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All 20 Islamorada hotels

Chesapeake Beach Resort

2.5 of 5 Resort   |   83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036
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Chesapeake Beach Resort
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Ranked #12 of 20 hotels in Islamorada
A recent review
4 of 5 stars reviewed 4 days ago
Dotneko Townsend, MA
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351 people have reviewed this hotel

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Rating summary
  • Location
    4.5 of 5 stars
  • Sleep Quality
    4 of 5 stars
  • Rooms
    3.5 of 5 stars
  • Service
    4 of 5 stars
  • Value
    3.5 of 5 stars
  • Cleanliness
    4 of 5 stars
Traveler tips help you choose the right room.   Room tips (95)
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English first
Savannah, Georgia
4 reviews 4 reviews
3 hotel reviews
7 helpful votes 7 helpful votes
1 of 5 stars Reviewed 3 days ago NEW

Only because the front desk people there are so rude, I rated this place Terrible! The views are wonderful and the housekeepers are okay but the front desk people hurry to check you in and get you out of the office quick and do not seem to care about the guests! When I checked in they gave me a map... More

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Townsend, MA
Top Contributor
86 reviews 86 reviews
19 hotel reviews
66 helpful votes 66 helpful votes
4 of 5 stars Reviewed 4 days ago NEW

Stayed in a deluxe oceanfront and the room was typical older resort room. Could definitely use an upgrade. Nice view, small waterfront. Good under building parking. Terrible breakfast - bacon sliced so thin you could see through it with no flavor. Horrible wifi. Got kicked off regularly.

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Atlanta, Georgia
2 reviews
1 helpful vote 1 helpful vote
4 of 5 stars Reviewed 2 weeks ago

A very friendly staff on a busy holiday weekend and a great experience throughout our stay. Overall, a good value and experience. Stayed in a Deluxe Ocean-view room. The room was clean each day on our return and the view from the room was as advertised. The bath counter and sink were updated as well as the room itself but... More

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Sollentuna, Sweden
Senior Reviewer
10 reviews 10 reviews
6 hotel reviews
1 helpful vote 1 helpful vote
2 of 5 stars Reviewed 2 weeks ago

Maybe we just had bad luck. We arrived late to the hotel and put our luggage in the room / cabin and went away and ate. When we came back the room was full of cockroaches. They crawled on our bags and into our beds. The children refused to sleep in that room so we had to switch rooms. This... More

Was this review helpful? Yes 1
Port Saint Lucie, Florida
1 review
1 helpful vote 1 helpful vote
2 of 5 stars Reviewed 2 weeks ago via mobile

We stayed 3 nights here. The grounds were ok,and the rooms were typical of the keys ( which by the wayis our favorite vacation spot) however, i was on the hammock on our last night,fell off and hurt my back. The hammock was not properly installed,and the hook came out of the tree. The staff did absolutly nothing about it.... More

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Tampa, Florida
Top Contributor
130 reviews 130 reviews
20 hotel reviews
64 helpful votes 64 helpful votes
3 of 5 stars Reviewed 2 weeks ago

I found a great rate for this place and read Trip Advisor reviews that were good, so I was thrilled. We arrived and the gentleman in the office was really not very personable although he got a bit better when we asked questions about where to fish. It just seemed that I had to pull each answer out of him.... More

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1 review
1 helpful vote 1 helpful vote
2 of 5 stars Reviewed 3 weeks ago

Nice view but that is all. Room had layers of dirt behind furniture. Found a pair of pants in room from previous guest. Balcony door wouldn't lock. Electrical plug in over center of sink. Mold in heat/ac unit. On the plus, the view was great and nice to have a kayak available if u wanted to paddle. Discussed my concerns... More

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Woodstock, Georgia
20 reviews 20 reviews
4 hotel reviews
11 helpful votes 11 helpful votes
5 of 5 stars Reviewed 3 weeks ago

Great stay for 5 nights. Room was clean and view was great. Water sports included and guy who works the water sport checkout hut is very helpful, even had us follow him out on kayaks to show us starfish. Hotel is close to all islamorada activities. Great rates and a very relaxing hotel. Would stay again for sure!

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Danville, Illinois
3 reviews 3 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed 3 weeks ago

We stayed 3 nights in this little paradise on the recommendation of a neighbor. Everything around the resort was beautiful! We loved the hammocks out on the little "islands" on each side of the lagoon. The pools and hot tub were wonderful and our villa was very comfortable and tidy. Area was easy to walk around to find places, the... More

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5 reviews 5 reviews
4 hotel reviews
7 helpful votes 7 helpful votes
5 of 5 stars Reviewed 3 weeks ago

Only negative comments I have are : No vent in the bathroom (we really needed one xD) and It seemed a bit more run down than it was at Christmas. We've stayed here every year,twice a year 2 or 3 days per visit. We love to walk around at night with flash lights and look in the water and see... More

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Additional Information about Chesapeake Beach Resort

Address: 83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036
Phone Number:
Location: United States > Florida > Florida Keys > Islamorada
Price Range (Based on Average Rates): $$
Hotel Class:2.5 star — Chesapeake Beach Resort 2.5*
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Also Known As:
Chesapeake Beach Hotel Islamorada

255 photos of this hotel

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All traveler photos (234)
Pool/beach area (38)
Hotel & grounds (53)
View from room (19)
Room/suite (35)
Bathroom (7)
Dining (1)
Videos (1)
Other (80)

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View from room (3)
Pool/beach area (10)
Room/suite (5)
Other (4)


Beach Fitness Center with Gym / Workout Room Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Kitchenette Room Service Suites Swimming Pool Wheelchair access
Hotel Style
#4 Top resorts Hotel in Islamorada #8 On the Beach Hotel in Islamorada
Hotel Class
Official Description (provided by the hotel)
Islamorada’s famous beach and fishing destination, Chesapeake Beach Resort, rests on 6.5 acres of oceanfront sands and gardens halfway between Miami and Key West, in the Florida Keys. Our property is now exquisitely remodeled to deliver state-of-the-art amenities and luxurious accommodations to our guests. We are proud to offer 37” HDTV, Stereo radio/CD/alarm with MP3 docking capabilities and wireless internet connection, along with new carpeting, furniture and remodeled bathrooms and kitchens including granite countertops and vanities; all to make your stay more enjoyable and relaxing. ... more   less 
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