See all properties

Drop Anchor

3.0 star property

Choose dates to view prices

Photo gallery for Drop Anchor

Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view
Oceanfront King Suite w/ Kitchen & Private Balcony | 1 bedroom, premium bedding, individually decorated
Exterior
Oceanfront King Suite w/ Kitchen & Private Balcony | Water view
Oceanfront King Suite w/ Kitchen & Private Balcony | Terrace/patio

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Pool
  • Pet friendly
  • Housekeeping
  • Air conditioning
  • Parking included
  • Free WiFi
$220
includes taxes & fees
Oct 22 - Oct 23

Explore the area

View in a map
84959 Overseas Highway, 222, Islamorada, FL, 33036
  • Place, Windley Key Fossil Reef Geological State Park
    ‪6 min walk‬
  • Place, Theater of the Sea
    ‪9 min walk‬
  • Place, Islamorada County Park
    ‪4 min drive‬

Room options

View all photos for Ocean View Double Queen w/ Kitchen & Private Balcony

Ocean View Double Queen w/ Kitchen & Private Balcony | 1 bedroom, premium bedding, individually decorated

Ocean View Double Queen w/ Kitchen & Private Balcony

9.6 out of 10
Exceptional
(5 reviews)
  • Sleeps 4
  • 2 Queen Beds

View all photos for Oceanfront Trailer

Oceanfront Trailer | 1 bedroom, premium bedding, individually decorated

Oceanfront Trailer

8.0 out of 10
Very good
(8 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for Resort View ADA King Room

Resort View ADA King Room | 1 bedroom, premium bedding, individually decorated

Resort View ADA King Room

  • Sleeps 2
  • 1 King Bed

View all photos for Oceanfront King Suite w/ Kitchen & Private Balcony

1 bedroom, premium bedding, individually decorated

Oceanfront King Suite w/ Kitchen & Private Balcony

10.0 out of 10
Exceptional
(19 reviews)
  • 1 bedroom
  • Beach view
  • Sleeps 4
  • 1 King Bed

View all photos for Ocean View Double Queen Room

Ocean View Double Queen Room | 1 bedroom, premium bedding, individually decorated

Ocean View Double Queen Room

8.8 out of 10
Excellent
(15 reviews)
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

View all photos for Resort View Family Suite w/ Kitchen

Resort View Family Suite w/ Kitchen | Private kitchen | Coffee/tea maker

Resort View Family Suite w/ Kitchen

7.4 out of 10
Good
(3 reviews)
  • 1 bedroom
  • Resort view
  • Sleeps 6
  • 2 Queen Beds and 2 Twin Beds

View all photos for Resort View Queen Room w/ Kitchen & Private Porch

Resort View Queen Room w/ Kitchen & Private Porch | 1 bedroom, premium bedding, individually decorated

Resort View Queen Room w/ Kitchen & Private Porch

9.6 out of 10
Exceptional
(7 reviews)
  • Resort view
  • Sleeps 2
  • 1 Queen Bed

View all photos for Oceanfront Queen Room

Oceanfront Queen Room | 1 bedroom, premium bedding, individually decorated

Oceanfront Queen Room

  • Ocean view
  • Sleeps 2
  • 1 Queen Bed

View all photos for Oceanfront King Suite w/ Beach Walkout & Kitchen

Oceanfront King Suite w/ Beach Walkout & Kitchen | 1 bedroom, premium bedding, individually decorated

Oceanfront King Suite w/ Beach Walkout & Kitchen

9.6 out of 10
Exceptional
(11 reviews)
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed

View all photos for Oceanfront Family Suite w/ Kitchen

Flat-screen TV

Oceanfront Family Suite w/ Kitchen

  • 2 bedrooms
  • Ocean view
  • Sleeps 6
  • 1 King Bed, 2 Twin Beds and 1 Queen Futon

View all photos for Resort View Queen Family Suite w/ Kitchen

Resort View Queen Family Suite w/ Kitchen | 1 bedroom, premium bedding, individually decorated

Resort View Queen Family Suite w/ Kitchen

10.0 out of 10
Exceptional
(1 review)
  • 2 bedrooms
  • Resort view
  • Sleeps 6
  • 1 Queen Bed, 1 Double Bed and 1 Queen Sofa Bed

Similar properties

Private beach, white sand, sun loungers, beach towels
Chesapeake Beach Resort
  • On private beach
  • Pool
  • Breakfast included
  • Pet friendly
4.6 out of 5, Wonderful, 1,552 reviews
Chesapeake Beach Resort

About this property

Drop Anchor

3-star Islamorada hotel with outdoor pool
Along with an outdoor pool, this hotel has coffee/tea in a common area and a business center. Free WiFi in public areas and free self parking are also provided. Additionally, free use of bicycles, wedding services, and a garden are onsite. Limited housekeeping is available.
Drop Anchor offers 18 air-conditioned accommodations with coffee/tea makers and hair dryers. Each accommodation is individually furnished and decorated. Beds feature premium bedding. Flat-screen televisions come with premium cable channels.

