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Drop Anchor

3.0 star property
3-star Art Deco hotel with private beach

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Photo gallery for Drop Anchor

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

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Pool
  • Pet friendly
  • Housekeeping
  • Air conditioning
  • Parking included
  • Free WiFi

Explore the area

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

Room options

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

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 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 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 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 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 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 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 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 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
(18 reviews)
  • 1 bedroom
  • Beach 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

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About the neighborhood

Islamorada

Oceanside stay.Stay at this Islamorada hotel and you'll be within half a mile (1 km) of Windley Key Fossil Reef Geological State Park and 2 miles (3 km) of Rain Barrel Village. Founders Park and Islamorada County Park are also within 3 miles (5 km).

What's nearby

  • Windley Key Fossil Reef Geological State Park - 6 min walk - 0.4 miles
  • Theater of the Sea - 9 min walk - 0.5 miles
  • Founders Park - 4 min drive - 2.5 miles
  • Islamorada County Park - 4 min drive - 2.7 miles
  • Florida Keys Brewing Co. - 7 min drive - 4.6 miles

Getting around

  • Miami Intl. Airport (MIA) - 89 min drive

Restaurants

  • ‪Tiki Bar - ‬18 min walk
  • ‪Lorelei Restaurant & Cabana Bar - ‬5 min drive
  • ‪Wendy's - ‬4 min drive
  • ‪Starbucks - ‬15 min walk
  • ‪The Trading Post - ‬5 min drive

About this property

Drop Anchor

3-star Art Deco hotel with private beach
A private beach is featured. Drop Anchor offers its guests an outdoor pool and complimentary bicycles. You'll find a business center on site.

WiFi is free in public spaces. Barbecue grills, a vending machine, and a garden are also featured at Drop Anchor. Free self parking is available.

Smoking is allowed in designated areas at this 3-star Islamorada hotel.

  • 18 guestrooms or units
  • 2 levels
  • 6 buildings
  • Built in 1963
  • Beach lounge chairs
  • Towels for the beach
  • Umbrellas for the beach
  • Poolside lounge chairs
  • Business facilities
  • Coffee in lobby
  • Front desk (limited hours)
  • Front-desk safe
  • Wedding services available
  • Garden
  • BBQ grill(s)
  • Outdoor picnic space
  • Smoking in designated areas
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.

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  • Pool
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Property amenities

Family friendly

  • Outdoor pool

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

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

Room amenities

Entertainment

  • Flat-screen TV with premium cable channels

Bedroom

  • Premium bedding

Bathroom

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

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: USD 25 per pet, per day
  • Only dogs are allowed
  • Service animals are exempt from fees

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

Guests will be asked to pay the following charges at the property:

  • 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've listed all charges provided to us by the property.

Optional extras

The fees and deposits listed below will be charged at the time of service, check-in, or check-out.

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

This may not be a comprehensive list. Fees and deposits are subject to change and might not include tax.

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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. 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. This property accepts Visa, Mastercard, American Express, Discover, debit cards, and cash. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, and a smoke detector in each accommodation.

We should mention

  • Pool access available from 7:30 AM to 6:30 PM.
  • Connecting/adjoining rooms are subject to availability and can be requested by contacting the property at the number on your booking confirmation.

Property is also known as

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

Frequently asked questions

How close is Drop Anchor to the airport?

Drop Anchor is 76.1 mi (89-min drive) away from the Miami Intl. Airport (MIA) airport, the closest popular airport to the property.

Does Drop Anchor have an airport shuttle?

Airport shuttle services are not available at Drop Anchor.

How close is Drop Anchor to the beach?

This hotel is 10.5 mi (14-min drive) from Sunset Drive Beach and 11.5 mi (16-min drive) from Anne's Beach. Don't forget your sunscreen!

Does Drop Anchor offer free breakfast?

Drop Anchor does not offer free breakfast.

Is there a casino at Drop Anchor?

No, there is no casino at this hotel.

What time is check-in at Drop Anchor?

Check-in start time: 3:00 PM; Check-in end time: 6:00 PM.

Is there free parking at Drop Anchor?

This hotel offers free self parking.

Does Drop Anchor have a pool?

Drop Anchor features an outdoor pool. Guests can enjoy pool access from 7:30 AM to 6:30 PM.

Does Drop Anchor have a spa?

There are no spa services available at this hotel.

How close is Drop Anchor to downtown Islamorada?

Drop Anchor is 2.6 mi away from Islamorada.

