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83409 Overseas Hwy, Islamorada, FL 33036-3526
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Prices are provided by our partners, and reflect average nightly room rates, including taxes and fees that are fixed, known to our partners, and due at time of booking. Other miscellaneous taxes and hotel fees which are not fixed or due at time of booking may be payable at the property at time of stay. Please see our partners for more details.
Traveller (92)
360
Panoramas (12)
Room & Suite (186)
What is Travellers’ Choice?
Tripadvisor gives a Travellers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travellers and are ranked within the top 10% of properties on Tripadvisor.
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What you can expect during your stay
  • All linens sanitised in high-temperature wash
  • Individually wrapped toiletries
Updated 24/09/20 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.
Updated 24/09/20 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.

About

#18 of 20 in Islamorada
Location
Cleanliness
Service
Value
Travellers' 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 bath
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
Ocean View
Marina View
Languages Spoken
English, Spanish
63Reviews27Q+A14Room tips
Traveller rating
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aquadicted66 wrote a review Yesterday
San Pedro, Belize10 contributions9 helpful votes
Booked this hotel as the images looked great and it was on the water. The price was pretty high so figured with breakfast included and all the amenities it would still be a great place to stay. Upon check in the staff and manager were super friendly and I give them 5 stars for sure. The room was in great shape but again for price some what basic and lacking in some amenities. The biggest problem was breakfast. Paying over 350 a night and having a box breakfast with a you microwave frozen egg biscuit thing and bottle of juice and an old muffin. Absolutely uneatable! I would leave the breakfast out of it all together. The beach area was clean and chairs available and pool was nice but still way over priced for current state of property and operations
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Date of stay: May 2022
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Lynne R wrote a review 9 May
13 contributions3 helpful votes
The hotel (can't really call it a resort) is very obviously undergoing a major rebuild. The views from our room were the only really pleasing part. There are no dining facilities at all. You fill in a form for breakfast and give it in to the desk. Next morning you go the front desk and pick up a box with a prepackaged muffin,Jimmy Dean Breakfast sandwich or granola bar.. Not what we were expecting. The front desk staff were very nice and friendly. You do have to text in the morning if you require anything. This also means if you want your room serviced. The decor of the rooms is ok but I nearly lost my finger to the barn door several times. There is one teeny tiny dresser to put your clothes, I didn't bother. Also one hanging closet. The pools were nice and the views excellent.
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Date of stay: May 2022
Value
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Service
Room Tip: Ask for ocean or pool facing
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Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 5 days ago
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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sunnsea302 wrote a review Apr 2022
Miami, Florida90 contributions15 helpful votes
Checked in w/ Annie asked if the 2 rooms I booked could be split. I pay for 1 room my friends pay for theirs. She said no problem and we took out two credit cards. Just got my Amex bill and both rooms are on it! Ugh now I have to ask these other people for $$$ for this room which was totally avoidable! In addition, my room key continuously didn’t work. In the morning it took 4 trips to the office to get it straightened out. Then I checked out. The place looks clean but housekeeping really needs to bend down and wipe the lower portion of the bathroom. Breakfast was a jimmy dean sausage biscuit , my bag had 4 don’t know why I was only 1. Nice place for 1 night but they need to get it together!
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Date of stay: April 2022Trip type: Travelled
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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. Your comments have been shared with the team in hopes to prevent any future disappointment. Thanks again and we hope to see you soon.
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Annette W wrote a review Mar 2022
Elmhurst, Illinois6 contributions1 helpful vote
If you are looking for a hotel on the water this is a perfect place. The ocean and two pools are just steps away from the hotel rooms. The sandy beach area is small but not crowded and pretty well maintained. The hotel Is also convenient to many restaurants and activities on the island. The bad things about this hotel are cleanliness of the rooms ( our floor wasn’t cleaned from the previous guest ) and no “in room “safes. Housekeeping is done on request. I wish the breakfast was optional because we didn’t eat it once .
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Date of stay: April 2022Trip type: Travelled
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Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 4 Apr 2022
Thank you for taking the time to share your experience. Your comments have been shared and addressed with the team in the hopes of preventing any future disappointment.
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Ellen M wrote a review Mar 2022
Westampton, New Jersey1 contribution
Beautiful location and views of the ocean. Clean room, 2 pools, and beaches. Staff were friendly and responsive. Breakfast was minimal but adequate. Wahoos bar/restaurant a short walk and a great spot for lunch or dinner. An easy Uber ride to other restaurants.
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Date of stay: March 2022Trip type: Travelled
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Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 25 Mar 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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Susan S wrote a review Mar 2022
New York, New York, United States14 contributions14 helpful votes
The motel calls itself a resort but it has no amenities. It says it has a beach but the area is too rocky to swim in and the sand has so many shells and rocks you have to wear shoes to walk around, they say that have complimentary breakfast but we had to fill out a sheet which had granola bars, cereal or blueberry muffins and then pick it up in the lobby.
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Date of stay: March 2022
Rooms
Service
Sleep Quality
Room Tip: This resort is way to expensive for what it has to offer.
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Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 21 Mar 2022
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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AnnieBag wrote a review Mar 2022
Butler, Pennsylvania146 contributions34 helpful votes
Chesapeake was one of the few hotels we could find in Islamorada where we could book a one night stay - every other hotel (in season) required 3 to 4 nights! It couldn't have been more perfect!!! The hotel is conveniently located - perfect for us to visit family who lives there - as well as convenient to restaurants, night life, shopping - AND did I mention they have their own beautiful beach as well as 2 swimming pools!!! Anna at the front desk was awesome - she gave us dining tips and some of the "must see" places in Islamorada, and she made check-in a breeze. Our room was spotless, lots of parking and had an ocean view. We will definitely book again. Thank you Chesapeake Beach Resort for a beautiful stay.
