Chesapeake Beach Resort Islamorada Beach photoChesapeake Beach Resort Islamorada Exterior photoChesapeake Beach Resort Islamorada Exterior photo

CHESAPEAKE BEACH RESORT, Islamorada

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From$149 /night
Check-in
24Jul
Check-out
25Jul
Rooms and Guests2 Guests, 1 Room
Key details

About spa resort

83409 Overseas Highway, Islamorada, 33036
-
Near Whale Harbor Marina
Great
8.6
9.1
/10
3.9
4.2
/5

3-star beachfront resort in Islamorada with private beach access

Amenities & Activities

Chesapeake Beach Resort offers a private beach area with loungers exclusively for guests. Complimentary kayaking and paddleboarding are included in the stay, with equipment available for daily use. Two heated outdoor pools, one with ocean views, and a hot tub provide additional relaxation options, while yoga classes and live music performances are scheduled on-site.

Rooms & Accommodations

Guests can choose from spacious two-bedroom villas or premium villas, many with ocean views and private balconies. Each room includes a 37-inch flat-screen cable TV, a small refrigerator, and select rooms offer a balcony. The property is pet-friendly, allowing pets in designated accommodations, and wheelchair-accessible rooms feature raised toilets, grab rails, and Braille visual aids.

Dining & Breakfast

A complimentary breakfast is served daily until 11:00 AM, featuring made-to-order omelets, pancakes, and French toast alongside a continental buffet. The on-site restaurant offers a snack bar and serves wine and champagne, with a small bar for drinks throughout the day. Personalized breakfast delivery service is available for guests staying in villas, ensuring a relaxed start to the day.

Location & Nearby Attractions

The resort is located on the oceanfront along Highway 1 in Islamorada, with the History of Diving Museum a 3-minute walk away. Windley Key Fossil Reef Geological State Park is 2 miles from the property, and Theater of the Sea is a 4-minute drive. Several restaurants and a supermarket are within walking distance, and a free city cab service provides local transportation.

Services & Special Features

Management sends regular text messages to guests to check on their stay and address any needs. AAA and CAA members receive benefits at check-in, and the property offers private check-in/check-out for convenience. A 24-hour front desk, concierge service, daily housekeeping, and luggage storage are available, along with a minimarket on site for essentials.

Highlights

Private beach: Exclusive guest-only loungers and beach area

Water sports: Complimentary kayaks, paddleboards, and fishing poles

Breakfast: Made-to-order omelets, pancakes, French toast until 11 AM

Villas: Two-bedroom and premium villas with ocean views and balconies

Pet-friendly: Pets allowed in designated rooms

Location: Steps from History of Diving Museum, 2 miles from Windley Key State Park

Must-do experiences

  • Snag fresh seafood at the Islander Watersports Grill for lunch.
  • Visit the History of Diving Museum for a unique local experience.
  • Enjoy sunset at the Morada Bay Beach Cafe with live music.
  • Explore the hidden trails of Windley Key Fossil Reef State Park.
  • Don't miss the artisanal goodies at the Islamorada Farmer's Market.

Select your room type

The resort offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
  • Ocean View Two Queens
    2 persons
    32 sq. feet
    2 Double beds
    Air conditioning
    Balcony
  • Ocean View King
    2 persons
    32 sq. feet
    1 King-size bed
    Air conditioning
    Balcony
  • Deluxe King Suite
    2 persons
    55 sq. feet
    1 King-size bed
    Air conditioning
    Balcony
Show all rooms

Price and Room Availability Calendar

Check availability and prices for your dates now!
July 2026 - July 2027
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Check-in/ Check-out

Facilities

The resort offers amenities for your comfortable stay and unforgettable experiences
Facilities: Great
8.6/10Review score

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
  • Fire extinguishers
  • Key card access

Sports & Fitness

  • Yoga class
  • Fishing

Guest Parking

  • Cookware/ Kitchen utensils

Services

  • Housekeeping
  • Shops/Commercial services
  • Welcome drink

Dining

  • Snack bar

Children

  • Board games

Facilities for people with disabilities

  • Toilet for disabled
  • Bathroom for disabled

Spa & Leisure

  • Heated swimming pool
  • Outdoor swimming pool
  • Beach access
  • Sun loungers
  • Live entertainment
  • Pool with view
  • Shallow end

Room features

  • Air conditioning
  • Heating
  • Sitting area
  • Garden furniture
  • Dining table

