Chesapeake Beach Resort Islamorada | Private Beach & Paddleboarding

Name: Book Chesapeake Beach Resort - Premium Seaview Hotel in Islamorada
Address: 83409 Overseas Highway, Islamorada, Florida, 33036
Price range: US$149+
Rating: 8.6

75 photos

Chesapeake Beach Resort Islamorada Beach photo

Chesapeake Beach Resort Islamorada Exterior photo

Book on our site

up to 10% cheaper

than Booking.com

Key details

About the Hotel

83409 Overseas Highway, Islamorada, 33036

Next to Whale Harbor Marina

Great

8.6

9.1

/10

3.9

4.2

Loved by Chesapeake Beach Resort guests

Waterfront location

Cooked-to-order breakfast

Comfortable beds

Attentive staff

"Beautiful views from balcony of ocean, nice beach with fresh towels, great breakfast daily and service, great suite with large balcony, Clean facilities and great service"

ctaylor2024 from United States

read full review

"The glass of bubbly upon arrival after a long day of travel set the tone for an excellent visit."

Don B from United States

read full review

"The property has been improved since we first started visiting about four years ago."

Joyce from United States

read full review

"Location, beautiful view of beach and ocean."

Daniel from United States

read full review

3-star beachfront retreat in Islamorada

Accommodations

Chesapeake Beach Resort offers various room types including waterfront rooms that feature full kitchenettes. Guests can enjoy private balconies with views of the stunning Florida Bay. The Comfort Suites is available with family-friendly options accommodating up to six guests.

Waterfront Activities

The hotel boasts a large Grand Pool Complex equipped with lounge chairs and umbrellas covering all family needs. A private beach area allows for water activities such as swimming or sunbathing with ease. Guests have access to kayaks, paddleboards, and other water sports without additional costs.

Dining Options

Chesapeake Beach Resort features the Blue Moon Fish Company with an outdoor dining experience overlooking the marina. Guests can enjoy a diverse menu including fresh seafood and tropical drinks. The hotel also provides a complimentary hot breakfast each morning for its guests.

Family-Friendly Amenities

Families benefit from a children's play area equipped with games and activities suitable for all ages. The hotel includes an exciting array of water sports geared towards family enjoyment. Additionally, there are organized activities that foster family bonding moments.

Event Space

Chesapeake Beach Resort offers versatile event spaces accommodating occasions such as weddings and corporate functions. The waterfront pavilion provides a unique setting for gatherings against a scenic backdrop. Audiovisual equipment and catering services are available for all event needs.

Highlights

Location: Direct access to Florida Bay

Dining: Blue Moon Fish Company with outdoor seating

Activities: Complimentary kayak and paddleboard rentals

Rooms: Waterfront rooms with full kitchenettes

“Chesapeake Beach Resort presents a genuinely tranquil escape with its updated, clean rooms and particularly the ocean-view accommodations that provide an immersive coastal experience. The complimentary breakfast, featuring made-to-order omelets, complements the resort's well-maintained private beach and complimentary water sports, making for a restorative stay.”

James DavidEditor-in-Chief at Seaviewhotels

Location: Perfect

9.0/10Review score

View hotel on map

Highlights from guests

DiningBreakfast Bliss

Chef Chris crafts amazing omelets and pancakes to order. Enjoy delicious breakfast with a stunning water view.

CulinaryExplorer from United States

Review on

Room FeaturesOceanfront Serenity

Our ocean-view room boasted a spectacular beachfront vista, perfect for watching sunrises and the water.

ViewSeeker from Canada

Review on

Spa & LeisureWaterfront Fun

Complimentary kayaks and paddleboards are available to explore the calm, warm waters right from the beach.

AdventureCouple from Australia

Review on

Guest ParkingEffortless Arrival

Parking was simple, convenient, and covered, making arrival and departures stress-free.

EasyPark from United Kingdom

Review on

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
32 sq. feet
2 Double beds
Air conditioning
Balcony
room details
Ocean View King
2 persons
32 sq. feet
1 King-size bed
Air conditioning
Balcony
room details
Deluxe King Suite
2 persons
55 sq. feet
1 King-size bed
Air conditioning
Balcony
room details

Show all rooms

Price and Room Availability Calendar

Check availability and prices for your dates now!

July 2026 - July 2027

Sun

Mon

Tue

Wed

Thu

Fri

Sat

July 2026

August 2026

September 2026

October 2026

November 2026

December 2026

January 2027

February 2027

March 2027

April 2027

May 2027

June 2027

Choose dates to see prices

Check-in/ Check-out

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
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, 33036

Explore Islamorada

History of Diving Museum

12 minutes' walk

Diving history exhibits showcase artifacts and photographs. Guided tours enhance the experience for all ages.

