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Drop Anchor

3.0 star property
Travelers dive into water adventures or unwind poolside at this coastal retreat, with complimentary bikes available for exploring the surrounding attractions

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Photo gallery for Drop Anchor

Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view - Drop Anchor (Islamorada)
Exterior - Drop Anchor (Islamorada)
Water view - Drop Anchor (Islamorada)
Terrace/patio - Drop Anchor (Islamorada)
Oceanfront King Suite w/ Kitchen & Private Balcony | Water view - Drop Anchor (Islamorada)
Drop Anchor offers a laid-back beach vibe with an outdoor pool and comfy sun loungers. Free bike rentals help you explore, while paddleboards and motorboating cater to adventurers. In-room WiFi keeps everyone connected.

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Pool
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services

Room options

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Showing 11 of 11 rooms

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
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

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
(16 reviews)
  • Ocean view
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

View all photos for Oceanfront Queen Room

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

Oceanfront Queen Room

  • Ocean view
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

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
(14 reviews)
  • Ocean view
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

About the neighborhood

Located in Islamorada, Drop Anchor is on the waterfront. Hurricane Monument and Indian Key Historic State Park are local landmarks, and the area's natural beauty can be seen at Windley Key Fossil Reef Geological State Park and San Pedro Underwater Archaeological Preserve State Park. Ready for a night out? Consider Hog Heaven and Lorelei Restaurant & Cabana Bar. Discover the area's water adventures with scuba diving and snorkeling nearby, or enjoy the great outdoors with hiking/biking trails and ecotours. Visit our Islamorada travel guide
Map
84959 Overseas Highway, 222, Islamorada, FL, 33036

What's nearby

  • Windley Key Fossil Reef Geological State Park
    Windley Key Fossil Reef Geological State Park
    6 min walk - 0.4 miles
  • Theater of the Sea
    Theater of the Sea
    9 min walk - 0.5 miles
  • Founders Park
    Founders Park
    3 min drive - 2.5 miles
  • Hog Heaven
    7 min walk - 0.4 miles
  • Baker's Cay Resort Beach
    19 min drive - 15.5 miles

Getting around

  • Miami Intl. Airport (MIA)
    89 min drive

Restaurants

  • Wahoo's Bar & Grill
    2 min drive
  • Hog Heaven
    7 min walk
  • Wendy's
    4 min drive
  • Starbucks
    15 min walk
  • Tiki Bar
    18 min walk

Similar properties

Exterior
Fisher Inn Resort & Marina
Islamorada
  • On private beach
  • Pool
  • Breakfast included
  • Pet friendly
8.2 out of 10, Very Good, 1,005 reviews
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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

Pets allowed for an extra charge of USD 26 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 26 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

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 26 per pet, per day. Service animals are exempt from fees.

How much is parking?

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 within a 10-minute walk of Windley Key Fossil Reef Geological State Park and Hog Heaven. Rain Barrel Village and Founders Park are also within 3 mi (5 km).

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Reviews

Drop Anchor Reviews

8.8

Excellent

9.0

Cleanliness

9.0

Location

9.0

Staff & service

8.4

Property conditions & facilities
Rating 10 - Excellent. 609 out of 1000 reviews
Rating 8 - Good. 224 out of 1000 reviews
Rating 6 - Okay. 79 out of 1000 reviews
Rating 4 - Poor. 43 out of 1000 reviews
Rating 2 - Terrible. 45 out of 1000 reviews

Reviews

Verified

10/10 Excellent

Melissa

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great stay for boaters! right on the water and easy to launch. The rooms were clean and had the essentials. The staff was super friendly and helpful.
Stayed 1 night in Jun 2026
Verified

10/10 Excellent

Anna Marie

Liked: Staff & service, amenities, property conditions & facilities
What a wonderfully kitschy Florida Keys hotel! The property was beautifully manicured and well taken care of. Our room was clean and very comfortable. We can’t wait to book another stay!
Stayed 3 nights in Apr 2026
Verified

10/10 Excellent

Amy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great room. Staff was very helpful and kind. Enjoyed the beachfront
Stayed 2 nights in Apr 2026
Verified

10/10 Excellent

Jill

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location! Super cute every room is close to the water. Would stay here again for sure.
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

vanessa

Liked: Cleanliness, staff & service, property conditions & facilities
We loved our stay and definitely will be back . Staff was great, hotel was clean and comfortable, the view amazing, great location. The only thing to improve is the water pressure when taking showers but everything else was fantastic .
Our view
From the pool
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

