CHESAPEAKE BEACH RESORT | Islamorada ★ Seaside Luxury & Beachfront Bliss

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About the Hotel

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

“The beautiful beachfront view made our stay truly nice.”view full review

Chesapeake Beach Resort - A family-friendly oceanside resort with private beach access, newly renovated rooms, and proximity to Theater of the Sea

Chesapeake Beach Resort offers newly renovated accommodations, including garden-view rooms with private balconies and ocean-view villas featuring king beds and sleeper sofas. The property includes a private beach, two outdoor pools, and water sports rentals such as kayaks and paddleboards. Guests at Chesapeake Beach Resort can enjoy fresh seafood at nearby restaurants like Wahoo's Bar and Grill, located 0.3 miles away. The resort is 1 mile from Theater of the Sea, where visitors can swim with dolphins. Each room has a flat-screen TV, coffee maker, and walk-in shower, while select villas include kitchenettes with stovetops and dishwashers. A $50 nightly resort fee covers breakfast, water sports rentals, and Wi-Fi.

Pros

Newly renovated rooms with private balconies and ocean or garden views.

Private beach access and two outdoor pools with lounge chairs.

Proximity to Theater of the Sea, a 4-minute drive for dolphin encounters.

Pet-friendly policy and on-site water sports rentals.

Group rates available for weddings and events.

Cons

The $50 nightly resort fee is mandatory.

Limited dining options directly on-site.

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Select your room type

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Ocean View Two Queens

Max:

4 persons

345 sq. feet

Bed options:

2 Double beds

Shower

Coffee machine

room details

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Ocean View King

Max:

2 persons

345 sq. feet

Bed options:

1 King-size bed

Shower

Coffee machine

room details

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Deluxe King Suite

Max:

4 persons

595 sq. feet

Bed options:

1 King-size bed

Shower

Coffee machine

room details

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Prices and availability

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How to get around?

Explore our comprehensive transport guide

City Centre

Islamorada 1.2 mi

Bus

Bus stop 3.3 mi

Facilities

Enjoy modern comforts, from ocean-view suites to family-friendly options with breakfast included

Free Water Activities

“I loved that the resort offered complimentary use of kayaks and paddleboards for the first two hours. It was a fantastic way to explore the water while soaking up the sun. It made my stay feel extra special to have such fun activities included in the package.” view full review

Convenient Breakfast Options

“The boxed breakfast option was a game-changer! I appreciated being able to order breakfast the night before and having it ready for pickup. This meant I could enjoy my morning without wasting time running out for food, maximizing my beach and pool time instead.” view full review

Immaculate Room Design

“Our room was simply furnished yet immaculate, with a fine bathroom that featured a huge walk-in shower. And a microwave and fridge was incredibly convenient for storing snacks and drinks during our stay. It truly was like a home away from home.” view full review

Fine Bathroom Upgrade

“I was really impressed by the bathroom facilities-it was spacious and beautifully designed with plenty of water pressure in the shower. It definitely added a touch of luxury to our stay, making it feel more than just a regular hotel experience.” view full review

General

No smoking on site
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

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

1.8 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

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CHESAPEAKE BEACH RESORT, Islamorada

About the Hotel

Chesapeake Beach Resort - A family-friendly oceanside resort with private beach access, newly renovated rooms, and proximity to Theater of the Sea

Pros

Cons

Select your room type

Prices and availability

How to get around?

Facilities

General

Sports & Fitness

Guest Parking

Services

Children

Facilities for people with disabilities

Spa & Leisure

Room features

Bathroom

Self-catering

Media

Location

Next best alternative