Skip to main content
Beginning of main content

Chesapeake Beach Resort

2.5 out of 5.0

Recent guest reviews

This hotel was dirty and not at all what the pictures and portray. We also tried to upgrade the room as our room was small and dirty but they wouldn't allow us to do that because we booked through Orbitz. I've stayed in Islamorada over 20 times and would not recommend this place that's for sure.

Mom always told me, if you can't say any thing nice, don't say anything at all. So, I grapple with this. Our stay was less than pleasurable because of the accommodations. The grounds are very nice. The cooked breakfasts were convenient but not very appealing. The same tired eggs and sausage and ham every day. The eggs were barely warm if there were any left at all. It was in our room that we had the most to complain about .The road noise was terrible! The front door was so hard to open that my husband actually had to put his shoulder into it to open it! The air conditioning unit was up so high that we had to stand on a suitcase to adjust it! The lampshade looked like a cat had gotten to it ! One of the mattresses had a really horrible sagginess to it. The room came with a broken light bulb, it took us a day and a half to get a replacement. For the money we paid we surely expected better!

We really liked the resort and the scenic location. The staff was nice friendly and helpful...shout out to Desmond, Becky and the rest of the staff. Dominique at the front desk on the other hand, was simply not too friendly or helpful. Rooms were a nice size and very quiet and comfortable, and the breakfast was a plus as well. Will definitely stay here again

Great staff great water views will definitely come back

Stayed for 4 nights during Thanksgiving week and had a very nice time with family.. The kids really loved it. Hotel staff were very nice and friendly. Very nice place to stay would recommend to everyone.

Lowanda and Caesar were terrific at the front desk and all of the employees were friendly and accommodating. All of the water sports were included [paddle boards, paddle boats, kayaks, etc,] as well as Wi-Fi and hot breakfast. We would definitely recommend this family-owned resort to all of our friends and family. It is right next door to a fabulous restaurant [Wahoo's] that is within walking distance so you don't even have get dressed up or drive to eat a great seafood lunch or dinner! There was even a separate pool for the kiddies which was only 4FT at the deepest part. And a hot tub for the adults.

The hotel itself could use some renovations. The paint was peeling in the bathroom, the fan in the bathroom doesn't work, had a few issues with the toilet not flushing. The porch is screened in but there was a hole in the screen. One of the pools, the one with the hot tub was closed for maintenance. There is no sandy beach. There is a sandy area with lots of chairs to sit or lay out in but not an actual beach. We did use the kayaks and that was nice. And we used their poles for 24 hours and fished off a bridge down the road. The staff was great and the rooms were clean. It was a friendly and decent motel, just not exactly what I expected based on the pictures and the site.

Upon arriving we found all of our towels in a garbage bag outside of our room. We had to question if they were clean or dirty. The room was clean. The wifi was free but so limited that we couldn't use it. They don't have a lot to do so I wouldn't bring kids here. It was ok for a night but I wouldn't stay longer.

The hotel is in an excellent location in Islamorada! Received a great rate for the night and room was ocean-facing. Definitely recommend this hotel, perfect for a night or two and close to Islamorada's greatest restaurants and nightlife!

We took a Charter Boat out of Whale Harbor ("NEW BLUE CHIP TOO"- AWESOME FISHING!) The hotel was right next door (you could walk over to Whale Harbor. The resort had two pools and a nice relaxing area. Great for fishing right from shore. Breakfast was better than expected. Only downside was the ice machine by our room was not working so had to go to the next building. Good news was we caught a lot of fish on the Blue Chip Too so the ice was needed and eventually we were able to get in. The restaurant (all you can eat Seafood) is being rebuilt but WAHOOS (upstairs) was great! We caught a 30 lb barracuda right by the bridge and my son caught a 70 lb tarpon on the Blue Chip right there also. Holiday Isle Tiki Bar is over the bridge. This Resort is nice because you don't really have to leave. Do recommend taking the family to Robbie's Marina to "feed the tarpon". Nothing like having a 100 lb fish take bait from your hand.

You won't get the oceanfront rooms that the hotel is known for with the discount. You get road noise rooms. And, the $160 per night was really $200 with additional charges. But, nice to have kayaks, and paddleboat, and catamaran at the beach.

