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Top Luxury Islamorada Hotels

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

8 min drive from Theater of the Sea

Cheeca Lodge & Spa is a Islamorada luxury 5-star beach property where you can treat yourself to Champagne service, massage services, and more. The 2 poolside ...

9.2/10 Wonderful! (1,319 reviews)

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Reviewed on 2026/4/29

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

12 min drive from Theater of the Sea

Amara Cay Resort is a Islamorada luxury 4-star beach property where you can treat yourself to pillowtop beds, Egyptian cotton sheets, and more. Notable amenities ...

8.8/10 Excellent! (1,270 reviews)

We had the most amazing stay at Amara Cay in Islamorada for our honeymoon! From the moment we arrived, everything felt effortless, relaxing, and truly special. The property is absolutely beautiful—clean, modern, and perfectly captures that laid-back luxury island vibe. The rooms were comfortable ...

Reviewed on 2026/4/29

Drop Anchor

84959 Overseas Highway, 222 Islamorada FL

8 min walk from Theater of the Sea

Discover luxurious lodging at Drop Anchor, where you can enjoy amenities like plush bedding, premium channels, and more. Notable amenities include an outdoor ...

8.8/10 Excellent! (1,000 reviews)

Our room was comfortable and clean. The grounds and pool were really nice. The entire staff were awesome. It was really cool having the kayaks on the property. We had a great stay.

Reviewed on 2026/4/26

See all 2,211 properties in Islamorada

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.