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Chesapeake Beach Resort

US$175
/ night

Avg. for September

Chesapeake Beach Resort - Image 1
Chesapeake Beach Resort - Room
Chesapeake Beach Resort - Room
Chesapeake Beach Resort - Reception
Chesapeake Beach Resort - Bathroom

Select dates to see prices and availability

US$175
/ night

Avg. for September

Monthly average prices

Nightly prices at Chesapeake Beach Resort average US$175 in the cheapest month (September) and US$460 in the most expensive month (March), based on the last 12 months.

Average nightly price at Chesapeake Beach Resort by month, last 12 months (USD)
MonthAverage price
JanuaryUS$325
FebruaryUS$455
MarchUS$460
AprilUS$395
MayUS$315
JuneUS$272
JulyUS$278
AugustUS$217
SeptemberUS$175
OctoberUS$189
NovemberUS$256
DecemberUS$325

Most expensive: March (~US$460)

Cheapest: September (~US$175)

About this property

Spend the day on the private beach or dip into one of the 2 outdoor pools. This hotel also features complimentary wireless internet access and concierge services.
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  • Parking

  • Swimming pool

  • Non-smoking rooms

  • Housekeeping

  • Private beach

  • Beach (nearby)

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Location

83409 Overseas Highway, Matecumbe, Islamorada, Florida, United States of America

History of Diving Museum (0.6 Miles)

Windley Key Fossil Reef Geological State Park (1.1 Miles)

Islamorada Brewery & Distillery (1.2 Miles)

Lorelei Restaurant & Cabana Bar (1.7 Miles)

Keys History & Discovery Center (1.7 Miles)

Hog Heaven (1.9 Miles)


