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Drop Anchor

Property class: 3

Choose dates to view prices

Photo gallery for Drop Anchor

A beachside patio with white furniture, palm trees, and a thatched umbrella.
A deck with white lounge chairs and a bench, overlooking a beach with palm trees and a thatched roof structure.
A pool area with lounge chairs and a sign indicating a drop-off zone.
A wooden boardwalk leading to a building with a brick wall and a white roof.
A beach with palm trees, a thatched umbrella, and lounge chairs.

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services

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, Hog Heaven
    ‪7 min walk‬
  • Place, Theater of the Sea
    ‪9 min walk‬

Room options

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

A hotel room with two beds, a ceiling fan, and a view of the outdoors.

Ocean View Double Queen w/ Kitchen & Private Balcony

9.8 out of 10
Exceptional
(7 reviews)
  • Sleeps 4
  • 2 Queen Beds

View all photos for Oceanfront Trailer

A neatly made bed with white and pink linens, a wooden headboard, and a mirror on the wall.

Oceanfront Trailer

8.4 out of 10
Very good
(9 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for Resort View ADA King Room

A bedroom with a bed, a desk with a microwave, a chair, and artwork on the walls.

Resort View ADA King Room

  • Garden view
  • Sleeps 2
  • 1 King Bed

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

A hotel room with a bed, a blue sofa, a small table, a ceiling fan, a white nightstand, and a bathroom visible through an open door.

Oceanfront King Suite w/ Kitchen & Private Balcony

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

View all photos for Ocean View Double Queen Room

A room with two beds, teal walls, and artwork.

Ocean View Double Queen Room

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

View all photos for Resort View Family Suite w/ Kitchen

A modern kitchen with white cabinetry, a stainless steel oven, a microwave, and a white countertop.

Resort View Family Suite w/ Kitchen

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

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

A bedroom with a bed, bedside tables, a desk, and a chair.

Resort View Queen Room w/ Kitchen & Private Porch

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

View all photos for Oceanfront Queen Room

A bedroom with a bed, a teal door, a white wall, and a window.

Oceanfront Queen Room

  • Ocean view
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

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

A bedroom with a large bed, a nightstand with a lamp, a painting of a starfish on the wall, and a window with blinds.

Oceanfront King Suite w/ Beach Walkout & Kitchen

9.0 out of 10
Wonderful
(16 reviews)
  • Ocean view
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed

View all photos for Oceanfront Family Suite w/ Kitchen

A dining area with a green table and white chairs, a ceiling fan, a kitchen in the background, and a colorful painting on the wall.

Oceanfront Family Suite w/ Kitchen

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

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

A hotel room with a bed, a small round table, and a white door leading to a bathroom.

Resort View Queen Family Suite w/ Kitchen

10.0 out of 10
Exceptional
(3 reviews)
  • Resort view
  • 2 bedrooms
  • 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 a 15-minute stroll of Hog Heaven. 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
  • Hog Heaven - 7 min walk - 0.4 miles
  • Theater of the Sea - 9 min walk - 0.5 miles
  • Bud n' Mary's Dive Center - 8 min drive - 6.9 miles
  • Anne's Beach - 18 min drive - 14.9 miles

Getting around

  • Miami Intl. Airport (MIA) - 98 min drive

Restaurants

  • ‪Hog Heaven - ‬7 min walk
  • ‪Lorelei Restaurant & Cabana Bar - ‬5 min drive
  • ‪Wahoo's Bar & Grill - ‬2 min drive
  • ‪Wendy's - ‬4 min drive
  • ‪Starbucks - ‬15 min walk

About this property

Drop Anchor

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.

Similar properties

A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.
Fisher Inn Resort & Marina
Islamorada
  • On private beach
  • Pool
  • Breakfast included
  • Pet friendly
8.2 out of 10, Very good, 1,004 reviews
$188 nightly
The price is $212
Oct 18 - Oct 19
Total with taxes and fees
Fisher Inn Resort & Marina

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 - 6:00 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 28 per pet, per day
  • Dogs only
  • Service animals exempt from fees

Property payment types

  • American Express
  • Discover
  • Mastercard
  • Visa

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 28 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 in Islamorada is within a 10-minute walk of Windley Key Fossil Reef Geological State Park and Hog Heaven. You'll also find Founders Park and Florida Keys Brewing Co. within a short drive.

How much does it cost to stay at Drop Anchor?

As of Oct 17, 2026, prices found for a 1-night stay for 2 adults at Drop Anchor on Oct 18, 2026 start from $174, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is there parking available 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.

What amenities will couples enjoy at Drop Anchor?

Amenities that appeal to couples at this waterfront hotel include premium bedding as well as an outdoor pool and wedding services.

Are there hot tubs at Drop Anchor?

No, there isn't a spa tub at this hotel.

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 28 per pet, per day.

Are there connecting rooms at Drop Anchor?

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

Are there rooms with balconies at Drop Anchor?

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

Does Drop Anchor offer wedding services?

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

Drop Anchor Reviews

Reviews

8.6

Excellent

Rating 10 - Excellent. 606 out of 1000 reviews
Rating 8 - Good. 216 out of 1000 reviews
Rating 6 - Okay. 81 out of 1000 reviews
Rating 4 - Poor. 42 out of 1000 reviews
Rating 2 - Terrible. 55 out of 1000 reviews

9.0/10

Cleanliness

9.0/10

Staff & service

8.4/10

Amenities

8.4/10

Property conditions & facilities

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Fun place to stay - clean rooms , well maintained property with pool and sitting areas over looking the water.
Stayed 1 night in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
A very cozy, small hotel in a quiet location by the sea. Perfect for a holiday with children. Highly recommended!
Stayed 1 night in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 1 night in Jun 2026
Verified review

10/10 Excellent

Quiet, great staff, plenty to do.
Stayed 4 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 3 nights in Jun 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We could walk to hog heaven They had complementary bikes, paddle boards, and kayaks.
Stayed 1 night in Jun 2026
Verified review

8/10 Good

Liked: Staff & service, amenities, property conditions & facilities
Great for a two night stay in Islamorada!
Stayed 2 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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 🙏
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great room. Staff was very helpful and kind. Enjoyed the beachfront
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Staff & service, amenities, property conditions & facilities
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!
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, property conditions & facilities
Loved this place
Stayed 2 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location! Super cute every room is close to the water. Would stay here again for sure.
Stayed 3 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service
Excellent
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities
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 .
Our view
From the pool
Stayed 2 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, property conditions & facilities
Clean room, beautiful view and loved being able to walk out to the beach.
Stayed 1 night in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities
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.
Stayed 1 night in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
View from Room 16
Wonderful place to enjoy the night sky
Stayed 4 nights in Mar 2026
Verified review

10/10 Excellent

The staff was personable, great location, having the bicycles and kayaks were a great touch
Stayed 3 nights in Dec 2025
Verified review

6/10 Okay

Liked: Cleanliness
Disliked: Amenities
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.
Stayed 7 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful … clean… great location!
Stayed 1 night in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities
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 !
Stayed 1 night in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities
Great staff
Stayed 2 nights in Feb 2026
Verified review

6/10 Okay

Disliked: Cleanliness, staff & service, property conditions & facilities
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
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities
The View was amazing!
Stayed 1 night in Feb 2026