Drop Anchor

Islamorada beach hotel with outdoor pool

Choose dates to view prices

Where to?

Dates

October 2025

November 2025

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 | 1 bedroom, premium bedding, individually decorated

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.

Excellent

Popular amenities

Connecting rooms available
Pet friendly
Pool
Air conditioning
Free parking
Free WiFi

Main amenities (12)

Daily housekeeping
Private beach
Outdoor pool
Free use of bicycles
Beach umbrellas
Beach sun loungers
Beach towels
Business center
Coffee/tea in a common area
Air conditioning
Garden
Front-desk safe

Feel at home (6)

Connecting/adjoining rooms available
Private bathroom
Premium TV channels
Garden
Daily housekeeping
Coffee/tea maker

$152 nightly

Oct 12 - Oct 13

Total with taxes and fees

Room options

Check availability for these dates

Tonight

Oct 10 - Oct 11

Tomorrow

Oct 11 - Oct 12

All rooms

1 bed

2 beds

3+ beds

Showing 11 of 11 rooms

Ocean View Double Queen w/ Kitchen & Private Balcony

Exceptional

Highlights

Balcony

Individually furnished

Individually decorated

Air conditioning

Connecting rooms available

Kitchen

Flat-screen TV

Separate bedroom

Sleeps 4
2 Queen Beds

Oceanfront Trailer

Very good

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

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

1 bedroom, premium bedding, individually decorated

Oceanfront King Suite w/ Kitchen & Private Balcony

Exceptional

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

Ocean View Double Queen Room

Excellent

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

Resort View Family Suite w/ Kitchen

Good

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

Resort View Queen Room w/ Kitchen & Private Porch

Exceptional

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

Oceanfront Queen Room

Highlights

Individually furnished

Individually decorated

Air conditioning

Connecting rooms available

Mini-fridge

Flat-screen TV

Separate bedroom

Ceiling fan

Ocean view
Sleeps 2
1 Queen Bed

Oceanfront King Suite w/ Beach Walkout & Kitchen

Exceptional

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

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

Resort View Queen Family Suite w/ Kitchen

Exceptional

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

Similar properties

Private beach, white sand, sun loungers, beach towels

Pool
Free breakfast
Pet friendly
Free WiFi

$192 nightly

Oct 14 - Oct 15

Total with taxes and fees

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About the neighborhood

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
‪Hog Heaven - ‬7 min walk
‪Wahoo's Bar & Grill - ‬2 min drive
‪Starbucks - ‬15 min walk
‪Whale Harbor Buffet - ‬2 min drive

About this property

Drop Anchor

Situated by the ocean, Drop Anchor is a great choice for a stay in Islamorada. Guests can enjoy the outdoor pool, along with onsite kayaking. Other highlights at this Art Deco hotel include free bike rentals and a garden. Fellow travelers love the helpful staff.

At a glance

Hotel size

- 18 rooms
- Arranged over 2 floors

Arriving/Leaving

- 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 time is 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

Required at check-in

- Credit card, debit card, or cash deposit required for incidental charges
- Government-issued photo ID may be required
- Minimum check-in age is 18

Children

- No cribs (infant beds)

Pets

- Pets allowed (dogs only)*
- Service animals welcome

Internet

- Free WiFi in public areas
- Free WiFi in rooms

Parking

- Free onsite self parking
- Onsite parking includes off-street options

Other information

- Designated smoking areas

Property amenities

Food and drink

Coffee/tea in a common area
Barbecue grills

Traveling with children

Paddleboard on site

What to do

Kayaking
Motor boating
Paddleboard on site
Private beach nearby
Ecotours nearby
Hiking/biking trails nearby
Parasailing nearby
Scuba diving nearby
Scooter/moped rentals nearby

Working away

Business center

Services

Front desk (limited hours)
Wedding services
Free bicycle rentals
Beach sun loungers
Beach towels
Beach umbrellas
Pool loungers
Paddleboard on site

Facilities

6 buildings/towers
Built in 1963
Safe-deposit box at front desk
Garden
Picnic area
An outdoor pool
Banquet hall
Dock
Walkway to water
Art Deco architecture

Accessibility

Upper floors accessible by stairs only
Well-lit path to entrance
Stair-free path to entrance

Room amenities

Be entertained

Flat-screen television
Premium cable channels

Home comfort

Air conditioning
Ceiling fan
Coffee/tea maker
Iron/ironing board

Sleep well

Premium bedding

What to enjoy

Individually furnished and decorated

Freshen up

Private bathroom
Shower only
Free toiletries
Hair dryer
Towels

Stay connected

Free WiFi

Daily housekeeping
Connecting/adjoining rooms available

Fees & policies

Mandatory fees

You'll be asked to pay the following charges by the property at check-in or check-out. Fees may include applicable taxes:

Resort fee: USD 35 per accommodation, per night

Resort fee inclusions:

Beach access
Beach loungers
Beach towels
Housekeeping
In-room coffee
Pool access

Pets

Service animals exempt from fees
Pets are allowed for an extra charge of USD 25 per pet, per day

Pool, spa, & gym (if applicable)

Pool access available from 7:30 AM to 6:30 PM

Policies

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.

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.

This property does not have elevators.

Guests can rest easy knowing there's a carbon monoxide detector, a fire extinguisher, and a smoke detector on site.

This property accepts credit cards, debit cards and cash.

Credit cards accepted: Visa, Mastercard, American Express, Discover

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Frequently asked questions

Is there a pool at Drop Anchor?

Yes, there's an outdoor pool. Guests have pool access from 7:30 AM to 6:30 PM.

Are pets allowed at Drop Anchor?

Yes, dogs are welcome. There's a charge of USD 25 per pet, per day. Service animals are exempt from fees.

Is parking offered on site at Drop Anchor?

Yes, there's free self parking.

What are the check-in and check-out times at Drop Anchor?

Check-in start time: 3:00 PM; Check-in end time: 6:00 PM. Check-out time is 11 AM. Contactless check-out is available.

What is there to do at Drop Anchor and nearby?

Have fun with onsite activities like kayaking, cycling, and motor boating. Additional recreation nearby includes ecotours. Enjoy a swim in the outdoor pool or use the hotel's other amenities, which include a picnic area and a garden.