Drop Anchor Reviews

Reviews

8.8

Excellent

Rating 10 - Excellent. 604 out of 1002 reviews
Rating 8 - Good. 247 out of 1002 reviews
Rating 6 - Okay. 76 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

8.4/10

Property conditions & facilities

8.6/10

Eco-friendliness

Reviews

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

10/10 Excellent

Michael

Traveled with pets, Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Always friendly and helpful staff. Private beach area is a major plus.
Stayed 1 night in May 2025

8/10 Good

Blake

Liked: Cleanliness, staff & service, amenities
Air conditioner was inadequate. Probably why they had box fans in the rooms.
Stayed 1 night in May 2025

10/10 Excellent

Kim

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Good price and clean

Great place. I enjoyed the beach area and how we could walk to a few good dive bars w live music. Very clean and included a kitchen snd good size shower. Only complaint would be the blinds did not close all the way and parking lot coyld see in at night.
Stayed 1 night in Apr 2025

10/10 Excellent

Niurka

Stayed 1 night in Apr 2025

6/10 Okay

Yelitza

Traveled with family
Disliked: Cleanliness, property conditions & facilities, room comfort

Overpriced and basic

Really over priced. The rooms were tiny and bathroom was even more so. Bed the step out of the door was not very safe. My daughter fell down and twisted both ankles.
Stayed 2 nights in Jan 2025

8/10 Good

Morayma P.

Traveled with partner, Traveled with pets
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Really cute and quiet, rooms were clean and the premises are nice. It is not a beach location although is water front.
Stayed 2 nights in Apr 2025

2/10 Terrible

Zachary

Liked: Cleanliness
Internet Bad, 1 bar w/ 2 min., walking outside, Guest above noise every time walked on floor, Sea Grape bush banged back window & elevated A/c compressor all night, #4 Room, 2 queen beds all most furthest unit from highway still noisy, Room & bathroom very clean, w/ clean towels, Nicely decorated w/ good paint, Bathroom very small, 1 person, No space for shelf under mirror, Small home depo type vanity, no space even for small tolitry bag, aprx. 4" ledge around, Top of toilet inches away for placement, Shower, w/ shower curtain, No bar for wash cloth/bathing suit, razor, shampoo etc., Wall mounted hair dryer, Ok shampoo, soap, etc. No door on closet visible across from beds, w/. ironing board and iron, hangers rattled from ceiling fan, No phone, front desk only 8AM-6PM, no one else on property, only phone # to call before 8AM & after 6PM, No Security, Nice Pool, no pool/ beach towels, lots & lots of Sand around complex, well keep, beautiful unobstructed view of Atlantic Ocean, no entries to ocean, rocks below, No dinning/ bar. No vending machine, Ice Machine, $37.63 per day "Resort Fee", Room size OK, Good mattress, w/ clean sheets & 4 pillows on beds, Small empty Refrigerator, small micro, & Coffee maker w/ Coffee Packets & uninsulated Ice bucket, Ice Machine, Electric for switches by door in pertruding channel, Old small TV, w/dark picture. OK remodel for 30 year building, Entire Complex very clean. Better choices in Islamorada in same price range. Zachary Bentley
Stayed 1 night in Apr 2025

8/10 Good

Richard

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

10/10 Excellent

Dustin

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 3 nights in Mar 2025

10/10 Excellent

Charlee

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
On the third night of our 3-night stay and wishing we could stay forever! We splurged on a direct ocean front room and it is worth every penny. This place is by no means fancy but it is old Florida at its finest: cozy, chill, unpretentious. Add in a heated pool and a drip (not pod!!) coffeemaker and all boxes have been checked. As with most of the upper keys there is no true walkout sandy beach but you can use the kayak ramp to get in an ocean swim. Note mucky bottom so mann up or wear swim shoes! Received lovely service from Daniel at front desk and housekeeper could not have been kinder. DROP ANCHOR IS A GEM
Stayed 2 nights in Mar 2025

10/10 Excellent

Douglas

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

8/10 Good

Nikki

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Cute spot.

The front desk guy was so nice, really just a very friendly guy and I appreciate that. The room was a bit hot -the ac wasn’t working right, it was blowing but not cold air unfortunately. The room itself and bathroom were super cute, the bed and pillows were very comfy, it was nice and quiet and I rested very well other than being a little hot.
Stayed 1 night in Mar 2025

10/10 Excellent

Jennifer

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 3 nights in Mar 2025

10/10 Excellent

Jamie

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Mar 2025

6/10 Okay

Vanessa

Disliked: Staff & service, property conditions & facilities
My boyfriend and I stayed here one night on Saturday, March 8th. The property was okay...but not anywhere near worth $400 for the night..even on a Saturday during spring break. Biggest issue was the old TV in the room - the screen died after 15mins of use. It came back on after 5minutes, and then died again promptly after that.. I let the office know, and the next day they called me saying "the TV is perfectly fine." So, they don't believe their guests when they say something is wrong. No refund either. So if you stay in Room 16, beware that the old TV dies after 15 minutes of being on.
Stayed 1 night in Mar 2025

2/10 Terrible

Armando

Stayed 2 nights in Mar 2025

8/10 Good

PETER

Liked: Cleanliness, staff & service, property conditions & facilities
Good location on the old highway, water pressure could use improvement.
Stayed 7 nights in Mar 2025

8/10 Good

Verified traveler

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Disappointing. Not as pictured. It’s not really a beach and you can’t get in the water from property. It’s on a sea wall. Very clean. Bathroom was tiny and futon/couch very uncomfortable as a couch.
Stayed 1 night in Mar 2025