Meg's Keys — your three, compared 🐬

Islander, Baker's Cay and Three Waters — side by side. Worth knowing: Three Waters is Amex Fine Hotels + Resorts (the one with free breakfast + a guaranteed 4pm checkout); Islander and Baker's Cay are in Amex's Hotel Collection (a $100 credit + upgrade, but no breakfast or guarantee). Each card shows exactly what you get. Fly Delta into Miami, then a short, gorgeous drive.

✨ deep dive · real reviews · verified Amex programs

At a glance

Three WatersIslanderBaker's Cay
Amex programFine Hotels + ResortsHotel CollectionHotel Collection
Free breakfast✓ for two✗✗
Guaranteed 4pm out✓✗ (not guaranteed)✗ (not guaranteed)
$100 credit✓✓ (2+ nights)✓ (2+ nights)
Rating★4.6 (860)★4.5 (1570)★4.3 (3004)
From /night$$398$$448$$517
Drive from MIA~1.5 hr~1.5 hr~1 hr

The three, in detail

BEST VALUE · THE FHR ONEFreshly reimagined

Three Waters Resort & Marina

Islamorada · Marriott Tribute Portfolio
★ 4.6 · 860 reviewsfrom $$398/nt
🚗 ~1.5 hr from Miami (MM 84)

Pool. Oceanfront pool across 15 waterfront acres, spa + a full marina.

Wildlife. Sportfishing capital — tarpon, snorkel & eco-tours from the marina; Theater of the Sea and Robbie's tarpon-feeding minutes away.

Vibe. Newly reimagined, island-chic, nine dining spots — lively but refined.

💬 What guests say. Highest rating of the three (4.6). Reviewers rave about service and the food.

Amex Fine Hotels + Resorts
  • 🍳 Free daily breakfast for two
  • 💵 $100 property credit
  • ⬆️ Room upgrade (when available)
  • 🕓 Guaranteed 4pm checkout
See it & reviews →
SPACE + A REAL BEACHClassic laid-back Keys

Islander Resort, a Guy Harvey Outpost

Islamorada · 24 oceanfront acres
★ 4.5 · 1570 reviewsfrom $$448/nt
🚗 ~1.5 hr from Miami (MM 82)

Pool. Two pools + a saltwater lagoon and a rare private sandy beach.

Wildlife. Guy Harvey marine-conservation vibe; dolphins & sea lions at Theater of the Sea and tarpon at Robbie's up the road.

Vibe. Spacious, easygoing, kitchenettes in many rooms, golf — room to breathe.

💬 What guests say. Guests love the dining, bar and breakfast; steady 4.5 across 1,570 reviews.

Amex The Hotel Collection
  • 💵 $100 credit (stays of 2+ nights)
  • ⬆️ Room upgrade (when available)
  • — no free breakfast
  • — 4pm checkout not guaranteed
See it & reviews →
NATURE + REEFWrapped in a nature preserve

Baker's Cay Resort

Key Largo · Curio Collection by Hilton
★ 4.3 · 3004 reviewsfrom $$517/nt
🚗 ~1 hr from Miami (MM 104) — closest

Pool. Two pools + hot tub, private beach, set in a tropical hardwood hammock.

Wildlife. Next to John Pennekamp — snorkel the only living coral reef in the US; manatees & tarpon in the marina, birds & mangroves on-site.

Vibe. Upscale and nature-immersed, and the closest to the airport.

💬 What guests say. By far the most reviewed (3,004) — reviewers single out the NATURE (554 mentions) and service.

Amex The Hotel Collection
  • 💵 $100 credit (stays of 2+ nights)
  • ⬆️ Room upgrade (when available)
  • + earns Hilton Honors points
  • — no free breakfast / no guaranteed checkout
See it & reviews →

Wullie's take 🪣

🏆 Best all-round + best Amex value: Three Waters — the highest rating (4.6), the freshest look, the friendliest price, AND the only one of the three in Fine Hotels + Resorts, so it's the one where you actually get free breakfast and the guaranteed 4pm checkout.

🐢 If wildlife's the point: Baker's Cay — reviewers mention the nature above all, it's by the coral reef, closest to Miami. (Hotel Collection, so a $100 credit + upgrade, no breakfast.)

🏖️ Most space + a real sandy beach: Islander. (Also Hotel Collection.)

Tell me your dates and your favourite and I'll price it with the Amex benefits applied and hold the room.

Amex programs verified against American Express's own listings (Jul 2026); the definitive check is your Amex Travel account. Fine Hotels + Resorts & Hotel Collection benefits apply only when booked through Amex Travel.