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From149US$ /night
Check-in
14Feb2026Select date
Check-out
15Feb2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

Property overview

83409 Overseas Highway, Islamorada, Florida, United States, 33036
-
Next to Whale Harbor Marina
Great
8.5
9.1
/10
3.1
4.2
/5

Rooms, Suites & Villas

Chesapeake Beach Resort offers rooms, suites, and villas. Each room has comfortable beds and a tranquil atmosphere. Garden View rooms feature a private balcony. Suites and villas are available for long-term stays or large groups. Rooms provide air conditioning, a private entrance, and a private bathroom with a walk-in shower and a hairdryer. Each room features a balcony, a coffee machine, a wardrobe, and a flat-screen TV with cable channels. Suites add a living room and a separate bedroom.

Onsite Dining Options

The Chesapeake Beach Resort provides dining options. Guests can enjoy fresh seafood, pasta, salads, garlic bread, spaghetti, and pizza. Tiki-covered bars, dockside fish houses, beachfront cafes and island bistros all offer meals. AAA and CAA members receive benefits.

Activities and Amenities

Guests at Chesapeake Beach Resort have access to amenities, including outdoor pools with ocean views and a private beach. Kayak, paddle board, and fishing rod rentals are available. The resort provides Wi-Fi in public areas and rooms. Boat and trailer parking is available. The resort is pet-friendly. A daily resort fee of $50 includes cooked-to-order omelets, continental breakfast, a welcome drink, in-room robes and slippers, high-speed internet, pool/beach towels, pool/beach lounge chairs, two hours of water sports rentals per room, seasonal resort activities, beach games, fish cleaning stations, 24-hour coffee and tea in the lobby, self-parking, and local calls. Special itineraries for two, three, or five-plus nights offer planned activities.

Location and Proximity

Chesapeake Beach Resort is located in Islamorada, between Everglades National Park and the Florida Strait. Islamorada is made up of Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key, Indian Key, and Lignumvitae Key. The resort is close to seafood restaurants, bars, taverns, and pubs. Nearby landmarks include Carysfort Reef (3 km), Windley Key (2 km), Whale Harbor Marina (0.3 km), and Hurricane Monument (3 km).

Hotel Services

Chesapeake Beach Resort offers wedding and event services. Special group rates are available. The resort provides waterfront access. The property is compliant with ADA standards.

“This resort's prime benefit lies in its location, close to local attractions and boasting its own slice of private beach. While some areas show wear, the spacious rooms and ocean views still appeal, especially for families and those seeking watersports; the dedicated breakfast service is a highlight, although I noted some mixed reports on overall cleanliness.”
Hotel logo
David MillerEditor, UsFlorida
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Choose your preferred room

The property features double rooms, family rooms, and suites, often including breakfast, free cancellation, and special offers
Ocean View King
2 persons
345 sq. feet 
1 King-size bed
Shower
Coffee machine
Deluxe King Suite
2 persons
595 sq. feet 
1 King-size bed
Shower
Coffee machine
Standard Queen Room
2 persons
315 sq. feet 
2 King Size Beds
Shower
Coffee machine
Hearing impaired Ocean view Two Queen Beds
2 persons
370 sq. feet 
2 King Size Beds
Shower
Coffee machine
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Calendar of room availability and rates

See current availability and pricing for your dates

Facilities

Amenities are designed to ensure comfort and memorable stays

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
  • 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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Chesapeake Beach Resort Location

83409 Overseas Highway, Islamorada, Florida, United States, 33036
Map view
83409 Overseas Highway, Islamorada, Florida, United States, 33036
Nearby
Marina
Whale Harbor Marina
700 ft
Restaurants
Wahoo's Bar and Grill
700 ft
83413 Overseas Hwy
Whale Harbor Seafood Buffet
700 ft
83413 Overseas Hwy
The Sand Bar
700 ft
83413 Overseas Hwy
Shuck N Dive
700 ft
83413 Overseas Hwy
Casa Mar Seafood
1900 ft
97001 Oversea Hwy Islamorada
Ziggie & Mad Dog's
3000 ft
83000 Overseas Hwy
Explore Islamorada
Explore Nearby Attractions
Top Attractions
Activities
Dining
Entertainment
History of Diving Museum
12 minutes' walk
Museum showcasing the history of diving, featuring artifacts and exhibits. Enjoy family-friendly educational activities.
Florida Keys History and Discovery Center
25 minutes' walk
Local history exhibits and engaging programs reveal the culture of the Florida Keys. Great for families and history buffs.
Windley Key Fossil Reef Geological State Park
25 minutes walking
Park featuring ancient fossilized coral reefs and nature trails. Unique geological features are great for hiking and exploration.
Snorkeling Tours
3 minutes' drive
Exciting snorkel tours at nearby reefs. Rentals and guided tours available at Whale Harbor Marina for all skill levels.
Yoga on the Beach
3 minutes' drive
Relaxing outdoor yoga classes at beautiful beaches. Classes suitable for all levels, with mats available for rent.
Wahoo's Bar and Grill
3 minutes' walk
Casual dining with a seafood focus. Known for fresh catches and local flavors, outdoor seating adds to the experience.
Whale Harbor Seafood Buffet
3 minutes' walk
All-you-can-eat seafood buffet featuring local specialties. Family-friendly atmosphere with a view of the marina.
Lobster Trap Art Gift Shop and Gallery
5 minutes' drive
Gallery and shop presenting local art and crafts. Offers family-friendly events and unique souvenir options.
Islamorada Brewing Company
10 minutes' drive
Local brewery featuring craft beers. Hosts live music events and tastings, great for enjoying with friends or on a date.
Local transportation
City Centre
Islamorada24 min  ·  1.2 mi
Bus
Bus stop8 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
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 are the check-in and check-out times at Chesapeake Beach Resort?
Check-in is at 16:00 and check-out is at 11:00.
What is the distance of Chesapeake Beach Resort from the nearest airport?
The resort is approximately 100 km from Miami International Airport.
Which attractions are located near Chesapeake Beach Resort?
Nearby attractions include the History of Diving Museum (0.5 km) and Theater of the Sea (5 km).
What amenities are available at Chesapeake Beach Resort?
Amenities include free Wi-Fi, outdoor heated swimming pool, private beach access, and a 24-hour reception.
What dining options does Chesapeake Beach Resort offer?
The resort features an on-site restaurant and snack bar, as well as nearby diners such as Wahoo's Bar and Grill (0.5 km) and Shuck N Dive (0.5 km).
Are there parking facilities at Chesapeake Beach Resort?
Free private parking is available on-site, and a reservation is needed.
Does Chesapeake Beach Resort offer family-friendly amenities?
The resort includes board games, a children's playground, and pet-friendly accommodations.
What room features can guests expect at Chesapeake Beach Resort?
Rooms are equipped with a flat-screen TV, air conditioning, and some feature balconies.
Is Chesapeake Beach Resort accessible for guests with limited mobility?
The property is wheelchair accessible.
What activities are available on-site at Chesapeake Beach Resort?
Guests can enjoy fishing, swimming in the heated pool, and complimentary water sports equipment rentals.

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