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See prices from 13 sites
from$201
See prices from 13 sites
from$201
  • Surroundings
  • Room details

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About Chesapeake Beach Resort

  • Heated oceanfront swimming pools

    Relax in two distinct heated pools, including a family-friendly option and a more private retreat, both surrounded by loungers and palm trees.

  • Modern coastal villas and suites

    Unwind in recently renovated accommodations featuring screened-in balconies, walk-in showers, and premium touches like plush robes and slippers.

  • Wellness and relaxation amenities

    Immerse yourself in tranquility with on-site beach yoga sessions or a soothing soak in the outdoor hot tub after a day of island adventures.

  • Central Islamorada lifestyle access

    Explore the Sport Fishing Capital of the World with a short walk to the History of Diving Museum and local favorites like Wahoo’s Bar & Grill.

  • On-site boat and trailer facilities

    Utilize the rare guest-only boat launch and dedicated trailer parking, perfect for travelers arriving with their own watercraft for reef excursions.

  • Oceanfront made-to-order breakfast

    Savor personalized omelets and fresh waffles prepared by Chef Chris while enjoying a sunrise view over the Atlantic from the outdoor dining patio.

The 3-star Chesapeake Beach Resort is an oceanfront property in Islamorada, recently renovated and offering pet-friendly accommodations. Located in the "Sport Fishing Capital of the World," the resort provides lagoon access for fishing and boating, and is a short walk from the History of Diving Museum. Guests can enjoy two heated oceanfront pools, a private beach with complimentary water sports, and made-to-order breakfast with ocean views. The resort has a review score of 8.8 based on over 3,000 reviews, with atmosphere, location, and overall experience highlighted positively by guests.

This summary was created by AI and might not be 100% accurate.

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    Select dates to see exact prices

    • Free WiFi
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    • Pool
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Price trend

Based on lowest prices on trivago from the last 30 days
$579
$290
$0

Sun, 10/18/26

$273

Mon, 10/19/26

$296

Tue, 10/20/26

$312

Wed, 10/21/26

$312

Thu, 10/22/26

$479

Fri, 10/23/26

$530

Sat, 10/24/26

$540

Sun, 10/25/26

$501

Mon, 10/26/26

$459

Tue, 10/27/26

$324

Wed, 10/28/26

$339

Thu, 10/29/26

$465

Fri, 10/30/26

$377

Sat, 10/31/26

$338

Sun, 11/01/26

$314

Mon, 11/02/26

$295

Tue, 11/03/26

$286

Wed, 11/04/26

$453

Thu, 11/05/26

$459

Fri, 11/06/26

$531

Sat, 11/07/26

$579

Sun, 11/08/26

$314

Mon, 11/09/26

$467

Tue, 11/10/26

$298

Wed, 11/11/26

$214

Thu, 11/12/26

$543

Fri, 11/13/26

$452

Sat, 11/14/26

$398

Sun, 11/15/26

$288

Mon, 11/16/26

$467

Tue, 11/17/26

$462

Wed, 11/18/26

$241

Thu, 11/19/26

$268

Fri, 11/20/26

$393

Sat, 11/21/26

$556

Sun, 11/22/26

$349

Mon, 11/23/26

$337

Tue, 11/24/26

$351

Wed, 11/25/26

$429

Thu, 11/26/26

$531

Fri, 11/27/26

$555

Sat, 11/28/26

$466

Sun, 11/29/26

$282

Mon, 11/30/26

$317

Tue, 12/01/26

$310

Reviews

8.8
Excellent
based on 4,033 ratings from top 
sites
sites

Review summary

Summarized by AI from 1,000+ reviews

A tranquil waterfront escape for active couples and families.


This resort serves as a serene haven for travelers seeking a coastal getaway defined by relaxation and recreation. The property sits alongside notable points of interest in Islamorada and is rounded out by well-maintained outdoor facilities including pristine pools and a private beach. Guests consistently praise the comfortable beds for a restful night’s sleep, and those booking an ocean-view balcony can enjoy a picturesque setting for morning coffee. The complimentary breakfast remains a guest favorite, particularly the popular made-to-order omelet station that provides a high-quality start to the day.


Some guests mentioned: limited sound insulation, occasional parking complexity, breakfast shortages.

Rated above average for Islamorada

Guest reviews

Excellent69%
Very good17%
Good8%
Fair4%
Poor2%

Top amenities

  • WiFi in lobby
  • WiFi in rooms
  • Pool
  • Parking
  • Pets
  • A/C
  • Hotel bar

All amenities

Property amenities

  1. Business centre
  2. Entrance hall/lobby
  3. Express check-in/check-out
  4. Parking

Accessibility

  1. Wheelchair accessible
  2. Accessible parking

Room amenities

  1. Shower
  2. Ironing board
  3. Openable windows
  4. Television

Sports facilities

  1. Volleyball
  2. Yoga
  3. Fishing

Location

Highlight
Central Islamorada lifestyle access
Explore the Sport Fishing Capital of the World with a short walk to the History of Diving Museum and local favorites like Wahoo’s Bar & Grill.

Distance from Chesapeake Beach Resort

History of Diving Museum:1 km

Theater of the Sea:1.3 km

Islamorada Train Caboose:1.7 km

Quarry Station:2.4 km

Island Adventures:4.9 km

Islamorada:7.4 km

The Laura Quinn Wild Bird Sanctuary:15.4 km

Dolphins Plus:23.9 km

African Queen:25.1 km

Florida Keys Marathon International Airport:50 km

Dadeland South:88.5 km

Explore nearby attractions

Property info

83409 Overseas Hwy, Islamorada, 33036-3526, USA

Frequently Asked Questions about Chesapeake Beach Resort

  • Is there a pool area at Chesapeake Beach Resort?

    Yes, Chesapeake Beach Resort offers 2 pool areas.

  • Are pets allowed at Chesapeake Beach Resort?

    Yes, Chesapeake Beach Resort has a pet policy that may vary based on the room type or availability. Please check with the hotel directly to learn about their pet policy.

  • Is parking available at Chesapeake Beach Resort?

    Yes, Chesapeake Beach Resort provides Parking, Accessible parking for guests.

  • What time is check-in and check-out at Chesapeake Beach Resort?

    Check-in at Chesapeake Beach Resort is available from: . Check-out time is by .

  • Where is Chesapeake Beach Resort located?

    Chesapeake Beach Resort is located in 83409 Overseas Hwy, 33036-3526, Islamorada, USA.

The prices and availability we receive from booking sites change constantly. This means you may not always find the exact same offer you saw on trivago when you land on the booking site.

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