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Chesapeake Beach Resort

3.5 star property

Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun-loungers, beach towels
Water view
1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace
Balcony
Outdoor spa tub

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Bar
  • 24/7 front desk

Explore the area

Map
83409 Overseas Hwy, Islamorada, FL, 33036
  • Windley Key Fossil Reef Geological State Park
    ‪2 min drive‬
  • Theater of the Sea
    ‪2 min drive‬
  • Florida Keys Brewing Co.
    ‪4 min drive‬

Room options

View all photos for 2-Bedroom Villa

2-Bedroom Villa

2-Bedroom Villa

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

View all photos for Standard King

Standard King

Standard King

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

View all photos for King Efficiency Villa

King Efficiency Villa

King Efficiency Villa

10.0 out of 10
Exceptional
(1 review)
  • 48 sq m
  • Resort view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard Doubles

Standard Doubles

Standard Doubles

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

View all photos for Standard King with Sleeper Sofa

Standard King with Sleeper Sofa

Standard King with Sleeper Sofa

9.0 out of 10
Wonderful
(18 reviews)
  • 29 sq m
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Hearing Impaired Ocean View Queens

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Hearing Impaired Ocean View Queens

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

View all photos for Hearing Impaired Ocean View King Suite

43-inch flat-screen TV with cable channels, TV

Hearing Impaired Ocean View King Suite

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

View all photos for ADA King Efficiency Villa

ADA King Efficiency Villa

ADA King Efficiency Villa

  • 48 sq m
  • Resort view
  • Sleeps 3
  • 1 King Bed

View all photos for Premium 1-Bedroom Ocean View Villa

Premium 1-Bedroom Ocean View Villa

Premium 1-Bedroom Ocean View Villa

  • 65 sq m
  • Ocean view
  • Sleeps 6
  • 2 Double Beds and 1 Double Sofa Bed

View all photos for Deluxe Ocean View Two Queen Suite

Balcony

Deluxe Ocean View Two Queen Suite

8.8 out of 10
Excellent
(8 reviews)
  • 60 sq m
  • Ocean view
  • Sleeps 6
  • 2 Queen Beds

View all photos for Ocean View King

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King

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

View all photos for Ocean View King Suite

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King Suite

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

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

9.8 out of 10
Exceptional
(41 reviews)
  • 34 sq m
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

Ocean View King Efficiency Villa

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

View all photos for Standard Queens

Standard Queens

Standard Queens

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

View all photos for Standard King Villa

Standard King Villa

Standard King Villa

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

View all photos for Premium Ocean View King Villa

Premium Ocean View King Villa | Living area

Premium Ocean View King Villa

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

View all photos for ADA Ocean View Queens

ADA Ocean View Queens

ADA Ocean View Queens

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

View all photos for ADA Ocean View King Suite

ADA Ocean View King Suite | Balcony

ADA Ocean View King Suite

10.0 out of 10
Exceptional
(2 reviews)
  • 50 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed

View all photos for ADA Ocean View King

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

ADA Ocean View King

8.6 out of 10
Excellent
(16 reviews)
  • 34 sq m
  • Ocean view
  • Sleeps 3
  • 1 King Bed

Similar properties

Exterior

Amara Cay Resort

  • On private beach
  • Pool
  • Pet-friendly
  • Restaurant
4.4 out of 5, Excellent, (1222)
The price is AU$478
for 1 room
includes taxes & fees
9 July - 10 July
Amara Cay Resort

About the area

Islamorada

Located in Islamorada (Matecumbe), Chesapeake Beach Resort is within a 5-minute drive of History of Diving Museum and Windley Key Fossil Reef Geological State Park. .This beach hotel is 1.2 mi (2 km) from Islamorada Brewery & Distillery and 1.7 mi (2.8 km) from Keys History & Discovery Center.

