Chesapeake Beach Resort

Property class: 3.5

Choose dates to view prices

Consider a stay at Chesapeake Beach Resort and take advantage of free continental breakfast, a marina, and a bar. This hotel is a great place to bask in the sun with a private beach, sun loungers, and kayaking. Enjoy onsite activities like fishing and boat tours. Guests can connect to free in-room WiFi.

Reviews

9.4 out of 10
Exceptional

Popular amenities

  • Free WiFi
The current price is SAR 526
SAR 803 total
includes taxes & fees
3 Nov - 4 Nov

Room options

Available filters for rooms
Showing 20 of 20 rooms

View all photos for Ocean View Queens

A balcony with two blue chairs and a small table, overlooking a beach with palm trees and the ocean.

Ocean View Queens

9.6 out of 10
Exceptional
(55 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Ocean View King

A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the outdoors through a sliding glass door.

Ocean View King

9.6 out of 10
Exceptional
(112 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for ADA Ocean View King Suite

A balcony with a view of the ocean and palm trees, featuring a chair, a small table, and a bench.

ADA Ocean View King Suite

8.4 out of 10
Very good
(9 reviews)
  • Ocean view
  • 50 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed

View all photos for ADA Ocean View King

A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the outdoors through a sliding glass door.

ADA Ocean View King

9.0 out of 10
Wonderful
(23 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for ADA Ocean View Queens

A hotel room with two beds, a ceiling fan, a large window with a view of palm trees, and a balcony with a chair.

ADA Ocean View Queens

9.0 out of 10
Wonderful
(7 reviews)
  • Ocean view
  • 34 sq m
  • Sleeps 4
  • 2 Queen Beds

View all photos for Hearing Impaired Ocean View Queens

A hotel room with two beds, a desk, a TV, and a balcony with a view of palm trees.

Hearing Impaired Ocean View Queens

10.0 out of 10
Exceptional
(4 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Hearing Impaired Ocean View King Suite

A modern living room with a grey sofa, wooden chairs, a round coffee table, and a large TV on the wall.

Hearing Impaired Ocean View King Suite

8.8 out of 10
Excellent
(5 reviews)
  • Ocean view
  • 50 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Standard Queens

A hotel room with two beds, a desk, a chair, a TV, and a ceiling fan.

Standard Queens

9.4 out of 10
Exceptional
(79 reviews)
  • 29 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard Doubles

A hotel room with two beds, a ceiling fan, an air conditioning unit, a TV, a desk with a chair, and a view of greenery through the windows.

Standard Doubles

9.2 out of 10
Wonderful
(117 reviews)
  • 25 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Double Beds

View all photos for Standard King with Sleeper Sofa

A hotel room with a large bed, a ceiling fan, an air conditioning unit, a bedside table with a lamp, and a view of the outside through large windows.

Standard King with Sleeper Sofa

9.2 out of 10
Wonderful
(30 reviews)
  • 29 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard King

A hotel room with a large bed, a desk with a chair, a ceiling fan, and an air conditioning unit.

Standard King

9.4 out of 10
Exceptional
(44 reviews)
  • 25 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for Ocean View King Suite

A modern bedroom with a large bed, a ceiling fan, bedside lamps, a bench, and a view through a sliding door.

Ocean View King Suite

9.4 out of 10
Exceptional
(24 reviews)
  • Ocean view
  • 49 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Deluxe Ocean View Two Queen Suite

A wooden balcony overlooking a beach with palm trees and a sunset.

Deluxe Ocean View Two Queen Suite

9.2 out of 10
Wonderful
(14 reviews)
  • Ocean view
  • 60 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds

View all photos for 2-Bedroom Villa

A bedroom with a bed, bedside table, lamp, and a dresser with a mirror.

2-Bedroom Villa

10.0 out of 10
Exceptional
(1 review)
  • Resort view
  • 60 sq m
  • 2 bedrooms
  • Sleeps 6
  • 1 King Bed, 1 Double Bed and 1 Double Sofa Bed

View all photos for Standard King Villa

A neatly made bed in a hotel room with a wooden headboard, two bedside tables with lamps, and a door to the right.

Standard King Villa

  • Resort view
  • 30 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for King Efficiency Villa

A neatly arranged hotel room with a large bed, a bedside table with a lamp, a chair, and a mirror.

