Drop Anchor in Islamorada | Best Rates & Deals on Orbitz

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Waterfront hotel with a nearby private beach and an outdoor pool

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Where to?

Dates

May 2025

June 2025

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

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

Overview
Rooms
Location
Policies

Excellent

Popular amenities

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
‪4 min walk‬
Theater of the Sea
‪7 min walk‬
Founders Park
‪3 min drive‬

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Room options

Resort View Queen Family Suite w/ Kitchen

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

Oceanfront King Suite w/ Beach Walkout & Kitchen

Ocean view
Sleeps 4
1 King Bed

Oceanfront Trailer

Sleeps 2
1 Queen Bed

Ocean View Double Queen w/ Kitchen & Private Balcony

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

Resort view
Sleeps 2
1 Queen Bed

Resort View Family Suite w/ Kitchen

Resort view
Sleeps 6
2 Queen Beds and 2 Twin Beds

Ocean View Double Queen Room

Ocean view
Sleeps 4
2 Queen Beds

Oceanfront King Suite w/ Kitchen & Private Balcony

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 - 4 min walk - 0.3 miles
Theater of the Sea - 7 min walk - 0.4 miles
Islamorada County Park - 3 min drive - 1.9 miles
Founders Park - 3 min drive - 1.9 miles
Florida Keys Brewing Co. - 5 min drive - 3.6 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

Similar properties

Private beach, white sand, sun loungers, beach towels

On private beach
Pool
Breakfast included
Pet friendly

includes taxes & fees

$296 per night

May 11 - May 12

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

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

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Drop Anchor Hotel Islamorada

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Drop Anchor Resort Marina

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Drop Anchor Hotel

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Drop Anchor

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Hotel Drop Anchor

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Drop Anchor Resort Marina

Drop Anchor Hotel

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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 2, 2025, prices found for a 1-night stay for 2 adults at Drop Anchor on May 4, 2025 start from $174.0, 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

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

6/10 Okay

Verified traveler

Jan 26, 2025

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

Jan 25, 2025

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

Jan 25, 2025

Stayed 5 nights in Jan 2025

2/10 Terrible

Michael

Jan 25, 2025

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

Resort fee my @ss

Stayed 1 night in Jan 2025

8/10 Good

Sean

Jan 23, 2025

Liked: Cleanliness, property conditions & facilities, room comfort

Stayed 1 night in Jan 2025

2/10 Terrible

Evelyn, Lake Ariel

Jan 21, 2025

Disliked: Cleanliness, property conditions & facilities

Stayed 3 nights in Jan 2025

10/10 Excellent

John

Traveled with partner

Jan 8, 2025

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

Jan 7, 2025

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

Jan 6, 2025

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

Stayed 2 nights in Jan 2025

6/10 Okay

Michelle

Jan 6, 2025

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

Jan 6, 2025

Stayed 4 nights in Dec 2024

10/10 Excellent

Maria Fernanda

Traveled with family

Jan 2, 2025

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

10/10 Excellent

Sara

Dec 31, 2024

I have stayed at drop anchor inn several times and will keep going back. It’s so typical of what the Florida Keys has to offer. I just love it there. I live in Fort Lauderdale and going down to the Keyes is the perfect getaway. I highly recommend drop anchor Inn.

Stayed 2 nights in Dec 2024

10/10 Excellent

Jami

Traveled with family

Dec 30, 2024

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

Very clean. Nice beach area and friendly staff.

Stayed 1 night in Dec 2024

10/10 Excellent

Sonja

Traveled with family

Dec 30, 2024

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

Stayed 1 night in Dec 2024

4/10 Poor

FABIO, NORTH MIAMI

Dec 29, 2024

Disliked: Property conditions & facilities

Our big problem was the room. It was small, the bed was too high, very uncomfortable, there was no ventilation or fan in the bathroom, completely overpriced. The bed is exposed in a way that I hate myself twice with it in the leg that I had to protect it with a towel, not to hate it during the night.

Stayed 2 nights in Dec 2024

10/10 Excellent

Ashley

Traveled with family

Dec 29, 2024

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

Will be back

Beautiful view, spacious, clean rooms. Only stayed 2 nights as we were visiting family so we did not use the pool or resort activities offered but we will definitely be adding this property to our list for future stays!

Stayed 2 nights in Dec 2024

10/10 Excellent

jose

Dec 27, 2024

Liked: Staff & service, property conditions & facilities

This place had an amazing view and sunrise will most definitely me back to this place

Stayed 2 nights in Dec 2024

8/10 Good

Craig

Traveled with family

Dec 21, 2024

The location was beautiful, rooms should be updated. My biggest complaint is a paid for two rooms, same price for both, but one was very much smaller than the other and no balcony in that same room either ?!?!

Stayed 1 night in Dec 2024

8/10 Good

Noreen

Traveled with family

Dec 6, 2024

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

Amazing place! Beautiful area with great amenities. Only thing was really stiff beds. But if you like very firm mattresses…it’s a 5 star. That aside …we will definitely be back!!

Stayed 2 nights in Nov 2024