Chesapeake Beach Resort, Islamorada ⇒ Browse rooms, reviews & rates for 2026

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About the Hotel

83409 Overseas Highway, Islamorada, Florida, United States, 33036

Near Whale Harbor Marina

Great

8.4

9.1

/10

3.9

4.2

Loved by Chesapeake Beach Resort guests

Boutique hotel
Private hotel
Friendly staff
Beachfront location

"There is a private beach at the resort that is absolutely beautiful."

Paula from United States

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"You get 2 hours complementary water sports every day and we used the kayaks and paddle boards."

Michael P from United Kingdom

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"Make sure to use the 2 hours free paddle boarding that comes with your reservation, we seen sharks, manatees and lots of fish and hermit crabs."

Tracy from United States

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Oceanfront Venue

Chesapeake Beach Resort offers direct access to a private beach with crystal blue waters, making it a prime location for outdoor events such as weddings and reunions. Guests can enjoy affordable rates while celebrating special moments against a stunning backdrop. The on-site event space provides a seamless experience for both corporate and social gatherings.

Accommodations

The hotel offers newly renovated rooms, suites, and villas, each equipped with private balconies featuring superb ocean or garden views. Options include spacious two-bedroom villas suitable for families and groups, each designed for longer stays. All accommodations provide rainfall showerheads, ensuring a refreshing start to any day.

Location

Situated in Islamorada, also known as the Sport Fishing Capital of the World, Chesapeake Beach Resort places guests at the crossroads of adventure and relaxation. The resort is conveniently close to local attractions, seafood restaurants, and unique shopping experiences. Visitors can engage in various water activities right from the resort.

Family-Friendly Amenities

Chesapeake Beach Resort provides a family-friendly atmosphere, featuring outdoor pools and beach games that cater to guests of all ages. The resort offers complimentary fishing rods and water sports rentals for exciting family activities. Children can enjoy engaging events scheduled throughout the year, adding to the vacation experience.

Dining Options

The on-site dining venue, Wahoo's Bar & Grill, serves fresh seafood and offers a laid-back marina setting for guests. Additionally, a complimentary continental breakfast is included, featuring items like cooked-to-order omelets. Guests can enjoy dining with beautiful views of the water at nearby local restaurants as well.

Highlights

Location: Private beach access for exclusive events

Accommodations: Newly renovated rooms, suites, and villas

Family-Friendly: Water sports rentals and fishing rods

Dining: On-site Wahoo's Bar & Grill with fresh seafood

Events: Beachside weddings with local vendor support

Must-do experiences

Dine at Morada Bay for sunset views and delicious Caribbean fare.
Kayak through the mangroves at Florida Keys Kayak Tours.
Visit the History of Diving Museum to learn about underwater adventures.
Go snorkeling at Alligator Reef for vibrant marine life encounters.
Check out the local art scene during the Islander Watersports gallery walk.

Location: Perfect

9.0/10Review score

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Highlights from guests

Sports & FitnessWater Fun!

We loved the free water sports! Kayaks and paddle boards were available to explore the ocean, spotting manatees and sharks.

Kevin B from Canada

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Guest ParkingEasy Parking

Parking was abundant and close to the rooms. Covered parking was a plus for keeping the car cool.

Jessica R from United States

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DiningBreakfast Rocks!

Breakfast was a highlight, especially the omelets. Made to order with fresh ingredients, they started our day perfectly!

Carlos M from Spain

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Room FeaturesOcean Views!

The ocean view room had a balcony with comfortable chairs and a stunning sunrise view every morning. Breathtaking!

Emily S from Australia

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Select your room type

Chesapeake Beach Resort offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals

Ocean View Two Queens

2 persons

345 sq. feet

2 Double beds

Shower

Coffee machine

room details

Ocean View King

2 persons

345 sq. feet

1 King-size bed

Shower

Coffee machine

room details

Deluxe King Suite

2 persons

595 sq. feet

1 King-size bed

Shower

Coffee machine

room details

ADA Ocean View Two Queens

2 persons

370 sq. feet

2 Double beds

Shower

Coffee machine

room details

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Facilities

Chesapeake Beach Resort offers amenities for your comfortable stay and unforgettable experiences

