Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL 33036-3526
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$439
$439
Free cancellation until 03/30/23
$464
$396
Hotels.com$439
Travelocity$439
Agoda.com$464
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About
#12 of 21 hotels in Islamorada
Location
Cleanliness
Service
Value
Travelers' Choice
The Key to Paradise - It’s not often you find a resort that exceeds your wildest dreams. The newly renovated Chesapeake Beach Resort takes everything you’ve ever wanted in a seaside vacation and places it in one scenic, majestic location. Celebrated as the Sport Fishing Capital of the World, Islamorada’s relaxed atmosphere provides an unmatched year-round destination. Visitors flock here for family vacations, group tours, corporate retreats, romantic escapes and more.
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Property amenities
Parking
Wifi
Pool
Vending machine
Beach
Fishing
Non-smoking hotel
Sun loungers / beach chairs
Hot tub
Pool / beach towels
Pool with view
Outdoor pool
Heated pool
Fence around pool
First aid kit
24-hour check-in
24-hour front desk
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Room features
Air conditioning
Private beach
Private balcony
Telephone
Coffee / tea maker
Refrigerator
Flatscreen TV
Walk-in shower
Iron
Private bathrooms
Wake-up service / alarm clock
Complimentary toiletries
Hair dryer
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Room types
Ocean view
Non-smoking rooms
Good to know
HOTEL CLASS
HOTEL STYLE
Marina View
Ocean View
Languages Spoken
English, Spanish
Location
63Somewhat walkable
Grade: 63 out of 100
11Restaurantswithin 1 km
2Attractionswithin 1 km
121Reviews27Q+A23Room tips
Reviews
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Beautiful view on a peaceful beach. Felt like our own private island beach. Friendly and helpful staff. Rooms were great....new...clean...spacious! great view fro. Our deck. Definitely coming back.
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Date of stay: February 2023Trip type: Traveled with friends
Value
Location
Service
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Helpful
Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 3 weeks ago
Thank you for taking the time to share your experience with us and with others. We are pleased you enjoyed your stay and thank you for highly recommending our hotel. Thanks again and we hope to see you soon!
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Garrett H wrote a review Feb 2023
The staff was awesome. So friendly!! The rooms were new and very clean. All have balconies. The surrounding area is laid back but also a nice drive either way lands you in a lot of great places. The beach was great for view and laying out. Heated pool was great and jacuzzi was a bonus. Overall for price and location and the setup I couldn’t asked for better. Definitely will be going back again
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Date of stay: January 2023Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Helpful
Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 13 Feb 2023
Thank you for taking the time to share your experience with us and with others. We are pleased you enjoyed your stay and thank you for highly recommending our hotel. Thanks again and we hope to see you soon!
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Nice property but not a resort. The check in was very slow & disorganized. The poor young girl at front desk was overwhelmed. Her "managers" just watched. No assistance was offered to her. The morning boxed breakfast was a joke. Making guest sign out beach towels is like staying @ Motel 6.
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Date of stay: February 2023Trip type: Traveled as a couple
Value
Location
Service
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
1 Helpful vote
Helpful
Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 6 Feb 2023
Thank you for taking the time to share your experience with us. We appreciate your feedback. Your comments have been shared with the team in hopes to prevent any future disappointment.
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Awesome place on the water to unwind. Not a beach for swimming really but the views are great and the pool and hottub were nice. Much quieter than key west and very laid back feel. Unit was very clean
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Date of stay: January 2023Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
1 Helpful vote
Helpful
Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 27 Jan 2023
Thank you so much for taking the time to share your experience. It means so much to know that you had such a wonderful time and hope to see you again soon!
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Pretty seasoned traveler coming to the keys for 35 plus years. Love the Cheeca bit for a one night pass through between Christmas and new years in key west decided not to spend $1500 for a night at Cheeca in a basic room. Booked an ocean from suite for three of us and while renovated and indeed a great view was disappointed in furnishing and cleanliness. Not terrible but as a pet friendly hotel it was indeed obvious more needed to be done in the housekeeping department. Super nice people working here but otherwise a lot is lacking . Not worth the $675 night for sure . I would put it on par with the courtyard Marriott in key largo. I can see why it would appeal online but in my opinion it’s a pass.