King Efficiency Villa

8.8 out of 10
Excellent
(6 reviews)
  • Resort view
  • 48 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for ADA King Efficiency Villa

A bedroom with a bed, a sofa, a dresser, a TV, and a ceiling fan.

ADA King Efficiency Villa

10.0 out of 10
Exceptional
(1 review)
  • Resort view
  • 48 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for 2 Full Beds, 1-Bedroom Villa

A hotel room with two beds, a large window with a view, and a ceiling with exposed beams.

2 Full Beds, 1-Bedroom Villa

7.0 out of 10
Good
(2 reviews)
  • Ocean view
  • 65 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Double Beds and 1 Double Sofa Bed

View all photos for Premium Ocean View King Villa

A spacious room with large windows offering a view of the beach and ocean.

Premium Ocean View King Villa

  • Ocean view
  • 77 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Ocean View King Efficiency Villa

A modern kitchen with white cabinets, stainless steel appliances, and a tiled backsplash.

Ocean View King Efficiency Villa

10.0 out of 10
Exceptional
(2 reviews)
  • Ocean view
  • 48 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

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About the neighborhood

Located on a private beach, Chesapeake Beach Resort is in Matecumbe, a neighborhood in Islamorada. Hurricane Monument and Indian Key Historic State Park are local landmarks, and some of the area's activities can be experienced at Islamorada Brewery & Distillery and Florida Keys Brewing Co.. Ready for a night out? Consider Lorelei Restaurant & Cabana Bar and Hog Heaven. With jet skiing and snorkeling nearby, you'll find plenty of adventures in the water. Visit our Islamorada travel guide
Map
83409 Overseas Hwy, Islamorada, FL, 33036

What's nearby

  • A building with a blue facade, a large mural of a diving scene, and a statue of a diver.
    History of Diving Museum
    12 min walk - 1.1 km
  • An archaeological site with stone structures and metal machinery.
    Windley Key Fossil Reef Geological State Park
    2 min drive - 2.0 km
  • A waterfall at SeaWorld, with text reading "I eat the sea" and "Marine Mammal Park, Islamorada, Florida".
    Theater of the Sea
    2 min drive - 2.4 km
  • A wooden deck with benches overlooking a clear blue sea.
    Anne's Beach
    16 min drive - 20.6 km
  • Islamorada Brewery & Distillery
    2 min drive - 2.7 km

Getting around

  • Miami Intl. Airport (MIA)
    100 min drive

Restaurants

  • Hog Heaven
    3 min drive
  • Lorelei Restaurant & Cabana Bar
    3 min drive
  • Wahoo's Bar & Grill
    2 min walk
  • Wendy's
    2 min drive
  • Starbucks
    15 min walk

About this property

Chesapeake Beach Resort

  • Hotel located in Matecumbe
  • Free continental breakfast, a marina, and a bar are just a few of the amenities provided at Chesapeake Beach Resort. With a private beach, sun loungers, and kayaking, this hotel is the perfect place to soak up some sun. Enjoy onsite activities like fishing and boat tours. Stay connected with free in-room WiFi.
  • You'll also enjoy the following perks during your stay:
    • 2 outdoor pools along with sun loungers
    • Free bicycle rentals, smoke-free premises, and multilingual staff
    • Concierge services, coffee/tea in the lobby, and a 24-hour front desk
    • Beach towels and a computer station
    • Guest reviews give top marks for the breakfast, beach locale, and pool
  • Room features
  • All 60 rooms offer comforts such as laptop-friendly workspaces and air conditioning, in addition to perks like free WiFi. Guest reviews speak positively of the clean, spacious rooms at the property.
  • More amenities include:
    • Hypo-allergenic bedding and pillowtop mattresses
    • Designer toiletries, showers, and hair dryers
    • 43-inch HDTVs with cable channels
    • Wardrobes/closets, microwaves, and coffee/tea makers

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Frequently asked questions

Does Chesapeake Beach Resort have a pool?

Yes, this property has 2 outdoor pools. Pool access is from 8:00 AM–6:00 PM.

How much does it cost to stay at Chesapeake Beach Resort?

As of 24 Shawwal 2026, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on 3 Dhuʻl-Qiʻdah 2026 start from SAR 526, excluding taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Chesapeake Beach Resort pet-friendly?

Yes, this property allows pets (limit 2 total) with a maximum weight of up to 50 lbs per pet. There's a deposit of USD 50.00 per night and a fee of USD 50.00 per accommodation, per night. Service animals are exempt from fees. Some restrictions may apply, so please contact the property for more details.

