Drop Anchor

Waterfront hotel with a nearby private beach and an outdoor pool

Choose dates to view prices

Where to?

Dates

July 2025

August 2025

Relax in a semi-circular seating area overlooking the beach, surrounded by palm trees and a thatched umbrella.

Enjoy a serene ocean view from the comfort of your room, featuring a large window and a plush bed.

Enjoy cooking in this well-equipped kitchen with a stainless steel microwave, oven, and sink.

Relax by the pool surrounded by palm trees and lounge chairs.

Relax in a beachfront haven with a covered outdoor seating area and balcony overlooking the ocean.

Overview
Rooms
Location
Policies

Excellent

Popular amenities

Pool
Pet friendly
Housekeeping
Air conditioning
Parking included
Free WiFi

Explore the area

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

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Room options

Resort View Queen Family Suite w/ Kitchen

Exceptional

Resort view
Sleeps 6
1 Queen Bed, 1 Double Bed and 1 Queen Sofa Bed

Oceanfront King Suite w/ Beach Walkout & Kitchen

Exceptional

Ocean view
Sleeps 4
1 King Bed

Oceanfront Trailer

Very good

Sleeps 2
1 Queen Bed

Ocean View Double Queen w/ Kitchen & Private Balcony

Exceptional

Sleeps 4
2 Queen Beds

Oceanfront Queen Room

Ocean view
Sleeps 2
1 Queen Bed

Resort View ADA King Room

Sleeps 2
1 King Bed

Resort View Queen Room w/ Kitchen & Private Porch

Exceptional

Resort view
Sleeps 2
1 Queen Bed

Resort View Family Suite w/ Kitchen

Good

Resort view
Sleeps 6
2 Queen Beds and 2 Twin Beds

Ocean View Double Queen Room

Wonderful

Ocean view
Sleeps 4
2 Queen Beds

1 bedroom, premium bedding, individually decorated

Oceanfront King Suite w/ Kitchen & Private Balcony

Exceptional

Beach view
Sleeps 4
1 King Bed

Oceanfront Family Suite w/ Kitchen

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

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 a picnic area.

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

Similar properties

Relax on the beach with a tranquil ocean view and comfortable sun loungers.

On private beach
Pool
Breakfast included
Pet friendly

$199 nightly

Aug 14 - Aug 15

Total includes taxes and fees

Relax by the oceanfront pool surrounded by palm trees and lounge chairs.

On private beach
Pool
Pet friendly
Free WiFi

$330 nightly

Aug 11 - Aug 12

Total includes taxes and fees

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

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

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

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

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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 Jul 16, 2025, prices found for a 1-night stay for 2 adults at Drop Anchor on Jul 23, 2025 start from $161.25, 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 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 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.

Are there connecting rooms at Drop Anchor?

Yes, this hotel has connecting guestrooms 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 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

8.8

Excellent

9.0/10

Cleanliness

9.2/10

Staff & service

8.6/10

Amenities

8.6/10

Property conditions & facilities

8.6/10

Eco-friendliness

10/10 Excellent

John

Traveled with partner

Jul 11, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Parking could be better

Stayed 2 nights in Jul 2025

6/10 Okay

Yelitza

Traveled with family

Apr 12, 2025

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

Apr 9, 2025

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

Apr 8, 2025

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

Apr 3, 2025

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

Stayed 1 night in Apr 2025

10/10 Excellent

Dustin

Mar 31, 2025

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

Stayed 3 nights in Mar 2025

10/10 Excellent

Charlee

Traveled with group

Mar 30, 2025

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

Mar 25, 2025

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

Stayed 1 night in Mar 2025

8/10 Good

Nikki

Mar 22, 2025

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

Mar 21, 2025

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

Stayed 3 nights in Mar 2025

10/10 Excellent

Jamie

Traveled with family

Mar 20, 2025

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

Stayed 2 nights in Mar 2025

6/10 Okay

Vanessa

Mar 17, 2025

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

Mar 16, 2025

Stayed 2 nights in Mar 2025

8/10 Good

PETER

Mar 15, 2025

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

Mar 14, 2025

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

10/10 Excellent

Terri

Mar 12, 2025

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

Stayed 2 nights in Mar 2025

8/10 Good

Cynthia

Mar 11, 2025

Liked: Cleanliness, staff & service

Stayed 1 night in Jan 2025

10/10 Excellent

Deney

Mar 10, 2025

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

Hood

Stayed 1 night in Mar 2025

10/10 Excellent

Nicole

Traveled with group, Traveled with partner

Mar 8, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Great place! We pretymuch had the placf to ourselves so it was really relaxing! Beautiful property as well and the pool was like bathwater!

Stayed 4 nights in Feb 2025

10/10 Excellent

Ivis

Mar 6, 2025

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

Stayed 1 night in Mar 2025

10/10 Excellent

stephanie ann

Mar 3, 2025

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

Stayed 4 nights in Feb 2025

4/10 Poor

Adinarayan

Traveled with family

Feb 27, 2025

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

Feb 25, 2025

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