Chesapeake Beach Resort
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1 night
1 room, 2 adults, 0 children
All properties in Islamorada
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, Florida, 33036, United States
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Highlights
Pets welcome
Free parking
Delicious breakfast
Lots to doAmenities
Private parkingFree
24-hour front desk
Luggage storage
Wi-Fi in public areasFree
Private beach area
Pool with view
Heated pool
Concierge service
All amenities
Property Description
Located in Islamorada (Matecumbe), Chesapeake Beach Resort is within a 5-minute drive of History of Diving Museum and Windley Key Fossil Reef Geological State Park. This beach hotel is 1.2 mi (2 km) from Islamorada Brewery & Distillery and 1.7 mi (2.8 km) from Keys History & Discovery Center.
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8.8/10
Cleanliness8.8
Amenities8.7
Location8.9
Service8.7
All 104 reviews
Surroundings
Landmarks: Dog House Charters
(160m)
Landmarks: Islamorada Watersports Company
(160m)
Landmarks: Hound Dawg Charters
(160m)
Landmarks: Drop Back Charters
(170m)
Landmarks: Sea Horse Private Charters
(210m)
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Overview
Rooms
Guest Reviews
Services & Amenities
Policies
11
Standard King Room With Sofa Bed
1 King bed and 1 Sofa bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Electric fan
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11
Queen Room with Ocean View
2 Queen bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
TV
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14
King Suite with Ocean View
1 King bed and 1 Sofa bed
Non-smoking
Air conditioning
Refrigerator
TV
Ocean view
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7
Ada King Efficiency Villa
1 King bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Electric fan
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11
Standard Double Room
2 Double bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Electric fan
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9
Standard King Room
1 King bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Electric fan
Check Availability
12
Ada Ocean View Queens
2 Queen bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Ocean view
Check Availability
7
Deluxe Ocean View Two Queen Suite
2 Queen bed
Non-smoking
Air conditioning
Refrigerator
TV
Ocean view
Check Availability
6
Standard King Villa
1 King bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Electric fan
Check Availability
20
Hearing Impaired Ocean View King Suite
Bedroom 1:1 Sofa bed and 1 King bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Ocean view
Check Availability
12
Standard Queen Room
2 Queen bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Electric fan
Check Availability
Ocean View King Efficiency Villa
Bedroom 1:1 King bed ● Living Room 1:1 Sofa bed
Non-smoking
Air conditioning
Refrigerator
Ocean view
Electric fan
Check Availability
11
Hearing Impaired Ocean View Queens
2 Queen bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Ocean view
Check Availability
15
King Room with Ocean View
1 King bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Ocean view
Check Availability
7
King Efficiency Villa
1 King bed and 1 Sofa bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Electric fan
Check Availability
6
Premium Ocean View King Villa
Bedroom 1:1 King bed ● Living Room:1 Sofa bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Ocean view
Check Availability
10
Ada Ocean View Suite King
1 King bed
Non-smoking
Air conditioning
Refrigerator
TV
Ocean view
Check Availability
6
Two-Bedroom Villa
Bedroom 1:1 King bed ● Bedroom 2:1 Double bed ● Living Room:1 Sofa bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Electric fan
Check Availability
13
Ada Ocean View King
1 King bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Ocean view
Check Availability
7
Premium 1-Bedroom Ocean View Villa
Bedroom 1:2 Double bed ● Living Room:1 Sofa bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Ocean view
Check Availability
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Guest Reviews
8.8/10
Very Good
104 reviews
- Cleanliness8.8
- Amenities8.7
- Location8.9
- Service8.7
Average for similar properties in Islamorada
Review summary
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Location: Most reviews highlight proximity to the beach, with some noting it as "right on the beach" or "great location." The property is described as "dog-friendly" and near local restaurants.
Gianny
August 23, 2025
The place is beautiful and very clean. There were a couple of hiccups but the hotel was quick to fix it. The only part that is upsetting is using on the amenities: fish rod, it kept tangling up. But overall, we will be returning. The breakfast was like no other.
Guest User
August 6, 2023
Very bad experience I paid for a room with 2 beds and they gave me a room with an air bed and their answer was that everything was full and there were no towels in the pool I asked no one answered the beach very bad
Guest User
January 3, 2025
It was great because there was a hot spring and hot spa! Free kayak and paddle boats were available and breakfast was good. The price was really bad because it was the end of the year.
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GrandTour31200623971
August 27, 2025
This is truly our favorite getaway! Adriana and the entire team are so warm and welcoming. We always enjoy our stays here, especially with the convenient location near all the great local restaurants. The views are breathtaking, and I love stargazing at night. Breakfast is fantastic, with plenty of delicious options to choose from. Every year we return, this resort is truly the best in Islamorada.
Adam T
July 25, 2025
We just got bk from 3 nts here: 2adults 1 child. We absolutely loved this hotel, it was clean, the staff were friendly and the rooms were very clean and the AC was perfect for escaping from the Florida heat and humidity. The breakfast offerings were plentiful, huge shout out to the chef for his waffles for the kids. The outdoor breakfast area was perfect for sitting and staring out to sea and the Islamorada lighthouse. Make sure you check out the entry to the little marina where it narrows at the entry from the sea - looking into the crystal clear water at dawn and dusk we saw Nurse Sharks, Eels, Horseshoe crabs and so many small and media sized coloured fish. Get up early one morning to checkout the sunrise too!! So worth it! Would highly recommend and we will use again when we are next in Islamorada. A wonderful place to stay.
