Islamorada Adventure Holidays 2026

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Top Adventure Islamorada Hotels

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

21 min drive from Anne's Beach

Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff ...

9.2/10 Wonderful! (1,288 reviews)

For a five star hotel, the grounds should be kept up better

Reviewed on 14 Jan 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

84001 Overseas Hwy Islamorada FL

27 min drive from Anne's Beach

Stay at this beach resort in Islamorada. Enjoy free Wi-Fi, 3 outdoor pools and 4 restaurants. Our guests praise the helpful staff and the clean rooms in their ...

9/10 Wonderful! (132 reviews)

All staff members were great!

Reviewed on 16 Jan 2026

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

16 min drive from Anne's Beach

Stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach and 3 bars/lounges. Our guests praise the pool and the helpful staff in their reviews. ...

8.8/10 Excellent! (1,264 reviews)

Beautiful grounds, very comfortable beds, provided water taxi between their 3 resorts, pool area with tiki bar very nice.

Reviewed on 17 Jan 2026

See all 2,220 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.