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Drop Anchor

3.0 star property
Waterfront 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 | Premium bedding, individually decorated, individually furnished
Oceanfront King Suite w/ Kitchen & Private Balcony | Premium bedding, individually decorated, individually furnished
Property grounds
Oceanfront King Suite w/ Kitchen & Private Balcony | Water view

Reviews

8.8 out of 10
Excellent

Popular amenities

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

Explore the area

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
  • Founders Park
    ‪4 min drive‬

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Room options

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

  • 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 | Premium bedding, individually decorated, individually furnished

Oceanfront King Suite w/ Beach Walkout & Kitchen

  • Ocean view
  • Sleeps 4
  • 1 King Bed

View all photos for Oceanfront Trailer

Oceanfront Trailer | Premium bedding, individually decorated, individually furnished

Oceanfront Trailer

  • 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 | Premium bedding, individually decorated, individually furnished

Ocean View Double Queen w/ Kitchen & Private Balcony

  • Sleeps 4
  • 2 Queen Beds

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 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 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

  • 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

  • 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 | Premium bedding, individually decorated, individually furnished

Ocean View Double Queen Room

  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

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

Premium bedding, individually decorated, individually furnished

Oceanfront King Suite w/ Kitchen & Private Balcony

  • Beach view
  • Sleeps 4
  • 1 King Bed

View all photos for Oceanfront Family Suite w/ Kitchen

Flat-screen TV

Oceanfront Family Suite w/ Kitchen

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

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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 - 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

  • ‪Lorelei Restaurant & Cabana Bar - ‬5 min drive
  • ‪Hog Heaven - ‬7 min walk
  • ‪Wahoo's Bar & Grill - ‬2 min drive
  • ‪Whale Harbor Restaurant Marina - ‬2 min drive
  • ‪Islamorada Beer Company - ‬4 min drive

About this property

Drop Anchor

Waterfront 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 wedding services.
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.

Languages

English

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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

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
  • 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.
  • 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.

How much does it cost to stay at Drop Anchor?

As of May 29, 2025, prices found for a 1-night stay for 2 adults at Drop Anchor on Jun 8, 2025 start from $230.0, excluding 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 parking available on site 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 a good place to stay 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, 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 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.

Are there rooms with balconies that I can book 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.

Drop Anchor Reviews

Reviews

8.8

Excellent

Rating 10 - Excellent. 617 out of 1000 reviews
Rating 8 - Good. 234 out of 1000 reviews
Rating 6 - Okay. 75 out of 1000 reviews
Rating 4 - Poor. 37 out of 1000 reviews
Rating 2 - Terrible. 37 out of 1000 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

4/10 Poor

Adinarayan

Traveled with family
Liked: Cleanliness, property conditions & facilities, room comfort
Disliked: Staff & service
Stayed 5 nights in Dec 2024

2/10 Terrible

Amanda

Traveled with family and small children, Traveled with group, Traveled with partner, Traveled with pets, Traveled with family
Air conditioners are fully of mold, blowing directly into your face in bed. I refused to let me family stay there. Checked out as fast as I checked in. Still have not received a refund from Expedia or the property for the resort and pet fee.
Stayed 3 nights in Feb 2025

10/10 Excellent

Yadira

Stayed 1 night in Feb 2025

8/10 Good

Timothy

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

8/10 Good

Steven

Liked: Cleanliness, staff & service, room comfort

Retro trailer

We stayed in the single wide retro trailer. Definitely added a unique experience. Old trailer in much need of updates but the views, property, and staff make up for what the trailer lacks.
Stayed 4 nights in Feb 2025

10/10 Excellent

Angela

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in Feb 2025

10/10 Excellent

Judith

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was very nice.
Stayed 2 nights in Jan 2025

10/10 Excellent

Tom

Liked: Cleanliness, staff & service, property conditions & facilities
Great staff. Very clean and wonderful waterfront setting.
Stayed 2 nights in Feb 2025