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Date of stay: February 2022
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Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 9 Mar 2022
Thank you for taking the time to share your experience with us and with others. We aim to provide the best service and accommodations in the hospitality industry and are pleased we met our goal! 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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Donald M wrote a review Mar 2022
6 contributions2 helpful votes
This is a hard review to write because the setting is ideal, the staff is very nice -- but the level of service makes it feel like the owners are trying to squeeze out profits by spending as little as possible on basic housekeeping. First the good part: Islamorada is a fishing mecca with fun activities. The Diving Museum is surprisingly great. The island is still homey, not full of franchise joints like Key West. The Chesapeake is a beautiful setting on the northern tip of Islamorada where it meets Whale Harbor Channel so there is a constant flow of boats going by and lots of birds -- pelicans, cormorants, even an osprey hunting from a palm tree on the property. If you have an Ocean View room, you see sunrise over the ocean and can go out on the walkway outside your door to see the sunset. The Chesapeake is small and cozy, not sprawling like the Islander Resort. The rooms are new -- it's been rebuilt since it was trashed by a hurricane -- and they are quite nice. There is a pretty beach and two pools and a hot tub. Do wear sandals -- it's crushed coral mixed with sand. The Wahoo Grill, a good fish restaurant with a bar with boat-harbor views is a five minute walk away. The Publix supermarket is nearby. Be careful crossing the road -- the traffic is relentless. Parking at the Chesapeake is free and sometimes in the shade. The hotel is family-friendly and pet-friendly. Others complain about thin walls; they didn't bother us. There is traffic noise, yes, but the Keys are narrow with a busy highway going through so that's pretty much inevitable. The staff, especially Anna and Shaniqua at the front desk when we were there, could not have been nicer. Now for the reason this is not a five-star review and why I thought about three stars: The week we went -- first week of March -- our room cost $550 a night. When you're paying that much, you sort of expect someone will drop by once during the day to make the bed, sweep the room, take away the garbage and change the towels. You think you can put one of those "Please Make Up The Room" tags on the doorknob and it will happen. But here's the Chesapeake Trick: unless you specifically send the front desk a text each day requesting each thing you want -- towels, sweeping, make beds, etc: THEY DON'T DO IT. It looks like they have a cleaning service drop by from 9 AM to 3 PM and the overworked ladies race to make up the vacated rooms and have very little time to do anything for the multi-day guests. When you check in, the hotel DOES NOT make this clear. They say they do -- but they don't. Even when we figured out the game and asked that our room be swept while we were out, whoever came in and changed the towels clearly didn't sweep. I could tell because the dragonfly wing that was in the middle of the floor when we left was still there when we came back. This is not being done for Covid safety -- because if you insist loud enough, they will get it done. It just seems like an attempt to not spend as much money on staff as they should. Other drawbacks: if you don't pay for an ocean view room, you will not be looking at a Garden View. You will be looking at a broken tennis court with pickup trucks parked on it and at the construction site next door. The beach is very pretty and you can walk into the water, but be careful -- I went swimming and found the tide pushing me hard toward the inlet. I put my feet down in the sandy grass and pushed my way back. A small child could have been swept away. Since the place is pet-friendly, your sunrise beach view includes other guests taking their dogs out for a morning poop. Everyone I saw seemed to pick up after their dogs. May you be so lucky. There is a breakfast included, which is nice, but it's a box that contains a Jimmy Dean sausage and egg sandwich, a banana or an orange, and some cereal. So, overall, it's a beautiful resort setting with resort prices, but Motel 6 service. Dress accordingly.
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Date of stay: March 2022
Value
Location
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Room Tip: Pay for an ocean view. Higher is nicer.
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2 Helpful votes
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Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 9 Mar 2022
Thank you for taking the time to share your experience with us and with others. We appreciate your feedback and hope you have the chance to visit us again.
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Ashlee E wrote a review Jan 2022
Des Moines, Iowa4 contributions
We loved our stay! Amenities were close and loved it being pet friendly! Would suggest another ice machine in each building or lobby. We only found one in a different building but no big deal. Would definitely stay again and recommend
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Date of stay: January 2022Trip type: Travelled
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Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 19 Jan 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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DivineTravelDesigns wrote a review Jan 2022
Washington, Illinois8 contributions3 helpful votes
A beyond wonderful staff, clean rooms, a restaurant 🍴 and a bar on property. Oceanfront 🏖 beach. Quiet as well while we were there. The Chesapeake Bay is the only hotel I stay at in the early Keys. Reasonably priced considering where you are traveling. Amy Sons Divine Travel Designs
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Date of stay: December 2021
Cleanliness
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Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 17 Jan 2022
Thank you for taking the time to share your experience with us and with others. We are delighted you enjoyed your stay and we hope to see you again!
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Previous
PRICE RANGE
$316 - $496 (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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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.
Is parking available at Chesapeake Beach Resort?
Yes, parking is available to guests.
What are some restaurants close to Chesapeake Beach Resort?
Conveniently located restaurants include Wahoo's Bar and Grill, Ciao Hound, and Ziggie & Mad Dog's.
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 enquiries, we recommend calling ahead to confirm.