Drop Anchor Resort & Marina – Islamorada Resort Review
Last updated: August 28, 2026
Choose Drop Anchor Resort & Marina if...
- You're an angler wanting marina dock access with direct Florida Bay backcountry fishing
- You're a couple wanting a quiet waterfront cottage with kitchen and bay views
- You're a boater needing on-site marina slips near Islamorada's fishing grounds
Skip Drop Anchor Resort & Marina if...
- You want a private beach — Drop Anchor is bayside with marina access, not beachfront
- You expect on-site dining, pool bar, spa, or fitness center
- You want organized kids' programs — the property is small and independent
AskTheKeys Traveler Match
How well does Drop Anchor Resort & Marina fit your trip?
Before you book — the one trade-off
Drop Anchor is a classic marina-cottage property — you get dock access and bay character, but no beach, dining, or resort amenities.
AskTheKeys Decision SummaryDrop Anchor Resort & Marina is best for anglers, boaters, and couples wanting a classic Florida Keys marina cottage property with dock access, waterfront views, and a laid-back atmosphere in Islamorada at mid-range pricing. It is not ideal for guests wanting a private beach, full-service amenities, or modern design.
Choose Drop Anchor if you're an angler wanting marina dock access with direct backcountry fishing. Skip it if you want a private beach, on-site dining, or resort amenities.
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Before You Book
The details that matter after you've narrowed down your options.
Best for
- Anglers wanting marina dock access with boat slips and direct Florida Bay backcountry fishing
- Couples seeking a quiet waterfront cottage with kitchen, private porch, and bay views
- Boaters needing on-site marina slips with easy access to Islamorada's fishing grounds
- Repeat Keys visitors who prefer classic cottage character over modern resort design
Not ideal for
- Guests wanting a private beach — Drop Anchor is bayside with marina access, not beachfront
- Travelers expecting on-site dining, pool bar, spa, or fitness center — none are available on-property
- Families wanting organized kids' programs or resort-scale activities — the property is small and independent
Quick facts
| Address | 84959 Overseas Highway, Islamorada, FL 33036 |
|---|---|
| Phone | (305) 664-4863 |
| Check-in / Out | 3:00 PM / 11:00 AM |
| Parking | On-site (complimentary) |
| Pets | Yes (fee may apply) |
| Beach access | No |
| Pool(s) | Yes |
| Spa | No |
| EV charging | No |
Location & nearby
Drop Anchor Resort & Marina is located in Windley Key within Islamorada.
What's nearby
- Theater of the Sea(0.3 mi, 6 min walk)
- Whale Harbor Channel(1.5 mi, 30 min walk)
- Islamorada Fish Company(2 mi, 40 min walk)
- Robbie's Marina (Tarpon Feeding)(4 mi, 80 min walk)
- History of Diving Museum(1 mi, 20 min walk)
- Bud N' Mary's Marina(2.5 mi, 50 min walk)
- Founders Park(3.5 mi, 70 min walk)
- Hurricane Monument(2 mi, 40 min walk)
Amenities overview
Property highlight features
- On-site marina with boat slips
- Waterfront cottages with full kitchens
- Private porches with bay views
- Heated freshwater pool
- Pet-friendly accommodations
- Complimentary on-site parking
Pricing positioning
Typical nightly pricing tends to fall in the $$ range, depending on season and room type.
mid-range classic marina cottage property
Compare current room availability and secure member-only pricing.
We handle our lodging checks through Expedia's network engine so you can lock in hidden seasonal discounts and stack your One Key™ rewards points across different island brands.
Independent Decision Engine
Florida Keys Resorts operates as a fully objective, crowdsourced review system. We do not accept paid placements from hotels to alter their scoring records. Instead, we use standardized API connections to provide transparent third-party rate checks for our community.
How Drop Anchor Resort & Marina Compares to Other Islamorada Resorts
Drop Anchor Resort & Marina vs Three Waters Resort & Marina
- Drop Anchor Resort & Marina wins:classic bayside marina cottages with full kitchens, pet-friendly policy, and old-school Keys character
- Three Waters Resort & Marina wins:214-room oceanfront marina resort with 72 slips, nine dining venues, three beaches, swim-up bar, and The Cove adults-only retreat
Drop Anchor Resort & Marina vs Chesapeake Beach Resort
- Drop Anchor Resort & Marina wins:bayside marina cottage property with boat slips, pet-friendly policy, and self-catering kitchens
- Chesapeake Beach Resort wins:oceanfront lodge with private Atlantic beach, fishing dock, and villa options near Whale Harbor
Drop Anchor Resort & Marina vs Cheeca Lodge & Spa
- Drop Anchor Resort & Marina wins:small-scale marina cottages with classic Keys character, pet-friendly policy, and mid-range rates
- Cheeca Lodge & Spa wins:flagship luxury resort with spa, golf, private beach, fine dining, and comprehensive family programming
FAQs
Does Drop Anchor have a marina?
Yes. Drop Anchor Resort & Marina operates an on-site marina with boat slips and direct bayside access to Florida Bay. The marina provides access to Islamorada's backcountry flats fishing and offshore charter grounds.
Does Drop Anchor have a beach?
No. Drop Anchor is a bayside marina property without a private beach. The nearest public beach access is at Founders Park (3.5 miles) or Anne's Beach (7 miles). Guests wanting beachfront should consider Chesapeake Beach Resort or Islander Resort.
Does Drop Anchor have a restaurant?
No. There is no on-site restaurant or bar. All cottages have full kitchens for self-catering. Islamorada Fish Company, Whale Harbor Seafood, and other restaurants are within a 2–4 mile drive.
What types of accommodations does Drop Anchor offer?
Drop Anchor offers individual waterfront cottages with full kitchens, private porches, and direct bay views. Units are standalone — no shared corridors or hotel towers. The layout provides a residential cottage feel with marina access steps away.
Is Drop Anchor pet-friendly?
Yes. Drop Anchor welcomes pets in designated cottages. The waterfront grounds and cottage layout give pets outdoor space. It is one of three pet-friendly Islamorada properties alongside Cheeca Lodge & Spa and Islander Resort.
Is Drop Anchor good for fishing?
Yes. Drop Anchor is one of Islamorada's most convenient fishing-access properties. The on-site marina provides direct access to Florida Bay backcountry flats, and charter fishing coordination is available. Bud N' Mary's Marina is within a 5-minute drive for offshore deep-sea trips.
How does Drop Anchor compare to Three Waters?
Drop Anchor is smaller, more traditional, and less expensive than Three Waters. Three Waters is a 214-room oceanfront resort with 72 marina slips, nine dining venues, three beaches, and a swim-up bar. Drop Anchor offers classic Keys cottages, a smaller marina, and a quieter, more residential atmosphere at lower rates.
Do you need a car at Drop Anchor?
Yes. Islamorada is car-dependent. Drop Anchor provides free on-site parking. Full kitchens in cottages reduce dining trips, but a car is needed for restaurants, groceries, beaches, and attractions beyond Theater of the Sea next door.