Chesapeake Beach Resort Islamorada Beach photoChesapeake Beach Resort Islamorada Exterior photoChesapeake Beach Resort Islamorada Exterior photo

CHESAPEAKE BEACH RESORT, Islamorada

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Up to 10% Off
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From$149 /night
Check-in
16Jul
Check-out
17Jul
Rooms and Guests2 Guests, 1 Room
Key details

Overview & Features

83409 Overseas Highway, Islamorada, 33036
-
Close to Whale Harbor Marina
Great
8.6
9.1
/10
3.9
4.2
/5

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.

“This oceanfront property in Islamorada distinguishes itself with a private beach and complimentary water sports, ideal for families and couples; spacious villas and personalized service add to the appeal. It's a place that balances relaxation with a wide array of activities, though the marina situation needs to be addressed. I'd recommend it for a laid-back beach vacation.”
Hotel logo
Edward HayesEditor-in-Chief at Beachresort

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
  • Ocean View Two Queens
    2 persons
    32 sq. feet
    2 Double beds
    Air conditioning
    Balcony
  • Ocean View King
    2 persons
    32 sq. feet
    1 King-size bed
    Air conditioning
    Balcony
  • Deluxe King Suite
    2 persons
    55 sq. feet
    1 King-size bed
    Air conditioning
    Balcony
Show all rooms

Check Prices & Room Availability

See what's available for your travel dates now!
July 2026 - July 2027
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Check-in/ Check-out

Facilities

Enjoy comfortable stays and unforgettable experiences at our beach resorts
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
Show more

Location & Nearby Attractions

83409 Overseas Highway, Islamorada, 33036
Explore Islamorada
Local Highlights
  • Top Attractions
  • Activities
  • Dining
  • Entertainment
History of Diving Museum
History of Diving Museum
12 minutes' walk
A tribute to the sport of diving featuring artifacts and exhibits, showcasing the history and technology of underwater exploration.
Windley Key Fossil Reef Geological State Park
Windley Key Fossil Reef Geological State Park
4 minutes' drive
A stunning geological park with fossilized coral reefs and nature trails perfect for hiking and observing local wildlife.
Florida Keys History and Discovery Center
Florida Keys History and Discovery Center
5 minutes' drive
Offers an in-depth look at Florida Keys history with interactive exhibits and films about the region's culture and environment.
Snorkeling Adventures
3 minutes' drive
Join local operators for thrilling snorkeling excursions to vibrant reefs, rentals and guided tours available for all skill levels.
Yoga on the Beach
3 minutes' walk
Relaxing beachfront yoga sessions that cater to all levels, perfect for recharging after a day of exploring.
Wahoo's Bar and Grill
3 minutes' walk
Casual dining with fresh seafood, renowned for its vibrant atmosphere and signature wahoo tacos, popular among guests.
Whale Harbor Seafood Buffet
3 minutes' walk
A feast of flavors with an extensive buffet featuring local seafood and dishes that appeal to diverse palates, reservations recommended.
The Sand Bar
3 minutes' walk
A lively beachfront bar with live music and a relaxed vibe, offering cocktails and snacks for a fun night out.
Shuck N Dive
3 minutes' walk
Known for its laid-back atmosphere and fresh seafood dishes, often featuring local bands for entertainment on weekends.
Getting around beach destinations
  • 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 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:
45

Guest Ratings & Coastal Resort Reviews

See What Past Guests Had to Say About Their Stay
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
Clean rooms
Comfortable beds
Oceanfront location
Cons
Noisy A/C
Guest reviews
based on 88 reviews
4/5
based on 734 reviews
8.6/10
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
Questions of the users
About Chesapeake Beach Resort
Is fishing permitted on the beach at Chesapeake Beach Resort?
10 April 2024
Fishing is allowed in the inlet area where guests can enjoy the activity.
Are furry companions welcomed at Chesapeake Beach Resort?
22 May 2024
Pets are welcome, with a fee of $50 plus tax per pet per night, allowing for up to two dogs per room.
Can guests enjoy swimming in the beach area?
15 June 2024
Yes, there is access to a beautiful beach where swimming is encouraged.
What kind of cooking facilities are available in the rooms?
30 July 2024
Rooms are equipped with mini refrigerators and coffee makers, but do not include stovetops.
Can pets accompany guests on the beach and property?
12 August 2024
Yes, pets can access most areas of the property, except for the pools, as long as they are leashed.
Are there private balconies available in the guest rooms?
25 September 2024
Each room features its own non-connected private balcony for guests to enjoy.
What is the earliest check-in time available for day visitors?
3 October 2024
Early check-in depends on availability. Guests can use pool and beach amenities anytime, with access to bathrooms while waiting for their room.
Is there an on-site restaurant available for meals?
18 November 2024
Currently, there is no restaurant on the property. However, there are three dining options just a minute's walk away.
Are there any accommodations on the ground floor for easier access?
14 December 2024
Some double queen and king rooms are located on the first floor, with seven steps to reach them.
Is there a fee for parking and docking boats at the resort?
6 January 2025
Yes, there is a parking and docking fee of $60 per day for boats.

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