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Chesapeake Beach Resort

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83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036
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1 room 1 adult
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Chesapeake Beach Resort
Chesapeake Beach Resort
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542 Reviews from our TripAdvisor Community

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Port Charlotte, Florida
Level Contributor
316 reviews
68 hotel reviews
common_n_hotel_reviews_1bd8 128 helpful votes
4 of 5 stars Reviewed 3 days ago NEW

Driving through the Keys, first stop Islamorada. We checked out several places and decided on the Chesapeake Beach Resort. Fair price for this time of year, it's high season. Our room was a good size and comfortable, we had an ocean view. The resort is older, as are lots of the hotels in the keys. This one has be well... More 

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1 Thank Karen W
Virginia
Level Contributor
25 reviews
19 hotel reviews
common_n_hotel_reviews_1bd8 31 helpful votes
4 of 5 stars Reviewed 4 days ago NEW

My husband and I spent one night here after a weekend in Key West. We LOVE Islamorada. It is just beautiful. This property is spread along the beautiful ocean and worked out wonderfully for us. We arrived late in the afternoon and ran right to the Kayaks. The water was a gorgeous blue and we paddled all over the place.... More 

Helpful?
Thank FootballFanTampa
Turin, Italy
Level Contributor
32 reviews
23 hotel reviews
common_n_hotel_reviews_1bd8 29 helpful votes
4 of 5 stars Reviewed 1 week ago via mobile

It started bad because they didn't have our reservation made by booking.com But the manager gave us an upgrade to ocean view room which was lovely. Rooms are spacious clean with big bathroom and the balcone. View is stunning . WiFi working ok. Big tv, water daily housekeeping daily. Resort is lovely there are 2 swimming pools with heated water... More 

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1 Thank sniegula
new york
Level Contributor
133 reviews
30 hotel reviews
common_n_hotel_reviews_1bd8 91 helpful votes
4 of 5 stars Reviewed 1 week ago

We had never been to the Florida Keys and were invited to a 'destination wedding' in Islamorada. We were looking for a moderately priced place to stay and found this Resort. We opted for a garden-view Villa. Nothing fancy, but quite adequate for our needs. 2 double beds, a full kitchen, table and 2 chairs, couch, sofa bed and flat-screen... More 

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1 Thank NewYorkelena
Nottingham, UK
Level Contributor
17 reviews
8 hotel reviews
common_n_hotel_reviews_1bd8 9 helpful votes
4 of 5 stars Reviewed 1 week ago via mobile

We stayed here for two nights after leaving Miami and heading down to key west. It's was a great little stop off with the rooms being very comfy. It's a quiet resort with ample pool and beach areas. The breakfast was great in terms of choice and layout of items. Staff were always helpful too. We found a great free... More 

Helpful?
2 Thank HollieV
Level Contributor
3 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 6 helpful votes
3 of 5 stars Reviewed 1 week ago via mobile

We stayed for our 25th wedding anniversary. So disappointing. Smelly room, dirty carpets, dated, no real sand just gritty cement. Disgusting breakfast served in a filthy room in black polystyrene bowls, plastic cutlery. No pool bar. The only good thing was the restaurant next door!

Helpful?
1 Thank Shelser
woodbridge, va
Level Contributor
11 reviews
8 hotel reviews
common_n_hotel_reviews_1bd8 9 helpful votes
4 of 5 stars Reviewed 2 weeks ago

They use the term "resort" very loosely and to charge $20 a day is ridiculous. The property has gorgeous views but no restaurant or bar on "resort" and rooms are adequate, not resort like at all. The breakfast is ok for one or two mornings and is more than you get at other hotels down there, but we went out... More 

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1 Thank cant25
Miami, Florida
Level Contributor
3 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed 3 weeks ago

Chesapeake resort has breathtaking views. I really enjoyed my stay. I stayed in the garden view room with two double beds. It had a full kitchen, sofa bed, and a screened porch. The property is gorgeous and has a lot of areas where you can kick back and relax. I highly recommend this to someone who wants a nice view... More 

Helpful?
1 Thank Yvette H
Cranston, Rhode Island
Level Contributor
8 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 2 helpful votes
4 of 5 stars Reviewed 3 weeks ago

We brought our daughters - ages 10 and 12 - and all of us really liked this place. It was chilly (for south Florida) during our stay, so we enjoyed spending time in the hot tub and the warmer pool. (The other was too cold for the adults to enjoy, but the kids liked it.) The free breakfast wasn't fancy,... More 

Helpful?
2 Thank Joe G
2 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
3 of 5 stars Reviewed 4 weeks ago

The room was clean, but very old. I'm not hard to please so this was fine, but they charge you $20/day, on top of an expensive nightly rate. This extra charge is not included in the nightly rate. Why? Almost false advertisement, I think. The "free" breakfast, that you actually pay for is bad to say the least. One of... More 

Helpful?
Thank Maxkyl
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Efficiency Villa (30)
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