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Drop Anchor

3.0 star property

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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 | Water view
Oceanfront King Suite w/ Kitchen & Private Balcony | Premium bedding, individually decorated, individually furnished
Exterior
Water view

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Pool
  • 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, Theater of the Sea
    ‪9 min walk‬
  • Place, Lignumvitae Key Botanical State Park

Room options

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

9.6 out of 10
Exceptional
(5 reviews)
  • Sleeps 4
  • 2 Queen Beds

View all photos for Oceanfront Trailer

Oceanfront Trailer | Premium bedding, individually decorated, individually furnished

Oceanfront Trailer

8.0 out of 10
Very good
(8 reviews)
  • 1 bedroom
  • 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

  • Garden view
  • Sleeps 2
  • 1 King Bed

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

Premium bedding, individually decorated, individually furnished

Oceanfront King Suite w/ Kitchen & Private Balcony

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

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

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

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

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

Resort View Queen Room w/ Kitchen & Private Porch | Premium bedding, individually decorated, individually furnished

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

Oceanfront Queen Room | Premium bedding, individually decorated, individually furnished

Oceanfront Queen Room

7.0 out of 10
Good
(7 reviews)
  • Ocean view
  • 1 bedroom
  • Sleeps 2
  • 1 Queen 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

9.6 out of 10
Exceptional
(12 reviews)
  • Ocean view
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed

View all photos for Oceanfront Family Suite w/ Kitchen

Flat-screen TV

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

Resort View Queen Family Suite w/ Kitchen | Premium bedding, individually decorated, individually furnished

Resort View Queen Family Suite w/ Kitchen

10.0 out of 10
Exceptional
(1 review)
  • Resort view
  • 2 bedrooms
  • Sleeps 6
  • 1 Queen Bed, 1 Double Bed and 1 Queen Sofa Bed

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Exterior

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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
  • Bud n' Mary's Dive Center - 8 min drive - 6.7 miles
  • Baker's Cay Resort Beach - 18 min drive - 14.2 miles
  • Anne's Beach - 19 min drive - 14.4 miles

Getting around

  • Miami Intl. Airport (MIA) - 89 min drive

Restaurants

  • ‪Tiki Bar - ‬18 min walk
  • ‪Wahoo's Bar & Grill - ‬2 min drive
  • ‪Hog Heaven - ‬7 min walk
  • ‪Wendy's - ‬4 min drive
  • ‪Bayside Gourmet of Islamorada - ‬3 min drive

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 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.

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Hadley Resort and Marina
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  • On private beach
  • Pool
  • Breakfast included
  • Pet friendly
7.6 out of 10, Good, 1,000 reviews
$190 nightly
The price is $214
May 4 - May 5
Total with taxes and fees
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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
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 26 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 26 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 Florida Keys Brewing Co. within a short drive.

How much does it cost to stay at Drop Anchor?

As of Apr 3, 2026, prices found for a 1-night stay for 2 adults at Drop Anchor on Apr 6, 2026 start from $391, 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.

Will I be able to park 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.

Are there hot tubs at Drop Anchor?

No, this hotel doesn't have a spa tub.

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 26 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

Reviews

8.8

Excellent

Rating 10 - Excellent. 604 out of 1000 reviews
Rating 8 - Good. 231 out of 1000 reviews
Rating 6 - Okay. 79 out of 1000 reviews
Rating 4 - Poor. 44 out of 1000 reviews
Rating 2 - Terrible. 42 out of 1000 reviews

9.0/10

Cleanliness

9.2/10

Staff & service

8.6/10

Amenities

8.4/10

Property conditions & facilities

Reviews

10/10 Excellent

Ron

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

6/10 Okay

Raman

Liked: Cleanliness
Disliked: Amenities
Overpriced! No breakfast available and room was falling apart- needed maintenance. The only thing we liked was the location- beautiful view from balcony.
Stayed 1 night in Dec 2025

10/10 Excellent

Brook

Traveled with family
Liked: Cleanliness, staff & service, amenities
Amazing and peaceful lady at front desk was amazing and friendly
Stayed 1 night in Dec 2025

10/10 Excellent

Traci

Traveled with pets, Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
The room was very clean and the staff was great. We didn’t cook. The kitchen was small but it would work if we needed it…full size appliances and a microwave. The place is right on the water. There isn’t a beach but they have sand and they rake it every morning. Pool is small but nice enough. A small place, never crowded while we were there even though it was fully booked. We enjoyed the hotel and Islamorada more than Key West…to crowded to enjoy.
Stayed 2 nights in Dec 2025

10/10 Excellent

miguel

Stayed 2 nights in Dec 2025

10/10 Excellent

Melissa

Liked: Cleanliness, amenities, property conditions & facilities
Staff was wonderful! Location and amenities were great! Room was clean and comfortable!
Stayed 4 nights in Nov 2025

10/10 Excellent

William

Stayed 2 nights in Dec 2025

10/10 Excellent

Laura, Gibsonton

Liked: Cleanliness, amenities, property conditions & facilities
Had a wonderful stay at Drop Anchor! Very adorable and super clean. Loved the amenities and the hotel staff were amazing!
Stayed 2 nights in Nov 2025

8/10 Good

Dustin, Sartell

Traveled with family
The staff was very nice. Thanks
Stayed 1 night in Nov 2025

8/10 Good

fiona

Liked: Cleanliness
Spotless, simple room. Quiet, peaceful resort. Daniel (GM) was super helpful. Very pleasant stay. Very Dog friendly. Everyone chilled and relaxed — the Key vibe you look for! Enjoy!
Stayed 2 nights in Nov 2025

10/10 Excellent

John

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

10/10 Excellent

John

Stayed 2 nights in Nov 2025

10/10 Excellent

Robert

Stayed 1 night in Nov 2025

6/10 Okay

Robert

Liked: Cleanliness, staff & service
Toilet problem
Stayed 1 night in Nov 2025

10/10 Excellent

ANNIA

Quiet peaceful nice beds view kitchen 😍
Stayed 1 night in Oct 2025

2/10 Terrible

Thomas

Disliked: Cleanliness, staff & service, property conditions & facilities, room comfort
Due to a family emergency, my brother passed suddenly, we had to cancel the room. I was not refunded, even though I had insurance and documentation on why. Manager was rude and dismissive when i contacted them.
Stayed 2 nights in Jul 2025

10/10 Excellent

Thalia

Liked: Cleanliness
Great
Stayed 2 nights in Oct 2025

10/10 Excellent

Paula

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Comfy bed! Pretty tiled shower!
Stayed 1 night in Oct 2025

10/10 Excellent

Paula

Stayed 2 nights in Oct 2025

10/10 Excellent

Dianna

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean, comfortable room, friendly staff. Grounds clean and properly taken care of. Would stay here again.
Stayed 1 night in Sep 2025

10/10 Excellent

Natacha

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Aug 2025

10/10 Excellent

juan

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Sep 2025

10/10 Excellent

Greg

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was a perfect little cottage and peace and quiet. Lots of Palm trees and perfect boat launch
Stayed 2 nights in Sep 2025

8/10 Good

Ariel

Traveled with pets, Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It is very convenient. It has fun and relaxing surroundings. Pet friendly. The dining places are a must.
Stayed 1 night in May 2025

10/10 Excellent

Manuel

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

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