See all properties

Chesapeake Beach Resort

3.5 star property
Travelers relax on sun-kissed beaches or take refreshing swims in outdoor pools at this peaceful Florida Keys resort with private waterfront access

Choose dates to view prices

Photo gallery for Chesapeake Beach Resort

A beach with palm trees and lounge chairs. - Chesapeake Beach Resort (Islamorada)
A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees. - Chesapeake Beach Resort (Islamorada)
A waterfront hotel with multiple floors, palm trees, and a calm reflective pool. - Chesapeake Beach Resort (Islamorada)
A swimming pool with clear blue water, surrounded by a white deck and a black metal fence. - Chesapeake Beach Resort (Islamorada)
A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the beach through the window. - Chesapeake Beach Resort (Islamorada)
Chesapeake Beach Resort offers a quiet escape in Matecumbe. Start your day with a leisurely breakfast, then head to the private beach with sun loungers and kayaking. Enjoy two outdoor pools, while multilingual staff and concierge services help plan the perfect stay.

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Free WiFi

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
(52 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds
  • Free WiFi

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
(104 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free WiFi

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

8.6 out of 10
Excellent
(8 reviews)
  • Ocean view
  • 50 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

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
(3 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds
  • Free WiFi

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
  • Free WiFi

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
(73 reviews)
  • 29 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds
  • Free WiFi

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
(109 reviews)
  • 25 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Double Beds
  • Free WiFi

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
(26 reviews)
  • 29 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Free WiFi

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
(41 reviews)
  • 25 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

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

8.4 out of 10
Very good
(5 reviews)
  • Resort view
  • 48 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Free WiFi

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
  • Free WiFi

View all photos for Premium 1-Bedroom Ocean View Villa

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

Premium 1-Bedroom Ocean View 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
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

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 - 0.7 miles
  • A small green leaf growing on a rough, textured surface.
    Windley Key Fossil Reef Geological State Park
    2 min drive - 1.3 miles
  • A waterfall at SeaWorld, with text reading "I eat the sea" and "Marine Mammal Park, Islamorada, Florida".
    Theater of the Sea
    2 min drive - 1.5 miles
  • A marina with boats docked, a motel, and a cafe.
    Bud n' Mary's Dive Center
    6 min drive - 4.8 miles
  • Islamorada Brewery & Distillery
    2 min drive - 1.7 miles

Getting around

  • Miami Intl. Airport (MIA)
    91 min drive

Restaurants

  • Lorelei Restaurant & Cabana Bar
    3 min drive
  • Hog Heaven
    3 min drive
  • Wahoo's Bar & Grill
    2 min walk
  • Wendy's
    2 min drive
  • The Oceanview Inn & Sports Pub
    2 min drive

Similar properties

Room, 1 King Bed with Sofa bed, Oceanfront (Alligator Reef, Lanai) | View from room
Amara Cay Resort
Matecumbe
  • On private beach
  • Pool
  • Pet friendly
  • Restaurant
8.8 out of 10, Excellent, 1,286 reviews
Amara Cay Resort
Compare similar properties

Property amenities

Internet

  • Available in all rooms: Free WiFi
  • In-room WiFi speed: 100+ Mbps (good for 1–2 people or up to 6 devices)
  • Available in some public areas: Free WiFi

Parking and transportation

  • Wheelchair-accessible parking available
  • Onsite parking includes off-street options

Food and drink

  • Free continental breakfast available daily 6:00 AM to 10:00 AM
  • A bar/lounge
  • Coffee and tea in common areas

Restaurants on site

  • Tiki Bar

Things to do

  • 2 outdoor pools
  • Boat tours
  • Fishing
  • Free bicycle rentals
  • Kayaking

Family friendly

  • 2 outdoor pools
  • Fenced pool
  • In-room microwave
  • Pool gate

Conveniences

  • 24-hour front desk

Guest services

  • Concierge services
  • Housekeeping (daily)
  • Multilingual staff

Business services

  • Computer station

Outdoors

  • Beach loungers
  • Beach towels
  • Marina
  • On a private beach
  • Pool loungers

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Assistive listening devices
  • Braille/raised signage
  • Handrails in hallways
  • Handrails in stairways
  • Lever door handles
  • Pool hoist on site
  • Upper floors accessible by stairs only
  • Visual alarms in hallways
  • Well-lit path to entrance
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible parking
  • Wheelchair-accessible pool
  • Wheelchair-accessible public washroom

More

  • 2 floors
  • 9 buildings
  • Built in 2020
  • Smoking not allowed
  • Traditional architecture

Room amenities

Bedroom

  • Bedsheets provided
  • Blackout drapes
  • Hypo-allergenic bedding
  • Pillowtop mattress

Bathroom

  • Designer toiletries
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • 43-inch flat-screen TV with cable channels

Food and drink

  • Coffee/tea maker
  • Microwave

More

  • Access via exterior corridors
  • Air conditioning
  • Ceiling fan
  • Free local calls
  • Iron/ironing board
  • Laptop workspace
  • Phone

Policies

Check-in

Check-in start time: 4:00 PM; Check-in end time: 3:00 AM
Contactless check-in available
Late check-in subject to availability
Minimum check-in age: 18

Check-out

Check-out before 11 AM
Contactless check-out available
A late check-out fee will be charged

Special check-in instructions

Front desk staff will greet guests on arrival at the property
Information provided by the property may be translated using automated translation tools