Facilities: Great

8.6/10Review 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

Chesapeake Beach Resort Location

83409 Overseas Highway, Islamorada, Florida, United States, 33036

Map view

83409 Overseas Highway, Islamorada, Florida, United States, 33036

City landmarks

Museum

History of Diving Museum

3200 ft

Landmark

Windley Key Fossil Reef Geological State Park

1.4 mi

Gallery

Lobster Trap Art Gift Shop and Gallery

1.4 mi

Museum

Florida Keys History and Discovery Center

1.4 mi

Island

Upper Matecumbe Key

1.8 mi

Island

Windley Key

1.5 mi

Monument

Hurricane Monument

1.9 mi

Gallery

Michelle Nicole Lowe Art Gallery

1.7 mi

Landmark

Keys History & Discovery Center

1.5 mi

Landmark

In the Doghouse Art Studio

1.8 mi

Gallery

Pasta Pantaleo Signature Gallery

2.1 mi

Gallery

Gallery Morada

2.1 mi

Landmark

Carysfort Reef

1.8 mi

Island

Plantation Key

1.8 mi

Island

Raccoon Key

1.8 mi

Church

Matecumbe United Methodist Church

1.9 mi

Gallery

Elena Madden Studio Gallery

2.0 mi

Gallery

Portside Studio & Gallery

2.1 mi

Landmark

Cheeca Rocks

2.2 mi

Landmark

Indian Key State Historic Site

2.6 mi

Landmark

Lignumvitae Key Botanical State Park

2.6 mi

Landmark

Rain Barrel Village

3.1 mi

Landmark

FNX Club by Islamorada Fitness

2.7 mi

Landmark

Rain Barrel Sculpture Gallery

3.1 mi

Landmark

Crossland Gallery

2.8 mi

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

History of Diving Museum

12 minutes walking

Diving history exhibits showcase over 4,000 years, highlighting techniques and equipment. Guided tours are available.

Windley Key Fossil Reef Geological State Park

4 minutes drive

Fossilized coral formations and hiking trails provide insights into the geological history of the Florida Keys.

Florida Keys History and Discovery Center

5 minutes drive

Local history immerses guests in the cultural heritage of the Keys. Special exhibits and curator led tours enhance visits.

Lobster Trap Art Gift Shop and Gallery

4 minutes drive

Unique art and gifts created by local artisans. A vibrant space showcasing the creativity and culture of the Florida Keys.

Snorkeling & Diving

3 minutes drive

Various local shops offer gear rentals for snorkeling and diving tours. Explore reefs teeming with marine life.

Relaxing at the Beach

3 minutes walking

Nearby beaches provide tranquil settings, perfect for sunbathing, picnics, and scenic views of the turquoise waters.

Fishing Charters

5 minutes drive

Charters available for deep-sea or backcountry fishing. Excellent opportunities for catching local fish species.

Kayaking Tours

3 minutes walking

Guided kayaking tours explore mangroves and wildlife. Rentals accessible for self-guided adventures.

Wahoo's Bar and Grill

3 minutes walking

Casual atmosphere with seafood specialties. Must-tries include grilled fish tacos and local craft beers.

Whale Harbor Seafood Buffet

3 minutes walking

Bountiful seafood buffet featuring fresh dishes and a relaxed setting. Reservations recommended for busy evenings.

The Sand Bar

3 minutes walking

Charming beachside bar offering light bites and refreshing beverages. Perfect for sunset views and laid-back vibes.

Casa Mar Seafood

7 minutes walking

Authentic seafood dishes with a tropical twist. Signature dishes include coconut shrimp and grilled snapper.

Green Turtle Inn

6 minutes drive

Well-known for live music and a lively atmosphere. Hosts regular events, including live jazz and local artist showcases.

Morada Way Arts and Cultural District

5 minutes drive

Cultural hub featuring art galleries, craft fairs, and live performances. Family-friendly events held throughout the year.

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

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:

Reviews and Ratings

Feedback about Chesapeake Beach Resort from previous guests about their experience.

Review score

Based on 935 verified reviews

8.9/10

Great

88%

Recommend

Breakfast

7.9/10

Cleanliness

9.1/10

Comfort

9.0/10

Facilities

8.6/10

Free Wi-Fi

7.5/10

Location

9.0/10

Paid Wi-Fi

8.3/10

Staff

8.5/10

Value for money

7.9/10

Pros

Villa upgrade

Heated tub

Good breakfast

Cons

Door issues

Rotten fruit

based on 88 reviews

4/5

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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 at 11:00.

Which airports are closest to Chesapeake Beach Resort?

The nearest airport is Florida Keys Marathon Airport, located 27 km away.

What dining options are available at Chesapeake Beach Resort?

The property features an on-site restaurant and is conveniently located near Whale Harbor Seafood Buffet, Wahoo's Bar and Grill, and Shuck N Dive, all within 0.5 km.

Is there beach access at Chesapeake Beach Resort?

The resort offers private beach access along with sun loungers and complimentary water sports equipment rentals.

What amenities are included in the rooms at Chesapeake Beach Resort?

Rooms are equipped with a 37-inch flat-screen TV, a small refrigerator, air conditioning, and free Wi-Fi.

Is parking available at Chesapeake Beach Resort?

Free on-site private parking is available, and reservation is needed.

What recreational facilities are available at Chesapeake Beach Resort?

Guests can enjoy an outdoor heated pool, beach activities, fishing, and board games.

What nearby attractions can guests visit during their stay at Chesapeake Beach Resort?

Nearby attractions include the History of Diving Museum (0.5 km), Theater of the Sea (4 km), and Windley Key Fossil Reef Geological State Park (3 km).