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From149US$ /night
Check-in
16Jan2026Select date
Check-out
17Jan2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

83409 Overseas Highway, Islamorada, Florida, United States, 33036
-
Near the History of Diving Museum
Great
8.6
9.1
/10
3.2
4.2
/5

Amenities

Chesapeake Beach Resort offers direct private beach access along with two outdoor pools that provide ocean views. Guests can enjoy water sports rentals on-site, including kayaking and paddleboarding, promoting an active getaway. The hotel also provides complimentary welcome drinks, beach towels, and lounge chairs for all guests.

Rooms

The hotel includes a variety of newly renovated accommodations, including ocean view rooms, spacious suites, and villas. Each room comes with its own private balcony, allowing guests to enjoy views of the ocean or captivating garden surroundings. The villas feature additional amenities, such as kitchenettes perfect for extended stays or family gatherings.

Location

Located in Islamorada, known as the Sport Fishing Capital of the World, the hotel offers a scenic backdrop and easy access to local attractions. Guests can explore nearby coral reefs through snorkeling and diving adventures just a short boat ride away. The hotel's proximity to restaurants and shopping allows for a leisure-filled experience.

Dining

The property features on-site dining options, including Wahoo's Bar & Grill, known for its fresh seafood and laid-back atmosphere. Guests can enjoy breakfast items and cooked-to-order omelets included in the resort fee. Numerous nearby seafood restaurants offer additional dining experiences with local flavors.

Family-Friendly Features

Families can take advantage of children's activities and access to outdoor games like cornhole and oversized chess on the beach. The hotel also provides complimentary fishing rods at the front desk, enhancing family bonding experiences. Families will find spacious accommodations perfect for group stays.

Highlights

Location: Sport Fishing Capital of the World

Rooms: Ocean view rooms with private balconies

Dining: Wahoo's Bar & Grill with fresh seafood

Family-Friendly: Children's activities & spacious accommodations

Must-do experiences

  • Snorkel at the John Pennekamp Coral Reef State Park for vibrant marine life.
  • Taste fresh Key lime pie at Mrs. Mac's Kitchen, a local favorite.
  • Visit the Theater of the Sea for marine animal encounters and shows.
  • Kayak through Florida Bay at sunset for breathtaking views.
  • Explore the history at the Florida Keys History and Discovery Center.
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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
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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Price and Room Availability Calendar

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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
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 the Local Scene
Top Attractions
Activities
Dining
Entertainment
History of Diving Museum
History of Diving Museum
12 minutes' walk
Diving history showcased through artifacts and exhibits. Unique guided tours available to enrich your visit.
Florida Keys History and Discovery Center
Florida Keys History and Discovery Center
25 minutes walking
Interactive exhibits on Florida Keys' culture and history. Family-friendly with educational programs and events.
Windley Key Fossil Reef Geological State Park
Windley Key Fossil Reef Geological State Park
25 minutes walking
Explore stunning fossilized reefs. Features scenic trails and picnic areas, perfect for nature lovers.
Lobster Trap Art Gift Shop and Gallery
Lobster Trap Art Gift Shop and Gallery
25 minutes walking
Local art and crafts using recycled materials. A great spot for unique souvenirs and art appreciation.
Water Sports at Whale Harbor Marina
3 minutes' walk
Thrilling water sports available, including boating and fishing. Rentals and tours accessible on-site.
Wellness at FNX Club
10 minutes' drive
Relaxation-focused classes, including yoga and fitness sessions. Perfect for unwinding after a busy day.
Biking along Upper Matecumbe Key
30 minutes walking
Scenic biking trails with picturesque views of the Keys. Rentals are easily available nearby for convenience.
Local Fishing Tours
3 minutes' drive
Guided fishing tours for both novices and experts. Experience local fisheries and enjoy the Florida atmosphere.
Wahoo's Bar and Grill
Wahoo's Bar and Grill
3 minutes' walk
Casual atmosphere with tasty seafood and tropical drinks. Reservations recommended during peak hours.
Whale Harbor Seafood Buffet
Whale Harbor Seafood Buffet
3 minutes' walk
Delicious seafood buffet featuring local specialties. Family-friendly with options for various dietary preferences.
Shuck N Dive
Shuck N Dive
3 minutes' walk
Relaxed vibe offering fresh seafood and key lime pie. Great for casual dining and local seafood lovers.
Casa Mar Seafood
Casa Mar Seafood
7 minutes' walk
Authentic seafood dishes with a cozy atmosphere. Offers options for various dietary needs; reservations recommended.
Live Music at Shuck N Dive
3 minutes' walk
Weekly live music events create a lively atmosphere. All ages welcome for a fun evening with family and friends.
Whale Harbor Marina
Whale Harbor Marina
3 minutes' walk
Vibrant nightlife with bars and entertainment events. Regular gatherings and activities make it a lively destination.
Funky Fish Art Cafe
10 minutes' drive
Art-themed café offering occasional live performances. Kid-friendly with a colorful atmosphere and delicious bites.
Local Art Galleries
10 minutes' drive
Showcases local artists' work; great for cultural exploration. Regular exhibitions and events provide family-friendly fun.
Getting around
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
Questions of the users
About Chesapeake Beach Resort
Can guests enjoy fishing along the beach at Chesapeake Beach Resort?
5 November 2024
Fishing is permitted in the inlet area of the resort, offering a great experience for fishing enthusiasts.
Are pets allowed to accompany guests at the resort?
12 September 2024
Yes, up to two dogs are welcome per room, with a pet fee of $50 plus tax per pet, per night.
Is swimming permitted on the private beach?
1 January 2025
Swimming is allowed on the beautiful private beach along the oceanside, providing a perfect spot for guests to relax.
Do the rooms include kitchen facilities?
18 December 2024
Rooms feature mini-refrigerators and coffee makers, but they do not include full kitchen facilities like a stove.
Are dogs allowed on the beach and throughout the property?
22 March 2025
Pets are permitted on the beach and in many areas of the property, except for the swimming pools, as long as they are leashed.
Do the accommodations come with private balconies?
8 February 2025
Yes, each room offers its own private balcony, perfect for enjoying the seaside views.
If I arrive early, can I access the resort's amenities while waiting for my room?
15 April 2025
Early check-in is based on availability, but guests can enjoy the pools and beach area and utilize bathroom facilities until their room is ready.
Are there specific areas where my small dog can accompany me?
3 July 2024
Small dogs can access all guest areas on the property except for the pools, but must be on a leash.
Have all the guest rooms been recently updated?
27 November 2024
All rooms available for rent have been updated, though the property is still going through some renovations.
Is there a restaurant on-site at the resort?
30 June 2024
Currently, there are no dining options on the property, but several restaurants are located just a short walk away.
Are there rooms available on the ground floor?
11 September 2024
Yes, standard double queen and king rooms are available on the first floor, accessed via seven stairs.
Is there parking available for boats and trailers?
19 August 2024
Boat trailer parking and docking services are available for a fee of $60 per day.
Can I expect the views in the room to match what is shown in the photos on the website?
29 October 2024
Photos of the rooms illustrate various angles and direct views of the ocean, with options for the best ocean views indicated next to room types.
Does each guest room include a bathroom?
24 January 2025
Indeed, each room features a private bathroom for guests' convenience and comfort.
Is the resort accessible for guests with mobility impairments?
16 October 2024
The property provides ADA-compliant accommodations and welcomes guests of all abilities with accessible features.
Check-in
16Jan2026Select date
Check-out
17Jan2026Select date
Rooms and Guests2 Guests, 1 Room
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