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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! (1,288 reviews)

Overall our stay was fabulous. Some small gripes are the shower heads were built up with mineral deposits and didn’t spray properly and there was a leak in our ceiling above the toilet. However it is a beautiful resort. Lots of amenities, fun for the whole family

Reviewed on 2026/1/11

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! (1,260 reviews)

This resort exceed our expectations. Wonderful for families , very clean and amazing staff. We did a free fishing lesson with captain Patrick and he was wonderful-also great with kids. Loved the free water taxi to visit the sister resorts . We will definitely be back

Reviewed on 2026/1/10

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 ...

8.6/10 Excellent! (1,000 reviews)

The staff was personable, great location, having the bicycles and kayaks were a great touch

Reviewed on 2026/1/1

See all 2,213 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.