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Drop Anchor

3.0 star property
Waterfront hotel with a nearby private beach and an outdoor pool

Choose dates to view prices

Photo gallery for Drop Anchor

Relax in a semi-circular seating area overlooking the beach, surrounded by palm trees and a thatched umbrella.
Relax on the balcony with comfortable lounge chairs and a picnic table, taking in the serene beach view.
Relax by the pool surrounded by palm trees and lounge chairs.
Enjoy a serene ocean view from the comfort of your room, featuring a large window and a plush bed.
Relax on the beach with a thatched-roof structure and comfortable seating.

Reviews

8.8 out of 10
Excellent

Popular amenities

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

Room options

Available filters for rooms
Showing 11 of 11 rooms

View all photos for Resort View Queen Family Suite w/ Kitchen

1 bedroom, premium bedding, individually decorated

Resort View Queen Family Suite w/ Kitchen

10.0 out of 10
Exceptional
(1 review)

Highlights

Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Kitchen
Full-sized refrigerator/freezer
Flat-screen TV
Separate bedroom
  • 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

1 bedroom, premium bedding, individually decorated

Oceanfront King Suite w/ Beach Walkout & Kitchen

9.8 out of 10
Exceptional
(8 reviews)

Highlights

Deck/patio
Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Kitchen
Full-sized refrigerator/freezer
Flat-screen TV
  • Ocean view
  • Sleeps 4
  • 1 King Bed

View all photos for Oceanfront Trailer

1 bedroom, premium bedding, individually decorated

Oceanfront Trailer

8.0 out of 10
Very good
(8 reviews)

Highlights

Patio
Separate dining area
Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Kitchenette
Full-sized refrigerator/freezer
  • Sleeps 2
  • 1 Queen Bed

View all photos for Ocean View Double Queen w/ Kitchen & Private Balcony

1 bedroom, premium bedding, individually decorated

Ocean View Double Queen w/ Kitchen & Private Balcony

9.6 out of 10
Exceptional
(5 reviews)

Highlights

Balcony
Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Kitchen
Flat-screen TV
Premium bedding
  • Sleeps 4
  • 2 Queen Beds

View all photos for Oceanfront Queen Room

1 bedroom, premium bedding, individually decorated

Oceanfront Queen Room

Highlights

Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Mini-fridge
Flat-screen TV
Premium bedding
Separate bedroom
  • Ocean view
  • Sleeps 2
  • 1 Queen Bed

View all photos for Resort View ADA King Room

1 bedroom, premium bedding, individually decorated

Resort View ADA King Room

Highlights

Patio
Yard
Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Refrigerator
Flat-screen TV
  • Sleeps 2
  • 1 King Bed

View all photos for Resort View Queen Room w/ Kitchen & Private Porch

1 bedroom, premium bedding, individually decorated

Resort View Queen Room w/ Kitchen & Private Porch

9.4 out of 10
Exceptional
(6 reviews)

Highlights

Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Kitchen
Full-sized refrigerator/freezer
Flat-screen TV
Premium bedding
  • Resort view
  • Sleeps 2
  • 1 Queen Bed

View all photos for Resort View Family Suite w/ Kitchen

Private kitchen

Resort View Family Suite w/ Kitchen

7.4 out of 10
Good
(3 reviews)

Highlights

Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Kitchen
Full-sized refrigerator/freezer
Flat-screen TV
Separate bedroom
  • Resort view
  • Sleeps 6
  • 2 Queen Beds and 2 Twin Beds

View all photos for Ocean View Double Queen Room

1 bedroom, premium bedding, individually decorated

Ocean View Double Queen Room

9.4 out of 10
Exceptional
(12 reviews)

Highlights

Balcony
Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Mini-fridge
Flat-screen TV
Premium bedding
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

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

1 bedroom, premium bedding, individually decorated

Oceanfront King Suite w/ Kitchen & Private Balcony

10.0 out of 10
Exceptional
(18 reviews)

Highlights

Balcony
Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Kitchenette
Full-sized refrigerator/freezer
Flat-screen TV
  • Beach view
  • Sleeps 4
  • 1 King Bed

View all photos for Oceanfront Family Suite w/ Kitchen

Flat-screen TV

Oceanfront Family Suite w/ Kitchen

Highlights

Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Kitchen
Full-sized refrigerator/freezer
Flat-screen TV
Separate bedroom
  • Ocean view
  • Sleeps 6
  • 1 King Bed, 2 Twin Beds and 1 Queen Futon

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About the neighborhood

Map
84959 Overseas Highway, 222, Islamorada, FL, 33036

What's nearby

  • Windley Key Fossil Reef Geological State Park - 6 min walk - 0.5 km
  • Theater of the Sea - 9 min walk - 0.8 km
  • Founders Park - 4 min drive - 4.0 km
  • Islamorada County Park - 4 min drive - 4.3 km
  • Florida Keys Brewing Co. - 7 min drive - 7.3 km

