8.4 Very Good Based on 728 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
15 Nov 2026
Check-out
16 Nov 2026
Guests
2 guests

Adults:

2

Children:

0
  • Free cancellation
    on many rooms
  • No booking fees
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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

The 3-star oceanfront Chesapeake Beach Resort Islamorada offers quick access to Whale Harbor Marina, which is a mere 5 minutes' walk away. Located 1.4 miles from Lobster Trap Art Gift Shop and Gallery, this Islamorada hotel features 45 rooms with views of the sea.

Anne s Beach is about a 10-minute drive from the resort, while Rain Barrel Sculpture Gallery is located approximately 15 minutes' drive away. Located on a private beach, the Chesapeake Beach Resort Islamorada is 0.4 miles from Wilson Key. Guests will also enjoy proximity to Whale Harbor, situated around 15 minutes' stroll away. Staying at the accommodation, you can also enjoy natural sights such as Upper Matecumbe Key Island, which is 1.8 miles away.

A small refrigerator along with a flat-screen TV with satellite channels are provided in each of the allergy-friendly rooms at Chesapeake Beach Resort. A walk-in shower and a separate toilet along with such comforts as a hairdryer and bath sheets are featured in the private bathrooms.

Wahoo's Bar and Grill is in close proximity to the hotel.

  • 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
15 Nov 2026
Check-out
16 Nov 2026
Guests
2 guests

Adults:

2

Children:

0
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