Windley Key Fossil Reef Geological State Park

25 minutes' walk

Unique fossilized coral reef formations and scenic trails. Perfect for nature lovers and geology enthusiasts.

Florida Keys History and Discovery Center

25 minutes' walk

Interactive exhibits detail the history of the Florida Keys. Regular programs enhance visitor engagement.

Lobster Trap Art Gift Shop and Gallery

25 minutes' walk

Local art showcasing marine-themed pieces in a quirky setting. Great for finding unique souvenirs.

Discover the local attractions near Chesapeake Beach Resort

Explore the unique attractions near Chesapeake Beach Resort that offer diverse experiences for guests.

Great for nature lovers exploring geological formations: Windley Key Fossil Reef Geological State Park

Ideal for art enthusiasts looking for local talent: Michelle Nicole Lowe Art Gallery

Best for history buffs wanting to learn about the region's past: Hurricane Monument

Suited for outdoor adventures and wildlife observation: Raccoon Key

Works well for unique shopping experiences and local crafts: Lobster Trap Art Gift Shop and Gallery

Perfect for scenic drives and picturesque views: Upper Matecumbe Key

Well suited for an immersive art experience: Pasta Pantaleo Signature Gallery

Ideal for snorkeling and marine exploration: Carysfort Reef

Great for creative workshops and local art immersion: In the Doghouse Art Studio

Snorkeling at Carysfort Reef

5 minutes' drive

Thrilling underwater adventures with colorful marine life. Tours available; equipment rentals can be arranged.

Yoga at FNX Club

10 minutes' drive

Relaxing yoga classes in a serene environment. Ideal for wellness seekers; pre-registration recommended.

Fishing Charters at Whale Harbor Marina

3 minutes' walk

Exciting fishing charters for all skill levels. Catch local fish on guided tours, with all gear provided.

Wahoo's Bar and Grill

3 minutes' walk

Casual dining with fresh seafood and tropical drinks. Signature fish tacos and beautiful sunset views.

Whale Harbor Seafood Buffet

3 minutes' walk

Variety of seafood dishes in a relaxed setting. Perfect for families; reservations recommended on weekends.

The Sand Bar

3 minutes' walk

Laid-back atmosphere with pub-style food, ideal for casual bites and drinks. Local craft beers on tap.

Discover dining options near Chesapeake Beach Resort

Enjoy diverse dining options near Chesapeake Beach Resort that cater to various tastes and preferences.

Best for seafood lovers seeking a hearty meal: Whale Harbor Seafood Buffet

Perfect for casual dining with a local flavor: Wahoo's Bar and Grill Restaurant

Great for those craving laid-back coastal bites: Shuck N Dive

Islander Watersports

5 minutes' drive

Live music and events create a fun atmosphere. Offers water sports rentals along with great food and drinks.

Islamorada Beer Company

5 minutes' drive

Brews and live music events with local vibes. Family-friendly environment with plenty of outdoor seating.

Getting around

City Centre
Islamorada 24 min · 1.2 mi
Bus
Bus stop 8 min · 3.3 mi

Want to see Exclusive Early Booking Rate?

Get exlusive rates right now!

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

Wireless internet is available in the entire hotel 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 993 verified reviews

8.9 /10

Great

89 %

Recommend

Cleanliness

9.0/10

Comfort

8.9/10

Facilities

8.6/10

Free WiFi

8.5/10

Location

9.0/10

Staff

8.6/10

Value for money

7.8/10

Pros

Private beach

Large pools

Friendly staff

Clean facility

Cons

Thin walls

Uncomfortable beds

Inconsistent breakfast hours

based on 88 reviews

4/5

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.

Open reviews

Show more reviews

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.

Is parking available at Chesapeake Beach Resort?

Private parking is available on-site for free, but a reservation is needed.

Does Chesapeake Beach Resort provide Wi-Fi access?

Free Wi-Fi access is available throughout the property.

What recreational activities can guests enjoy at Chesapeake Beach Resort?

Guests can enjoy activities such as fishing, access to a private beach, and complimentary kayaking and paddleboarding.

What types of amenities can be found in the rooms at Chesapeake Beach Resort?

Rooms feature air conditioning, a 37-inch flat-screen TV, a small refrigerator, and complimentary toiletries.

What dining options are available at Chesapeake Beach Resort?

The hotel has an on-site restaurant, and nearby dining options include Whale Harbor Seafood Buffet, Wahoo's Bar and Grill Restaurant, and Shuck N Dive, all within 0.5 km.

Which popular attractions are nearby Chesapeake Beach Resort?

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

Does Chesapeake Beach Resort have a pool?

The hotel features a heated outdoor swimming pool with ocean views.

What is the distance from Chesapeake Beach Resort to the nearest airport?

The hotel is approximately 80 km from Miami International Airport.