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All 15 Islamorada hotels »

Chesapeake Beach Resort

2.5 of 5
83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036
Hotel amenities
Chesapeake Beach Resort
Ranked #10 of 15 hotels in Islamorada
4.0 of 5 stars 181 Reviews
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181 reviews from our community

    Trip type
Traveller rating
    55
    70
    21
    20
    15
Date Rating
s.c.
Contributor
15 reviews 15 reviews
Reviews in 8 cities Reviews in 8 cities
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed 21 May 2012

And it was awesome. Everything was very clean and the maids never once bothered us but seemed to know when we left the room and whisked in and straightened up. We had a great huge balcony and a living room with a flat screen TV. Small kitchen area, but I wasn't cooking.The bed room was lovely and the bed was... More

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See 2 more reviews by ellettfoodie for Islamorada
Fort Lauderdale, Florida
Senior Reviewer
7 reviews 7 reviews
Reviews in 2 cities Reviews in 2 cities
2 helpful votes 2 helpful votes
2 of 5 stars Reviewed 14 May 2012
1
person found this review helpful

Two nights at this hotel, mid week. One couple in the least expensive room with view of greenery, the other in a suite with view of the ocean. The welcome was friendly and fast. Oddly at a hotel with these prices they hand you two towels for the beach and ask you to return them at checkout. The budget room... More

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See 5 more reviews by acawray for Islamorada
Key West, Florida
Senior Reviewer
9 reviews 9 reviews
Reviews in 3 cities Reviews in 3 cities
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed 13 May 2012

We loved this resort! Great, friendly staff. Clean, well maintained. Awesome for families or couples!! Thank you for a wonderful stay!

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See 2 more reviews by lovellem7 for Islamorada
Washington DC
Senior Reviewer
10 reviews 10 reviews
Reviews in 7 cities Reviews in 7 cities
10 helpful votes 10 helpful votes
4 of 5 stars Reviewed 1 May 2012

Our group was there for the fishing. I cannot imagine a more convenient location. We walked to the docks (50 yards). About five great bars/restaurants within walking distance. The hotel accommodations are adequate for those all about fishing and carousing (very little time in room). Unfortunately, we did not have the best weather or catch many fish. Still, I would... More

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fairfield ct
Contributor
14 reviews 14 reviews
Reviews in 8 cities Reviews in 8 cities
8 helpful votes 8 helpful votes
4 of 5 stars Reviewed 27 April 2012

A great time here. We choose the perfect week to come- April 18. Spring break families were gone. We had the place almost to ourselves, which is probably very unusual. The setting was beautiful and everything was very clean. Two pools to choose from and there was a great outdoor pavilion to sit and eat or just relax in. If... More

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See 4 more reviews by parentswithfourkids for Islamorada
Covington, GA
Reviewer
5 reviews 5 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed 27 April 2012
1
person found this review helpful

I had no idea what we were going to experience. The reviews on here were mixed but the pictures looked good. The Resort is beautiful. Small but charming and well cared for. Very convenient (next door) to 3 great restaurants. We stayed in 602, had a fabulous view and the suite was clean and comfortable. I highly recommend this resort... More

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See 4 more reviews by CMask for Islamorada
Ny
Reviewer
3 reviews 3 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed 19 April 2012
1
person found this review helpful

Immediately after seeing the lagoon I booked this resort without a second thought. I then looked at trip advisor and became nervous very quickly. I read more then a few reviews that made me second guess my choice. I started looking into other resorts and saw a few that impressed me but I still had something drawing me to Chesapeake.... More

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See 2 more reviews by Vincent R for Islamorada
Astoria, Oregon
Contributor
19 reviews 19 reviews
Reviews in 12 cities Reviews in 12 cities
7 helpful votes 7 helpful votes
5 of 5 stars Reviewed 17 April 2012

We had a great 3 night stay at this resort. It was right on the highway, but was well hidden from all the traffic by lots of landscaping and palm trees. They served a basic free breakfast each morning with croissants, rolls, bagels, cereal, and some scrambled eggs, sausage & bacon. The unit we were in was small with 2... More

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See 3 more reviews by SBHOregon for Islamorada
marquette
Reviewer
3 reviews 3 reviews
1 helpful vote 1 helpful vote
4 of 5 stars Reviewed 12 April 2012

A bit expensive for the size of room, but clean, safe and lots to offer. Loved the free b-fast and water activities. Kids loved the clean pools and beachfront. Very clean rooms. Cesar was very helpful upon check-in. Great location. Marathon and Key Largo too "towny," Key West too "crazy," Islamorada just right.

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See 2 more reviews by lfarns for Islamorada
Colorado
Contributor
13 reviews 13 reviews
Reviews in 12 cities Reviews in 12 cities
14 helpful votes 14 helpful votes
3 of 5 stars Reviewed 8 April 2012
1
person found this review helpful

My wife and I were making a quick trip to the Keys and booked for a couple of nights.The views from this resort are beautiful. The grounds are not extensive but adequate. We rented an ocean view king bed suite and the ocean view was as billed and is certainly impressive. The problem for us was that the structure is... More

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Additional Information about Chesapeake Beach Resort

83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036
Price range (per night):* S$253 - 377

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