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Drop Anchor

3.0 star property
Art Deco hotel with a nearby private beach and an outdoor pool

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Photo gallery for Drop Anchor

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

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
  • Place, Windley Key Fossil Reef Geological State Park
    ‪6 min walk‬
  • Place, Theater of the Sea
    ‪9 min walk‬
  • Place, Bud n' Mary's Dive Center
    ‪14 min drive‬

Room options

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

Ocean View Double Queen w/ Kitchen & Private Balcony | Premium bedding, individually decorated, individually furnished

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 | Premium bedding, individually decorated, individually furnished

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 | Premium bedding, individually decorated, individually furnished

Resort View ADA King Room

  • Sleeps 2
  • 1 King Bed

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

Premium bedding, individually decorated, individually furnished

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 | Premium bedding, individually decorated, individually furnished

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 | Premium bedding, individually decorated, individually furnished

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 | Premium bedding, individually decorated, individually furnished

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 | Premium bedding, individually decorated, individually furnished

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 | Premium bedding, individually decorated, individually furnished

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

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About the neighborhood

Islamorada

Located within a 5-minute walk of Windley Key Fossil Reef Geological State Park, Drop Anchor is within 2 miles (3 km) of Rain Barrel Village. This 18-room, 3-star hotel has conveniences like a private beach, an outdoor pool, and free in-room WiFi.

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 - 5 min drive - 2.3 miles
  • Bud n' Mary's Dive Center - 14 min drive - 6.8 miles
  • Anne's Beach - 28 min drive - 14.4 miles

Getting around

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

Restaurants

  • ‪Tiki Bar - ‬18 min walk
  • ‪Hog Heaven - ‬7 min walk
  • ‪Wahoo's Bar & Grill - ‬2 min drive
  • ‪Starbucks - ‬15 min walk
  • ‪Marathon Bagel Co - ‬3 min drive

About this property

Drop Anchor

Art Deco hotel with a nearby private beach and an outdoor pool
Guests of Drop Anchor enjoy an outdoor pool, free WiFi in public areas, and a business center. If you drive, put free parking to good use. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Additional amenities include coffee/tea in a common area, free use of bicycles, and a garden.
Guests can expect to find free WiFi and flat-screen TVs with cable channels. Beds sport premium bedding and bathrooms offer hair dryers and free toiletries. Other standard amenities include coffee makers, ceiling fans, and ironing boards. Limited housekeeping is available.
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.

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Dec 1 - Dec 2
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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
Information provided by the property may be translated using automated translation tools

Access methods

Front desk (limited hours)

Pets

  • This property welcomes pets for USD 25 per pet, per day
  • Dogs only
  • Service animals exempt from fees

Property payment types

Important information

Fees

You'll be asked to pay these 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

These are all of the charges provided to us by the property.

Optional extras

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

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

This list may not be comprehensive. Fees and deposits might 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
  • Check-in: 3:00 PM—-6:00 PM
  • Check-out: 11 AM
  • Minimum check-in age: 18
The front desk is available during limited hours. Driving? This property offers free parking.

We should mention

Details about charges, deposits, or other important information:

  • 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.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • This property accepts credit cards, debit cards, and cash.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, and a smoke detector.

Additional information about polices, regulations, and more:

  • Pool access available from 7:30 AM to 6:30 PM.
  • Connecting or adjoining rooms can be requested, but all rooms are subject to availability. Contact the property using the phone number on your booking confirmation.
  • There are no elevators.
  • No cribs or infant beds are available.
  • No rollaway or extra beds are available.

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

Frequently asked questions

What's there to do near Drop Anchor?

This hotel is located in Islamorada within a short 4-minute walk of Windley Key Fossil Reef Geological State Park. You'll also find Founders Park and Islamorada County Park within a short drive.

Will I be able to park at Drop Anchor?

Yes, self parking is offered for free at the hotel.

Does Drop Anchor have a casino?

No, Drop Anchor doesn't have a casino.

Is there an indoor pool at Drop Anchor?

No, this hotel doesn't have an indoor pool; however, there is an outdoor pool. Guests have pool access between 7:30 AM and 6:30 PM.

Is Drop Anchor good for couples?

Amenities that appeal to couples at this waterfront hotel include premium bedding as well as an outdoor pool and a nearby private beach.

Does Drop Anchor have a hot tub?

No, this hotel doesn't have a spa tub.

Does Drop Anchor have a restaurant that serves breakfast?

No, Drop Anchor doesn't have a restaurant that serves breakfast.

Does Drop Anchor allow pets to stay free of charge?

Although they can't stay for free, dogs are welcome at Drop Anchor for a fee of USD 25 per pet, per day.

Does Drop Anchor have connecting rooms?

Yes, this hotel has connecting guestrooms you can book for your group event or vacation.

Can I book a room with a balcony at Drop Anchor?

Yes, some guestrooms at this hotel offer either a balcony or a deck where guests can enjoy ocean or garden views.

Does Drop Anchor offer wedding services?

There are wedding services available at Drop Anchor if that's in your vacation plans.

Reviews

Drop Anchor Reviews

8.8

Excellent

9.0/10

Cleanliness

9.2/10

Staff & service

8.6/10

Amenities

8.4/10

Property conditions & facilities

8.6/10

Eco-friendliness
Rating 10 - Excellent. 605 out of 1004 reviews
Rating 8 - Good. 245 out of 1004 reviews
Rating 6 - Okay. 78 out of 1004 reviews
Rating 4 - Poor. 37 out of 1004 reviews
Rating 2 - Terrible. 39 out of 1004 reviews

Reviews

8/10 Good

John

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful property and the staff was amazing.
Stayed 1 night in Aug 2025

2/10 Terrible

William

Stayed 1 night in Aug 2025

10/10 Excellent

Jennifer

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

10/10 Excellent

Anisley

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The hotel is very quiet and that are we need for relax
Stayed 2 nights in Aug 2025

10/10 Excellent

STEPHEN

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 1 night in Aug 2025

8/10 Good

Anindya, Miramar

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Aug 2025

10/10 Excellent

Lisa

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

10/10 Excellent

Ninoslav

Traveled with pets, Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful and quiet place!
Stayed 1 night in Aug 2025

8/10 Good

Raul

Traveled with family and small children, Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The property was well maintained. The staff was excellent.
Stayed 3 nights in Aug 2025

10/10 Excellent

Jose

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

8/10 Good

Susan

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

8/10 Good

Kendra

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

10/10 Excellent

Jodie

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

10/10 Excellent

Silvia

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Love it!!
Stayed 1 night in Aug 2025

8/10 Good

ERIKA

Liked: Cleanliness
Stayed 1 night in Aug 2025

8/10 Good

David

Traveled with family
Liked: Staff & service, property conditions & facilities
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
Stayed 1 night in Jul 2025

8/10 Good

GALE

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

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.
Stayed 2 nights in Jul 2025

8/10 Good

Wendy Hanks

Stayed 5 nights in Jul 2025

4/10 Poor

Tanya

Traveled with family
Disliked: Staff & service, property conditions & facilities
The motel is quite old and run down. The king suite with walk out to the beach; isn’t really a walk out to the beach at all - instead you are facing the boat ramp. The futon is so uncomfortable that it shouldn’t be considered an option for an extra place to sleep. My kids couldn’t sleep all night which was also due to the neighboring room being very loud late into the night.
Stayed 1 night in Jul 2025

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

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