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All 19 Islamorada hotels

Chesapeake Beach Resort

2.5 of 5 Resort   |   83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036
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15% off room rate
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Ranked #13 of 19 hotels in Islamorada
A recent review
5 of 5 stars reviewed yesterday
Thea M Chagrin Falls, Ohio
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319 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 (79)
Date | Rating
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English first
Chagrin Falls, Ohio
4 reviews 4 reviews
5 of 5 stars Reviewed yesterday NEW

We enjoyed four nights at this great place. We used the beach, pools, bikes, kayaks and tennis courts. The common areas are very well kept with plenty of chairs, hammocks and area for all. The staff was wonderful and ready to help in every way. We stayed in both the double room and the efficiency. The efficiency was a little... More

Was this review helpful? Yes 1
4 reviews 4 reviews
1 helpful vote 1 helpful vote
3 of 5 stars Reviewed yesterday NEW via mobile

Recently stayed at the resort for 4 nights w my husband and daughters. Had an ocean view room with a stunning view. The outdoor balcony was spacious and the best part of the room. The inside of the room was dated, tired and had the worst mattresses I think I have ever experienced. My husband slept on the floor. I... More

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Punta Gorda, Florida
Top Contributor
106 reviews 106 reviews
4 hotel reviews
10 helpful votes 10 helpful votes
4 of 5 stars Reviewed 2 days ago NEW via mobile

We really enjoyed our 3 night stay at the Chesapeake. Everything was clean and nice. It is right on the water with great views of the sunrise. The breakfast was included and it is all I'd hope for. There are 2 pools, a hot tub and great sunning areas on the water front. Most resorts offer kayaks, sailing equipment and... More

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Ponte Vedra, Florida, United States
4 reviews 4 reviews
3 hotel reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed 3 days ago NEW

Although the hotel office is right on US1, our ocean front room was quiet and very relaxing. My teenage son and I stayed 4/11-4/15 for spring break. Convenient location for access to Bud n' Mary's marina for fishing, Robbie's for the snorkeling trip, and lots of local restaurants. Room and grounds were well maintained and staff was friendly, especially the... More

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Long Branch, New Jersey
4 reviews 4 reviews
3 hotel reviews
4 of 5 stars Reviewed 5 days ago NEW

We traveled to Islamorada for 10 days and spent 8 days at this hotel. It was quiet, clean and we had a nice ocean view. They also had under building parking so your car wasn't roasting in the sun. The hotel offers a free breakfast every morning consisting of a nice variety of choices...eg. Scrambled eggs, bacon, sausage, toast, cereal,... More

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18 reviews 18 reviews
4 hotel reviews
8 helpful votes 8 helpful votes
5 of 5 stars Reviewed 1 week ago

Stayed in a room with 2 double beds and a balcony with a great ocean view. We had a four night stay and didn't want to leave. It's in a good location for exploring further up and down the Keys. Desk staff were friendly and knowledgeable - happy to share tips about local restaurants, snorkelling locations, etc. The facilities available... More

Was this review helpful? Yes 1
Senior Reviewer
7 reviews 7 reviews
2 helpful votes 2 helpful votes
4 of 5 stars Reviewed 3 weeks ago via mobile

Had a great time staying at the resort. The rooms are huge and we had a balcony that faced the ocean. It was nice that the bikes, kayaks and paddle boats are included in the price. We had fun riding around the island. The free breakfast is well "free" so don't expect too much, but the place is quite charming.... More

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Bear, Delaware
Senior Contributor
33 reviews 33 reviews
5 hotel reviews
8 helpful votes 8 helpful votes
4 of 5 stars Reviewed 3 weeks ago

Stayed for 5 nights. Great location - it is beautiful looking out over the ocean. The grounds are well kept. We had an ocean front room which was clean and perfect. Bed was firm but comfortable. This is not a luxury resort - but we weren't looking for that - we were looking for clean, comfortable, relaxing. This place met... More

Was this review helpful? Yes 1
13 reviews 13 reviews
10 hotel reviews
19 helpful votes 19 helpful votes
3 of 5 stars Reviewed 3 weeks ago via mobile

Stayed here for two nights. It really is a great location but the decor to the garden room which was allocated to us was very poor. The curtains did not match the pelmet but this matched the bed valances. The balcony door would not lock and the air conditioning units were very noisy. The bathtub enamel was chipped, electrical socket... More

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Medford, New Jersey
4 reviews 4 reviews
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed 4 weeks ago

We did not know much about Islamorada so we decided to visit. Unsure where to stay, we logged into Trip Advisor and chose Chesapeake Beach Resort. It was perfect. The hotel is funky (that is a plus), very clean and the staff was very friendly. Even though there was no vacancy, there is so much beach room that we never... More

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Additional Information about Chesapeake Beach Resort

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