We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
The latest reviews. The lowest prices. The perfect place to shop for hotels.

“Keys to your heart?”

Best prices for -
Check In dd/mm/yyyy Check Out dd/mm/yyyy
Prices are for 1 room, 2 adults
Show Prices
Compare best prices from top travel sites
and 9 more sites!
Chesapeake Beach Resort
Ranked #13 of 19 Hotels in Islamorada
Winter Springs, Florida
Level Contributor
33 reviews
9 hotel reviews
common_n_hotel_reviews_1bd8 12 helpful votes
“Keys to your heart?”
Reviewed 3 September 2013

Delightful, small resort style hotel on the beach in beautiful Islamorada. Nice, laid back atmosphere with plenty of excellent seafood restaurants nearby. The front desk staff were very helpful and pleasant, as were the local herons and pelicans inhabiting the beach and pool area.

The continental breakfast could be spruced up a bit and the antiquated universal weight machine (outdoors) would be best left in the local scrap yard.

Altogether a very pleasant experience.

  • Stayed August 2013, travelled as a couple
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
1 Thank roadwarar
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Write a Review

684 reviews from our community

Traveller rating
    197
    268
    122
    48
    49
See reviews for
209
298
20
9
Rating summary
  • Location
    4.5 of 5 bubbles
  • Sleep Quality
    4 of 5 bubbles
  • Rooms
    3.5 of 5 bubbles
  • Service
    4 of 5 bubbles
  • Value
    3.5 of 5 bubbles
  • Cleanliness
    4 of 5 bubbles
Traveller tips help you choose the right room.   Room tips (201)
Date | Rating
  • Danish first
  • English first
  • French first
  • German first
  • Italian first
  • Norwegian first
  • Portuguese first
  • Russian first
  • Spanish first
  • Any
English first
Fort Morgan, Colorado
Level Contributor
106 reviews
15 hotel reviews
common_n_hotel_reviews_1bd8 41 helpful votes
Reviewed 2 September 2013

I booked my stay based on Tripadvisor reviews and was not disappointed! In fact, I found Chesapeake exceeded my expectations. Several posted reviews dissed the cleanliness, condition, and bedding qualities of the rooms, so I arrived with a few hesitations.

Checking in at night I was helped by a friendly front desk person. In fact, I called before I arrived thinking I was lost. She coached me with a few simple directions and I arrived safe and secure. Check in was a breeze. I appreciated a real key on a wristband that wouldn't get lost - 2 sets in fact.

My ocean side king suite was immaculate, the bed and pillows very comfortable, and the furnishings quite nice. This is indeed an 'old Florida' style facility, which is what I prefer. The living area had a sofa and 2 arm chairs, as well as storage furniture and large screen tv. The adjacent dining area had a 30" round table w/ 4 side chairs. Two balcony areas, one off the living, another off the bedroom, had 2 arm chairs with side tables. The housekeeping staff were helpful and friendly, not in your face. I left my 'privacy please' tag on several different days and they didn't bother me, but left clean linens in a bag outside my door.

A real treat was the jacuzzi in the king room just steps from the bed; I thought it would be in the bathroom, but it was a second tub altogether. Wonderful for honeymoon romance I would imagine! Relaxing for me before hitting the bed.

The small kitchen was adequate for simple food prep, though remember it only has a 2 burner cooktop, microwave, and NO OVEN. Decent size refrigerator (think small apartment), and adequate utensils, etc. if you peek in the cupboards to find them all.

The main pool is large enough to swim laps, no deep end or diving board. I actually liked the shallower depth for standing around and visiting with other guests. Plenty of nice quality chaise loungers, umbrella tables with arm chairs, and a large hot tub in the pool area. I didn't go to the second smaller pool, but others seemed to be enjoying it.

There is a beach, though small, but still exists, and you can wade out into the shallow water to enjoy the ocean. Wear shoes as there is seaweed and some gravely rocks as you enter. Not shelling beaches like Sanibel, but still the same wonderful calm, warm ocean water. Low tide was in the morning and was great to get out into the water. Loungers and hammocks and chairs/tables are located along the property's length by the water.

