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 do
Amenities
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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8.7/10
Very Good
Cleanliness8.7
Amenities8.8
Location8.8
Service8.6
All 103 reviews
Surroundings
Landmarks: Hound Dawg Charters
(150m)
Landmarks: Dog House Charters
(160m)
Landmarks: Islamorada Watersports Company
(160m)
Landmarks: Drop Back Charters
(170m)
Landmarks: Sea Horse Private Charters
(210m)
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Overview

Rooms

Guest Reviews

Services & Amenities

Policies

Standard King Room With Sofa Bed
8

Standard King Room With Sofa Bed

1 King bed and 1 Sofa bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Electric fan
Room Details
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Queen Room with Ocean View
11

Queen Room with Ocean View

2 Queen bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
TV
Room Details
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King Suite with Ocean View
14

King Suite with Ocean View

1 King bed and 1 Sofa bed
Non-smoking
Air conditioning
Refrigerator
TV
Ocean view
Room Details
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Ada King Efficiency Villa
7

Ada King Efficiency Villa

1 King bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Electric fan
Room Details
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Standard Double Room
9

Standard Double Room

2 Double bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Electric fan
Room Details
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Standard King Room
7

Standard King Room

1 King bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Electric fan
Room Details
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Ada Ocean View Queens
12

Ada Ocean View Queens

2 Queen bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Ocean view
Room Details
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Deluxe Ocean View Two Queen Suite
7

Deluxe Ocean View Two Queen Suite

2 Queen bed
Non-smoking
Air conditioning
Refrigerator
TV
Ocean view
Room Details
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Standard King Villa
6

Standard King Villa

1 King bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Electric fan
Room Details
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Hearing Impaired Ocean View King Suite
21

Hearing Impaired Ocean View King Suite

Bedroom 1:1 King bed and 1 Sofa bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Ocean view
Room Details
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Standard Queen Room
9

Standard Queen Room

2 Queen bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Electric fan
Room Details
Check Availability
Ocean View King Efficiency Villa

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
Room Details
Check Availability
Hearing Impaired Ocean View Queens
11

Hearing Impaired Ocean View Queens

2 Queen bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Ocean view
Room Details
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King Room with Ocean View
15

King Room with Ocean View

1 King bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Ocean view
Room Details
Check Availability
King Efficiency Villa
7

King Efficiency Villa

1 King bed and 1 Sofa bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Electric fan
Room Details
Check Availability
Premium Ocean View King Villa
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
Room Details
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Ada Ocean View Suite King
10

Ada Ocean View Suite King

1 King bed
Non-smoking
Air conditioning
Refrigerator
TV
Ocean view
Room Details
Check Availability
Two-Bedroom Villa
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
Room Details
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Ada Ocean View King
13

Ada Ocean View King

1 King bed
Non-smoking
Air conditioning
Private bathroom
Refrigerator
Ocean view
Room Details
Check Availability
Premium 1-Bedroom Ocean View Villa
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
Room Details
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Guest Reviews

8.7/10
Very Good
103 reviews
  • Cleanliness8.7
  • Amenities8.8
  • Location8.8
  • Service8.6
Average for similar properties in Islamorada
Most Mentioned
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.
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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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
July 26, 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
February 29, 2024
On pourrait plutôt parler d’un motel amélioré que d’ un véritable hôtel tant celui-ci semble déshumanisé. Comme dans les Motels, on se gare devant ou dessous sa chambre. Caractère renforcé par le mode de communication de l’hotel (via sms) et par le principe des petits déjeuners qu’il faut commander en détail la veille et venir chercher dans des box le matin. Aucun lieu de convivialité dans l’hôtel qui est situé en bord de highway que l’on entend bien le matin. Néanmoins les chambres sont grandes et bien équipées et les deux piscines très fonctionnelles. Les photos sont trompeuses, il n’existe pas de véritable plage (pas de sable) et la mer n’est pas très encourageante à cet endroit (pleine de posidonies). Enfin , la vue promise sur le jardin donnait en fait sur un chantier….
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G‍u‍e‍s‍t‍ ‍U‍s‍e‍r
June 28, 2025
The Place is beautiful and in an excellent location in Islamorada. The staff is friendly and accommodating. The complementary breakfast is great with a wide variety. The is a quaint marina on property for some small boats. Can't wait to revisit...
L‍o‍c‍a‍l‍G‍M‍a‍n
June 10, 2025
Absolutely horrible experience. There are so many great places to stay in the Keys — this is not one of them. Our room was filthy (hairs in the bed and shower — disgusting), the property was rundown, and loud guests were yelling in the middle of the night with no staff intervention. It didn’t feel safe or peaceful — at one point there was even a screaming match between two boaters inside the front office. Even worse: they bait-and-switched our room. We booked one with a sofa bed for extra sleeping space — only to find out that night when trying to open the sofa they’d downgraded us to a smaller room with no sofa bed. That left some of my guests sleeping on the dirty floor. Management admitted it, but refused to fix the issue and offered only a small, insulting refund. I'm disputing the charge with my credit card. I’ve been to the Keys many times — I go to relax, not deal with lies, filth, and chaos. Do yourself a favor and stay anywhere else. Amara Cay for one is a thousand times better and the staff there actually cares about their guests.
t‍l‍c‍o‍o‍p‍e‍r‍6‍5
June 1, 2025
Resort is nice with a paddle boards, kayaks, and fishing poles to used. Two restaurants next door so you don't need to drive. Room was great! Breakfast included custom made to order omelets.
r‍o‍n‍a‍l‍d‍c‍Q‍8‍5‍3‍1‍S‍I
May 23, 2025
We have stayed here several times, back in the 90's and early 2000s. been away for about 20 Years, was happy the property was totally remodeled, but kept the charm of what we enjoyed years ago.

Services & Amenities

Private beach area
More Amenities
Internet
Outdoor swimming pool
Parking
Private (exclusively for guests) is available On-site parking. Reservation needed.
Front Desk Services
Languages Spoken
Food & Drink
Public Areas
Health & Wellness
Activities
Accessibility
Safety & Security

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
AgeFee
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
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.

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 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.

Does Chesapeake Beach Resort provide breakfast?

Yes, Breakfast is offered at Chesapeake Beach Resort. Breakfast option(s): Western.

Can I bring my pet inside the Chesapeake Beach Resort?

Pets are allowed on request at Chesapeake Beach Resort. Charges may be applicable.

About This Property

Average Price FromPHP27284
Hotel Star Rating2