What time is check-in at Chesapeake Beach Resort?

Check-in start time: 4:00 PM; Check-in end time: 3:00 AM. Late check-in is available during limited hours.

What time is check-out at Chesapeake Beach Resort?

Check-out is at 11 AM. Late check-out is available for a fee.

Where is Chesapeake Beach Resort located?

Nestled on the beach, this Matecumbe hotel is within 1 mi (2 km) of History of Diving Museum and Windley Key Fossil Reef Geological State Park. Islamorada Brewery & Distillery and Lorelei Restaurant & Cabana Bar are also within 2 mi (3 km).

Can I cancel my reservation for free and receive a full refund?

Yes, this property offers free cancellation on select room rates, because flexibility matters! Please refer to the property cancellation policy on our site for more details about any exclusions or requirements.

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Reviews

Chesapeake Beach Resort Reviews

9.4

Exceptional

9.6

Cleanliness

9.2

Amenities

9.4

Staff & service

9.4

Property conditions & facilities
Rating 10 - Excellent. 1354 out of 1804 reviews
Rating 8 - Good. 282 out of 1804 reviews
Rating 6 - Okay. 96 out of 1804 reviews
Rating 4 - Poor. 43 out of 1804 reviews
Rating 2 - Terrible. 29 out of 1804 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I like that everything looks clean and really nice staff, good breakfast
Stayed 2 nights in Oct 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Breakfast was excellent and the view and private beach was amazing
Stayed 4 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very professional reception, room clean staff very polite
Stayed 1 night in Oct 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent location, nice breakfast.
Stayed 1 night in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
All staff members are wonderful, and the rooms were clean and spacious. Overall, the property was wonderful.
Stayed 1 night in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
They offer a free breakfast which is super convenient/ The rooms are clean and the common areas are well maintained.
Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Had a great stay. Room was very comfortable and clean. Breakfast was better than expected, with omelets on demand. Dora was helpful and friendly. Will definitely stay here again.
Stayed 1 night in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nice pool, great breakfast with seating outside with nice views
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Amazing breakfast, clean room and very friendly staff.
Stayed 5 nights in Aug 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff were friendly and accommodating. Room was spotless, refrigerator and microwave useful, bathroom small but nice. Loved the lounge chairs all across the ocean side. They were great for sunrise viewing and relaxing. Breakfast and Tiki Bar were convenient. Enjoyable casual getaway.
Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This resort was beautiful & very well maintained. The view from my room was absolutely breathtaking. I will definitely stay here again when I go back to the Keys
Stayed 3 nights in Aug 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very quiet and peaceful stay. Amazing water and beach views from the balcony.
Stayed 4 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved the view and the private beach
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
After many years we came to celebrate our anniversary, the place is amazing. Yes we will come back again. Keep the good job.
Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everyone was friendly and we had a good time.
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great beach for the keys and great breakfast! The bar food is minimal and they don’t always open but Wahoo next door is amazing. Would definitely come back to this hotel.
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities
Excellent location we had a Waterview room, which was extremely clean well maintained with a beautiful view of the ocean and beach from our balcony. Both swimming pools were well maintained. Only glitch was hot tub was not working.. would definitely stay again .
Stayed 4 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I always stay here with my sisters & mom for our girls trip! Always so relaxing!!
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location, we loved having the little beach area and swimming in the pool looking at the ocean. Apparently it's dog friendly too and we loved that, may come down with the pups next time! Also it smelled great and clean without smelling like actual cleaners. The staff was also very friendly as well, and there is a bar right next to the pool too!
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The views were great and the location was perfect. The staff was friendly and helpful.
Stayed 1 night in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved the kayak, and breakfast and the view! Everything!
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful ocean view from balcony. Small pool could use resurfacing. Overall a beautiful pace for a place to stay, and enjoy the Keys.
Stayed 4 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The room we had was exceptional, the view was awesome. The bar area was a nice amenity. Although this is a pet friendly hotel, seems like some people do not feel the need to pick up after their pets, if you know what I mean. So that was why I couldn’t give the grounds a five star.
Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
A great place to stay and very well located. Breakfast staff was wonderful and very accommodating. Check in staff as well. A beautiful property,
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The property was bery nice great location, its pet friendly staff was great and the breakfast was amazing...You have restaurants right next to the property that you dont need to drive anywhere...would be there again 🙏🙏
Stayed 2 nights in Aug 2026