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From149US$ /night
Check-in
09Jan2026Select date
Check-out
10Jan2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

83409 Overseas Highway, Islamorada, Florida, United States, 33036
-
Next to Whale Harbor Marina
Great
8.5
9.1
/10
3.2
4.2
/5

Rooms, Suites & Villas

Chesapeake Beach Resort offers a range of accommodations, including newly renovated rooms, suites, and villas, providing options for couples and families. Every unit comes with a private balcony and stunning ocean views, allowing guests to immerse themselves in the natural beauty of the Florida Keys. Guests can choose from one- or two-bedroom villas for longer stays, equipped with kitchenettes for added convenience.

Location

Located in Islamorada, known as the Sport Fishing Capital of the World, the resort offers direct access to white sandy beaches and crystal-clear waters. Guests can explore popular local attractions such as Theater of the Sea and the famous Islamorada Sandbar, all within a short drive. The hotel positions itself close to diverse dining and shopping options, all showcasing the flavors of the Florida Keys.

Amenities

The resort includes multiple outdoor pools with ocean views for relaxation and swimming. Guests can engage in various water sports, including complimentary kayak and paddleboard rentals, promoting an active outdoor experience. For beach gatherings or events, the resort provides an oceanfront venue, ensuring memorable celebrations right by the water.

Dining

Chesapeake Beach Resort features Wahoo's Bar & Grill, offering fresh seafood options in a relaxed atmosphere. Guests can enjoy a complimentary breakfast that includes cooked-to-order omelets and continental items to kick-start their day. Nearby dining options showcase a variety of cuisines, allowing guests to explore local flavors at their convenience.

Family-Friendly Activities

Families will find numerous activities to engage in, with beach games and live entertainment available throughout the week. The hotel provides access to water sports, making it easy for families to explore the surrounding waters together. Group rates are offered for families planning reunions or special gatherings, allowing for a collaborative experience.

Highlights

Location: Sport Fishing Capital of the World

Rooms: newly renovated rooms with balconies

Amenities: multiple outdoor pools with ocean views

Dining: Wahoo's Bar & Grill on-site

Family-Friendly: beach games and watersports access

Must-do experiences

  • Stop by Lorelei Restaurant for sunset views and live music.
  • Try the Key Lime Pie at Mrs. Mac's Kitchen - a local favorite!
  • Visit the History of Diving Museum for a unique underwater journey.
  • Explore the serene trails at the Windley Key Fossil Reef Geological State Park.
  • Join a guided eco-tour to see local wildlife in the tranquil waters.
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Select your room type

The hotel 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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Facilities

The hotel 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
Local Highlights
Top Attractions
Activities
Dining
Entertainment
Whale Harbor Marina
Whale Harbor Marina
3 minutes walking
A vibrant marina offering fishing charters, boat rentals, and stunning sunset views. Ideal for water lovers.
History of Diving Museum
History of Diving Museum
12 minutes walking
This museum showcases the history of underwater exploration with engaging exhibits. A unique experience for history buffs.
Windley Key Fossil Reef Geological State Park
Windley Key Fossil Reef Geological State Park
4 minutes drive
A geological wonder featuring fossilized coral reefs and nature trails. Perfect for nature enthusiasts and hikers.
Fishing Charters
3 minutes walking
Nearby charters provide deep-sea fishing experiences. Rentals and equipment are available for all skill levels.
Yoga at the Beach
5 minutes drive
Beachfront yoga sessions offer relaxation and stress relief with ocean views. Check for seasonal schedules and classes.
Wahoo's Bar and Grill
Wahoo's Bar and Grill
3 minutes walking
Casual dining with seafood specialties. Enjoy fresh catch and craft beers in a laid-back, welcoming atmosphere.
Whale Harbor Seafood Buffet
Whale Harbor Seafood Buffet
3 minutes walking
A seafood buffet with a wide array of dishes. Family-friendly with something for everyone, including gluten-free options.
Shuck N Dive
Shuck N Dive
3 minutes walking
An upbeat bar known for live music and karaoke nights. Great for an evening out with friends or family.
Florida Keys History and Discovery Center
Florida Keys History and Discovery Center
5 minutes drive
A family-friendly center showcasing the history of the Keys with interactive exhibits and educational programs.
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
FAQs
About Chesapeake Beach Resort
What is the check-in and check-out policy at Chesapeake Beach Resort?
Check-in is at 16:00 and check-out is by 11:00.
Is parking available at Chesapeake Beach Resort?
Private parking is available on-site for free, with a reservation needed.
What are some attractions near Chesapeake Beach Resort?
Nearby attractions include the History of Diving Museum (0.5 km), Theater of the Sea (3 km), and Windley Key Fossil Reef Geological State Park (3 km).
What amenities can guests enjoy at Chesapeake Beach Resort?
Amenities include free Wi-Fi, an outdoor swimming pool with ocean views, beach access, a Jacuzzi, and a fitness club.
What are the dining options available at Chesapeake Beach Resort?
The resort features an on-site restaurant and local dining options within walking distance, including Whale Harbor Seafood Buffet, Wahoo's Bar and Grill, and Shuck N Dive, all located 0.5 km away.
What room amenities are provided at Chesapeake Beach Resort?
Rooms come equipped with air conditioning, a flat-screen TV, a refrigerator, and complimentary toiletries.
Are there fitness facilities at Chesapeake Beach Resort?
There is a fitness club available for guests to use during their stay.
Can guests access any water sports activities at Chesapeake Beach Resort?
The resort offers complimentary kayaking and paddleboarding equipment rentals for guests.

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