Bathrooms include showers and complimentary toiletries. This Islamorada hotel provides complimentary wireless Internet access. Additionally, rooms include irons/ironing boards and ceiling fans. Housekeeping is provided daily.

Recreational amenities at the hotel include an outdoor pool and complimentary bicycles.

The recreational activities listed below are available either on site or nearby; fees may apply.

This Islamorada hotel has its very own private beach. Drop Anchor features an outdoor pool and complimentary bicycles. This 3-star property offers access to a business center.

Wireless Internet access is complimentary. This Art Deco hotel also offers barbecue grills, a vending machine, and a garden. Onsite self parking is complimentary.

Drop Anchor has designated areas for smoking.

Property amenities

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Free WiFi

Parking and transportation

  • Free self parking on site
  • Onsite parking includes off-street options

Food and drink

  • Coffee and tea in common areas

Things to do

  • Free bicycle rentals
  • Kayaking
  • Motor boating
  • Outdoor pool
  • Paddleboard

Family friendly

  • Outdoor pool

Conveniences

  • Limited-hour front desk
  • Safe at front desk
  • Vending machine

Guest services

  • Housekeeping (daily)
  • Wedding services

Business services

  • Business center

Outdoors

  • Barbecue grill
  • Beach loungers
  • Beach towels
  • Beach umbrellas
  • Dock
  • Garden
  • On the waterfront
  • Picnic area
  • Pool loungers

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Stair-free path to entrance
  • Upper floors accessible by stairs only
  • Well-lit path to entrance

More

  • 2 floors
  • 6 buildings
  • Art Deco architecture
  • Banquet hall
  • Built in 1963
  • Designated smoking areas

Room amenities

Bedroom

  • Premium bedding

Bathroom

  • Free toiletries
  • Hair dryer
  • Private bathroom
  • Shower
  • Towels provided

Entertainment

  • Flat-screen TV with premium cable channels

Food and drink

  • Coffee/tea maker

More

  • Air conditioning
  • Ceiling fan
  • Connecting rooms available
  • Individual decor
  • Individual furnishings
  • Iron/ironing board

Policies

Check-in

Check-in start time: 3:00 PM; Check-in end time: 6:00 PM
Late check-in subject to availability
Minimum check-in age: 18

Check-out

Check-out before 11 AM
Contactless check-out available

Special check-in instructions

The front desk is open daily from 8:00 AM - 8:00 PM
Front desk staffed during limited hours

Access methods

Front desk (limited hours)

Pets

Pets allowed for an extra charge of USD 25 per pet, per day
Service animals are welcome, and are exempt from fees
Welcoming dogs only

Children and extra beds

Children are welcome
Rollaway/extra beds are not available
Cribs (infant beds) are not available

Property payment types

Important information

Fees

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

  • Resort fee: USD 35 per accommodation, per night
The resort fee includes:
  • Beach access
  • Beach loungers
  • Beach towels
  • Housekeeping
  • In-room coffee
  • Pool access

We have included all charges provided to us by the property.

Optional extras

  • Pet fee: USD 25 per pet, per day
  • Service animals are exempt from fees

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

You need to know

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

We should mention

This property does not have elevators
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

Property is also known as

Drop Anchor
Drop Anchor Islamorada
Drop Anchor Resort
Drop Anchor Resort Islamorada
Drop Anchor Hotel Islamorada
Drop Anchor Hotel
Drop Anchor Islamorada
Hotel Drop Anchor Islamorada
Islamorada Drop Anchor Hotel
Hotel Drop Anchor
Drop Anchor Islamorada
Drop Anchor Resort Marina
Drop Anchor Hotel Islamorada
Drop Anchor Hotel
Drop Anchor Islamorada
Drop Anchor
Hotel Drop Anchor Islamorada
Islamorada Drop Anchor Hotel
Hotel Drop Anchor
Drop Anchor Islamorada
Drop Anchor Resort Marina
Drop Anchor Hotel
Drop Anchor Islamorada
Drop Anchor Hotel Islamorada