As for the grounds, they were very nice. Not a 5 star overdone resort property, but small gardens along the pathways between buildings. Plenty of parking even for Labor Day weekend, and room for boats to pull in and dock at the nice small harbor there. Lovely plantings and walkways to the pool, water sports area, tennis court, and covered workout weight equipment spot. Elevators that have been added at some point made getting from the first level parking up to my 3rd level room easy. The view of the ocean is spectacular.

I booked an all day off-shore fishing charter with Captains Parker and Grovier on the Danica Anne. My daughter from Miami visited for 2 days, and went fishing w/ me. We caught a lot of fish and had a nice ride with these two gentlemen. A very pleasant fishing experience. Good for singles, couples, family, or up to 6 friends on their nice large 42' boat that has an enclosed cabin, including an airplane size bathroom 'head'. We fisher ladies appreciate that!

I would return again for sure. A diverse crowd at the pool, with folks from Miami, New York, Ohio, and me from Colorado. If you have a boat, it seems a great place to dock and stay.

There were a number of young couples there, kind of a party type crowd, but they weren't noisy, or the noise didn't carry to my room.

Hot breakfast is complimentary and decent fare served in an A/C room on the way to the pool and boat area.

Ice and pop machines near the elevators at each level. Some gifts and things for sale in the Lobby. Closest grocery store is 20-30 minutes or so away, so maybe hit it on the way there to stock up if you are fixing for yourself. There is an ATM at the restaurant/harbor complex just to the north by the dockmaster office.

Room Tip: Ocean side upper level is recommended. They also have villas for more of a suite feel at ground lev...
See more room tips
  • Stayed August 2013, travelled solo
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
3 Thank ShariMcMinn
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
1 review
common_n_hotel_reviews_1bd8 2 helpful votes
Reviewed 13 August 2013

We had a great stay at the Chesapeake Beach Resort this weekend August 9th through the 12th. The front desk staff (Cesar and a girl) were very helpful and courteous. The stay got even better as we (there were 6 in our party) headed down to the waterfront to catch some sun and enjoy the ocean, hammocks, hotub, and pool. The person in charge of the waterfront activities (Bobby) made our trip that much more enjoyable! Being a sailor, I enjoyed being able to use the hotel's Hobie Wave to sail around behind the hotel and it was free at that. The grounds, and pool area were kept immaculately clean. Aside from the hotels's great amenities and staff the overall location of the hotel is perfect. The hotel is next door to two restaurants and walking distance from Holiday Isle tiki bar. In addition, it's only a few minutes drive to Robbie's marina where we hand fed tarpon and Bud N' Mary's where we rented a 26 foot deck boat. Last but not least there was free breakfast provided at the hotel. Eggs, bacon, sausage, muffins, cereal, bagels, waffles and fruit. Perfect, for getting a quick breakfast in before a day on the water in the sun. Keep up the great work! We will definitely be back!

  • Stayed August 2013
    • Value
    • Location
    • Rooms
    • Cleanliness
    • Service
Helpful?
2 Thank Josh5091
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Fairfield, CT
Level Contributor
6 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 5 helpful votes
Reviewed 12 August 2013

Great accommodations! Clean, relaxing and quiet, albeit we went in Aug and I can only imagine that it may be busier in the high season. The breakfast was not bad either, compared to some of the bad "continental" breakfasts that we had experienced prior to our arrival! We are glad we found this place and would stay here again.

  • Stayed August 2013, travelled as a couple
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
2 Thank Cotajim
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Orlando, Florida
Level Contributor
8 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
Reviewed 12 August 2013

We stayed at the Chesapeake for the last 3 days. It was awesome. We stayed in a standard hotel room, room 209. It was clean and recently remodeled. The beds were comfy. The breakfast in the morning was great and even included bacon and eggs. The property is very well maintained. We went fishing at night in the marina and caught a ton of mangrove snapper and grunts....the kids loved it. We saw sting rays and even a little 3 to 4 foot shark. They even had kayaks and paddle boats for the hotel guests to use free of charge. We would definitely stay again.

