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Drop Anchor

3.0 star property
Islamorada beach hotel with outdoor pool

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Photo gallery for Drop Anchor

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
Exterior
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

  • Connecting rooms available
  • Pool
  • Pet friendly
  • 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
$130 nightly
The total price is $142
Oct 1 - Oct 2
Total with taxes and fees

Room options

Check availability for these dates

Tonight

Sep 30 - Oct 1
Check availability for tonight Sep 30 - Oct 1

Tomorrow

Oct 1 - Oct 2
Check availability for tomorrow Oct 1 - Oct 2
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 | 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
  • 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 | 1 bedroom, premium bedding, individually decorated

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 | 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
  • 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 | 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
Ceiling fan
  • Sleeps 4
  • 2 Queen Beds

View all photos for Oceanfront Queen Room

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
Ceiling fan
Premium bedding
  • Ocean view
  • Sleeps 2
  • 1 Queen Bed

View all photos for Resort View ADA King Room

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

Resort View Queen Room w/ Kitchen & Private Porch | 1 bedroom, premium bedding, individually decorated

Resort View Queen Room w/ Kitchen & Private Porch

9.6 out of 10
Exceptional
(7 reviews)

Highlights

Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Kitchen
Full-sized refrigerator/freezer
Flat-screen TV
Ceiling fan
  • 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 | Coffee/tea maker

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 | 1 bedroom, premium bedding, individually decorated

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
Ceiling fan
  • 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
Separate bedroom
  • 2 bedrooms
  • Ocean view
  • Sleeps 6
  • 1 King Bed, 2 Twin Beds and 1 Queen Futon

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9.2 out of 10, Wonderful, 1,544 reviews
$165 nightly
The price is $186
Oct 2 - Oct 3
Total with taxes and fees
Chesapeake Beach Resort
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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

  • ‪Tiki Bar - ‬18 min walk
  • ‪Hog Heaven - ‬7 min walk
  • ‪Starbucks - ‬15 min walk
  • ‪Whale Harbor Buffet - ‬2 min drive
  • ‪Wahoo's Bar & Grill - ‬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

DONE

Hotel size

    • 18 rooms
    • Arranged over 2 floors
DONE

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
DONE

Special check-in instructions

    • The front desk is open daily from 8:00 AM - 8:00 PM
    • Front desk staffed during limited hours
DONE

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
DONE

Children

    • No cribs (infant beds)
DONE

Pets

    • Pets allowed (dogs only)*
    • Service animals welcome
WIFI

Internet

    • Free WiFi in public areas
    • Free WiFi in rooms
LOCAL_PARKING

Parking

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

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

More

  • 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

Also known as

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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.

What's the area around Drop Anchor like?

Drop Anchor is located on the waterfront, a short 4-minute walk from Windley Key Fossil Reef Geological State Park.

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