Name: Large Screened Porch, Professional Cleaning, Wifi
Address: Tavernier
Rating: 9.2

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Top Romantic Islamorada Hotels

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL

8 min drive from Theater of the Sea

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 ...

9/10 Wonderful! (1,222 reviews)

"I went there this weekend to celebrate my birthday. Great place, well kept, nice service, rooms are pretty and clean. The pools are nice. Loved the resort. Hope to come back soon. They had a room for me right away. Check in was very pleasant. The paddle boarding, and canoes are free with the stay. ..."

Reviewed on 12 Oct 2025

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

22 min walk from Theater of the Sea

Stay at this 3.5-star beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...

9.2/10 Wonderful! (1,536 reviews)

"I had a wonderful stay here with my pet! The hotel is super pet-friendly, which made our trip so easy and enjoyable. There’s plenty of parking, and the view from our room was amazing. I also loved that my favorite buffet was right in the parking lot next door — total bonus! Perfect spot for anyone ..."

Reviewed on 9 Oct 2025

Large Screened Porch, Professional Cleaning, Wifi

Tavernier

13 min drive from Theater of the Sea

Book a stay at this beach condo in Tavernier. Enjoy private pools, a beach locale, and a sauna. Popular attractions Florida Keys Dive Center and Old Road Gallery ...

9.2/10 Wonderful! (63 reviews)

Awesome condo

"AMAZING! This condo has EVERYTHING that you are looking for in a short or extended stay! The property amenities are great and the balcony view is beautiful. The owner was extremely helpful with any questions we had and was very responsive. Will stay here again in the future."

Reviewed on 2 Feb 2025

See all 2,212 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.