  • Stayed August 2013, travelled with family
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
Thank Jodie G
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Pompano Beach, Florida
Level Contributor
28 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 20 helpful votes
Reviewed 2 August 2013

This resort is a great family spot. Breakfast, use of kayaks and paddle boats is included in a daily resort fee of 19 bucks per room, well worth it! The property has 2 pools and you can also wade with water shoes just off the shore. This resort does not have a bar or restrauant on the property but you can walk or borrow a free bike to go anywhere on the island. There is also a boat ramp on the property and docking available that is in a cove.

Room Tip: we had a garden room, it had a screened in patio. if you choose an ocean view some rooms do not have...
See more room tips
  • Stayed July 2013, travelled as a couple
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
Thank photoMOMontheGO
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Level Contributor
13 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 6 helpful votes
Reviewed 1 August 2013 via mobile

Chesapeake Beach is a great resort. This is my 3rd trip to Islamorada and I've stayed at The Hampton Inn before which is also very nice. I would rate Chesapeake above it because it feels more homey and has an old school Keys-feel. We stayed in room 314 which is an upstairs villa with an efficiency. It overlooks the water and a small lagoon. I really think we lucked out with this room. It's quaint and picturesque. I would definitely stay here again. If you're party crazy, I would stay somewhere else. It's more of a family/couples environment.

  • Stayed July 2013
    • Value
    • Location
    • Rooms
    • Cleanliness
    • Service
Helpful?
2 Thank Richard32796
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Hotels you might also like...
Travellers also viewed these Islamorada hotels
3.6 mi away
Amara Cay Resort
Amara Cay Resort
#6 of 19 in Islamorada
1,277 reviews
0.6 mi away
Postcard Inn Beach Resort & Marina
0.8 mi away
Pelican Cove
Pelican Cove
#5 of 19 in Islamorada
633 reviews
Show Prices
Show Prices
Show Prices
1.9 mi away
Cheeca Lodge & Spa
Cheeca Lodge & Spa
#7 of 19 in Islamorada
3,180 reviews
1.6 mi away
Islander Resort, a Guy Harvey Outpost
1.4 mi away
Drop Anchor Resort
Drop Anchor Resort
#4 of 19 in Islamorada
709 reviews
Show Prices
Show Prices
Show Prices

Been to Chesapeake Beach Resort? Share your experiences!

Write a Review Add Photos & Videos

Additional Information about Chesapeake Beach Resort

Property: Chesapeake Beach Resort
Address: 83409 Overseas Hwy, P.O. Box 909, Islamorada, FL 33036-3526
Region: United States > Florida > Florida Keys > Islamorada
Amenities:
Beach Business Centre with Internet Access Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Kitchenette Room Service Suites Swimming Pool Wheelchair access
Hotel Style:
#6 Top resorts Hotel in Islamorada
#11 On the Beach Hotel in Islamorada
Price Range (Based on Average Rates): ££
Hotel Class:2.5 star — Chesapeake Beach Resort 2.5*
Number of rooms: 65
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 delivers state-of-the-art amenities and luxurious accommodations to our guests. We are proud to offer HDTV, Stereo radio/CD/alarm and wireless internet connection, along with carpeting, furniture, bathrooms and kitchens including granite countertops and vanities; all to make your stay more enjoyable and relaxing. ... more   less 
Reservation Options:
TripAdvisor is proud to partner with Hotels.com, Booking.com, Travel Republic (UK), Expedia, TravelUp, Odigeo, TripOnline SA, Traveltool, S.L.U., Evoline ltd and HotelQuickly so you can book your Chesapeake Beach Resort reservations with confidence. We help millions of travellers each month to find the perfect hotel for both holiday and business trips, always with the best discounts and special offers.
Also Known As:
Chesapeake Beach Hotel Islamorada
Chesapeake Beach Resort Islamorada, Florida - Florida Keys

Is This Your TripAdvisor Listing?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing