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Top Romantic Islamorada Hotels

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

8 min drive from Theater of the Sea

Fall in love again at this upscale resort. You and your special someone are sure to love the hot tub, spa, and in-room massages. You'll also appreciate the ocean-view ...

9.2/10 Wonderful! (1,266 reviews)

Couples like: full-service spa, couples spa treatments, beachfront dining, hot tub

Travelers say...

Everything was awsome

Reviewed on 2025/12/7

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

22 min walk from Theater of the Sea

A private beach and premium mattresses await at this romantic hotel, which also offers 2 outdoor pools and a white sand beach.

9.2/10 Wonderful! (1,598 reviews)

Couples like: bar, on the beach

Travelers say...

The entire resort was wonderful.

Reviewed on 2025/12/17

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

12 min drive from Theater of the Sea

Ocean-view dining, a garden, and happy hours await visiting couples at this romantic resort. The property also offers a private beach and romance packages.

8.8/10 Excellent! (1,265 reviews)

Couples like: restaurant with ocean view, on the beach, romance packages available

Travelers say...

very nice staff, quiet and comfortable

Reviewed on 2025/12/10

See all 2,221 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.