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From149US$ /night
Check-in
28Dec2025Select date
Check-out
29Dec2025Select date
Rooms and Guests2 Guests, 1 Room
Key details

About spa resort

83409 Overseas Highway, Islamorada, Florida, United States, 33036
-
Near Whale Harbor Marina
Great
8.6
9.1
/10
3.2
4.2
/5

Offering spa therapy, barbecue grills, and a garden terrace, as well as the views of the garden, the premium Chesapeake Beach Resort Islamorada is located 1.7 miles from Lobster Trap Art Gift Shop and Gallery. Offering a fitness center, this traditional hotel is within 5 minutes' walk of Wilson Key.

Location

The 3-star smoke-free resort has an oceanfront setting 2.8 miles from Rain Barrel Sculpture Gallery. In close proximity to the oceanfront accommodation, Whale Harbor Marina is located.

Nature lovers will appreciate proximity to Windley Key Fossil Reef Geological State Park, which is about 25 minutes' walk away.

Rooms

There are 45 rooms comprising an adjoining terrace and a balcony. Some of them offer a ceiling fan and an ironing set along with a coffee machine. Some of the premium rooms also come with a microwave, coffee and tea making facilities, and a stovetop. Bathrooms include a walk-in shower and a separate toilet, along with comforts such as a shower cap and bath sheets.

Eat & Drink

Jaws Raw Bar is 0.7 miles from the hotel.

Leisure & Business

A tennis court and a play area are available for additional fees. The Chesapeake Beach Resort boasts 2 outdoor swimming pools.

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.
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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 King
2 persons
32 m² 
1 King-size bed
Shower
Coffee machine
Deluxe King Suite
2 persons
55 m² 
1 King-size bed
Shower
Coffee machine
Standard Queen Room
2 persons
29 m² 
2 King Size Beds
Shower
Coffee machine
Hearing impaired Ocean view Two Queen Beds
2 persons
34 m² 
2 King Size Beds
Shower
Coffee machine
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Price and Room Availability Calendar

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Facilities

The resort offers amenities for your comfortable stay and unforgettable experiences

General

  • No smoking on site
  • Free 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
  • Patio
  • Garden furniture
  • Dining table

Bathroom

  • Free toiletries
  • Sink

Self-catering

  • Cookware/ Kitchen utensils

Media

  • Flat-screen TV
  • AM/FM alarm clock
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Location

83409 Overseas Highway, Islamorada, Florida, United States, 33036
Map view
83409 Overseas Highway, Islamorada, Florida, United States, 33036
Nearby
Marina
Whale Harbor Marina
210 m
Restaurants
Wahoo's Bar and Grill
190 m
83413 Overseas Hwy
Whale Harbor Seafood Buffet
210 m
83413 Overseas Hwy
The Sand Bar
210 m
83413 Overseas Hwy
Shuck N Dive
210 m
83413 Overseas Hwy
Casa Mar Seafood
560 m
97001 Oversea Hwy Islamorada
Ziggie & Mad Dog's
910 m
83000 Overseas Hwy
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
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
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
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
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
Islamorada24 min  ·  2.0 km
Bus
Bus stop8 min  ·  5.3 km
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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
is available in 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
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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