6/10 Okay

Chris

Traveled with partner
Disliked: Cleanliness, staff & service, property conditions & facilities
I felt like an employee having to get fresh towels, cleaning the room and bathroom, delivering dirty towels, asking and finding staff for coffee packets, and toiletries. Noisy room with very early traffic noise, and an air conditioning unit in the bedroom closet that was absolutely filthy with dust and as loud as the traffic. No staff on the premises in the evening. If you needed help you had to call. No phone in the room, so cell phone needed to be charged for any emergency.
Stayed 7 nights in Jan 2025

2/10 Terrible

Delisa

Disliked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in Jan 2025

10/10 Excellent

Sarah

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

Awesome spot! Beautiful location!

Wonderful ocean front spot! Clean, comfortable bed and linens, great balcony and view, friendly staff! Loved the paddle boards and heated pool. Grounds have hammocks, games and loungers on the beach. Incredible sunrise and sunset, good location and easy to access. Can’t wait to stay again!
Stayed 1 night in Feb 2025

8/10 Good

Kurt

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
No hot water. Otherwise all nice. No beach. No fishing pier. Great view though. Nice pool. Not crowed.
Stayed 6 nights in Feb 2025

6/10 Okay

Dale billing

Stayed 1 night in Feb 2025

6/10 Okay

Verified traveler

Disliked: Property conditions & facilities

Not worth it

Not what I expected. Expensive for a run-down motel pretending to be a three-star hotel with “resort” amenities. Everything felt like it was done with minimal effort. Staff was helpful enough but definitely, again, with minimal effort. Do not recommend.
Stayed 3 nights in Jan 2025

10/10 Excellent

Scott

Liked: Cleanliness, staff & service, property conditions & facilities
Small hotel, nice and quiet staff was great
Stayed 1 night in Jan 2025

6/10 Okay

pedro. Jr, Indianapolis

Stayed 5 nights in Jan 2025

2/10 Terrible

Michael

Disliked: Staff & service, property conditions & facilities, room comfort

Resort fee my @ss

Stayed 1 night in Jan 2025

8/10 Good

Sean

Liked: Cleanliness, property conditions & facilities, room comfort
Stayed 1 night in Jan 2025

2/10 Terrible

Evelyn, Lake Ariel

Disliked: Cleanliness, property conditions & facilities
Stayed 3 nights in Jan 2025

10/10 Excellent

John

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Good value for the money. Enjoyed using the kayaks and paddle boards. Friendly staff. Very good location on the water.
Stayed 2 nights in Jan 2025

10/10 Excellent

Howard

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very clean, friendly resort. Very personal attention. The room was terrific. Loved that we had an ocean view balcony and a kitchen and the beds were very comfortable. The staff was SO friendly and helpful. Did not like that bikes had to be returned by 5pm Apparently a drunk guest from some time ago got into an accident on bicycle. We did not have a car and that limited our early evening access to free and easy transport to dinner. Also... though it has a marina for boaters, the resort has no beach. It does have a great pool and free kayaks which we made great use of, but we came to the Keys for the beach and the clear water. We had to take a two mile bike ride (which was nice exercise) to a small local beach and a 45 minute Uber (expensive!) to a really large beach.
Stayed 5 nights in Jan 2025

10/10 Excellent

hilary

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

6/10 Okay

Michelle

Liked: Property conditions & facilities
Disliked: Room comfort

Pretty

Property was pretty but couch was full of sand and uncomfortable chairs were uncomfortable as well. No security at night
Stayed 3 nights in Jan 2025

10/10 Excellent

Tony

Stayed 4 nights in Dec 2024

10/10 Excellent

Maria Fernanda

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

Perfect boutique style hotel

This hotel is a real gem. Location is ideal, right on the water with a pool and very comfortable spots to take in the breathtaking views of the ocean. You truly feel like you are off the grid at this very tranquil spot. The staff is extremely kind, and they even let you borrow kayaks to explore.
Stayed 1 night in Dec 2024

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