Chesapeake Beach Resort Islamorada Beach photoChesapeake Beach Resort Islamorada Exterior photoChesapeake Beach Resort Islamorada Exterior photo
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From149US$ /night
Check-in
04May2026Select date
Check-out
05May2026Select 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
3.9
4.2
/5

Amenities

Chesapeake Beach Resort offers a private beach with direct access to the ocean. Guests can enjoy an outdoor pool that provides stunning views of the water. Additionally, the hotel provides complimentary water sports rentals, including kayaks and paddleboards.

Rooms

The newly renovated accommodations at Chesapeake Beach Resort include garden view rooms, suites, and deluxe villas. Every room comes with a private balcony overlooking the beach, providing a space to relax outdoors. The spacious one and two-bedroom villas feature kitchenettes suitable for longer stays and family gatherings.

Location

Situated in Islamorada, the hotel is part of the Florida Keys, renowned as the Sport Fishing Capital of the World. Guests can explore nearby attractions such as the Islamorada Sandbar, perfect for swimming and relaxation. The resort's central location allows convenient access to local seafood restaurants and shopping experiences.

Pet-Friendly

Chesapeake Beach Resort welcomes pets, ensuring that guests can bring their furry companions along on their vacation. The hotel accommodates various pet sizes, allowing for a comfortable stay for all types of travelers. This policy enhances the overall family-friendly atmosphere of the resort.

Dining

On-site dining options include the Sunrise Room, which offers a complimentary breakfast featuring cooked-to-order items. Guests can sample fresh seafood and local fare at nearby restaurants within walking distance. The hotel facilitates memorable beachfront dining experiences just steps from the water.

Highlights

Location: Sport Fishing Capital of the World

Rooms: Newly renovated rooms with balconies

Diving: Nearby excellent snorkeling & diving sites

Dining: On-site complimentary breakfast

Events: Oceanfront venue for gatherings

Pet-Friendly: Welcomes pets of various sizes

“The oceanside location makes it perfect for families seeking relaxation, with its private beach access and complimentary water sports; plus, it's within walking distance of local dining options. The villas are spacious, suitable for families, and offer personalized breakfast delivery. For those planning beach weddings or vacations, it presents itself as a scenic and affordable option.”
Hotel logo
Olivia SmithEditor-in-Chief at Cheaphotels
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Select your room type

The hotel provides a selection of rooms—doubles, family rooms, and suites—with perks like free cancellation, breakfast options, and great value deals
Ocean View Two Queens
2 persons
345 sq. feet 
2 Double beds
Ocean view
Shower
Coffee machine
Ocean View King
2 persons
345 sq. feet 
1 King-size bed
Ocean view
Shower
Coffee machine
Deluxe King Suite
2 persons
595 sq. feet 
1 King-size bed
Shower
Coffee machine
ADA Ocean View Two Queens
2 persons
370 sq. feet 
2 Double beds
Ocean view
Shower
Coffee machine
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Amenities & services

Real traveler stories and honest reviews—no glossy ads, just authentic feedback to guide your booking
Facilities: Great
8.5/10Review score

General

  • No smoking on site
  • Wi-Fi
  • Free 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 the Surroundings
Top Attractions
Activities
Dining
Entertainment
History of Diving Museum
History of Diving Museum
12 minutes' walk
Museum showcasing diving history with artifacts and immersive exhibits. Special talks occasionally available.
Windley Key Fossil Reef Geological State Park
Windley Key Fossil Reef Geological State Park
4-minute drive
Park featuring fossilized coral reefs, nature trails, and stunning views. Educational programs offered regularly.
Florida Keys History and Discovery Center
Florida Keys History and Discovery Center
5-minute drive
Center that highlights the history and culture of the Florida Keys. Interactive displays engage guests of all ages.
Lobster Trap Art Gift Shop and Gallery
Lobster Trap Art Gift Shop and Gallery
4-minute drive
Art gallery featuring local artisans. Unique gifts and artworks promote local culture and craftsmanship.
Snorkeling at Carysfort Reef
5-minute drive
Thrilling snorkeling adventure with vivid sea life. Tours available; reservations recommended during peak seasons.
Yoga on the Beach
0.2 km
Relaxing beach yoga sessions for all skill levels. Classes offered daily; check the schedule for times.
Bike Rentals
3-minute walk
Biking along scenic routes in Islamorada. Rentals available nearby; explore at your own pace.
Kayaking Tours
0.2 km
Guided kayaking tours available through local rental providers. Great way to see wildlife up close.
Wahoo's Bar and Grill
Wahoo's Bar and Grill
3 minutes' walk
Casual atmosphere serving fresh seafood. Popular for their fish tacos and craft beers.
Whale Harbor Seafood Buffet
Whale Harbor Seafood Buffet
3 minutes' walk
Buffet-style dining featuring an array of seafood and local dishes. Family-friendly with plentiful options.
Casa Mar Seafood
Casa Mar Seafood
7 minutes' walk
Intimate seafood restaurant known for its fresh catch. Offers vegetarian options and stunning sunset views.
Shuck N Dive
Shuck N Dive
3 minutes' walk
Relaxed spot serving oysters and classic Keys fare. Casual vibe makes it a favorite among locals.
Morada Bay Beach Cafe
5-minute drive
Live music venue with a relaxed beach atmosphere. Hosts weekly events, perfect for unwinding after a busy day.
Islamorada Beer Company
5-minute drive
Brewery with craft beers and local flavors. Offers tours and tastings; suitable for all ages.
Theater of the Sea
10-minute drive
Marine park featuring animal shows and exhibits. Family-friendly and educational experiences await.
Jazz Night at the Buzzard's Roost
5-minute drive
Weekly jazz nights with local musicians. Cozy vibe makes it a great spot for music lovers of all ages.
Getting around town
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
Wireless 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

Reviews and Ratings

What past guests shared about their stay
Review score
Based on 963 verified reviews
8.9/10
Great
88%
Recommend
Cleanliness
8.9/10
Comfort
8.9/10
Facilities
8.5/10
Free Wi-Fi
8.5/10
Location
8.9/10
Staff
8.4/10
Value for money
7.7/10
Pros
Oceanfront room
Comfortable beds
Private beach
Complimentary watersports
Cons
Expensive fees
Unfriendly staff
Poor breakfast
Guest reviews
based on 88 reviews
4/5
based on 771 reviews
8.5/10
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.
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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 by 11:00.
Is parking available at Chesapeake Beach Resort?
Private parking is available on-site for free, but a reservation is needed.
What amenities can guests expect in their rooms at Chesapeake Beach Resort?
Rooms are equipped with air conditioning, a 37-inch flat-screen TV, a refrigerator, and complimentary Wi-Fi.
Which nearby attractions are close to Chesapeake Beach Resort?
Attractions include the History of Diving Museum (0.5 km), Theater of the Sea (6 km), and Windley Key Fossil Reef Geological State Park (3 km).
What dining options are available near Chesapeake Beach Resort?
Nearby restaurants include Whale Harbor Seafood Buffet, Wahoo's Bar and Grill Restaurant, and Shuck N Dive, all located within 0.5 km.
What recreational facilities are available at Chesapeake Beach Resort?
Facilities include an outdoor heated swimming pool, private beach access, and complimentary water sports equipment rentals.
Does Chesapeake Beach Resort offer any business services?
The hotel provides free Wi-Fi, a lobby area, and a convenience store, which can facilitate business activities.

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Check-in
04May2026Select date
Check-out
05May2026Select date
Rooms and Guests2 Guests, 1 Room