Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, United States - Near local attractions
4.0 88 reviews

The oceanfront Chesapeake Beach Resort Islamorada has 45 rooms and is located around 5 minutes' walk from the Whale Harbor Marina. Offering a lounge bar, this 3-star smoke-free resort also has a heated swimming pool beckoning guests to dive in.

Location

The traditional hotel has a private setting 2.8 km from the Lobster Trap Art Gift Shop and Gallery, while natural sights like the Windley Key Fossil Reef Geological State Park are about 2 km away. The History of Diving Museum is a popular place to visit within a few blocks of the Chesapeake Islamorada. Along with other cultural attractions the Rain Barrel Sculpture Gallery is nestled approximately 10 minutes' drive from the property.

Rooms

Some of the air-conditioned rooms of this Islamorada hotel face the sea, and comprise a balcony and a sitting area. Guests can make use of a microwave, and relax with Wi-Fi.

Food & Drinks

A free continental breakfast is offered each morning at the Chesapeake. This accommodation is within reach of Jaws Raw Bar serving American dishes.

Leisure & Activities

The hotel also offers a tennis court and a play area for extra charge. There is private access to an own beach with free Wi-Fi access, lounge chairs, and beach towels. Guests can enjoy a diving club at Chesapeake Beach Resort, which is located on a private beach.

Why choose Chesapeake Beach Resort Islamorada

Select room

  • Oceanfront venue with scenic views

  • Complimentary water sport rentals available

  • Private beach access for guests

  • Spacious rooms with balconies

Main amenities

  • Free Wi-Fi

  • 24-hour services

  • Swimming Pool

  • Private beach

  • Sports activities

  • Spa and relaxation

  • Wheelchair access

  • Air conditioning

  • Pets

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

Internet

  • Free Wi-Fi

Parking options

  • Free 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 cots provided in a room.

Enter dates to see availability

From USD 149 per night
Check-in 6 Dec 2025
Check-out 7 Dec 2025
Guests 2 guests

Adults:

2

Children:

0

Beautiful Experience

Exceptional stay! The staff's warmth and ocean view from the balcony made our mornings unforgettable.

Nicholas A. stayed in June 2025

Fantastic Location

Conveniently located by the marina and beach, our family loved the spacious room with awesome views.

Edward B. stayed in July 2025

Joyful Memories

Our reunion here was perfect! Friendly staff and stunning ocean sights made it so special for us all.

Rosie C. stayed in August 2025

True Paradise

This resort exceeded my hopes! Every sunrise on the balcony was a breathtaking memory in the making.

Eric D. stayed in September 2024

Wonderful Hospitality

Outstanding service and a relaxed vibe made this an unforgettable getaway! We can't wait to return.

Steven E. stayed in October 2024

Summary:

4.0/5 88 reviews
Special offers & deals Limited offer

Early Booking Discount

Up to 20% off
Save up to 20% when you book at least 30 days before your trip.

Summer Deal

Up to 15% off
Make the most of summer with up to 15% off and free breakfast โ€“ limited-time offer.

Members Only Rate

Up to 15% off
Join now to unlock up to 15% off on your dates โ€“ visible to members only.

Mobile-Only Deal

An exclusive discount โ€“ get up to 10% off when you book from your phone.

Family Package Deal

Up to 20% off
Save up to 20% with special family packages that include your stay, meals, and fun for the kids..

Rooms

Photos of Chesapeake Beach Resort Islamorada

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Chesapeake Beach Resort
Chesapeake Beach Resort
Chesapeake Beach Resort
Chesapeake Beach Resort

Chesapeake Beach Resort Islamorada

Hotel offering oceanfront relaxation and activities

Location of Chesapeake Beach Resort Islamorada

83409 Overseas Hwy, Islamorada, United States

 -  Near local attractions
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    Guest reviews of Chesapeake Beach Resort Islamorada

    8.6 Fabulous
    853 reviews

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    100% Verified Reviews
    Enter dates to see availability
    From USD 149 per night
    Check-in 6 Dec 2025
    Check-out 7 Dec 2025
    Guests 2 guests

    Adults:

    2

    Children:

    0
    Check-in & out
    6 Dec 2025
    โ€”
    7 Dec 2025
    Guests
    2 guests
    Check availability
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    Details:

    83409 Overseas Hwy, 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 cots provided in a room.