Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL 33036 US
View Map Reservations: +1-800-219-2797
3.5 Star Property In Islamorada (Matecumbe)
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Select My Room
  • Pool hoist on site
  • Wheelchair-accessible pool
  • Free WiFi
  • Number of outdoor pools - 2
  • Free continental breakfast
  • Free bicycles on site
  • Free breakfast
  • Smoke-free property
  • Pool sun loungers
Select Your Room:
08/09/2026 - 08/10/2026
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2 bookings in the last 48 hours

Standard prices by room type for the next 60 days

Rates shown are nightly rates before taxes and do not necessarily reflect all discounts available. The chart provides the cheapest public rates available by room type.

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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.

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.

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.

Distances are displayed to the nearest 0.1 mile and kilometer.

History of Diving Museum - 0.9 km / 0.6 mi
Windley Key Fossil Reef Geological State Park - 1.8 km / 1.1 mi
Islamorada Brewery & Distillery - 2 km / 1.2 mi
Keys History & Discovery Center - 2.7 km / 1.7 mi
Matecumbe United Methodist Church - 3.1 km / 1.9 mi
Florida Keys Brewing Co. - 3.4 km / 2.1 mi
MoradaWay Arts & Cultural District - 3.5 km / 2.2 mi
Hurricane Monument - 3.6 km / 2.3 mi
Indian Key Historic State Park - 4.9 km / 3.1 mi
Rain Barrel Village - 5.1 km / 3.2 mi
Founders Park - 5.2 km / 3.2 mi
Islamorada County Park - 5.3 km / 3.3 mi
Bud n' Mary's Dive Center - 6.2 km / 3.8 mi
Old Road Gallery - 8.6 km / 5.4 mi
San Pedro Underwater Archaeological Preserve State Park - 10.1 km / 6.3 mi

The preferred airport for Chesapeake Beach Resort is Miami Intl. Airport (MIA) - 124.8 km / 77.5 mi

Featured amenities include a computer station, a 24-hour front desk, and multilingual staff.

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.

Amenities / Features

  • Check In: 4:00 PM
  • Check Out: 11:00 AM
  • Minimum age of oldest guest: 18
  • Wheelchair accessible (may have limitations)
  • Pool hoist on site
  • Wheelchair-accessible pool
  • Free WiFi
  • Wheelchair-accessible public washroom
  • Number of bars/lounges - 1
  • Well-lit path to entrance
  • Number of outdoor pools - 2
  • Braille or raised signage
  • Marina on site
  • Upper floors accessible by stairs only
  • Assistive listening devices available
  • Wheelchair accessible parking
  • Beach towels
  • Free continental breakfast
  • Boat tours on site
  • Fishing on site
  • Free bicycles on site
  • Off-street parking
  • Year Built - 2020
  • Number of buildings/towers - 9
  • Total number of rooms - 60
  • Number of floors - 2
  • Professional property host/manager
  • No rollaway/extra beds available
  • By ocean
  • No elevators
  • On private beach
  • Free breakfast
  • Visual alarms in hallways
  • Handrails in stairways
  • Multilingual staff
  • Handrails in hallways
  • 24-hour front desk
  • Personal motor watercraft nearby
  • Daily
  • Smoke-free property
  • Snorkeling nearby
  • Coffee/tea in common areas
  • Kayaking on site
  • Beach sun loungers
  • Computer station
  • Pool sun loungers
  • Fence around pool
  • Concierge services

Airport & Shuttle Information

2 hrs. from Miami or Key West

Airport Shuttle? Sorry, no airport shuttle available.

Breakfast Information

Included with your stay breakfast with cooked to order omelets and continental breakfast items

Pet Friendly?

Service animals complying with ADA Title lll regulations are allowed.

Maximum number of pets per room 2

Pet max weight (per pet) in lb is 50

Pet max weight (per pet) in kg is 23

Service animals are allowed

Service animals are exempt from fees/restrictions

Pets allowed

$50 per night per pet

Parking Info

Included in your stay

Internet / WiFI

Included in your stay

Misc Fees / Policies

  • Pet deposit: USD 50.00 per night
  • Pet fee: USD 50.00 per accommodation, per night
  • Service animals are exempt from fees
  • A late check-out fee will be charged

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

  • Pool access available from 8:00 AM to 6:00 PM.
  • Some facilities may have restricted access. Guests can contact the property for details using the contact information on the booking confirmation.
  • Construction is underway at a neighboring building and there may be noise disturbance from the construction work.
  • Guests can arrange to bring pets by contacting the property directly, using the contact information on the booking confirmation (surcharges apply and can be found in the Fees section).
  • Contactless check-in and contactless check-out are available.

Cleaning Policies

Contactless check-in is available

Contactless check-out is available

Essential workers only - NO

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