Pros

  • Heated, oceanfront pool shaded by palm trees
  • Boat launch and fishing pier for guests
  • Rooms include AC, flat-screen TVs, and coffeemakers with Green Mountain coffee
  • Some rooms have private patios or balconies, full kitchens, and ocean views
  • Picnic area and barbecue grills on-site
  • Free in-room Wi-Fi
  • Free self-parking
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Cons

  • No swimming allowed on the beach
  • No on-site restaurant, bar, or breakfast service
  • Room decor dated, and rooms show wear and tear
  • No fitness facilities
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Bottom Line

The two-and-a-half pearl, 18-room Drop Anchor Resort is located on Windley Key in Islamorada, "the fishing capital of the world." The resort, very much in the laid-back "Old Keys" style, includes a man-made beach surrounded by thatched-roof umbrellas, hammocks, palm trees, loungers, picnic tables, and Adirondack chairs, but the area is for boat launching and docking, not swimming. But there's a heated pool overlooking the waterfront, shaded by lush palm trees. Rooms are spread over several one- and two-story pastel-painted buildings, and include air-conditioning, free Wi-Fi, flat-screen TVs with premium channels, and coffeemakers. Some have full kitchens, private balconies or patios, and ocean views, but they're no-frills and decor is dated. Travelers might want to check rates at the Sands of Islamorada, a seven-minute drive from Drop Anchor, which offers similar amenities plus a hot tub.

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Oyster Hotel Review

Drop Anchor

Scene

"Old Keys" ambience with landscaped grounds and outdoor pool

This "Old Keys" resort has manicured, landscaped grounds with aromatic jasmine and gardenia and colorful bougainvillea, along with various native trees and other tropical plants. Most of the property is situated under a canopy of several coconut palms, which offer shade to the outdoor pool area. The beach leads  to the ocean-side dock, and a boat ramp and dockage are available to guests. Drop Anchor has no lobby or lounge -- the reception desk is in a small room with a soda machine in the corner, which leads to another room with sightseeing brochures and a convenience store with drinks, snacks, souvenirs, and free Green Mountain Coffee. Drop Anchor is in no way fancy, and there's no private beach for swimming. But it draws couples attracted to its laid-back vibe, families, and those serious about fishing.

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Location

At MM85 on Windley Key in Islamorada

Located in Islamorada, home to back-country fishing, the Drop Anchor is a four-minute walk to Windley Key Fossil Reef Geological State Park, which showcases the botany and geology of the Florida Keys, as well as its vast slabs frozen in stone. The History of Diving Museum, a three-minute drive from the hotel, features exhibitions and events all relating to diving. The Theater of the Sea, a seven-minute walk, hosts dolphin and sea lion shows, along with a chance to swim with them. Lignumvitae Key Botanical State Park is a 12-minute drive, and Founders Park is a five-minute drive. Founders is a huge public area that’s great for outdoor activities; it includes a marina, boat ramps, beaches, a baseball field, an Olympic-size pool, and a skate park. Restaurants are within walking distance or a short car trip, including Hog Heaven Sports Bar and Grill, which has a dance club, outdoor waterside seating, and a menu of classic pub food, and Ziggie & Mad Dog's, known for its steaks, chops, and local seafood served in a sports-bar setting. Jaws Raw Bar, a 13-minute walk, has a wooden terrace overlooking the lush water. Florida Keys Marathon Airport Is a 40-minute drive from the hotel, and Key West is a little under two hours away by car.

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Rooms

Rooms range from Standard to Suites with private patios or terraces, and full kitchens

The Drop Anchor's 18 rooms come with one to three beds, and some have balconies overlooking the ocean, or patios with gardens. Some rooms include heavy-wood wardrobes and matching elegant desks, and common areas with dining tables and chairs. Other, more stylish rooms have bedrooms with wood paneling or red-accent walls, with pulled-back curtains separating them from the living area. Two-bedroom units come with full-size kitchens. Connecting rooms are possible for groups or families. Standard amenities include flat-screen TVs, coffeemakers, and free Wi-Fi, and those without kitchens have mini-fridges. Decor has begun to show some wear and tear, especially in the kitchens. Bathrooms, with their kitschy coral or Pepto-Bismol-pink tiles, could especially use an update; all have toiletries, hairdryers, and shower stalls or shower/tub combos.