Room options

Ocean View King Suite

Room details

1 Extra-Large Double Bed
and
1 Sofa Bed

Sleeps 4

527 ft²

Balcony
Air Conditioning
Wi-Fi (Free)
Separate Living Room

Hearing Impaired Ocean View King Suite

Room details

1 Extra-Large Double Bed
and
1 Sofa Bed

Sleeps 4

540 ft²

Balcony
Air Conditioning
Wi-Fi (Free)
Separate Living Room

Adapted King Efficiency Villa

Room details

1 Extra-Large Double Bed

Sleeps 2

517 ft²

Separate Dining Area
Air Conditioning
Wi-Fi (Free)
Kitchenette

Adapted Ocean View King Suite

Room details

1 Extra-Large Double Bed

Sleeps 4

540 ft²

Balcony
Air Conditioning
Wi-Fi (Free)
Separate Living Room

2-Bedroom Villa

Room details

1 Extra-Large Double Bed
,
1 Double Bed
and
1 Sofa Bed

Sleeps 6

646 ft²

Air Conditioning
Wi-Fi (Free)
Kitchenette

Premium 1-Bedroom Ocean View Villa

Room details

2 Double Beds
and
1 Sofa Bed

Sleeps 6

700 ft²

Separate Dining Area
Air Conditioning
Wi-Fi (Free)
Kitchenette

Standard King with Sleeper Sofa

Room details

1 Extra-Large Double Bed
and
1 Sofa Bed

Sleeps 4

307 ft²

Deck or Patio
Air Conditioning
Wi-Fi (Free)
Microwave

Ocean View King

Room details

1 Extra-Large Double Bed

Sleeps 2

364 ft²

Balcony
Air Conditioning
Wi-Fi (Free)
Microwave

Standard King Villa

Room details

1 Extra-Large Double Bed

Sleeps 2

323 ft²

Air Conditioning
Wi-Fi (Free)
Kitchenette

Ocean View Queens

Room details

2 Large Double Beds

Sleeps 4

366 ft²

Balcony
Air Conditioning
Wi-Fi (Free)
Microwave

King Efficiency Villa

Room details

1 Extra-Large Double Bed
and
1 Sofa Bed

Sleeps 4

517 ft²

Separate Dining Area
Air Conditioning
Wi-Fi (Free)
Kitchenette

Ocean View King Efficiency Villa

Room details

1 Extra-Large Double Bed
and
1 Sofa Bed

Sleeps 4

517 ft²

Separate Dining Area
Air Conditioning
Wi-Fi (Free)
Kitchenette

Standard Doubles

Room details

2 Double Beds

Sleeps 4

272 ft²

Balcony
Air Conditioning
Wi-Fi (Free)
Microwave

Adapted Ocean View King

Room details

1 Extra-Large Double Bed

Sleeps 2

364 ft²

Balcony
Air Conditioning
Wi-Fi (Free)
Microwave

Adapted Ocean View Queens

Room details

2 Large Double Beds

Sleeps 4

366 ft²

Balcony
Air Conditioning
Wi-Fi (Free)
Microwave

Premium Ocean View King Villa

Room details

1 Extra-Large Double Bed
and
1 Sofa Bed

Sleeps 4

829 ft²

Separate Dining Area
Air Conditioning
Wi-Fi (Free)
Kitchenette
Patio

Hearing Impaired Ocean View Queens

Room details

2 Large Double Beds

Sleeps 4

366 ft²

Balcony
Air Conditioning
Wi-Fi (Free)
Microwave

Standard King

Room details

1 Extra-Large Double Bed

Sleeps 2

272 ft²

Balcony
Air Conditioning
Wi-Fi (Free)
Microwave

Standard Queens

Room details

2 Large Double Beds

Sleeps 4

307 ft²

Deck or Patio
Air Conditioning
Wi-Fi (Free)
Microwave

Deluxe Ocean View Two Queen Suite

Room details

2 Large Double Beds

Sleeps 6

650 ft²

Balcony
Air Conditioning
Wi-Fi (Free)
Separate Living Room

Guest reviews

What guests think

AI-generated summary based on recent guest reviews

Across recent reviews, Chesapeake Beach Resort is praised for clean, updated rooms, a scenic oceanfront setting, and a relaxed vibe with pools, a small beach, and included water activities, while service and amenities feel mostly friendly and convenient.

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Facilities

Good

Cleanliness

Clean

Rooms

Modern

Service

Friendly

Location

Scenic

Dining

Tasty

Was this helpful?

10

Debrah

IAN-logo

3 weeks ago

·

Stayed 3 nights

Beautiful property and great little breakfast!!
Beautiful property and great little breakfast!!

10

Janet

IAN-logo

3 weeks ago

·

Stayed 3 nights

Check-in went smoothly and the little touch of offering some champagne on arrival made me feel special! Loved the updated room! Beds comfy. Staff accommodating. Breakfast has many great hot /cold choices. Coffee was 👍One of the Pools was a little dirty but front desk had maintenance on it when I informed them ..
Check-in went smoothly and the little touch of offering some champagne on arrival made me feel special! Loved the updated room! Beds comfy. Staff accommodating. Breakfast has many great hot /cold choices. Coffee was 👍One of the Pools was a little dirty but front desk had maintenance on it when I informed them ..

8

Cheryl

IAN-logo

3 weeks ago

·

Stayed 1 night

We arrived one hour and twenty minutes before check in and were told there were no available rooms, although I am positive there were clean ready rooms. My husband and I went to the pool and enjoyed some music before checking into our room. Room was clean and comfortable. Continental breakfast served the next morning. The attendance were lovely and seemed happy to be at work. Check out soon after.
We arrived one hour and twenty minutes before check in and were told there were no available rooms, although I am positive there were clean ready rooms. My husband and I went to the pool and enjoyed some music before checking into our room. Room was clean and comfortable. Continental breakfast served the next morning. The attendance were lovely and seemed happy to be at work. Check out soon after.

10

Dawn

IAN-logo

3 weeks ago

·

Stayed 2 nights

Great place to stay, good location to restaurants and activities. Nice pool with tiki bar that mix a good drink. Full breakfast with made to order eggs and omelets which was a nice change from the normal continental breakfast. Stayed by the pool because Beach was full of sargassum but they work hard to clean it. Not much swimming room in the ocean…again a lot of seaweed.
Great place to stay, good location to restaurants and activities. Nice pool with tiki bar that mix a good drink. Full breakfast with made to order eggs and omelets which was a nice change from the normal continental breakfast. Stayed by the pool because Beach was full of sargassum but they work hard to clean it. Not much swimming room in the ocean…again a lot of seaweed.

10

Jamie

IAN-logo

3 weeks ago

·

Stayed 2 nights

The staff was excellent and the amenities were very convenient
The staff was excellent and the amenities were very convenient

Property policies

Check-in instructions

Everything you need to know for a smooth check-in.

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Check-in

Check-out

From 16:00 to 23:00

Before 11:00


Good to know

Additional policies and info about this property.

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Optional extras

Additional paid services you can request.

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FAQs about Chesapeake Beach Resort

Is parking available at the property?

Parking is available on-site and is free. However, it is limited, so guests are encouraged to arrive early.


What type of breakfast is offered and what are the serving hours?

A complimentary continental breakfast is served daily from 6:00 AM to 10:00 AM.


Does the property allow pets?

Pets are allowed at the property with a pet fee of USD 50.00 per accommodation, per night. Service animals are exempt from fees.


What are the standard check-in and check-out times?

Check-in time is at 4:00 PM and check-out time is at 11:00 AM. Early check-in and late check-out may be available upon request and may incur additional charges.

What accessibility features are available for guests with disabilities?

The property offers limited wheelchair accessibility, including accessible parking and public areas. Guests are encouraged to contact the property for specific needs.


What is the location of the property in relation to key landmarks?

Chesapeake Beach Resort is located in Islamorada (Matecumbe), within a 5-minute drive of the History of Diving Museum and Windley Key Fossil Reef Geological State Park. It is approximately 1.2 miles from Islamorada Brewery & Distillery and 1.7 miles from Keys History & Discovery Center.


Does the property have a swimming pool?

Yes, the property features two outdoor pools, including a heated pool. Pool access is available from 8:00 AM to 6:00 PM.


What are the policies for guests staying with children?

Children are welcome at the property. There is no minimum age requirement for children to stay for free.


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Prices for upcoming dates

September 2026
October 2026

Cheaper

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Average nightly price across deals, with taxes & fees.

Prices in USD for 2 guests, updated daily.



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