Drop Anchor

Waterfront hotel with a nearby private beach and an outdoor pool

Choose dates to view prices

Where to?

Dates

October 2025

November 2025

Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view

Oceanfront King Suite w/ Kitchen & Private Balcony | 1 bedroom, premium bedding, individually decorated

Oceanfront King Suite w/ Kitchen & Private Balcony | Terrace/patio

Oceanfront King Suite w/ Kitchen & Private Balcony | Water view

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

Place, Windley Key Fossil Reef Geological State Park
‪6 min walk‬
Place, Theater of the Sea
‪9 min walk‬
Place, Islamorada County Park
‪4 min drive‬

Room options

Ocean View Double Queen w/ Kitchen & Private Balcony

Exceptional

Sleeps 4
2 Queen Beds

Oceanfront Trailer

Very good

1 bedroom
Sleeps 2
1 Queen Bed

Resort View ADA King Room

Sleeps 2
1 King Bed

1 bedroom, premium bedding, individually decorated

Oceanfront King Suite w/ Kitchen & Private Balcony

Exceptional

1 bedroom
Beach view
Sleeps 4
1 King Bed

Ocean View Double Queen Room

Excellent

Ocean view
Sleeps 4
2 Queen Beds

Resort View Family Suite w/ Kitchen

Good

1 bedroom
Resort view
Sleeps 6
2 Queen Beds and 2 Twin Beds

Resort View Queen Room w/ Kitchen & Private Porch

Exceptional

Resort view
Sleeps 2
1 Queen Bed

Oceanfront Queen Room

Ocean view
Sleeps 2
1 Queen Bed

Oceanfront King Suite w/ Beach Walkout & Kitchen

Exceptional

1 bedroom
Ocean view
Sleeps 4
1 King Bed

Oceanfront Family Suite w/ Kitchen

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

Resort View Queen Family Suite w/ Kitchen

Exceptional

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

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

‪Tiki Bar - ‬18 min walk
‪Hog Heaven - ‬7 min walk
‪Starbucks - ‬15 min walk
‪Whale Harbor Buffet - ‬2 min drive
‪Wahoo's Bar & Grill - ‬2 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.

Similar properties

Private beach, white sand, sun loungers, beach towels

On private beach
Pool
Breakfast included
Pet friendly

$182 nightly

Oct 8 - Oct 9

Total with 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

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 Oct 4, 2025, prices found for a 1-night stay for 2 adults at Drop Anchor on Oct 6, 2025 start from $99.19, 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.

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 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.

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

8/10 Good

David

Traveled with family

Aug 1, 2025

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

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

10/10 Excellent

ellie

Traveled with partner

Jul 3, 2025

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

Compared to other choices in the area, I thought we ended with the best deal. We booked the ocean view king room, which is very spacious with sitting area and the view of the water is right there. Nice updated bathroom and a balcony overlooking the water too. Freshly painted inside and out - well kept grounds, loved sitting under one of several tiki umbrellas to enjoy that view and watch the boats. wished we were staying longer - but next time we will.

Stayed 1 night in Jul 2025

8/10 Good

Anthony

Traveled with partner

Jun 19, 2025

Liked: Cleanliness, property conditions & facilities

Disliked: Amenities

The property was a throw back to old motels, charming…

Stayed 1 night in Jun 2025

8/10 Good

David

Traveled with family

Jun 19, 2025

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

Quaint

Stayed 1 night in Feb 2025

2/10 Terrible

Monica

Jun 18, 2025

Disliked: Cleanliness, property conditions & facilities, room comfort

Terrible experience. The a/c is pointing directly towards the restroom and the bed is stuck in a whole with little ventilation. The pool was extremely dirty.

Stayed 1 night in Jun 2025

10/10 Excellent

Yarelys

Traveled with family

Jun 16, 2025

Liked: Cleanliness, amenities, property conditions & facilities

Stayed 2 nights in Jun 2025

10/10 Excellent

Virginia

Jun 10, 2025

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

Amazing stay from pre checkin to checkout. They easily accommondated a late night check in and the room was great.

Stayed 3 nights in May 2025

10/10 Excellent

hevelin

Traveled with family

May 26, 2025

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

May 26, 2025

Stayed 3 nights in May 2025

8/10 Good

Nikki

Traveled with family

May 23, 2025

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

Stayed 1 night in May 2025

4/10 Poor

Marlene

May 18, 2025

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

May 15, 2025

Stayed 1 night in May 2025

10/10 Excellent

Lynette

May 6, 2025

Stayed 1 night in May 2025

8/10 Good

Verified traveler

Traveled with family

May 5, 2025

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

May 4, 2025

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

May 4, 2025

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

Apr 23, 2025

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

Apr 22, 2025

Stayed 1 night in Apr 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