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Date of stay: January 2023Trip type: Traveled with family
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
2 Helpful votes
Helpful
Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 9 Jan 2023
Thank you for taking the time to share your experience with us. Your comments have been shared with the team in hopes to prevent any future disappointment.
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
This was a Good last minute stop Pricey but worth the location. We stopped just to see if room was available. Rent the canoes -we Saw dolphins and sting ray while canoeing Staff was friendly Beautiful location Cute little amenities just some small improvement and updates and it would be perfect
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Date of stay: January 2023Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
1 Helpful vote
Helpful
Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 3 Jan 2023
Thank you for taking the time to share your experience with us and with others. We are pleased you enjoyed your stay and hope to see you again!
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Seeking a getaway before Christmas we headed to the Florida Keys and Chesapeake Beach resort, formerly Chesapeake Bay resort on Islamorada. WE had shopped to find the best options for an inexpensive getaway in the prime real estate of the Florida keys in high season. Our costs for two was less than $170 per night including taxes, resort fee and fees. Most 3 star properties range higher. This included a light breakfast. WE appreciated the efforts at ADA accomodaiton including an elevator on the new unit we stayed in. This 64 room property went through major renovations over the past year It sits on a small private beach in Islamorada along the Overseas Highway which adds noise. The cove at the back of the property makes a secluded beach and allows a peninsula to it and watch sunrise and sunset. WE were upgraded to an "ocean front" room from one on the highway . This Atlantic has no surf or splashing waves as it laps at the sea wall and onto the 50 feet wide wading beach. Our balcony provided a second floor vision of sunrise and sunset. The noise of the highway was there but not in the room itself. The room was quite large , probably 300 sq ft with a very roomy bath with walk-in shower for two. Plenty of hot water. Everything was clean and new. The laminate floor was immaculate. The amenities includes refrigerator, microwave, Keurig coffee maker with cups , large full towels enough for four persons and bathroom stocks a plenty,. My first impression was a "four star hotel at a three star price". Our stay for two nights gave us more than we expected. The "continental breakfast" was a pre-printed menu filled out the day before to include fruit, cold cereal and milk, muffin, juice, and microwave Jimmy Dean sausage sandwich. All the supplies in the room were brand name from tissue to soap to breakfast. The two pools and hot tub were maintained and clean Men worked each day at sunrise to prep the pool for the guests,. The sand outside our room was raked each day. Every effort was made to make it look great. Toys like paddleboards were available for rent at the front desk. Beach towels were large and graciously signed out. Front desk staff made a difference. Q checked us in while handling three check ins at once. Each of us got her attention and follow-up. This property uses text liberally to check customers . Shaniqua the morning person checked in with us for our needs .This property does not do daily housekeeping unless asked for,. We had problems The toilet broke overnight. Shaniqua got the repair done while we were off to Key West. WE needed towels and coffee and that was supplied but we did not need our beds made or this very clean place to be wet mopped! Although our unit was less than a year old we had the toilet break( handle and flapper), the door lock on the patio fell apart and would not lock and the shower head leaked down the wall. The quality of the construction was sad although the units look great. The staff responded immediately to correct the problems but management needs to check the rooms for shoddy workmanship. My travel companion did not like the steep angle of the balcony chairs and the similar chairs out on the beach Not easy for older persons to get back out of,. WE enjoyed our stay and will return. As it is 2 hours south of Miami it is easy going. Key West is a two hour drive for a day of shopping and dining. Locally there are good restaurants. great location . .…
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Date of stay: December 2022
Cleanliness
Service
Sleep Quality
Room Tip: seek ocean view on farthest east building ours was 605 . All that building are second and third...
