8.4 Very Good Based on 725 reviews
Editor's Pick

"Kayaks and paddleboards rest on the private beach for guest use. Airy rooms feature ocean-view balconies. Best for weekend couples, less so for anyone sensitive to road noise."

From US$ 174 US$ 149 per night
Save 14%
Check-in
1 Oct 2026
Check-out
2 Oct 2026
Guests
2 guests

Adults:

2

Children:

0
  • Free cancellation
    on many rooms
  • No booking fees
    Pay at the hotel
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Why guests choose Chesapeake Beach Resort

  • Private Beach
    Guest-exclusive loungers
  • Water Sports
    Complimentary kayaks & paddleboards
  • Breakfast Delivery
    Order nightly to room
  • Family Villas
    Two-bedroom layouts
  • Live Music
    Weekly performances
  • Heated Pools
    Two with ocean views

Overview

Featuring a private location about 15 minutes by foot from Whale Harbor, the 3-star oceanfront Chesapeake Beach Resort Islamorada boasts access to a sand beach with free Wi-Fi and lounge chairs. Located 1.4 miles from Lobster Trap Art Gift Shop and Gallery, this Islamorada hotel offers views of the sea and a heated pool.

The resort is located approximately 5 minutes' walk from Whale Harbor Marina and Gallery Morada is approximately 10 minutes' drive away. The Chesapeake Beach Resort Islamorada is located 1.7 miles from Michelle Nicole Lowe Art Gallery. The nearby cultural attractions include History of Diving Museum, which is within reach of the accommodation.

The 45 allergy-free rooms are equipped with a flat-screen TV with satellite channels, along with a small refrigerator for guests' comfort. The spacious bathrooms come with hairdryers and towels as well as a walk-in shower and a separate toilet.

Chesapeake Beach Resort features a continental breakfast. The lounge bar will set you up nicely for enjoying your stay. Wahoo's Bar and Grill is adjacent to the hotel, around 5 minutes' walk away.

  • Check-in
    from 16:00 until 23:00
  • Check-out
    from 07:00 until 11:00
  • Hotel class
    3 stars
Chesapeake Beach Resort
Our tips

Should you book Chesapeake Beach Resort?

Perfect if you
  • Are looking for an outdoor pool with an ocean view.
  • Need free private parking available on site.
  • Are traveling with a pet, as the hotel is pet friendly.
Maybe skip if you
  • Need a full-service restaurant on site - the hotel only has a snack bar.
Best for
  • the complimentary kayaking and paddleboarding activities
  • the personalized breakfast delivery service

Facilities of Chesapeake Beach

General
  • No smoking on site
  • Wi-Fi
  • Parking
  • 24-hour reception
  • VIP check-in/ -out
  • Pets allowed
  • Rooms/ Facilities for disabled
  • Wheelchair access
  • Security
  • Luggage storage
  • Private beach
  • Allergy-free rooms
  • Lift
  • Smoke detectors
  • Toilet for disabled
  • Bathroom for disabled
  • Fire extinguishers
  • Key card access
Dining
  • Cookware/ Kitchen utensils
  • Snack bar
Leisure & Sports
  • Heated swimming pool
  • Outdoor swimming pool
  • Beach access
  • Sun loungers
  • Live entertainment
  • Yoga class
  • Fishing
  • Pool with view
  • Shallow end
Chesapeake Beach Guest Services
  • Housekeeping
  • Shops/Commercial services
  • Welcome drink
Room Amenities
  • Air conditioning
  • Heating
  • Sitting area
  • Garden furniture
  • Dining table
  • Free toiletries
  • Sink
  • Flat-screen TV
  • AM/FM alarm clock
  • Board games

Policies

Chesapeake Beach Resort applies these conditions to all bookings.
Check-in / Check-out
Check-in
from 16:00 until 23:00
Check-out
from 07:00 until 11:00
Important info
  • Children and extra beds
  • There are no extra beds provided in a room.
  • There are no cribs provided in a room.

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Check-in
1 Oct 2026
Check-out
2 Oct 2026
Guests
2 guests

Adults:

2

Children:

0
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