Skip to Main Content.
List your propertySupportTrips
Member discount illustration

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Sign in
Learn about Expedia Rewards
Give feedback

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

Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view
Oceanfront King Suite w/ Kitchen & Private Balcony
Exterior
Oceanfront King Suite w/ Kitchen & Private Balcony | Water view
Oceanfront King Suite w/ Kitchen & Private Balcony | Terrace/patio
Drop Anchor offers a relaxing beach vibe with an outdoor pool, sun loungers, and free bicycle rentals to explore the surrounding area. Enjoy paddleboards or motor boating activities while staying connected with in-room WiFi.

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Housekeeping
  • Pet-friendly
  • Pool
  • 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

Resort View Queen Family Suite w/ Kitchen

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
2 bedrooms
  • 2 bedrooms
  • 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

Oceanfront King Suite w/ Beach Walkout & Kitchen

Oceanfront King Suite w/ Beach Walkout & Kitchen

9.6 out of 10
Exceptional
(11 reviews)

Highlights

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

View all photos for Oceanfront Trailer

Oceanfront Trailer

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
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

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

Ocean View Double Queen w/ Kitchen & Private Balcony

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
Separate bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Oceanfront Queen Room

Oceanfront Queen Room

Oceanfront Queen Room

Highlights

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

View all photos for Resort View ADA King Room

Resort View ADA King Room

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

Resort View Queen Room w/ Kitchen & Private Porch

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
Separate bedroom
  • Resort view
  • Sleeps 2
  • 1 Queen Bed

View all photos for Resort View Family Suite w/ Kitchen

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
  • 1 bedroom
  • Resort view
  • Sleeps 6
  • 2 Queen Beds and 2 Twin Beds

View all photos for Ocean View Double Queen Room

Ocean View Double Queen Room

Ocean View Double Queen Room

8.8 out of 10
Excellent
(15 reviews)

Highlights

Balcony
Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Mini-fridge
Flat-screen TV
Separate bedroom
  • 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
  • 1 bedroom
  • 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
2 bedrooms
  • 2 bedrooms
  • Ocean view
  • Sleeps 6
  • 1 King Bed, 2 Twin Beds and 1 Queen Futon

You may also like

Ad
Private beach, sun loungers, beach umbrellas, beach towels

Cheeca Lodge & Spa

Matecumbe
  • On private beach
  • Pool
  • Hot tub
  • Spa
9.0 out of 10, Wonderful, 1,156 reviews
The price is CA $212
CA $333 total
includes taxes & fees
Aug 24 - Aug 25
Cheeca Lodge & Spa
Mod logo
Sign in to view eligible discounts and perks. More rewards for more adventures!
Sign inSign up, it's free

About the area

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. 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 guideOpens in a new window
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

  • ‪Tiki Bar - ‬18 min walk
  • ‪Wendy's - ‬4 min drive
  • ‪Whale Harbor Restaurant Marina - ‬2 min drive
  • ‪Starbucks - ‬15 min walk
  • ‪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, a front-desk safe, and a banquet hall
  • Beach towels, wedding services, 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

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.

How much does it cost to stay at Drop Anchor?

As of Aug 22, 2025, prices found for a 1-night stay for 2 adults at Drop Anchor on Aug 24, 2025 start from CA $228.49, 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 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).

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Drop Anchor Reviews

Reviews

8.8

Excellent

Rating 10 - Excellent. 607 out of 1001 reviews
Rating 8 - Good. 244 out of 1001 reviews
Rating 6 - Okay. 76 out of 1001 reviews
Rating 4 - Poor. 36 out of 1001 reviews
Rating 2 - Terrible. 38 out of 1001 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

10/10 Excellent

Ninoslav

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful and quiet place!
Stayed 1 night in Aug 2025

10/10 Excellent

Lisa

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This place was great! Was a spur of the moment decision to stay here and we haven’t regretted it. Beautiful view and 2 restaurants within walking distance to property.
Stayed 1 night in Aug 2025

8/10 Good

Raul

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The property was well maintained. The staff was excellent.
Stayed 3 nights in Aug 2025

10/10 Excellent

Travis

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This was our second stay in a month. Great location, beautiful property on the water. We love it here and cant wait to go back.
View from the dock.
Stayed 2 nights in Jul 2025

8/10 Good

Jack

Liked: Cleanliness, amenities, property conditions & facilities
Clean and convenient
Stayed 2 nights in Jun 2025

10/10 Excellent

Silvia

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Love it!!
Stayed 1 night in Aug 2025

8/10 Good

Anthony

Liked: Cleanliness, property conditions & facilities
Disliked: Amenities
The property was a throw back to old motels, charming…
Stayed 1 night in Jun 2025

10/10 Excellent

Morgan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I loved this property. My husband and I stayed here for a quick getaway and it was perfect. Super clean and the staff was very responsive. We utilized the complimentary kayaks which was a nice touch. Will be returning
Stayed 2 nights in Jun 2025

8/10 Good

Paolo

Liked: Cleanliness, property conditions & facilities
It was that keys feeling that everyone looks for
Stayed 3 nights in Jul 2025

10/10 Excellent

Dixiana

Liked: Cleanliness, amenities, property conditions & facilities
Very quiet , nice views , excellent costumer service.
Stayed 2 nights in Jun 2025

8/10 Good

David

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Quaint
Stayed 1 night in Feb 2025

10/10 Excellent

ellie

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

10/10 Excellent

Michael

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Always friendly and helpful staff. Private beach area is a major plus.
Stayed 1 night in May 2025

8/10 Good

Verified traveller

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

Nice ocean views

Nice location with ocean views
Stayed 1 night in Apr 2025

6/10 Okay

Niurka

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

4/10 Poor

Tanya

Disliked: Staff & service, property conditions & facilities
The motel is quite old and run down. The king suite with walk out to the beach; isn’t really a walk out to the beach at all - instead you are facing the boat ramp. The futon is so uncomfortable that it shouldn’t be considered an option for an extra place to sleep. My kids couldn’t sleep all night which was also due to the neighboring room being very loud late into the night.
Stayed 1 night in Jul 2025

6/10 Okay

Cathy

Liked: Cleanliness, staff & service, property conditions & facilities
Wouldn't do it again
Stayed 1 night in Jul 2025

10/10 Excellent

hevelin

Liked: Cleanliness, amenities, property conditions & facilities
The boat dock is a little rough to enter and exit especially on low tide.
Stayed 3 nights in May 2025

8/10 Good

Morayma P.

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

Nicole

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

Kim

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

Good price and clean

Great place. I enjoyed the beach area and how we could walk to a few good dive bars w live music. Very clean and included a kitchen snd good size shower. Only complaint would be the blinds did not close all the way and parking lot coyld see in at night.
Stayed 1 night in Apr 2025

10/10 Excellent

Tom

Liked: Cleanliness, staff & service, property conditions & facilities
Great staff. Very clean and wonderful waterfront setting.
Stayed 2 nights in Feb 2025

10/10 Excellent

Judith

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was very nice.
Stayed 2 nights in Jan 2025

10/10 Excellent

Da

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

10/10 Excellent

jose

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