Nov 2025

Dustin

The staff was very nice. Thanks

Leisure Family

8/10

Excellent

23 Nov 2025

fiona

Spotless, simple room. Quiet, peaceful resort. Daniel (GM) was super helpful. Very pleasant stay. Very Dog friendly. Everyone chilled and relaxed — the Key vibe you look for! Enjoy!

10/10

Exceptional

23 Nov 2025

John

Wonderful … clean… great location!

Leisure Family

6/10

Pleasant

13 Nov 2025

Robert

Toilet problem

10/10

Exceptional

31 Oct 2025

ANNIA

Quiet peaceful nice beds view kitchen 😍

2/10

Poor

26 Oct 2025

Thomas

Due to a family emergency, my brother passed suddenly, we had to cancel the room. I was not refunded, even though I had insurance and documentation on why. Manager was rude and dismissive when i contacted them.

Partner

10/10

Exceptional

22 Oct 2025

Thalia

Great

10/10

Exceptional

19 Oct 2025

Paula

Comfy bed! Pretty tiled shower!

Partner

10/10

Exceptional

01 Oct 2025

Dianna

Clean, comfortable room, friendly staff. Grounds clean and properly taken care of. Would stay here again.

10/10

Exceptional

25 Sep 2025

Greg

It was a perfect little cottage and peace and quiet. Lots of Palm trees and perfect boat launch

Leisure Family

8/10

Excellent

23 Sep 2025

Ariel

It is very convenient. It has fun and relaxing surroundings. Pet friendly. The dining places are a must.

Leisure Pet

10/10

Exceptional

11 Sep 2025

Michael

Beach view

4/10

Poor

09 Sep 2025

Vicki

Disappointed

Did not have hot water in our room. Notified them the next day to see if they could at least take the resort fee off (which was a surprise fee of almost $40 btw) and called a couple times when no one reached out to me. Having a hot shower should be standard and something should have been done for us because of it. Disappointed in their neglect to make it right.

Friends_and_family Family

10/10

Exceptional

02 Sep 2025

Karen

Beautiful view!!!

8/10

Excellent

26 Aug 2025

John

Beautiful property and the staff was amazing.

Leisure Family

10/10

Exceptional

22 Aug 2025

Anisley

The hotel is very quiet and that are we need for relax

Leisure Partner

10/10

Exceptional

21 Aug 2025

STEPHEN

Liked the Atlantic bulkhead. Plenty of dock space and casting room. Tasteful atmosphere with clean grounds and pool. Boat launch looked safe and maintained. Outdoor lights gave a nice ambience. Room was clean and properly stocked. TV was outdated.

Leisure Partner

10/10

Exceptional

14 Aug 2025

Lisa

This place was great! Was a spur of the moment decision to stay here and we haven’t regretted it. Beautiful view and 2 restaurants within walking distance to property.

Leisure Family

10/10

Exceptional

11 Aug 2025

Ninoslav

Beautiful and quiet place!

Leisure Pet

8/10

Excellent

11 Aug 2025

Raul

The property was well maintained. The staff was excellent.

Leisure Family_with_children

10/10

Exceptional

04 Aug 2025

Silvia

Love it!!

Leisure Family

8/10

Excellent

01 Aug 2025

David

Check in and out super easy and front desk great. Room itself was roomy but older. No vent or ac in shower or bathroom area. Older window wall unit barely cooled room. However property itself and location were great so made it a win. Having Paddleboard’s and kayaks to use for free big bonus, pool at end of day was relaxing and sitting under tiki huts at night and in morning looking out to wide open water was awesome and super relaxing. Definitely not a resort but a very nice option to stay a night or two with a reasonable price

Leisure Family

8/10

Excellent

31 Jul 2025

GALE

Nice place to stay

Great location clean rooms and private beach adds this to our list of places we will book again. Also affordable rates. Upper keys easily accessible and lots of things to do in the immediate area.

Friends_and_family Family