Drop Anchor

Property class: 3

Choose dates to view prices

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.

Reviews

8.6 out of 10
Excellent

Popular amenities

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

Room options

Available filters for rooms
Showing 11 of 11 rooms

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

A hotel room with two beds, a ceiling fan, and a view of the outdoors.

Ocean View Double Queen w/ Kitchen & Private Balcony

9.8 out of 10
Exceptional
(7 reviews)
  • Sleeps 4
  • 2 Queen Beds

View all photos for Oceanfront Trailer

A neatly made bed with white and pink linens, a wooden headboard, and a mirror on the wall.

Oceanfront Trailer

8.4 out of 10
Very good
(9 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for Resort View ADA King Room

A bedroom with a bed, a desk with a microwave, a chair, and artwork on the walls.

Resort View ADA King Room

  • Garden view
  • Sleeps 2
  • 1 King Bed

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

A hotel room with a bed, a blue sofa, a small table, a ceiling fan, a white nightstand, and a bathroom visible through an open door.

Oceanfront King Suite w/ Kitchen & Private Balcony

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

View all photos for Ocean View Double Queen Room

A room with two beds, teal walls, and artwork.

Ocean View Double Queen Room

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

View all photos for Resort View Family Suite w/ Kitchen

A modern kitchen with white cabinetry, a stainless steel oven, a microwave, and a white countertop.

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

A bedroom with a bed, bedside tables, a desk, and a chair.

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

A bedroom with a bed, a teal door, a white wall, and a window.

Oceanfront Queen Room

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

View all photos for Oceanfront King Suite w/ Beach Walkout & Kitchen

A bedroom with a large bed, a nightstand with a lamp, a painting of a starfish on the wall, and a window with blinds.

Oceanfront King Suite w/ Beach Walkout & Kitchen

9.0 out of 10
Wonderful
(16 reviews)
  • Ocean view
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed

View all photos for Oceanfront Family Suite w/ Kitchen

A dining area with a green table and white chairs, a ceiling fan, a kitchen in the background, and a colorful painting on the wall.

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

A hotel room with a bed, a small round table, and a white door leading to a bathroom.

Resort View Queen Family Suite w/ Kitchen

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

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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

  • An archaeological site with stone structures and metal machinery.
    Windley Key Fossil Reef Geological State Park
    6 min walk - 0.4 miles
  • A waterfall at SeaWorld, with text reading "I eat the sea" and "Marine Mammal Park, Islamorada, Florida".
    Theater of the Sea
    9 min walk - 0.5 miles
  • An aerial view of a coastal area with a marina, tennis courts, a baseball field, and surrounding greenery.
    Founders Park
    3 min drive - 2.5 miles
  • A wooden deck with benches overlooking a clear blue sea.
    Anne's Beach
    18 min drive - 14.9 miles
  • Hog Heaven
    7 min walk - 0.4 miles

Getting around

  • Miami Intl. Airport (MIA)
    98 min drive

Restaurants

  • Hog Heaven
    7 min walk
  • Lorelei Restaurant & Cabana Bar
    5 min drive
  • Wahoo's Bar & Grill
    2 min drive
  • Wendy's
    4 min drive
  • Starbucks
    15 min walk

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 along with sun loungers
    • Free self parking
    • Free bicycle rentals, coffee/tea in the lobby, and beach umbrellas
    • 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

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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.

How much does it cost to stay at Drop Anchor?

As of Oct 24, 2026, prices found for a 1-night stay for 2 adults at Drop Anchor on Oct 27, 2026 start from $180, 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.

Is Drop Anchor pet-friendly?

Yes, dogs are allowed at this property. There's a fee of USD 28 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

8.6

Excellent

9.0

Cleanliness

9.0

Location

9.0

Staff & service

8.4

Property conditions & facilities
Rating 10 - Excellent. 605 out of 1000 reviews
Rating 8 - Good. 216 out of 1000 reviews
Rating 6 - Okay. 82 out of 1000 reviews
Rating 4 - Poor. 42 out of 1000 reviews
Rating 2 - Terrible. 55 out of 1000 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location,
Stayed 4 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was quite and clean. Feels like home
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was a great location on the Keys. The staff was friendly and helpful. The view from our room was amazing.
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This place was great! Donna is super nice. Went kayaking to the sandbar. Room is very spacious. Beautiful view. Very clean.
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
A very cozy, small hotel in a quiet location by the sea. Perfect for a holiday with children. Highly recommended!
Stayed 1 night in Jul 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We were greeted by Daniel when we checked in. He was kind and very respectful with many recommendations in the area. Our unit was GREAT. Perfect views of the bay and the kitchen had everything we needed for a short stay.
Stayed 3 nights in Jun 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We could walk to hog heaven They had complementary bikes, paddle boards, and kayaks.
Stayed 1 night in Jun 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

8/10 Good

Liked: Cleanliness, staff & service, amenities
This place was set in a beautiful location but you could not swim in the water - the swimming pool was a great substitute and well maintained. There were plenty of places to grill and enjoy the views on the property, and I loved that free bike rentals were included. The staff was very friendly and helpful - really satisfied there, but the standard of the rooms was average. Things were functional but there were several conveniences missing, like a towel rod in the bathroom, or unfinished walls in different parts of the villa. It was nice to be in walking distance to a couple of restaurants, an ice cream place, a pizza place, and a Starbucks.
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

Liked: Cleanliness, property conditions & facilities
Disliked: Amenities
Friendly Staff, relaxing pool, and great view. The wife and I would absolutely stay there again. Center all everything you would need. The downside, the room we booked (ocean walkout room with kitchen) was double booked. We were placed in a regular room with no kitchen, they offered to move us Saturday but it was not feasible as we had our dog and were on the water all day. They did give us a small refund and waive pet fee, it was just disappointing as we specifically booked the hotel for the walkout room with Kitchen. I would recommend calling to confirm the room booked will actually be your room.
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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

10/10 Excellent

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

8/10 Good

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

10/10 Excellent

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

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities
Disliked: Amenities
Very excellent location for staying
Stayed 1 night in Aug 2024