Drop Anchor rates, Islamorada

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Dates and guests	Current price	Customer link
Nov 13 to Nov 15, 2026 · 2 nights · 2 adults	Get current price for this stay	Customer link — Open hotel details
Nov 20 to Nov 22, 2026 · 2 nights · 2 adults	Get current price for this stay	Customer link — Open hotel details
Dec 8 to Dec 10, 2026 · 2 nights · 2 adults	Get current price for this stay	Customer link — Open hotel details
Dec 11 to Dec 13, 2026 · 2 nights · 2 adults	Get current price for this stay	Customer link — Open hotel details
Dec 25 to Dec 28, 2026 · 3 nights · 3 adults	Get current price for this stay	Customer link — Open hotel details
Jan 8 to Jan 10, 2027 · 2 nights · 2 adults	Get current price for this stay	Customer link — Open hotel details

Axel's take: 8.0/10

Strong on waterfront atmosphere, but choose your room carefully. a retro 3-star oceanfront motel and marina, scored for what it is.

Drop Anchor is a retro 3-star oceanfront motel and marina, not a full-service resort. We'd pick it for a relaxed Keys break: the waterfront pool, colorful grounds and kitchen-equipped suites give it more personality than a standard roadside stop. Expedia and Booking.com guests broadly praise the setting, cleanliness and friendly staff, with recent reviews reinforcing those strengths.

The main catch is inconsistency between rooms. Tripadvisor and Expedia reports flag dated interiors, plumbing problems and occasional mismatches between the accommodation expected and received. Those complaints don't outweigh the largely positive overall picture, but they make confirming the exact layout, view and kitchen worthwhile. Factor in the mandatory resort fee and arrange late arrival ahead of time. We'd skip it if you want polished, uniform rooms and round-the-clock service.

Best for: couples seeking old-Florida atmosphere; boaters and paddlers; families booking kitchen suites
Watch out for: uneven room condition and layouts; mandatory nightly resort fee; limited front-desk hours
Location: Oceanfront on Windley Key, with a few restaurants within walking distance.
Rooms: Retro rooms and kitchen suites; confirm the precise view and layout before booking.
Cleanliness: Strong overall guest ratings, though some recent reviews report housekeeping and maintenance lapses.
Service: Friendly staff earn repeated praise; problem resolution draws more mixed feedback.
Amenities: Waterfront outdoor pool, kayaks, paddleboards, bicycles, grills and free self-parking.
Fees and surprises: Mandatory resort fee and extra pet charges; arrange late check-in directly.

Axel's opinion of Drop Anchor, from the hotel's website and recent guest reviews. Sources: Hotel website · Expedia · Booking.com · Tripadvisor. Reviewed Oct 23, 2026.

About Drop Anchor

Property type: Hotel
3-star hotel
84959 Overseas Highway, 222, Islamorada
Amenities: Smoking areas, Garden, Reception desk, Family room, Accessibility features, Safe-deposit box, Coffee/tea for guests, Vending machine, Free Wi-Fi, English, Barbecue grill(s), Hiking
Check-in from: 15:00:00
Check-out by: 11:00:00
City page: Hotels in Islamorada

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3-star hotel · 84959 Overseas Highway, 222, Islamorada

Check-in from 15:00:00 · Check-out by 11:00:00

Smoking areas · Garden · Reception desk · Family room · Accessibility features · Safe-deposit box · Coffee/tea for guests · Vending machine · Free Wi-Fi · English · Barbecue grill(s) · Hiking

Hotels in Islamorada

Axel's take

a retro 3-star oceanfront motel and marina

8.0/10

Strong on waterfront atmosphere, but choose your room carefully.

Best for

couples seeking old-Florida atmosphere
boaters and paddlers
families booking kitchen suites

Watch out for

uneven room condition and layouts
mandatory nightly resort fee
limited front-desk hours

Location: Oceanfront on Windley Key, with a few restaurants within walking distance.
Rooms: Retro rooms and kitchen suites; confirm the precise view and layout before booking.
Cleanliness: Strong overall guest ratings, though some recent reviews report housekeeping and maintenance lapses.
Service: Friendly staff earn repeated praise; problem resolution draws more mixed feedback.
Amenities: Waterfront outdoor pool, kayaks, paddleboards, bicycles, grills and free self-parking.
Fees and surprises: Mandatory resort fee and extra pet charges; arrange late check-in directly.

Axel's opinion, from the hotel's website and recent guest reviews, scored for what the hotel is. Sources: Hotel website · Expedia · Booking.com · Tripadvisor. Reviewed Oct 23, 2026.

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