Chesapeake Beach Resort Islamorada | Private Beach from $149

Name: CHESAPEAKE BEACH RESORT, Islamorada
Address: 83409 Overseas Highway, Islamorada, Florida, 33036
Price range: US$149+
Rating: 8.4

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Chesapeake Beach Resort Islamorada Beach photo

Chesapeake Beach Resort Islamorada Exterior photo

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Key details

About the Hotel

83409 Overseas Highway, Islamorada, 33036

Next to the History of Diving Museum

Great

8.4

9.1

/10

3.9

4.2

Loved by Chesapeake Beach Resort 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

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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 States

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

Lia

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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.

Select your room type

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

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

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Prices and availability

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

September 2026 - September 2027

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Check-in/ Check-out

Facilities

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

Facilities: Great

8.4/10Review 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

Location

83409 Overseas Highway, Islamorada, 33036

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
Islamorada 24 min · 1.2 mi
Bus
Bus stop 8 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 the entire hotel for free.

Breakfast

A full breakfast is served at the price of USD 0.1 per person.

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 1056 verified reviews

9.0 /10

Perfect

89 %

Recommend

Cleanliness

8.8/10

Comfort

8.7/10

Facilities

8.4/10

Free WiFi

9.3/10

Location

9.0/10

Staff

8.5/10

Value for money

7.7/10

Pros

Free kayaking

Kind staff

Good location

Villa upgrade

Good restaurants

Cons

Uncomfortable chairs

Limited breakfast

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.

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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.