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

Hotel by the ocean
Drop Anchor provides amenities like a garden and a business center. Active travelers can enjoy amenities like motor boating and paddleboards at this hotel. Stay connected with free in-room WiFi.
Additional perks include:
  • An outdoor pool with sun loungers
  • Free self parking
  • Free bicycle rentals, barbecue grills, and a front-desk safe
  • A banquet hall, a vending machine, and a dock
  • Guest reviews say great things about the helpful staff
Room features
All guestrooms are individually furnished, and feature comforts such as premium bedding and air conditioning, as well as thoughtful touches like free WiFi. Guest reviews highly rate the clean rooms at the property.
Other amenities include:
  • Bathrooms with showers and free toiletries
  • Flat-screen TVs with premium channels
  • Coffee/tea makers, ceiling fans, and daily housekeeping

Languages

English

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Chesapeake Beach Resort

  • On private beach
  • Pool
  • Breakfast included
  • Pet friendly
9.2 out of 10, Wonderful, 1,491 reviews
The price is P13,898
P18,813 total
includes taxes & fees
Jul 23 - Jul 24
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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

Pets allowed for an extra charge of USD 25 per pet, per day
Service animals are welcome, and are exempt from fees
Welcoming dogs only

Children and extra beds

Children are welcome
Rollaway/extra beds are not available
Cribs (infant beds) are not available

Property payment types

Important information

Fees

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

  • Resort fee: USD 35 per accommodation, per night
The resort fee includes:
  • Beach access
  • Beach loungers
  • Beach towels
  • Housekeeping
  • In-room coffee
  • Pool access

We have included all charges provided to us by the property.

Optional extras

  • Pet fee: USD 25 per pet, per day
  • Service animals are exempt from fees

The above list may not be comprehensive. Fees and deposits may 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

We should mention

This property does not have elevators
Pool access available from 7:30 AM to 6:30 PM
The property has connecting/adjoining rooms, which are subject to availability and can be requested by contacting the property using the number on the booking confirmation

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

Does Drop Anchor have a pool?

Yes, this property has an outdoor pool. Pool access is from 7:30 AM–6:30 PM.

Is Drop Anchor pet-friendly?

Yes, dogs are allowed at this property. There's a fee of USD 25 per pet, per day. Service animals are exempt from fees.

How much is parking at Drop Anchor?

Self parking is free at this property.

What time is check-in at Drop Anchor?

Check-in start time: 3:00 PM; Check-in end time: 6:00 PM. Late check-in is available during limited hours.

What time is check-out at Drop Anchor?

Check-out is at 11 AM.

Where is Drop Anchor located?

Situated on the waterfront, this hotel is 0.2 mi (0.4 km) from Windley Key Fossil Reef Geological State Park and within 3 mi (5 km) of Rain Barrel Village and Founders Park. Islamorada County Park and History of Diving Museum are also within 3 mi (5 km).

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Drop Anchor Reviews

Reviews

8.8

Excellent

Rating 10 - Excellent. 616 out of 1005 reviews
Rating 8 - Good. 238 out of 1005 reviews
Rating 6 - Okay. 77 out of 1005 reviews
Rating 4 - Poor. 36 out of 1005 reviews
Rating 2 - Terrible. 38 out of 1005 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

8/10

The property was a throw back to old motels, charming…
Stayed 1 night in Jun 2025

10/10

Very quiet , nice views , excellent costumer service.
Stayed 2 nights in Jun 2025

8/10

Quaint
Stayed 1 night in Feb 2025

10/10

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

6/10

No parking and a little derty
Stayed 2 nights in Jul 2025

10/10

Always friendly and helpful staff. Private beach area is a major plus.
Stayed 1 night in May 2025

6/10

Wouldn't do it again
Stayed 1 night in Jul 2025

10/10

The boat dock is a little rough to enter and exit especially on low tide.
Stayed 3 nights in May 2025

8/10

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

10/10

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

Great staff. Very clean and wonderful waterfront setting.
Stayed 2 nights in Feb 2025

10/10

It was very nice.
Stayed 2 nights in Jan 2025

8/10

Good location on the old highway, water pressure could use improvement.
Stayed 7 nights in Mar 2025

8/10

Air conditioner was inadequate. Probably why they had box fans in the rooms.
Stayed 1 night in May 2025

10/10

This place had an amazing view and sunrise will most definitely me back to this place
Stayed 2 nights in Dec 2024

10/10

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

10/10

Very excellent location for staying
Stayed 1 night in Aug 2024

10/10

Love the location the property and views are amazing !
Stayed 2 nights in Oct 2024

10/10

Beutifull hotel
Stayed 1 night in Oct 2024

10/10

Hood
Stayed 1 night in Mar 2025

6/10

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

10/10

Very nice place to stay and relax
Stayed 1 night in Aug 2024

8/10

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

Is a beutifull place to relax .
Stayed 1 night in Oct 2024

10/10

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