8.4 Very Good Based on 722 reviews
Editor's Pick

"Kayaks and paddleboards are available for use at this beachfront property, which features villas and direct ocean views. Best for water-loving couples, less so for anyone requiring ground-level access."

From US$ 174 US$ 149 per night
Save 14%
Check-in
4 Sept 2026
Check-out
5 Sept 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-only loungers
  • Water Sports
    Complimentary kayaks & paddleboards
  • Breakfast Delivery
    Ordered night before
  • Text Check-Ins
    Morning service requests
  • Two Pools
    Oceanfront heated
  • Spacious Villas
    Two-bedroom suites

Overview

The 3-star Chesapeake Beach Resort Islamorada includes boat tours along with setting approximately a 5-minute stroll from Whale Harbor Marina. Located on a private beach, this Islamorada resort is 1.7 miles from Michelle Nicole Lowe Art Gallery.

The hotel lies about 15 minutes by foot from Whale Harbor and around 25 minutes' walk from Lobster Trap Art Gift Shop and Gallery. There is Indian Key State Historic Site 2.6 miles from the smoke-free Chesapeake Beach Resort. The nearby cultural experience includes History of Diving Museum, which is just a 12-minute walk away.

There are 45 allergy-free rooms featuring a flat-screen TV with satellite channels as well as a small refrigerator for self-catering. The private bathrooms, fitted with a walk-in shower and a separate toilet, also offer hairdryers and bath sheets. All rooms also boast views of the ocean.

Chesapeake Beach Resort serves a free breakfast daily. Guests are welcome to a lounge bar on site. While staying at the property, guests can choose from dining options nearby, such as Wahoo's Bar and Grill, located merely 650 feet away, or Shuck N Dive at a 5-minute walking distance.

  • 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
  • enjoy an outdoor pool with an ocean view.
  • prefer a room with a 37-inch flat-screen TV and a small refrigerator.
  • are a 3-minute walk from the History of Diving Museum and a 4-minute drive from the Theater of the Sea.
Maybe skip if you
  • expect a continental breakfast rather than a full hot buffet.
Best for
  • Complimentary kayaking and paddleboarding activities right from the property
  • A personalized breakfast delivery service ordered the night before

Facilities of Chesapeake Beach

General
  • No smoking on site
  • Wi-Fi
  • Free 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.

Frequently asked questions

The cost of a night's stay in Chesapeake Beach Resort is $397.
Guests of Chesapeake will reach the downtown within 25 minutes' walk.
Popular spots near Chesapeake Beach Resort Islamorada include Hurricane Monument, History of Diving Museum, Upper Matecumbe Key, among others.
Restaurants near Chesapeake Beach Resort include Wahoo's Bar and Grill Restaurant, and Shuck N Dive.
Chesapeake Beach Resort Islamorada will accept Visa, American Express and Mastercard as well as other payment methods.
Chesapeake Beach Resort offers a spa center, an outdoor swimming pool and a picnic area.
Some rooms of Chesapeake Beach Resort Islamorada welcome guests with the following facilities:
  • a seating area
  • a small refrigerator
  • a safe box
  • a flat-screen cable-TV
.
Pets are welcome in Chesapeake.
Guests of Chesapeake Beach Resort may arrive to check in at 4 PM, and check out until 11 AM.

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Check-in
4 Sept 2026
Check-out
5 Sept 2026
Guests
2 guests

Adults:

2

Children:

0
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