CHESAPEAKE BEACH RESORT

75 photos

Book on our site

up to 10% less

than Booking.com

Key details

About the Hotel

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

Next to the History of Diving Museum

Great

8.5

9.1

/10

3.2

4.2

Loved by guests

Ocean views
Helpful staff
Adequate breakfast
Beach area
Modern rooms

"Breakfast included deliscious omelets made to order and other typical items."

Michelle from United States

read full review

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

Michael P from United States

read full review

"The pool and beach area is so beautiful we did not want to go anywhere else."

Lia

read 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.

Must-do experiences

Snorkel at the nearby Alligator Reef for vibrant marine life.
Savor fresh key lime pie at Mrs. Macs Kitchen-locally loved!
Visit Windley Key Fossil Reef Geological State Park for hiking.
Enjoy live music and fresh seafood at Marker 88 on the beach.
Take a sunset cruise with Islander Watersports for stunning views.

Hotel on map

Guest Emotional Experience

Shine on SocialsSunrise views

“We booked an Ocean view, king room, which looked out on the beautiful sunrise every morning.”

Vincent P from United States

Explorers, Not TouristsSeagrass adventure

“Snorkeling from the beach was easy; they have a path through the sea grass that leads out from shore.”

Joe from United States

Perfect for Finding FriendsBubbly welcome

“At check in we were greeted with a champagne glass which was on point.”

Lia

View all

Select your room type

Find detailed information on rooms, amenities, and exclusive deals for your ideal beach holiday

Ocean View King

2 persons

32 m²

1 King-size bed

Shower

Coffee machine

room details

Deluxe King Suite

2 persons

55 m²

1 King-size bed

Shower

Coffee machine

room details

Standard Queen Room

2 persons

29 m²

2 King Size Beds

Shower

Coffee machine

room details

Hearing impaired Ocean view Two Queen Beds

2 persons

34 m²

2 King Size Beds

Shower

Coffee machine

room details

Click button to see more rooms

Show all rooms

Show all roomsLess

Prices and availability

View real-time room availability and secure the best rate for your travel dates

Facilities

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

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

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

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

Explore Islamorada

Explore Local Highlights

History of Diving Museum

12 minutes' walk

Museum showcasing diving's evolution with artifacts and interactive exhibits. Great for families and history enthusiasts.

Windley Key Fossil Reef Geological State Park

4 minutes' drive

Geological park featuring fossilized coral reefs and scenic hiking trails. Perfect for nature lovers and outdoor enthusiasts.

Florida Keys History and Discovery Center

5 minutes' drive

An excellent resource for understanding the Keys' history, culture, and ecology through interactive exhibits and guided tours.

Lobster Trap Art Gift Shop and Gallery

4 minutes' drive

Gallery and shop featuring unique local art. Ideal for picking up souvenirs or gifts while supporting local artists.

Snorkeling Excursions

3 minutes' drive

Adventurous snorkeling tours to vibrant coral reefs. Rentals available, suitable for thrill-seekers of all ages.

Yoga on the Beach

4 minutes' drive

Relaxing beach yoga sessions offered at sunrise. Accessible for all skill levels, with nearby rental services for mats.

Wahoo's Bar and Grill

3 minutes' walk

Casual seafood eatery known for fresh catches and a laid-back atmosphere. Signature dish: fish tacos. Reservations recommended.

Whale Harbor Seafood Buffet

3 minutes' walk

Vibrant buffet featuring an array of seafood dishes. Perfect for families and large groups. Check for dietary options.

The Sand Bar

3 minutes' walk

Charming beach bar with casual bites and cocktails. Known for its sunset views. Great for a relaxed evening with friends.

Islamorada Brewery & Distillery

5 minutes' drive

Local brewery offering craft beers and tours. Family-friendly with outdoor seating and live music events on weekends.

Morada Bay Beach Cafe

5 minutes' drive

Lively beach venue hosting music and special events. Perfect for enjoying a meal with entertainment in a tropical setting.

How to get around?

City Centre

Islamorada24 min · 2.0 km

Bus

Bus stop8 min · 5.3 km

Want to get the best booking rate?

Access special rates for early reservations and start planning your dream beach holiday

Check Rates

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:

Questions of the users

About Chesapeake Beach Resort

Is fishing permitted from the beach area?

10 November 2024

Fishing is allowed from the inlet area, providing a great spot for anglers.

Are pets allowed during our stay?

22 December 2024

Yes, pets are welcome with a fee of $50 plus tax per pet, per night, with a limit of two dogs per room.

Can guests swim at the private beach?

5 January 2025

Absolutely, swimming is permitted at the beautiful private beach on the Oceanside.

Do the rooms include kitchen facilities?

18 February 2025

Rooms feature a mini refrigerator and a coffee maker, but do not have stove access.

Are pets allowed at the beach?

27 March 2025

Yes, dogs can accompany guests at the beach and other areas on the property, excluding the pools, as long as they are leashed.

Do rooms come with a private balcony?

12 April 2025

All rooms have their own balconies that are not connected to other rooms.

If we arrive early, can we use the facilities before check-in?

30 May 2025

Early check-in is based on availability, but guests are welcome to use the pools and beach area at any time. Bathrooms are available for use until your room is ready.

What areas can my small dog access on the property?

17 June 2025

Small dogs are allowed in all guest-accessible areas except the pools, as long as they remain on a leash.

Are dining options available on the property?

8 July 2025

Currently, there are no dining options on-site, but three restaurants are conveniently located just a minute's walk away.

Are there any ground-floor rooms available for guests?

21 August 2025

There are double queen and king rooms located on the first floor, though they are accessible via stairs.