Guest User
September 25, 2025
The Chesapeake Resort was absolutely perfect for my wife and I on a trip through the FL Keys while celebrating our 50th wedding anniversary. The staff was
Christine C
March 24, 2025
Beautiful location with private beach. Very calm and casual. 2 pools are lovely Recently upgraded. Very comfortable bed and nice people at front desk. The chef at the omelette station in the morning is gruff and unfriendly, which isn’t in tune with the vibe of this little gem. If you are looking for a laid back experience in a lovely atmosphere then you are in the right place. They also have BYOB tiki huts seating 6 that will motor you out to the sandbar for a few hours.
Guest User
September 22, 2025
From check in to departure this expensive motel had broken a/c fixed three times still broken, never cleaned our room, phone not working, artwork missing because a/c leaked on it snd the couch. They took off one days $50 resort fee from $1250 bill for three nights. Stay at coconut in instead!!!!! Manager refused to reduce by 10% only $120. This nee renovation is a mess!!!!
Services & Amenities
Most popular amenities
Private parking
Free
24-hour front desk
Luggage storage
Wi-Fi in public areas
Free
Private beach area
Private beach area
More Amenities
Internet
Wi-Fi in public areas
Free
Outdoor swimming pool
Pool with view
Heated pool
Parking
Private (exclusively for guests) is available On-site parking. Reservation needed.
Private parking
Free
Front desk services
24-hour front desk
Concierge service
Luggage storage
VIP check-in service
Languages spoken
Spanish
Food & drink
Lobby bar
Convenience store/kiosk
Health & wellness
Kayaking
Motorized water sports equipment
Activities
Private beach area
Fishing
Public areas
No smoking in public areas
Elevator
Accessibility
Assistive listening devices
Handrails in hallways
Braille signs
Pool hoist available
Handrails on stairs
Accessible rooms available
Pool ramp available
Safety & security
First aid kit
Intruder alarm
Smoke detector
Fire extinguisher
Property Policies
Check-in and Check-out Times
Check-in: 16:00–23:00
Check-out: 07:00–11:00
Front desk hours: 24/7
Child policies
Children of all ages are welcome at this property.
Additional fees may be charged for children using existing beds. Add the number of children to get a more accurate price.
Cribs and Extra Beds
For all room types, extra beds cannot be added. Crib policies vary according to room type. Please refer to the relevant room type policy.
Breakfast
TypeWestern
| Age | Fee |
|---|---|
Adult | Contact property |
Additional breakfast fees are not included in the total and need to be paid at the property.
Pets
Pets are allowed on requestAdditional charge
Fee: Contact the property for details
Service animals
Service animals are allowed on request
Age Requirements
The main guest checking in must be at least 18 years old
Paying at the hotel
Property Description
- Opened: 2020
- Renovated: 2023
- Number of Rooms: 45
Phone:+1-305-6644662
Located in Islamorada (Matecumbe), Chesapeake Beach Resort is within a 5-minute drive of History of Diving Museum and Windley Key Fossil Reef Geological State Park. This beach hotel is 1.2 mi (2 km) from Islamorada Brewery & Distillery and 1.7 mi (2.8 km) from Keys History & Discovery Center.
Spend the day on the private beach or dip into one of the 2 outdoor swimming pools. This hotel also features complimentary wireless internet access and concierge services.
Wrap up your day with a drink at the bar/lounge. A complimentary continental breakfast is served daily from 6:00 AM to 10:00 AM.
Featured amenities include a computer station, a 24-hour front desk, and multilingual staff.
Make yourself at home in one of the 60 air-conditioned rooms featuring microwaves and flat-screen televisions. Your room comes with a pillowtop bed. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms feature showers, designer toiletries, and hair dryers.
Spend the day on the private beach or dip into one of the 2 outdoor swimming pools. This hotel also features complimentary wireless internet access and concierge services.
Wrap up your day with a drink at the bar/lounge. A complimentary continental breakfast is served daily from 6:00 AM to 10:00 AM.
Featured amenities include a computer station, a 24-hour front desk, and multilingual staff.
Make yourself at home in one of the 60 air-conditioned rooms featuring microwaves and flat-screen televisions. Your room comes with a pillowtop bed. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms feature showers, designer toiletries, and hair dryers.
Frequently Asked Questions
What is the cancellation policy for Chesapeake Beach Resort?
The cancellation policy for Chesapeake Beach Resort varies depending on the type of room and booking conditions.What is the cancellation policy for Chesapeake Beach Resort?
What are the check-in and check-out times at Chesapeake Beach Resort?
Standard check-in time at Chesapeake Beach Resort is 16:00-23:00 and check-out time is 11:00.What are the check-in and check-out times at Chesapeake Beach Resort?
Does Chesapeake Beach Resort provide breakfast?
Yes, Breakfast is offered at Chesapeake Beach Resort. Breakfast option(s): Western. Does Chesapeake Beach Resort provide breakfast?
Can I bring my pet inside the Chesapeake Beach Resort?
Pets are allowed on request at Chesapeake Beach Resort. Charges may be applicable.Can I bring my pet inside the Chesapeake Beach Resort?
About This Property
| Average Price From | PHP29011 |
|---|---|
| Hotel Star Rating | 2 |