Location.
Situated on the beach, this Islamorada property is close to Theater of the Sea on Islamorada and History of Diving Museum.
Features.
Chesapeake Beach Resort has a private beach and an outdoor pool. The property offers wireless Internet access. Guests are served a complimentary breakfast each morning. Guest parking is complimentary. The staff can arrange dry cleaning/laundry services. Additional amenities include laundry facilities, barbecue grills, and a picnic area. This is a smoke-free property (fines may apply for violations). A total renovation of this property was completed in 2008.
Guestrooms.
Amenities featured in guestrooms include air conditioning, coffee/tea makers, and clock radios. Business-friendly amenities include desks. All guestrooms provide refrigerators. Bathrooms feature hair dryers. Rollaway beds are available on request. All guestrooms at Chesapeake Beach Resort are non-smoking.
Guest Reviews: Chesapeake Resort
Provided by TripAdvisor
- Traveler Reviews brought to you by

- Chesapeake Beach Resort
-
83409 Overseas Highway, P.O. Box 909
| Islamorada, FL 33036
- TripAdvisor Traveler Rating:
-
Based on 96 traveler reviews
- Most Recent Traveler Reviews:
-
-
-
“Outstanding!”
-
Aug 23, 2010
RAShort, Jacksonville, Florida
- Newlywed couple (older and experienced). Wanted a well managed oasis in the Keys and were not disappointed. The resort is not new but is in immaculate condition. Grounds and facilities...
more »
- Newlywed couple (older and experienced). Wanted a well managed oasis in the Keys and were not disappointed. The resort is not new but is in immaculate condition. Grounds and facilities are professionally groomed and always in "eye candy" condition. Staff are professional, friendly, helpful and a joy to interface with. Lagoon, Beachfront (set off from the water), 2 pools, Tennis, Workout area, and garden walks are exactly what a Florida Keys experience should be. Wife & I are Florida long time residents and know what we should see. Chesapeake did not disappoint us. Try it! « less
-
-
“Don't waste your money”
-
Jul 25, 2010
ab1965, Hypoluxo, Florida
- We stayed at the Cottages at the "resort". You can get alot more for less money....we paid $210 for a weekday night. There is NO beach....their pictures are very deceiving....
more »
- We stayed at the Cottages at the "resort". You can get alot more for less money....we paid $210 for a weekday night. There is NO beach....their pictures are very deceiving. The front desk staff is extremely unfriendly. I wouldnt waste my money on this place, rather do some research and you can get a lot more and feel welcome. « less
-
-
“Chesapeake should be #1 just for the views alone!”
-
Jun 11, 2010
LFox14, New Orleans, LA
- I couldn't wait until the end of my trip to write. We are enjoying our second day here. We have a 2 bedroom suite with living room. I can't speak...
more »
- I couldn't wait until the end of my trip to write. We are enjoying our second day here. We have a 2 bedroom suite with living room. I can't speak for the smaller rooms, but this is an awesome place to relax. Hubby and son went deep sea fishing. They had to literally walk 20 feet to the gorgeous boat. Daughter and I went paddle boating. Very laid back, quiet, friendly staff... Come here to unwind. The kids beds weren't the most comfortable, but our king bed was great. The price for what we're paying (tons of room) is not cheap, but worth every dime. You won't be disappointed!! « less
-
-
“Very quiet and relaxing with great views!!”
-
Jun 2, 2010
Connie66, Germany
- We spend 3 nights in this hotel on our way to Key West. The resort is beautifully landscaped with great views of the ocean. There is not really anz beach...
more »
- We spend 3 nights in this hotel on our way to Key West. The resort is beautifully landscaped with great views of the ocean. There is not really anz beach there. Swimming is not possible unfortunately. This was a disappointment to me. Rooms however are really beautiful, lovely decor, great flat screen tv and lovely ocean front balcony. The included continental breakfast is okay. There is a nice jacuzzi and 2 nice pools for swimming. A great seafood restaurant with an all you can eat seafood buffett (for $ 28). We enjoyed it there. There is not really anything else in walking distance. There is a marina at the hotel and you can lay on the loungers or hammocks and watch the ocean. There is not really anything else to do there, so not good for a longer stay.... « less
-
-
“Relaxing and Leisurely”
-
Apr 23, 2010
Crystal5, New York City, New York
- My husband and I went away for the first time in many years, sans kids. I have to say that I was nervous going to the hotel, after reading the...
more »
- My husband and I went away for the first time in many years, sans kids. I have to say that I was nervous going to the hotel, after reading the extreme reviews. (It took me a week to even book a place in Islamorada, after scanning reviews.) But, I am glad we went to the Chesapeake. We were very happy with the hotel, the room, the grounds, and of course...the beautiful water views from our room. My advice is if you do go away as a couple, it's worth the splurge to just make sure you get the full ocean view or suite. The balcony was such a welcome addition to the experience. They also have hammocks lining the property and a central public "observatory" area, which is nice, if you don't have a balcony. I read reviews that said the rooms weren't well kept, but ours was freshly painted, though it was no frills, with the exception of the large flat screen t.v. We did change rooms, as our first room had an obscured view of the ocean, and the staff readily accomodated us.
O.K. Now for the 'could have been better': 1) They serve a continental breakfast, which is packaged bagels and pastries...could have been fresher 2) When it was bad weather and we asked a staff member what people do in the rain, she replied "Nothing"...and made no suggestions, which wasn't so helpful, as we didn't have a guide book with us. (We drove out to key west and stopped along the way, which was fun.)
And I just want to echo some other reviews for those who expect "resort-like luxury'... Islamorada just isn't that. For those of us familiar with the Jersey-shore or other shore-like towns, the ambiance of Islamorada will be familiar...only here there is absolutely stunningly beautiful water and palm trees. It's not upscale, but it's comfortable and leisurely. So many of the 'resorts' are road side motels, except that they are on the water. (And it's easy to be on the water as Islamorada is barely wider than the highway...but, you don't hear any highway noise at the Chesapeake). Chesepeake isn't a "resort" in it's truest sense, but it is definitely not a road side motel...It's lovely, overall, and much more upscale than other places calling themselves resorts in the area. P.S. The indepent cottage accomodations seem wonderful for families...we're going to take ours next year. « less
These reviews are the subjective opinions of individual travelers and not of TripAdvisor LLC nor of its partners.
© 2010 TripAdvisor LLC
Amenities: Chesapeake Resort
Hotel Services
Kitchen
24-Hour Security
Laundry Facilities
Recreational Services
Fitness Facility