Chesapeake Beach Resort

83409 Overseas Highway, Islamorada, United States - Close to local dining
4.0 88 reviews

Situated 1.7 miles from a shopping hub like Lobster Trap Art Gift Shop and Gallery, the 3-star oceanfront Chesapeake Beach Resort Islamorada provides guests with a convenience store and a lobby area. Located approximately 10 minutes' drive from Rain Barrel Sculpture Gallery, this hotel features 45 rooms with views of the pool.

Location

Located 2.1 miles from Upper Matecumbe Key Island, the smoke-free resort is also 2.8 miles from Rain Barrel Village. Located on a private beach, the Chesapeake Beach Resort Islamorada is about 5 minutes' walk from Wilson Key. Cultural experiences in the area feature Hurricane Monument, situated 2.3 miles from the traditional property.

Rooms

The rooms feature an air conditioner, along with a flat-screen TV with satellite channels for guests' utmost comfort. Guests will make use of hair dryers and towels in bathrooms equipped with a walk-in shower and a separate toilet.

Food & Drinks

Jaws Raw Bar is in the vicinity of Chesapeake Beach Resort and specializes in American cuisine.

Leisure & Activities

A tennis court and a playground can be booked at this Islamorada hotel at an extra charge. To relax after a busy day, a heated pool is provided on site.

Why choose Chesapeake Beach Resort Islamorada

Select room
  • Private beach access with lounge chairs

  • Renovated rooms with ocean views

  • On-site water sports rentals available

  • Outdoor pool with ocean view

Main amenities

  • Free Wi-Fi

  • 24-hour services

  • Swimming Pool

  • Private beach

  • Sports activities

  • Wheelchair access

  • Air conditioning

  • Pets

General
  • Free Wi-Fi
  • 24-hour services
  • Swimming Pool
  • Private beach
  • Sports activities
  • Wheelchair access
  • Air conditioning
  • Pets
1/17

Internet

  • Free Wi-Fi

Parking options

  • Parking

Activities

  • Yoga class
  • Fishing

Property services

  • 24-hour reception
  • VIP check-in/ -out
  • Security
  • Luggage storage
  • Housekeeping
  • Shops/Commercial services
  • Welcome drink

Dining options

  • Snack bar

In the kitchen

  • Cookware/ Kitchen utensils

For kids

  • Board games

Recreation

  • Private beach
  • Heated swimming pool
  • Outdoor swimming pool
  • Beach access
  • Sun loungers
  • Live entertainment
  • Pool with view
  • Shallow end

For disabled guests

  • Rooms/ Facilities for disabled
  • Wheelchair access
  • Toilet for disabled
  • Bathroom for disabled

In the rooms

  • Air conditioning
  • Heating
  • Sitting area
  • Garden furniture
  • Dining table

In the bathroom

  • Free toiletries
  • Sink

Devices

  • Flat-screen TV
  • AM/FM alarm clock

General facilities

  • No smoking on site
  • Allergy-free rooms
  • Lift
  • Smoke detectors
  • Fire extinguishers
  • Key card access

Pets

  • Pets allowed

Important information

Check-in:
from 16:00 until 23:00
Check-out:
from 07:00 until 11:00
  • Children and extra beds
  • There are no extra beds provided in a room.
  • There are no cribs provided in a room.

Enter dates to see availability

From USD 149 per night
Check-in 27 Feb 2026
Check-out 28 Feb 2026
Guests 2 guests

Adults:

2

Children:

0

Rooms

Photos of Chesapeake Beach Resort Islamorada

Location of Chesapeake Beach Resort Islamorada

83409 Overseas Highway, Islamorada, United States

 -  Close to local dining
Attractions
Great restaurants
Transportation

Places nearby

    Guest reviews of Chesapeake Beach Resort Islamorada

    8.4 Very Good
    802 reviews

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    100% Verified Reviews
    Enter dates to see availability
    From USD 149 per night
    Check-in 27 Feb 2026
    Check-out 28 Feb 2026
    Guests 2 guests

    Adults:

    2

    Children:

    0
    Check-in & out
    27 Feb 2026
    28 Feb 2026
    Guests
    2 guests
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    Details:

    83409 Overseas Highway, Islamorada, United States

    Important information
    Chesapeake Beach Resort
    Check-in:
    from 16:00 until 23:00
    Check-out:
    from 07:00 until 11:00
    • Children and extra beds
    • There are no extra beds provided in a room.
    • There are no cribs provided in a room.