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
1 Helpful vote
Helpful
Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 3 Jan 2023
Thank you for taking the time to share your experience with us and with others! We are pleased you enjoyed your stay and thank you for your feedback! We hope to see you again soon!
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
+1
From the moment we came to check in we were greeted with friendly hellos and big smiles. The rooms are gorgeous. Large clean and chock full of everything you need. The amenities offer are great. Right on the beach and 2 pools to boot. Everyone gets a boxed daily complimentary breakfast. Pet friendly as well. I definitely recommend this place.
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Date of stay: December 2022Trip type: Traveled with family
Room Tip: Close to everything and parking is plentiful. You can walk or just take your ride less than a...
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
1 Helpful vote
Helpful
Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 22 Dec 2022
Thank you for taking the time to share your experience with us and with others. We are pleased you enjoyed your stay and thank you for highly recommending our hotel. Thanks again and we hope to see you soon!
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
A lovely roadside hotel which had everything we wanted for a relaxing stay after 2 weeks in Orlando. The room were big enough for a family of 4, modern and very clean. The staff were fantastic and very welcoming and helpful. Sure, there is some construction work going on, but we totally accept that and didn't affect our stay in any way at all. The walls are thin, but if everyone remains respectful it isn't a problem. The pool areas were clean and that's where we spent most of our days. Beach wise, there isn't much of it and you'd struggle to get a beach towel on there. All in all a fantastic stay for us
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Date of stay: November 2022
Cleanliness
Service
Sleep Quality
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Helpful
Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 16 Dec 2022
Thank you for taking the time to share your experience with us and with others. We are delighted you enjoyed your stay! We hope to see you again soon!
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Great location and views. Pet friendly, my dog enjoyed her stay and the beach. Rooftop bar next door (sand bar). Lobby staff very friendly and helpful, use of text messages to check on needs every day. Box breakfast was a nice freebie. Will be going back!
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Date of stay: December 2022Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Helpful
Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 7 Dec 2022
Thank you for taking the time to share your experience with us and with others. We are pleased you enjoyed your stay! We will look forward to welcoming you back!
Read more
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
PRICE RANGE
US$257 - US$529 (Based on Average Rates for a Standard Room)
ALSO KNOWN AS
chesapeake beach hotel islamorada
LOCATION
United StatesFloridaFlorida KeysIslamorada
NUMBER OF ROOMS
65
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Claim Your ListingCHESAPEAKE BEACH RESORT - UPDATED 2023 Reviews & Price Comparison (Islamorada, FL) - Tripadvisor
Frequently Asked Questions about Chesapeake Beach Resort
Which popular attractions are close to Chesapeake Beach Resort?
Nearby attractions include History of Diving Museum (0.9 km), Whale Harbor Marina (0.2 km), and Stacie Krupa Studio Gallery of Art (1.0 km).
What are some of the property amenities at Chesapeake Beach Resort?
Some of the more popular amenities offered include a pool, a hot tub, and internet access.
Which room amenities are available at Chesapeake Beach Resort?
Top room amenities include air conditioning, a flat screen TV, and a refrigerator.
What are some restaurants close to Chesapeake Beach Resort?
Conveniently located restaurants include Wahoo's Bar and Grill, Whale Harbor Seafood Feast (Buffet), and Ciao Hound.
Are there opportunities to exercise at Chesapeake Beach Resort?
Yes, guests have access to a pool during their stay.
Which languages are spoken by the staff at Chesapeake Beach Resort?
The staff speaks multiple languages, including English and Spanish.
Are there any historical sites close to Chesapeake Beach Resort?
Many travellers enjoy visiting Indian Key State Historic Site (4.0 km) and Pasta Pantaleo Signature Gallery (3.3 km).
Does Chesapeake Beach Resort have any great views?
Yes, guests often enjoy the harbour view available here.
Is Chesapeake Beach Resort accessible?
Yes, it offers wheelchair access and facilities for disabled guests. For specific inquiries, we recommend calling ahead to confirm.