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Three Waters Resort and Marina Islamorada, Florida
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Hotel comparison guide

Three Waters Resort and Marina vs Drop Anchor

Three Waters Resort and Marina is a large, modern Tribute Portfolio marina resort in Islamorada with multiple pools, a full-service marina and a mix of family and adults-only spaces; read this if you want a full-service Keys resort with lots of on-site dining and water activities. Drop Anchor is a small, retro-style Islamorada beachfront motel-resort; read this if you prefer a compact, beachfront, no-frills stay with direct beach access and local character.

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Aerial view of Three Waters Resort and Marina pool, decks and oceanfront shoreline.

Three Waters Resort and Marina

Large marina resort · Many dining options · Family‑and‑adults mix

Best for travelers who want extensive on-site dining, multiple pools and a full-service marina for boating or fishing charters.

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Drop Anchor, Islamorada, Florida

Drop Anchor

Retro beachfront motel-resort · Small handful of rooms · Laid-back, local vibe

Best for travelers who want a small, beachfront, retro-style stay with direct water access and a compact set of amenities.

Quick Verdict: Three Waters Resort and Marina vs Drop Anchor

When Three Waters Resort and Marina wins: choose Three Waters if you want variety — multiple restaurants and bars, three year-round pools including an adults-only Cove, a 72-slip marina and more on-site programming and facilities for families and groups.

When Drop Anchor wins: choose Drop Anchor if you want a low-rise, small-property beach stay in Islamorada with an easy waterfront location, a single outdoor pool, and rooms named for oceanfront access and simple kitchens.

Bottom line: Three Waters is the choice for a full-service, larger-resort experience and boating/fishing access; Drop Anchor is the choice for a small, retro beachfront motel feel and straightforward waterfront lodging.

Call +1 (888) 605-1350Book Three Waters Resort and Marina

Three Waters Resort and Marina vs Drop Anchor – At a Glance

Side-by-side facts for Three Waters Resort and Marina and Drop Anchor
CategoryThree Waters Resort and MarinaDrop Anchor
Overall vibeResort-scale, marina-focused with modern Tribute Portfolio branding and many on-site venuesRetro-style, beachfront motel-resort with a local, come-as-you-are character
Location84001 Overseas Highway, Islamorada (15 waterfront acres, mile marker 84)84959 Overseas Highway, 222, Islamorada (waterfront address on Overseas Highway)
Size (rooms)214 rooms, suites, and cottages18 rooms
Audience / age policyAll ages overall; The Cove is a 21+ adults-only enclaveAll ages (not adults-only)
PoolsThree year-round pools (including an adults-only Cove pool and a swim-up Kokomo bar)1 outdoor pool
Restaurants & barsMultiple on-site options including Kindler Wood-Fired Fare (signature), Little Limón rooftop, Tiki Bar, Kokomo swim-up bar, Mercado Morada and moreNot published
Spa / wellnessOceanside massages and open-air fitness options (including Wave Motion Studio)Not published
Marina / boatingFull-service marina with 72 slips, fishing charters and water taxi access to sister propertiesDock and marina nearby; boating and motor-boat activity listed as on-site/nearby
BeachPrivate beaches (multiple), including a walk-in Cove beach for adultsPrivate beach nearby and direct waterfront access
Wi‑Fi & parkingFree Wi‑Fi in rooms/public areas; resort fee includes enhanced Wi‑Fi and self-parkingFree WiFi and free self parking on site

A Look Inside Three Waters Resort and Marina

Three Waters Resort and Marina: rooms & suitesRooms & suitesThree Waters Resort and Marina: pools & beachPools & beachThree Waters Resort and Marina: diningDiningThree Waters Resort and Marina: spa & wellnessSpa & wellness
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Location: Three Waters Resort and Marina vs Drop Anchor

Three Waters Resort and Marina – Location

Three Waters sits on 15 waterfront acres at mile marker 84 with easy access to Islamorada attractions and a full-service marina.

  • Address: 84001 Overseas Highway, Islamorada, FL 33036.
  • Close to Windley Key Fossil Reef Geological State Park and other local sights; Rum Runner water taxi connects to sister properties.
  • On-site marina and multiple private beaches; complimentary shuttle within a local radius.

Choose Three Waters for a larger waterfront property with marina access and easy links to nearby attractions.

Drop Anchor – Location

Drop Anchor is a small, waterfront motel-resort on the Overseas Highway with immediate beach access.

  • Address: 84959 Overseas Highway, 222, Islamorada, FL 33036.
  • Waterfront location near Windley Key Fossil Reef Geological State Park and other Islamorada points of interest.
  • Small property footprint that puts the water and local character close to your room.

Choose Drop Anchor if you want direct beachfront proximity in a compact, low-rise property.

Rooms: space, types and what to expect

Three Waters Resort and Marina – Rooms

Three Waters offers 214 rooms, suites and cottages across multiple room types, including Cove (21+) options.

  • Wide range of room types and sizes including suites and cottages; several Cove rooms are reserved for guests 21+.
  • Free Wi‑Fi in rooms; enhanced Wi‑Fi is part of the nightly resort fee.
  • Pet policy allows dogs with a $150 non-refundable fee (per room per stay) and a two-dog maximum.

Pick Three Waters for variety in room layouts and larger-suite or cottage choices, plus designated adults-only room options.

Drop Anchor – Rooms

Drop Anchor has 18 air-conditioned rooms with a mix of oceanfront and resort-view options, some with kitchens or balconies.

  • Room names include Oceanfront Queen Room; Oceanfront King Suite w/ Kitchen & Private Balcony; Oceanfront King Suite w/ Beach Walkout & Kitchen; and others.
  • Rooms include flat-screen TVs, complimentary WiFi, coffee/tea makers, daily housekeeping and private bathrooms with complimentary toiletries.
  • Some rooms offer kitchen facilities or private balconies and there are ADA-accessible room types listed.

Choose Drop Anchor for compact oceanfront rooms and suites (some with kitchens) when you want a simple, beach-oriented stay.

Dining & drinks: options and atmosphere

Three Waters Resort and Marina – Dining & drinks

Three Waters has a broad food-and-drink program with several distinct venues for different moods and occasions.

  • Signature restaurant: Kindler Wood-Fired Fare; rooftop Little Limón and waterfront Mercado Morada are other highlighted venues.
  • Casual options include Islamorada Pizza Co., Lucky Twist soft-serve and a swim-up Kokomo pool bar.
  • Hideaway offers a 21+ dining lounge inside The Cove; several venues host happy-hour promotions.

Three Waters is the pick for on-site dining variety — casual to elevated, plus multiple bars and an adults-only lounge.

Drop Anchor – Dining & drinks

Drop Anchor's supplier listing does not publish a roster of signature restaurants on site.

  • On-site amenities include coffee/tea in common areas and vending machines.
  • Room types include kitchen-equipped suites for guest self-catering in some cases.
  • Nearby dining and attractions are a short drive; Drop Anchor’s location is convenient to Islamorada restaurants.

Choose Drop Anchor if you plan to eat local or use in-room kitchens; the property itself is modest on on-site dining.

Pools & beach: what water access looks like

Three Waters Resort and Marina – Pools & beach

Three Waters provides beaches and three year-round pools with separate adult and family spaces.

  • Three outdoor pools: Kokomo (with swim-up bar), Overseas Pool, and The Cove (21+ adults-only) open year-round.
  • Multiple private beaches and beach amenities (loungers, umbrellas, towels) included in the resort fee.
  • Water activities and rentals are part of the resort fee or available on-site (kayaks, paddleboards, snorkeling).

Three Waters is best for guests who want multiple pool choices, family areas and a separate adults-only beach experience.

Drop Anchor – Pools & beach

Drop Anchor offers direct waterfront access, a private beachfront setting and one outdoor pool.

  • Private beach nearby and a single outdoor pool (listing shows number of outdoor pools = 1).
  • Property lists walkways to the water, a dock and fish-cleaning table for anglers.
  • Free beach umbrellas and sun loungers are noted in the amenities list.

Drop Anchor suits travelers who want simple beachfront access and a single pool rather than multiple resort pools.

Wellness & nightlife: relaxation and evening options

Three Waters Resort and Marina – Wellness & nightlife

Three Waters mixes wellness services with lively on-site nightlife options like live music at the Tiki Bar.

  • Oceanside massages and Ooh La La spa treatments are available; outdoor fitness center open early to late.
  • Tiki Bar hosts live music several evenings and Kindler/Little Limón offer evening dining and cocktails.
  • On-site nightlife ranges from the rowdier Tiki Bar to the quieter Hideaway 21+ lounge.

Three Waters fits guests who want both wellness services and an evening scene on property.

Drop Anchor – Wellness & nightlife

Drop Anchor focuses on a simpler, low-key stay; the supplier listing emphasizes waterfront recreation over formal wellness or nightlife facilities.

  • On-site recreation centers on water activities (snorkeling, paddleboarding, nearby scuba diving and fishing).
  • No dedicated spa or multiple evening venues are published in the supplier listing.
  • Close proximity to Islamorada bars and restaurants if you want an evening out.

Pick Drop Anchor if you prefer low-key evenings and getting off-property for most nightlife or spa services.

Who Wins? Best Pick by Travel Style

Best for boating and fishing
Three Waters Resort and Marina lobby seating area with green chairs and sculptural stone feature.

Three Waters Resort and Marina

Three Waters — full-service 72-slip marina and year-round fishing charters.

Best small beachfront motel experience
Drop Anchor, Islamorada, Florida

Drop Anchor

Drop Anchor — compact, retro-style beachfront property with direct water access.

Best on-site dining variety
Three Waters Resort and Marina lobby lounge with velvet chairs and wood display shelving.

Three Waters Resort and Marina

Three Waters — multiple restaurants and bars from wood-fired dining to a rooftop and swim-up bar.

Best for self-catered beachfront stays
Drop Anchor, Islamorada, Florida

Drop Anchor

Drop Anchor — several room types include kitchens or kitchenettes for in-room meals.

Frequently asked questions

Three Waters Resort and Marina vs Drop Anchor: FAQs

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Which property is better for families with kids?

Three Waters — it has multiple pools, family-friendly dining and activities; The Cove provides an adults-only option if needed.

Which is more budget-friendly or low-key?

Drop Anchor tends to be the lower-capacity, simpler option with basic on-site amenities and kitchen-equipped rooms for DIY meals.

Which property has a marina or better boating access?

Three Waters has a full-service marina with 72 slips and organized fishing charters; Drop Anchor lists a dock and nearby boating activity but not a full-service marina of that size.

Can I get spa services at both properties?

Three Waters publishes oceanside massage spa services; Drop Anchor’s supplier listing does not publish an on-site spa.

More Three Waters Resort and Marina Comparison Guides

Explore how Three Waters Resort and Marina stacks up against other hotels nearby:

Private pool cabana and loungers with ocean view at Three Waters Resort and Marina
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