CHESAPEAKE BEACH RESORT | Beach Resort in Islamorada | Book from 149$/Night

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Overview & Features

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

“The fine waterfront views made my stay truly nice.”view full review

Rooms & Villas

Chesapeake Beach Resort offers newly renovated rooms, suites, and villas with private balconies. Options include ocean-view rooms with king or queen beds, one-bedroom suites with sleeper sofas, and two-bedroom villas with kitchenettes. All accommodations feature rainfall showers, flat-screen TVs, and high-speed Wi-Fi. ADA-accessible rooms are available.

Dining & Bars

Guests can enjoy fresh seafood, Italian dishes, and local specialties at nearby restaurants, many within walking distance. The resort provides a cooked-to-order omelet breakfast, a welcome drink, and 24-hour coffee in the lobby. Nearby options include dockside fish houses, beachfront cafes, and tiki-covered bars.

Beach & Activities

The resort has a private beach, outdoor pools, and water sports rentals, including kayaks and paddleboards. Nearby attractions include Theater of the Sea for dolphin encounters, snorkeling at Alligator Reef, and the Islamorada Sandbar for boat gatherings. Anne's Beach, with its shallow waters and boardwalk, is a 10-minute drive.

Location & Access

Situated in Islamorada, the resort is between Everglades National Park and the Florida Strait. It's a 4-minute drive to Windley Key Fossil Reef Geological State Park and 3 km from the History of Diving Museum. The area is known for coral reefs, fishing, and dive shops like Hen and Chickens Reef.

Services & Events

The resort offers group rates for weddings, reunions, and meetings, with beachfront event spaces. Services include pet-friendly accommodations, boat parking, and daily housekeeping. AAA/CAA members receive discounts. Staff follow enhanced cleaning protocols, focusing on high-touch surfaces and in-room amenities.

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Pick the Room Type That Suits You

Choose from spacious beach suites, family rooms, or cosy couples’ retreats with perks like breakfast and free cancellation

Pokój typu superior z łóżkiem queen-size

Max:

2 persons

32 m²

Bed options:

1 Single Bed or 1 Double Bed

Prysznic

Ogrzewanie

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Pokój typu deluxe

Max:

2 persons

28 m²

Bed options:

Łóżko King Size

Prysznic

Ogrzewanie

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Pokój dwuosobowy typu deluxe

Max:

2 persons

28 m²

Bed options:

Łóżko King Size

Prysznic

Ogrzewanie

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Getting around beach destinations

All Transportation Methods Available

City Centre

Islamorada 2.0 km

Bus

Bus stop 5.3 km

Facilities

Enjoy comfortable stays and unforgettable experiences at our beach resorts

Spacious & Modern Rooms

“During my stay, I was kinda surprised by the spaciousness of our villa. The room was beautifully decorated and equipped with a kitchen, making it easy for us to prepare meals and save on dining expenses.” view full review

Beautiful Pool Area

“I really enjoyed spending time by the pool. It was impeccably clean and provided a tranquil atmosphere for relaxation. The hot tub was also a wonderful bonus for winding down after a day of activities.” view full review

Fun Activities for Kids

“The resort offered a variety of family-friendly activities, which kept my kids engaged and happy during our stay. We loved renting kayaks and paddleboards to explore the waters together.” view full review

Great Entertainment Options

“The resort's media options were great. Our room had a high-quality TV, and it was easy to access movies and shows for family movie nights after a long day in the sun.” view full review

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

Fishing

Guest Parking

Cookware/ Kitchen utensils

Services

Housekeeping
Shops/Commercial services
Welcome drink

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
Jacuzzi
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

Location & Nearby Attractions

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

Map view

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

City landmarks

Museum

History of Diving Museum

950 m

Landmark

Windley Key Fossil Reef Geological State Park

2.3 km

Gallery

Lobster Trap Art Gift Shop and Gallery

2.2 km

Museum

Florida Keys History and Discovery Center

2.3 km

Island

Upper Matecumbe Key

2.9 km

Island

Windley Key

2.4 km

Monument

Hurricane Monument

3.1 km

Gallery

Michelle Nicole Lowe Art Gallery

2.8 km

Landmark

Keys History & Discovery Center

2.4 km

Landmark

In the Doghouse Art Studio

3.0 km

Gallery

Pasta Pantaleo Signature Gallery

3.4 km

Gallery

Gallery Morada

3.4 km

Landmark

Carysfort Reef

3.0 km

Island

Plantation Key

3.0 km

Island

Raccoon Key

3.0 km

Church

Matecumbe United Methodist Church

3.1 km

Gallery

Elena Madden Studio Gallery

3.3 km

Gallery

Portside Studio & Gallery

3.4 km

Landmark

Cheeca Rocks

3.6 km

Landmark

Indian Key State Historic Site

4.1 km

Landmark

Lignumvitae Key Botanical State Park

4.1 km

Landmark

Rain Barrel Village

5.0 km

Landmark

FNX Club by Islamorada Fitness

4.4 km

Landmark

Rain Barrel Sculpture Gallery

5.0 km

Landmark

Crossland Gallery

4.6 km

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

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CHESAPEAKE BEACH RESORT, Islamorada

Overview & Features

Rooms & Villas

Dining & Bars

Beach & Activities

Location & Access

Services & Events

Pick the Room Type That Suits You

Check Prices & Room Availability

Getting around beach destinations

Facilities

General

Sports & Fitness

Guest Parking

Services

Children

Facilities for people with disabilities

Spa & Leisure

Room features

Bathroom

Self-catering

Media

Location & Nearby Attractions

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