We had a wonderful stay at Chesapeake Beach Resort. The hotel has a wonderful property with 2 pools, spa, tennis courts, kayaks, paddleboats and jungle gym - there was alot to do. It is located adjacent to alot of places of interest, especially Theatre of the Sea. Restaurants and access to renting boats,jet skis even hang gliding were just steps away. The rooms are directly on the water - with a great view of the ocean and very quiet. It had a B&B feel- with the breakfast that was offered every morning and the library room it was located in. We will definitely be back!

Good hotel, not really new but ok, only the restroom was seriously uncomfortable. Price for value appropriate, I don't think you'll be able to find anything better in the area.

At first glance we thought the bad reviews we read were answered with upgrades to the "resort". Not so much! When we arrived the man at the desk was less than helpful. We were definitely not his priority. After we checked in we asked him for dinner recommendations and he presented us with a prepared list of "near by" restaurants. I looked them up on my phone and they were all quite a distance from the hotel but they were recommended so we drove the distance (south). After stopping at 3 or 4 we noticed that none of them had average prices under $60 per plate. Just so we are clear… people who pay less than $200 per night at a hotel are not dining at these types of restaurants. When we got back to the room we noticed that there was a seafood buffet three doors to the north that did not make the list. REALLY?? Back to the hotel… The room itself was not so bad. But the bathroom was DISGUSTING!!! Words will not describe. In the morning we went to find the included breakfast buffet. We circled the property several times and asked several employees were it was. After finally finding it (through a door that looked like it was an employee only entrance) it wasn’t so bad, I’ll even be so kind to say it was average.

Nice place, but room location was disappointing so they charged me another $20 to move rooms so we had a better view. Also the $18 resort fee was a surprise after we already paid for the room. In total they added around $47 to our $268 room cost. Very expensive for what we got.

The view and surroundings were great. The outdoor activities looked fun, short stay unable to take advantage.

This is a small little hotel/villa complex. the grounds are clean and kept. They have free water sports and bycicles free of charge, but the staff is not to friendly to get you to use them. they give you excuses why you can not try them. There is really no beach for you to go out on. the sand is not sand its tiny gravel. this is a place to get away and relax because there is not much to do here. They have free parking but you get hit with $18 resourt fee per day that was not disclosed up front when you made resevations so be ware.

We only stayed here one night but it was a real treat. If we travel that way again we will be sure to make a point of staying for several days. Our room was very nicely appointed. You could tell it was an older hotel from the wear and tear of the buildings, swimming pool, hot tub etc. But the rooms had been newly decorated and were very nice. The activities that were offered were plentiful, but we did not have the time to participate in any. I would recommend this hotel to any one looking for a comfortable room in a nice location.

Nice stay. The rate was a bit expensive for the room but it could have been because I booked it on the week I was traveling. The fitness center was two Nautilus machines on the outdoors - not hardly a fitness center. The room and the view was very nice, however.

mostly slept got in late and had to leave at checkout didn't get to use all the wonderful things they got to offer It was a beautiful location and site

83409 Overseas Hwy Islamorada FL

Hotel highlights

  • Free buffet breakfast
  • Free WiFi in rooms and public areas
  • Free parking
  • Marina

Chesapeake Beach Resort places you within a short walk of History of Diving Museum and within a mile (2 km) of Theater of the Sea. This 65 -room resort has 2 outdoor pools along with a private beach and a marina. Also close to this Islamorada resort are Windley Key Fossil Reef Geological State Park and Hurricane Monument.


Start your day off right with a free buffet breakfast, served each morning from 7 AM to 10 AM. Satisfy your hunger from the comfort of your room with room service.


Chesapeake Beach Resort's 65 air-conditioned rooms provide balconies, refrigerators, and coffee makers. Guests can expect free WiFi and 37-inch flat-screen TVs with satellite channels. Pillowtop beds grant a restful night's sleep, and bathrooms offer hair dryers and free toiletries. Ceiling fans, safes, and phones are also standard.

Property features

Chesapeake Beach Resort features a private beach, a marina, and a full-service spa. If you drive, put free parking to good use. The front desk has multilingual staff that can answer questions about the accommodations, services, and more. Other amenities at this beach resort include 2 outdoor pools, a fitness center, and a spa tub.

Room options

Standard Room, 2 Double Beds, Balcony, Garden View

Full 2 | Sleeps 4

Premium Room, 1 King Bed, Ocean View

King 1 | Sleeps 2

Premium Suite, 1 King Bed with Sofa bed, Ocean View

King 1 | Full 1 | Sleeps 4

Large Two Bedroom Villa

Full 1 | Queen 1 | Sleeps 6