How payments to us affect ranking

How payments to us affect ranking

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

  • Walking access to local restaurants

    Walk to nearby dining options including Wahoo's Bar & Grill and the Whale Harbor Seafood Buffet located adjacent to the property.

  • Made-to-order breakfast with ocean views

    Start your morning with complimentary made-to-order omelets and waffles served in the outdoor breakfast area overlooking the water.

  • Seasonal beach seaweed and debris

    The private beach area occasionally accumulates seaweed and coral debris depending on seasonal conditions and maintenance schedules.

  • Renovated rooms with private balconies

    Enjoy updated accommodations featuring spacious layouts, private balconies, and provided bathrobes and slippers for added comfort.

  • Two heated oceanfront swimming pools

    Relax at either of the two heated outdoor pools or lounge on the private beach area equipped with chairs and umbrellas.

  • Outdoor-only breakfast seating area

    Breakfast service is provided exclusively in an outdoor setting, which may be inconvenient during inclement weather.

  • Potential noise from highway traffic

    Guest rooms located near the main highway may experience audible traffic noise throughout the day and night.

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.

Rooms

  • ADA Ocean View King Suite

    • 1 1 King Bed
    • Sleeps 4
    • 540 sq ft

  • Standard King

    • 1 1 King Bed
    • Sleeps 3
    • 272 sq ft

  • Ocean View Queens

    • 1 2 Queen Beds
    • Sleeps 4
    • 366 sq ft

  • Deluxe Ocean View Two Queen Suite

    • 1 2 Queen Beds
    • Sleeps 6
    • 650 sq ft

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    • Free WiFi
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    Select dates to see exact prices

    • Free WiFi
    • Pool
    • Parking
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    • Pool
    • Parking
    • A/C
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Price trend

Based on lowest prices on trivago from the last 30 days
$569
$285
$0

Tue, 10/13/26

$307

Wed, 10/14/26

$284

Thu, 10/15/26

$406

Fri, 10/16/26

$543

Sat, 10/17/26

$405

Sun, 10/18/26

$274

Mon, 10/19/26

$286

Tue, 10/20/26

$479

Wed, 10/21/26

$309

Thu, 10/22/26

$480

Fri, 10/23/26

$397

Sat, 10/24/26

$533

Sun, 10/25/26

$327

Mon, 10/26/26

$466

Tue, 10/27/26

$459

Wed, 10/28/26

$467

Thu, 10/29/26

$292

Fri, 10/30/26

$393

Sat, 10/31/26

$338

Sun, 11/01/26

$315

Mon, 11/02/26

$298

Tue, 11/03/26

$284

Wed, 11/04/26

$454

Thu, 11/05/26

N/A

Fri, 11/06/26

$529

Sat, 11/07/26

$569

Sun, 11/08/26

$313

Mon, 11/09/26

$462

Tue, 11/10/26

$285

Wed, 11/11/26

$215

Thu, 11/12/26

$478

Fri, 11/13/26

$401

Sat, 11/14/26

$403

Sun, 11/15/26

$274

Mon, 11/16/26

$322

Tue, 11/17/26

$262

Wed, 11/18/26

$242

Thu, 11/19/26

$269

Fri, 11/20/26

$393

Sat, 11/21/26

$556

Sun, 11/22/26

$350

Mon, 11/23/26

$338

Tue, 11/24/26

$323

Wed, 11/25/26

$430

Thu, 11/26/26

$529

Fri, 11/27/26

$528

Sat, 11/28/26

$474

Sun, 11/29/26

$283

Mon, 11/30/26

$318

Tue, 12/01/26

$307

Reviews

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

Review summary

Summarized by AI from 1,000+ reviews

This boutique-style resort is a tranquil historic hideaway, ideal for couples and luxury travelers seeking a relaxing and peaceful environment, and is also notably pet-friendly. The property boasts a prime Islamorada location with a private beach offering stunning ocean views and convenient access to local attractions. Guests can enjoy complimentary use of kayaks, paddleboards, and bicycles, perfect for exploring the surrounding waters. Guests consistently praise the exceptional staff and the complimentary breakfast, featuring made-to-order omelets and waffles. For a quieter stay, choose a room facing the garden to minimize road noise.

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

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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