What's nearby

  • History of Diving Museum - 12 min walk - 1.1 km
  • Windley Key Fossil Reef Geological State Park - 2 min drive - 2.0 km
  • Theater of the Sea - 2 min drive - 2.4 km
  • Islamorada Brewery & Distillery - 2 min drive - 2.4 km
  • Florida Keys Brewing Co. - 4 min drive - 4.0 km

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
  • ‪Florida Keys Brewing Co. - ‬3 min drive
  • ‪Whale Harbor Restaurant Marina - ‬2 min walk

About this property

Chesapeake Beach Resort

Hotel on the beach, with 2 outdoor pools
Chesapeake Beach Resort offers 60 air-conditioned accommodations, which are accessible via exterior corridors and feature coffee/tea makers and designer toiletries. Beds feature pillowtop mattresses. 43-inch flat-screen televisions come with cable channels. Bathrooms include showers, complimentary toiletries, and hair dryers.

This Islamorada hotel provides complimentary wireless Internet access, with a speed of 100+ Mbps (good for 1–2 people or up to 6 devices). Business-friendly amenities include phones along with free local calls (restrictions may apply). Additionally, rooms include irons/ironing boards and ceiling fans. Housekeeping is offered daily and hypo-allergenic bedding can be requested.

A private beach, a marina, and complimentary bicycles are featured at the hotel. 2 outdoor swimming pools are on site.

Children under 16 years old are not allowed in the swimming pool without adult supervision.

The recreational activities listed below are available either on site or nearby; fees may apply.

Make yourself at home in one of the 60 air-conditioned rooms featuring microwaves and flat-screen televisions. Your room comes with a pillowtop bed. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms feature showers, designer toiletries, and hair dryers.
Spend the day on the private beach or dip into one of the 2 outdoor swimming pools. This hotel also features complimentary wireless internet access and concierge services.
Wrap up your day with a drink at the bar/lounge. A complimentary continental breakfast is served daily from 6:00 AM to 10:00 AM.
Featured amenities include a computer station, a 24-hour front desk, and multilingual staff.
A complimentary continental breakfast is served each morning between 6:00 AM and 10:00 AM.
Tiki Bar - Onsite bar.

Languages

English, Spanish

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 transport

  • 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 bathroom

More

  • 2 floors
  • 9 buildings
  • Built in 2020
  • Renovated entire property - January 2020
  • Smoke-free property
  • 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

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 stay
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

Payment types

Important information

Optional extras

  • Pet deposit: USD 50.00 per stay
  • 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
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 7:00 AM to 10:30 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

Property is also known as

Chesapeake Beach Islamorada
Chesapeake Beach Resort
Chesapeake Beach Resort Islamorada
Chesapeake Resort
Chesapeake Beach Hotel Islamorada
Chesapeake Beach Resort Hotel
Chesapeake Beach Resort Islamorada
Chesapeake Beach Resort Hotel Islamorada

Chesapeake Beach Resort Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 1059 out of 1475 reviews
Rating 8 - Good. 245 out of 1475 reviews
Rating 6 - Okay. 93 out of 1475 reviews
Rating 4 - Poor. 44 out of 1475 reviews
Rating 2 - Terrible. 34 out of 1475 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

8.8/10

Amenities

9.2/10

Property conditions & facilities

9.0/10

Eco-friendliness

Reviews

8/10 Good

Carlos

Stayed 2 nights in Mar 2025

10/10 Excellent

Maria, Jupiter

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We were very happy here. Had almost everything except fine dining which we did not mind! Plenty of places to go!
Stayed 1 night in Mar 2025

8/10 Good

Jamie, Bloomington

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 5 nights in Mar 2025

10/10 Excellent

Federico

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in Mar 2025

8/10 Good

Ashley

Liked: Cleanliness
Stayed 2 nights in Mar 2025

2/10 Terrible

Michael

Travelled with family
Disliked: Cleanliness, staff & service, amenities, property conditions & facilities
This is not a resort. It is a motor lodge sandwiched between the highway and the water. You literally park under your room. There is a tiny pool. The “beach” is a joke. It’s not sand, but white dirt, and it’s a tiny area. The water is shallow and the bottom is weedy and rocky. I am a cheap person, but my wife and kid and I all decided to leave shortly after checking in (no refund despite the deceptive advertising) and go back to Eden ROC in Miami. Better room, real resort amenities, and less expensive. Chesapeake motor lodge felt like a prison.
Stayed 4 nights in Mar 2025