Wendy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very pleasantly surprised with the location and quality of this resort. The water view is available throughout the property and this resort is well taken care of. The pool was exceptionally clean and refreshing.
View from Room 16
Wonderful place to enjoy the night sky
Stayed 4 nights in Mar 2026
Verified

10/10 Excellent

Jasmine

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The room wasn’t the most luxurious and needed work. The pool needs a reface as well, but the location and the boat ramp was great and we were able to get across to the sand bar in no time! The staff was helpful, the location is absolutely amazing, the scenery is amazing, and the convenience of launching there was a great perk! Definitely recommend if you want something laid back, a great view, and convenient. Definitely call before booking and let them know about your plans for launching! They’re a little sticky about this!
Stayed 1 night in May 2026
Verified

10/10 Excellent

Ana

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything was clean and in good conditions
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

Brian

Liked: Cleanliness, property conditions & facilities
Clean room, beautiful view and loved being able to walk out to the beach.
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Markee

Liked: Cleanliness, staff & service, amenities
The View was amazing!
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

Shaney E

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We had a great room with a beautiful view of the beach in front of the ocean. Loved it!
Stayed 1 night in Mar 2026
Verified

10/10 Excellent

Erin

Liked: Cleanliness, amenities, property conditions & facilities
the staff was wonderful, the room was perfect, the location/view was awesome . the pool was wonderful. i am very very pleased with our stay !
Stayed 1 night in Jan 2026
Verified

8/10 Good

Alberto

Liked: Cleanliness, property conditions & facilities
Great room and amazing view
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Linda

Liked: Cleanliness, staff & service, property conditions & facilities
The ocean was right outside our door. The unit was very clean, very kept up and the quietness was amazing.
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

Cassie

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We could see the ocean from the bed so we'd wake up, open the curtains and watch the sunrise from the bed! Amazing!
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

Elena

Liked: Cleanliness, staff & service, amenities
Good times staying at the property. Great view out of the window.
Stayed 5 nights in Jan 2026
Verified

10/10 Excellent

James

Liked: Cleanliness, staff & service, amenities
So clean. Great room. Near everything and so so clean. I would stay here again. The people at the drop anchor are super nice.
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

Brook

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

10/10 Excellent

Laura

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
Verified

10/10 Excellent

Jeff

Liked: Cleanliness, property conditions & facilities
Staff member at front desk was friendly and courteous! Room was just what we wanted costal, cozy and clean. Coffee and a pastry or fruit at the office in the am would be a nice touch.
Stayed 2 nights in Jan 2026
Verified

4/10 Poor

Carol

Liked: Staff & service
Disliked: Cleanliness, amenities, property conditions & facilities
This place needs an entire makeover. The staff were super nice and the views were beautiful. It’s in a great location but the rooms are run down. The free kayaks and bikes were in terrible condition and the pool was dirty and had many visible concrete holes on the bottom. The WiFi and ice machine were both not working and the water pressure was almost nonexistent.
Stayed 5 nights in Mar 2026
Verified

10/10 Excellent

Christy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The room walked right out to water. Staff came around to ask if we needed anything. It was amazing!
Stayed 3 nights in Jan 2026
Verified

10/10 Excellent

Nina

Liked: Cleanliness, staff & service, amenities
Great stay, better than I even expected from the pictures. Quiet, quaint little place right on the water. The edge is actually a dock, but it looks like it’s right on its own, private, wide beach! The internet was good - I had a half day of doing Zoom work calls and had no problems. It’s quiet, the bed and pillows were comfortable, and the coffee in the room was strong and good. Close to a couple restaurants within walking distance, one of which was dockside with outdoor seating that was so relaxing (Island Grill). Definitely would stay again.
Stayed 2 nights in Jan 2026
Verified

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
Verified

10/10 Excellent

DeeDee

Liked: Cleanliness, amenities, property conditions & facilities
The room was clean, property is nice, pool is really heated and lovely to get in and out. Most places lie about heating their pool this one is for real! Daniel in the office is super great! They have bikes and kayaks to use, that is included in your resort fee.( which is reasonable). Definitely be back☀️.
Stayed 1 night in Jan 2026