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Chesapeake Beach Resort, Islamorada

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From149US$ /night
Check-in
29Apr2025Select date
Check-out
30Apr2025Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Resort

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

Chesapeake Beach Resort is an idyllic seaside escape in Islamorada, recognized for its breathtaking oceanfront views and unique blend of luxury and comfort. Tucked between the Everglades National Park and the Florida Strait, it offers guests a tranquil retreat focused on relaxation and recreation. The resort is celebrated for its family-friendly atmosphere, featuring expansive outdoor spaces and well-appointed accommodations designed for both leisure and social gatherings. Known for its proximity to various water sports and local attractions, the resort stands out as a premier destination for vacations and events alike.

Location

Situated in the heart of the Florida Keys, Chesapeake Beach Resort is conveniently located near several attractions, including local seafood restaurants and unique shopping experiences. The resort is only a short drive from notable landmarks such as Anne's Beach and the Theater of the Sea. The area's relaxed vibe, combined with stunning coastal scenery, offers an ideal backdrop for exploration and enjoyment.

Rooms

Chesapeake Beach Resort offers a variety of room types, including garden view rooms and spacious villas. Each room has big comfortable beds and a serene atmosphere, perfect for a restful stay. Guests can enjoy stunning ocean views from their private balconies or opt for garden views with direct access to the lush surroundings. The newly renovated rooms include plush bedding and modern amenities for a high level of comfort.

Eat & Drink

The resort features a range of dining options, including tiki-covered bars and gourmet beachfront cafes. Guests can savor fresh-from-the-dock seafood alongside landlubber favorites and ethnic dishes. Breakfast options include cooked-to-order omelets and continental items to start the day. The diverse culinary offering ensures there is something to please every palate, making dining at the resort a delightful experience.

Leisure & Business

Chesapeake Beach Resort provides an array of leisure activities, including access to private beach areas and outdoor pools with ocean views. Water sports rentals, such as kayaking and paddleboarding, are available onsite, allowing guests to explore the surrounding waters. Live entertainment is also a highlight, offering guests enjoyable performances amid a beach party atmosphere, enhancing the overall recreational experience.

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Select your room type

The hotel offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
Ocean View Two Queens
Max:
4 persons
32 m² 
Bed options:
2 Double beds
Sea view
Shower
Coffee machine
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Ocean View King
Max:
2 persons
32 m² 
Bed options:
1 King-size bed
Sea view
Shower
Coffee machine
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Deluxe King Suite
Max:
4 persons
55 m² 
Bed options:
1 King-size bed
Sea view
Shower
Coffee machine
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Price and Room Availability Calendar

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Getting around

Explore available ways to reach your dream destination

City Centre
Islamorada 2.0 km
Bus
Bus stop 5.3 km

Facilities

The hotel offers amenities for your comfortable stay and unforgettable experiences

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
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Location

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

Reviews and Ratings

Feedback from previous guests about their experience
70%
liked the resort and would come back again
Great beach access
Friendly staff
Limited dining options
Pricey Wi-Fi
7.0/10
Very good
Rooms
7.0
Location
9.0
Service
7.6
Dining
5.0
Guest reviews
7.0/10
based on 6 reviews
4/5 based on 88 reviews
8.5
8.5/10 based on 910 reviews
#16 of 21 hotels in Islamorada based on Tripadvisor
Karen
United States, December  2024
6.8/10

Staying at the hotel was a mixed bag for me. The location was absolutely stunning, with easy access to great food and activities. The rooms, while beautiful, did show some wear and tear. The staff were incredibly nice and attentive, making sure we had what we needed. However, the dining situation left much to be desired, as the breakfast options were quite limited and not very appealing. Overall, it was a decent value for money, but improvements could definitely be made.