10/10 Excellent

Lisandra

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very clean, very beautiful. Sea on the back side love it.
Stayed 1 night in Mar 2025

6/10 Okay

James

Liked: Cleanliness
Stayed 1 night in Mar 2025

10/10 Excellent

Jessica

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities
Beautiful property, comfy, and clean room and excellent service!
Stayed 1 night in Mar 2025

8/10 Good

Jim

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Convenient
Stayed 5 nights in Mar 2025

10/10 Excellent

Christopher

Stayed 1 night in Mar 2025

10/10 Excellent

Keziah

Travelled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
So accommodating. Love this place. I could be there all day
Stayed 1 night in Mar 2025

10/10 Excellent

Michelle

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This property fit all of our needs. Our Villa was immaculately clean. All the staff was extremely accommodating and went out of their way to be polite and warming. The arrival champagne glass was so nice after our trip and the beach was great, the water was amazing. I will definitely book this resort when we come back down to the Keys and that won’t be long because we live in Florida. If you want to stay in Islamorada, you should absolutely put this place in your top 3. They serve drinks and has two poles and people were snorkeling and just have a great time. Everyone that we spoke to absolutely loved this place. Robes and the shoes were so nice. I would absolutely give this place five stars out of five. For a 10 out of 10 experience for your trip in the Florida Keys trust me your hotel or resort you should not have any concerns or questions or drama.
Stayed 2 nights in Mar 2025

10/10 Excellent

theodore

Stayed 4 nights in Mar 2025

10/10 Excellent

Heike

Stayed 1 night in Mar 2025

10/10 Excellent

Liang Eva

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities
We had a great spring break. The resort is clean, conveniently located.
Stayed 5 nights in Mar 2025

8/10 Good

Robert

Liked: Cleanliness, staff & service, property conditions & facilities
Nice people, quiet resort.
Stayed 3 nights in Mar 2025

10/10 Excellent

max

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great stay, clean room!
Stayed 2 nights in Mar 2025

10/10 Excellent

Gladys

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities
Secluded quiet, excellent to relax
Stayed 1 night in Mar 2025

10/10 Excellent

Tracy

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff are super friendly. Our room was clean and well laid out. Make sure to use the 2 hours free paddle boarding that comes with your reservation, we seen sharks, manatees and lots of fish and hermit crabs. The breakfast in the morning is fresh and a great selection.
Stayed 2 nights in Mar 2025

10/10 Excellent

Rebecca, Okeechobee

Liked: Cleanliness, staff & service, property conditions & facilities
I love this place! Lovely maintained grounds, very clean and modern rooms. The sunrises are amazing. Front desk, cleaning staff, breakfast staff and bar staff were friendly and very accommodating. I am going to miss the great cooked to order omelets and drinks by the pool and beach. I would recommend this resort to anyone with families or adults only. We enjoyed the beautiful grounds which are lush and well maintained. The chess, checkers and kayak rentals plus the tiki boat rentals to the sandbar are an added bonus. This was betterthan an all inclusive resort in the Caribbean for us. Paradise in the Keys- close to shopping and great restaurants. Better than traveling south where it gets a little crazy for us. We plan to come back as often as we can.
Stayed 3 nights in Mar 2025

8/10 Good

Darlis

Stayed 2 nights in Feb 2025

10/10 Excellent

Sue Ellen

Liked: Cleanliness, staff & service, property conditions & facilities
We asked for & received early check-in. The staff was friendly & helpful & everything was immaculate! Wonderful breakfast included! Nice beach area with lots to do. We will definitely stay here again!
Stayed 1 night in Mar 2025

10/10 Excellent

Derick

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Most amazing views
Stayed 2 nights in Feb 2025

10/10 Excellent

Patrick

Liked: Cleanliness, amenities
Love this place
Stayed 2 nights in Feb 2025