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Features

Guests come to dock their boats, not swim in the ocean

The Drop Anchor Resort has a heated outdoor pool, a marina, and free self-parking, but there's no swimming on the beach -- the waterfront area is strictly for boat launching and dockage, and taking in the views. Guests can fish right from the pier, and charter fishing excursions and in-room massages can be arranged for a fee. There are barbecue grills and a picnic area on-site, but no fitness facilities, bar, coffee shop, or restaurant on-site. Free Wi-Fi is available in the rooms.

See More Features

Oyster Hotel Review

Drop Anchor

Scene

"Old Keys" ambience with landscaped grounds and outdoor pool

This "Old Keys" resort has manicured, landscaped grounds with aromatic jasmine and gardenia and colorful bougainvillea, along with various native trees and other tropical plants. Most of the property is situated under a canopy of several coconut palms, which offer shade to the outdoor pool area. The beach leads  to the ocean-side dock, and a boat ramp and dockage are available to guests. Drop Anchor has no lobby or lounge -- the reception desk is in a small room with a soda machine in the corner, which leads to another room with sightseeing brochures and a convenience store with drinks, snacks, souvenirs, and free Green Mountain Coffee. Drop Anchor is in no way fancy, and there's no private beach for swimming. But it draws couples attracted to its laid-back vibe, families, and those serious about fishing.

See More Scene

Location

At MM85 on Windley Key in Islamorada

Located in Islamorada, home to back-country fishing, the Drop Anchor is a four-minute walk to Windley Key Fossil Reef Geological State Park, which showcases the botany and geology of the Florida Keys, as well as its vast slabs frozen in stone. The History of Diving Museum, a three-minute drive from the hotel, features exhibitions and events all relating to diving. The Theater of the Sea, a seven-minute walk, hosts dolphin and sea lion shows, along with a chance to swim with them. Lignumvitae Key Botanical State Park is a 12-minute drive, and Founders Park is a five-minute drive. Founders is a huge public area that’s great for outdoor activities; it includes a marina, boat ramps, beaches, a baseball field, an Olympic-size pool, and a skate park. Restaurants are within walking distance or a short car trip, including Hog Heaven Sports Bar and Grill, which has a dance club, outdoor waterside seating, and a menu of classic pub food, and Ziggie & Mad Dog's, known for its steaks, chops, and local seafood served in a sports-bar setting. Jaws Raw Bar, a 13-minute walk, has a wooden terrace overlooking the lush water. Florida Keys Marathon Airport Is a 40-minute drive from the hotel, and Key West is a little under two hours away by car.

See More Location

Rooms

Rooms range from Standard to Suites with private patios or terraces, and full kitchens

The Drop Anchor's 18 rooms come with one to three beds, and some have balconies overlooking the ocean, or patios with gardens. Some rooms include heavy-wood wardrobes and matching elegant desks, and common areas with dining tables and chairs. Other, more stylish rooms have bedrooms with wood paneling or red-accent walls, with pulled-back curtains separating them from the living area. Two-bedroom units come with full-size kitchens. Connecting rooms are possible for groups or families. Standard amenities include flat-screen TVs, coffeemakers, and free Wi-Fi, and those without kitchens have mini-fridges. Decor has begun to show some wear and tear, especially in the kitchens. Bathrooms, with their kitschy coral or Pepto-Bismol-pink tiles, could especially use an update; all have toiletries, hairdryers, and shower stalls or shower/tub combos.

See More Rooms

Features

Guests come to dock their boats, not swim in the ocean

The Drop Anchor Resort has a heated outdoor pool, a marina, and free self-parking, but there's no swimming on the beach -- the waterfront area is strictly for boat launching and dockage, and taking in the views. Guests can fish right from the pier, and charter fishing excursions and in-room massages can be arranged for a fee. There are barbecue grills and a picnic area on-site, but no fitness facilities, bar, coffee shop, or restaurant on-site. Free Wi-Fi is available in the rooms.

See More Features

Best Rates

Amenities

  • Air Conditioner

  • Balcony / Terrace / Patio

  • Basic Television

  • Cabanas

  • Cable

  • Concierge

  • Cribs

  • Full Kitchen

  • Internet

  • Kids Allowed

  • Pool

  • Poolside Drink Service

  • Rental Car Service Desk Onsite

  • Separate Bedroom / Living Room Space

  • Swim-Up Bar

Disclaimer: This content was accurate at the time the hotel was reviewed. Please check our partner sites when booking to verify that details are still correct.