We stayed in the standard room--overlooking the gardens and tennis court. Bed linens and curtains are updated, Pretty view, even though not an ocean view. Pretty spot on the beach with plenty of room to yourself for sunning. Two pools--one with hot tub. Resort fee is mandatory and was not worth the fee. Mediocre breakfast, a few kayaks, and a... More

the best $400/night villa was outdated, dirty, bathroom was gross, simple thing like metal rail inside villa between the rooms that was thin and cut bottom of bare feet.. not worth it at all.. Then there is the main reason we chose this resort was because of the watersport items pictured in website and when talking to receptionist on the... More

Back at the Chesapeake this month with great satisfaction. Extremely clean, staff is very attentive, rooms are quite comfortable with a great view of the Atlantic. While there s no bar or restaurant on site, it adds to the quiet lifestyle of the Chesapeake. There are many spots within walking distance

Enjoyed our stay at Chesapeake, great location, right on the water, great sunrise view. Went with a group of friends lots of space in the villa. Pool and hot tub were nice. Loved relaxing on the hammocks. Walking distance to good bars. Continental breakfast-- simple nothing too exciting, same food every morning. Free rental of Hobie Cat was fun. Enjoyed... More

I loved everything about this Resort. We took a vacation to relax and we did just that. Laying by the calm breezy ocean, napping in hammocks, exploring the waters via free kayaks, and throwing a line in. This resort was clean, staff was friendly, and there was even a 16 year old Resident Kitty living on the property named Bob.... More

The desk cleark lied to me and said, one room left,the most expencive sweet. I know it wasen`t because i met a couple at the restraunt next to the hotel,they arived two hours after i did and they got a cheeper room,i was solo. The wifi didn`t work, there was crap in the tolite and when i flushed it it... More

We stayed in a pet friendly villa and we had a great time. The staff is very friendly and made sure we were comfortable and had what we needed. We didn't have our reservation confirmation with us and it ended up being more expensive than what I was expecting, but will come back and recommend to others. We brought our... More

I returned to the resort in March and spent a beautiful week. It is the best place to relax, enjoy the sun and the palm trees. And while I was there they were in the process of changing all the mattresses to double pillow top. !!! How comfortable is that !!! This time I stayed in a villa right by... More

This was my husband and I's 2nd stay at the Chesapeake. We are locals who live just 45 min. from Islamorada but like to "get out of town" and away from the kids for a weekend alone every now and then. Both times, we have had a room with a view of the ocean. The rooms are spacious and very... More