Drop Anchor Reviews

Reviews

8.8

Excellent

Rating 10 - Excellent. 606 out of 1002 reviews
Rating 8 - Good. 244 out of 1002 reviews
Rating 6 - Okay. 77 out of 1002 reviews
Rating 4 - Poor. 37 out of 1002 reviews
Rating 2 - Terrible. 38 out of 1002 reviews

9.0/10

Cleanliness

9.2/10

Staff & service

8.6/10

Amenities

8.6/10

Property conditions & facilities

8.6/10

Eco-friendliness

Reviews

8/10 Good

Paolo

Liked: Cleanliness, property conditions & facilities
It was that keys feeling that everyone looks for
Stayed 3 nights in Jul 2025

10/10 Excellent

Travis

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This was our second stay in a month. Great location, beautiful property on the water. We love it here and cant wait to go back.
View from the dock.
Stayed 2 nights in Jul 2025

10/10 Excellent

Celso

Stayed 1 night in May 2025

8/10 Good

alejandro

Liked: Cleanliness
Disliked: Staff & service, property conditions & facilities
Stayed 2 nights in Jul 2025

6/10 Okay

Dumitru

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Jul 2025

10/10 Excellent

Virginia

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Jul 2025

8/10 Good

Jack

Liked: Cleanliness, amenities, property conditions & facilities
Clean and convenient
Stayed 2 nights in Jun 2025

4/10 Poor

Yarelys

Stayed 2 nights in Jun 2025

10/10 Excellent

John

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Parking could be better
Stayed 2 nights in Jul 2025

10/10 Excellent

Morgan

Traveled with partner, Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I loved this property. My husband and I stayed here for a quick getaway and it was perfect. Super clean and the staff was very responsive. We utilized the complimentary kayaks which was a nice touch. Will be returning
Stayed 2 nights in Jun 2025

6/10 Okay

Niurka

Traveled with partner
Disliked: Amenities
No parking and a little derty
Stayed 2 nights in Jul 2025

6/10 Okay

Cathy

Traveled with group
Liked: Cleanliness, staff & service, property conditions & facilities
Wouldn't do it again
Stayed 1 night in Jul 2025

10/10 Excellent

ellie

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Compared to other choices in the area, I thought we ended with the best deal. We booked the ocean view king room, which is very spacious with sitting area and the view of the water is right there. Nice updated bathroom and a balcony overlooking the water too. Freshly painted inside and out - well kept grounds, loved sitting under one of several tiki umbrellas to enjoy that view and watch the boats. wished we were staying longer - but next time we will.
Stayed 1 night in Jul 2025

8/10 Good

Anthony

Traveled with partner
Liked: Cleanliness, property conditions & facilities
Disliked: Amenities
The property was a throw back to old motels, charming…
Stayed 1 night in Jun 2025

8/10 Good

David

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Quaint
Stayed 1 night in Feb 2025

2/10 Terrible

Monica

Disliked: Cleanliness, property conditions & facilities, room comfort
Terrible experience. The a/c is pointing directly towards the restroom and the bed is stuck in a whole with little ventilation. The pool was extremely dirty.
Stayed 1 night in Jun 2025

10/10 Excellent

Yarelys

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
Stayed 2 nights in Jun 2025

10/10 Excellent

Virginia

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Amazing stay from pre checkin to checkout. They easily accommondated a late night check in and the room was great.
Stayed 3 nights in May 2025

10/10 Excellent

hevelin

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
The boat dock is a little rough to enter and exit especially on low tide.
Stayed 3 nights in May 2025

8/10 Good

elizabeth, miami

Stayed 3 nights in May 2025

8/10 Good

Nikki

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in May 2025

4/10 Poor

Marlene

Disliked: Cleanliness, staff & service, property conditions & facilities
I booked a Resort Queen Family Suite with Kitchen. I thought we'd have an ocean view from the photos we saw on Expedia. We asked, but they said no. The room looked clean, but during the night, a cockroach came out. We couldn't sleep after that. We waited until dawn, and my husband told the front desk, and the response was that it wasn't under their control and that it was Florida. The hotel was expensive. The pool was fine, and the surrounding areas were clean.The experience was not good.
Stayed 1 night in May 2025

8/10 Good

TIMOTHY, ORLANDO

Stayed 1 night in May 2025

10/10 Excellent

Lynette

Stayed 1 night in May 2025

8/10 Good

Verified traveler

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities

Nice ocean views

Nice location with ocean views
Stayed 1 night in Apr 2025