Rooms
7.0
The rooms were beautiful, but they showed their age and could use some updates.
Service
9.0
The staff was very nice and attentive, making sure we had everything we needed during our stay.
Location
8.0
The location was incredible and close to everything we wanted to do, although the nearby restaurant did have some loud music on weekends.
Dining
5.0
The breakfast was not what I was expecting—just a microwaveable sandwich and a few packaged items.
Facilities
6.0
The facilities were decent but nothing extraordinary.
Carl
United States, November  2024
8.0/10

I stayed at this hotel and loved the proximity to the beach, which was a huge plus for me. The rooms were clean and spacious, offering perfect views of the ocean. The staff was friendly and attentive, making my stay even better. However, the dining options left a lot to be desired - they could definitely use some improvement. Overall, it's a good value for the location and amenities offered.

Rooms
9.0
The rooms were clean, spacious, and offered stunning views right on the sand.
Service
9.0
The staff was incredibly friendly and courteous, always ready to help when I needed anything.
Location
10.0
The location was absolutely beautiful, right on the beach with easy access to local attractions.
Dining
5.0
Unfortunately, the dining options were pretty poor and definitely something that needs to be improved.
Facilities
8.0
The facilities were nice, with a lovely pool area to relax by.
Great beach access
Limited dining options
Phillip
United States, September  2024
7.2/10

The hotel is situated in a great location for exploring the Keys, with easy access to snorkelling tours and major attractions. While my room was clean and had a decent view, it faced the parking lot, which made it quite noisy at times. The service was mostly friendly, although the mattress could really use an upgrade. The dining options could also use improvement, as they felt a bit bland. Overall, it was a fair value for the price considering the location but not without some drawbacks.

Rooms
7.0
The room was clean, but it faced the parking lot, so I dealt with some freeway noise.
Service
6.0
The staff was friendly and helpful, but the beds were quite uncomfortable.
Location
9.0
The hotel’s location is fantastic for activities and restaurants, right in the heart of the Keys.
Dining
5.0
Dining options were pre-packed and needed improvement; nothing special about the food offered.
Facilities
8.0
The facilities were satisfactory, with access to kayaks and paddle boats, which was a nice touch.
Daniel
United States, August  2024
7.0/10

I had a pleasant stay at this hotel which is conveniently located, but the rooms need some updates and the dining experience was lacking. The service was excellent with friendly and attentive staff, and while the facilities are good, the breakfast options left a bit to be desired. Overall, it’s a decent choice considering the location and friendly vibe.

Rooms
6.0
The rooms were clean at first glance, but I noticed quite a bit of dust in the corners and they felt older and tired, especially the bathrooms.
Service
9.0
The service was really attentive, with the staff making sure we had everything we needed. They were extra friendly and sent messages to check on us.
Location
9.0
The hotel is in a great location, very close to everything, which made getting around super easy.
Dining
5.0
Breakfast was quite limited with just a few choices available in a pickup box, and it wasn't really what I expected for a breakfast meal.
Facilities
7.0
The facilities were adequately maintained, but nothing particularly stood out as exceptional.
Dennis
United States, August  2024
6.6/10

The hotel is located in a nice area with beautiful views, but I was disappointed with the cleanliness of the rooms as they were in need of updating. The staff was generally friendly; however, I had a frustrating experience when they woke us up late at night for a credit card that was already on file. The dining options for breakfast were decent but could use more variety. Overall, while the location is breathtaking, the overall experience didn't quite match the price I paid.

Rooms
6.0
The rooms were clean but had a cute decor that feels outdated and definitely needed some renovations.
Service
5.0
The staff was friendly, but I was woken up at 10 PM for a credit card I had already provided at check-in, which was really frustrating.
Location
9.0
The location was absolutely beautiful, with spectacular views and the opportunity to see manatees swimming in the harbor.
Dining
7.0
Breakfast had a relaxed dress code and good choices, though I wish there were more options available.
Facilities
6.0
The facilities seemed adequate but didn’t really stand out; I would have liked to see a bit more modern amenities.
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Rooms and Guests2 Guests, 1 Room