Bathroom

  • Free toiletries
  • Sink

Self-catering

  • Cookware/ Kitchen utensils

Media

  • Flat-screen TV
  • AM/FM alarm clock
Show more

Location

83409 Overseas Highway, Islamorada, 33036
Explore Islamorada
Explore the Florida Keys
  • Top Attractions
  • Activities
  • Dining
  • Entertainment
History of Diving Museum
History of Diving Museum
12 minutes' walk
Museum dedicated to the history of diving; features exhibits and artifacts including free admission days.
Florida Keys History and Discovery Center
Florida Keys History and Discovery Center
25 minutes' walk
Cultural center showcasing local history through engaging exhibits; unique guided tours enhance the experience.
Windley Key Fossil Reef Geological State Park
Windley Key Fossil Reef Geological State Park
25 minutes' walk
Natural park with fossilized coral reefs and hiking trails; ideal for nature lovers and educational outings.
Lobster Trap Art Gift Shop and Gallery
Lobster Trap Art Gift Shop and Gallery
25 minutes' walk
Art gallery showcasing local artists; unique lobster-themed art pieces are perfect souvenirs to take home.
Water Sports
3 minutes' drive
Thrilling water sports including jet skiing and snorkeling; rentals and guides available at nearby marinas.
Yoga on the Beach
3 minutes' drive
Relaxing beach yoga sessions offered at local studios; classes suitable for all levels, often with ocean views.
Fishing Charters
3 minutes' drive
Chartered fishing trips for both beginners and experienced anglers; equipment rental and guided options available.
Wahoo's Bar and Grill
3 minutes' walk
Casual spot known for seafood classics and tropical cocktails; outdoor seating with a fun, laid-back vibe.
Whale Harbor Seafood Buffet
3 minutes' walk
Seafood buffet with a variety of fresh options; vibrant atmosphere, ideal for families and groups. Reservations recommended.
The Sand Bar
3 minutes' walk
Informal eatery specializing in burgers and local seafood; known for its lively tunes and friendly service.
Shuck N Dive
3 minutes' walk
Seafood joint famous for its oysters; casual dining atmosphere with options for all dietary needs.
Whale Harbor Marina
Whale Harbor Marina
3 minutes' walk
Scenic marina featuring live music events; a great spot for drinks and enjoying sunset views.
Morada Bay Beach Café
5 minutes' drive
Charming beach café with live music; ideal for enjoying a drink with friends or family in a picturesque setting.
Islamorada Historical Society
5 minutes' drive
Local museum hosting seasonal events and exhibits; educational fun for guests of all ages with a friendly atmosphere.
Getting around
  • City Centre
    Islamorada 24 min  ·  1.2 mi
  • Bus
    Bus stop 8 min  ·  3.3 mi
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Property information and rules
Check-in
from 16:00-23:00
Check-out
from 07:00-11:00
Guest Parking
Private parking is possible on site for free.
Internet
Wireless internet is available in the entire hotel for free.
Breakfast
A full breakfast is served at the price of US$0.10 per person per day.
Children & extra beds
There are no extra beds provided in a room.  There are no cots provided in a room. 
Pets
Pets are allowed on request.
Year renovated:
2008
Number of rooms:
45

Reviews and Ratings

Feedback about Chesapeake Beach Resort from previous guests about their experience.
Review score
Based on 982 verified reviews
8.9 /10
Great
89 %
Recommend
Cleanliness
9.0/10
Comfort
8.9/10
Facilities
8.6/10
Free WiFi
8.5/10
Location
9.0/10
Staff
8.6/10
Value for money
7.9/10
Pros
Comfortable beds
Good breakfast
Nice pools
Cons
Dirty rooms
Small beach
Guest reviews
based on 88 reviews
4/5
based on 735 reviews
8.6/10
No reviews yet on our siteUnfortunately, our guests have not yet left any reviews for this hotel, but you can read reviews from Booking.com.
Open reviews
Questions of the users
About Chesapeake Beach Resort
Can visitors fish from the beach area?
12 October 2024
Fishing is permitted in the inlet area where guests can enjoy casting their lines.
Are pets allowed at the resort, specifically dogs?
5 November 2024
Yes, up to two dogs are welcomed per room with a pet fee of $50 plus tax for each pet, per night.
Is it safe to swim at the beach?
18 November 2024
Yes! The private beach is accessible from the Oceanside, offering a beautiful swimming experience.
Do the rooms feature kitchenettes?
23 December 2024
Rooms include mini refrigerators and coffee makers, but they do not have full kitchenettes with stoves.
Are pets allowed to enjoy the beach?
7 January 2025
Yes, pets can access the beach and all areas of the property except for the pools, as long as they are leashed.
Do the accommodations come with private balconies?
14 January 2025
Each room includes its own private balcony, allowing guests to enjoy the fresh air.
How early can guests check in and use the facilities upon arrival?
25 January 2025
Check-in time is subject to availability, but guests are welcome to use the pools and beach area while waiting for their room.
Where can dogs roam freely on the property?
9 February 2025
Dogs are allowed in all guest-accessible areas on the property, except for the pools, as long as they remain leashed.
Are the renovated rooms all finished and available for booking?
3 March 2025
All rooms available for rent have been updated, although the property is still undergoing some renovations. The pools and beach bar are currently open.
Is there an on-site restaurant available for guests?
20 March 2025
Currently, there is no restaurant on the property, but three dining options are available within a minute's walk.
Are there accessible ground-floor rooms available?
15 April 2025
Standard rooms with double queen or king beds are available, but they are situated seven stairs above the ground level.
Is there available parking for boats and trailers?
22 April 2025
Yes, boat trailer parking and docking are available for a fee of $60 per day.
Do the room images accurately represent the views offered?
30 May 2025
Yes, the images showcase various angles from the rooms, highlighting the different ocean views available.
Will guests have private bathrooms in their accommodations?
1 June 2025
Each room is equipped with its own attached private bathroom for guests' convenience.
How many floors does the building have, and is there an elevator?
28 June 2025
The property has two floors in the garden view building, which is accessible only by stairs. The ocean view buildings offer elevator access.

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