Access methods

Staffed front desk

Pets

Pets allowed for an extra charge of USD 50.00 per accommodation, per night, plus a deposit of USD 50.00 per night
Service animals are welcome, and are exempt from fees
2 total (up to 50 lbs per pet)
Restrictions apply; for more information contact the property at the number on the booking confirmation

Children and extra beds

Children are welcome
Rollaway/extra beds are not available

Property payment types

Important information

Optional extras

  • Pet deposit: USD 50.00 per night
  • Pet fee: USD 50.00 per accommodation, per night
  • Service animals are exempt from fees
  • A late check-out fee will be charged

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts credit cards; cash is not accepted
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

We should mention

This property does not have elevators
Pool access available from 8:00 AM to 6:00 PM
Some facilities may have restricted access; guests can contact the property for details using the contact information on the booking confirmation
Construction is underway at a neighboring building and there may be noise disturbance from the construction work
Children under 16 years old are not allowed in the swimming pool without adult supervision

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.

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.

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Reviews

Chesapeake Beach Resort Reviews

9.2

Wonderful

9.6

Cleanliness

9.2

Amenities

9.4

Staff & service

9.2

Property conditions & facilities
Rating 10 - Excellent. 1307 out of 1746 reviews
Rating 8 - Good. 276 out of 1746 reviews
Rating 6 - Okay. 92 out of 1746 reviews
Rating 4 - Poor. 41 out of 1746 reviews
Rating 2 - Terrible. 30 out of 1746 reviews

Reviews

Verified review

10/10 Excellent

Elizabeth

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Love the place very clean and peaceful
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Christeen

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Awesome staff. Great location. Nice property.
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Deanna

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful place for family and friends. Breakfast is phenomenal. So many activities on site. Quiet location. No crowds. One of my favorites in the Keys!
Stayed 4 nights in Jun 2026
Verified review

10/10 Excellent

Melissa

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved that this property is right on the beach. Plenty of seating by the water.
Stayed 1 night in Jun 2026
Verified review

10/10 Excellent

Charlotte

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
A beautiful place to stay on the Florida Keys! The staff were all so nice, breakfast was good, and the views were unbeatable. We would definitely consider returning!
Stayed 4 nights in Jun 2026
Verified review

10/10 Excellent

Nathan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Perfect place to stay and a super friendly and helpful staff...definitely staying here again
Stayed 1 night in Apr 2026
Verified review

10/10 Excellent

Iliana

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was so kind and eager to please! The breakfast had everything you could desire, very pleasant stay , absolutely would return !
Stayed 1 night in May 2026
Verified review

10/10 Excellent

Randy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We recently stayed at this property and was a beautiful, clean and well maintained property. Staff was excellent!
Stayed 1 night in May 2026
Verified review

8/10 Good

Louis

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great and friendly staff, perfect location.
Stayed 1 night in Apr 2026
Verified review

10/10 Excellent

Brittany

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very clean, amazing breakfast, lovely staff.
Stayed 4 nights in Mar 2026
Verified review

10/10 Excellent

NIDAL

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Breakfast is very good Staff is amazing Private beach with a walk to sandbar is Beautiful
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Kenneth

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Breakfast was great, views were awesome, nice little private beach (rare in the keys) perfect location with plenty of night life walking distance and near by! Would stay again for sure!
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Jessica

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We really enjoyed the resort! They offered snacks and champagne during the day by the pool with live music. Also the breakfast was amazing! Especially the omelettes. We will definitely be back and bring the boat.
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Jerrod

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location and beautiful beach
Stayed 2 nights in Mar 2026
Verified review

10/10 Excellent

Laura

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very clean . Staff was very attentive . Loved the beach area. Breakfast was great !
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

Rob

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I liked that I could fish in peace with very good resuts.I also enjoyed the free omlette.
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

Patrick

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Awesome beachfront clean rooms walk to restaurants
Stayed 1 night in Mar 2026
Verified review

10/10 Excellent

Philip

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great room, very clean and comfortable, pool heated and very nice area to relax. The private beach area is very nice.
Stayed 4 nights in Apr 2026
Verified review

8/10 Good

Mauricio

Liked: Staff & service, amenities
Nice hotel, second time we stay there. Nice pool and jacuzzi.
Stayed 1 night in Apr 2026
Verified review

10/10 Excellent

Matthew

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Breakfast was great!
Stayed 3 nights in Mar 2026
Verified review

10/10 Excellent

Farah

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everyone was friendly and helpful, always available when needed. The breakfast was amazing, from the cooked Omelets to the delicious pancakes. Kayaking and canoes available and already included. Lounging chairs and beach were very relaxing, with nice view. And restaurant right next door with amazing views.
Stayed 1 night in Jun 2026
Verified review

10/10 Excellent

Sara

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff was very helpful and friendly. 2 pools are great as is free kayaks and paddle boards. Breakfast cooked to order and delicious. 6&4 yr old grandkids had a ball. This is our 2nd time staying here.
Stayed 1 night in Jun 2026
Verified review

10/10 Excellent

Eduardo

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I had a wonderful time on my getaway. The view from my room was beautiful. Everything was quite and pleasant perfect for a family. Everyone was polite, and the breakfast was delicious. The view of the breakfast was phenomenal.
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Latear

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Property was clean and very smooth check in process. I would definitely return.
Stayed 1 night in May 2026
Verified review

10/10 Excellent

Monica

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful facility. Great breakfast
Stayed 3 nights in Apr 2026