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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
Property preview
Water view
Balcony
1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Bar
  • 24/7 front desk
  • Pet-friendly
  • Pool

Explore the area

View 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
  • 2 bedrooms
  • 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

9.4 out of 10
Exceptional
(29 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
(2 reviews)
  • 48 sq m
  • 1 bedroom
  • 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
(88 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
(19 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
  • 1 bedroom
  • 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
  • 1 bedroom
  • 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
  • 1 bedroom
  • 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
(9 reviews)
  • 60 sq m
  • 1 bedroom
  • 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

9.4 out of 10
Exceptional
(80 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
(15 reviews)
  • 49 sq m
  • 1 bedroom
  • 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
(43 reviews)
  • 34 sq m
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

Ocean View King Efficiency Villa

  • 48 sq m
  • 1 bedroom
  • 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
(54 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
  • 1 bedroom
  • 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
  • 1 bedroom
  • 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
  • 1 bedroom
  • 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

8.0 out of 10
Very good
(3 reviews)
  • 50 sq m
  • 1 bedroom
  • 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
(17 reviews)
  • 34 sq m
  • Ocean view
  • Sleeps 3
  • 1 King Bed

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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
  • Florida Keys Brewing Co. - 4 min drive - 4.0 km
  • Bud n' Mary's Dive Center - 7 min drive - 7.3 km

Getting around

  • Miami Intl. Airport (MIA) - 91 min drive

Restaurants

  • ‪Tiki Bar - ‬13 min walk
  • ‪Lorelei Restaurant & Cabana Bar - ‬3 min drive
  • ‪Wendy's - ‬2 min drive
  • ‪Whale Harbor Restaurant Marina - ‬2 min walk
  • ‪Starbucks - ‬15 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.

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

Reviews

Chesapeake Beach Resort Reviews

9.2

Wonderful

9.4/10

Cleanliness

9.2/10

Staff & service

9.0/10

Amenities

9.2/10

Property conditions & facilities

9.0/10

Eco-friendliness
Rating 10 - Excellent. 1105 out of 1527 reviews
Rating 8 - Good. 258 out of 1527 reviews
Rating 6 - Okay. 94 out of 1527 reviews
Rating 4 - Poor. 39 out of 1527 reviews
Rating 2 - Terrible. 31 out of 1527 reviews

Reviews

8/10 Good

Annalien

Liked: Cleanliness, property conditions & facilities
The pools are amazing
Stayed 1 night in Jun 2025

10/10 Excellent

Shelly

Liked: Cleanliness, property conditions & facilities
The property is the best for family vacation and the staff is awesome
Stayed 1 night in Jun 2025

4/10 Poor

Cecilia, HALLANDALE BEACH

Travelled with family and small children
Disliked: Cleanliness, amenities, property conditions & facilities
We unfortunately found your resort lacking in good customer service. No one at the pools or beach to offer towels or to open an umbrella. Breakfast was mediocre at best, the coffee not that good, the cook was super angry looking and not courteous AT ALL. The AC in the rooms very annoying-antiquated. We were promised we could stay until 12, then the front desk changes their mind. NOT WORTH THE MONEY. 2 Stars at best.
Stayed 1 night in Jun 2025

10/10 Excellent

Marlene

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
We enjoyed all things involved. Pool breakfast room. Everything was wonderful
Stayed 2 nights in Jun 2025

10/10 Excellent

Elizabeth

Travelled with partner
Liked: Amenities
Dog poop in pool area Found hair in a lot of the towels used Staff were friendly and dependable
Stayed 1 night in Jun 2025

10/10 Excellent

Esther

Travelled with family
Stayed 1 night in May 2025

8/10 Good

Jasmine

Stayed 3 nights in Jun 2025

10/10 Excellent

Dailen

Business traveller, Travelled with family, Travelled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Excepcional
Stayed 3 nights in Jun 2025

10/10 Excellent

James, HOLLYWOOD

Stayed 2 nights in Jun 2025

8/10 Good

Isbet

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
In general, was fine, just not all staff was nice
Stayed 1 night in Jun 2025

6/10 Okay

Amanda

Liked: Cleanliness, property conditions & facilities
Disliked: Staff & service, room comfort
Honestly was expecting this place to be great given the price; however, that wasn’t true. Each room has a mini split for AC which did not cool our room very well given the Florida heat. Upon check in, we were told a room wasn’t ready yet and asked if we could use the kayaks in the meantime while waiting and the front desk attendant didn’t know the answer. Thankfully our room was ready minutes later. Overall, not very many amenities very available for the price paid.
Stayed 1 night in Jun 2025

10/10 Excellent

Katie

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Great stay!

We loved this property! We actually cancelled our second night at a different hotel in Marathon to come back to this one. The pools were great, rooms were clean and beautiful, front desk employees were kind and helpful. The breakfast was delicious and I loved the option to purchase a mimosa with breakfast. We went to Wahoo’s restaurant which is in walking distance to the hotel as well as Papa Joe’s and both were fantastic. We would definitely come back here!
Stayed 1 night in May 2025

10/10 Excellent

karen

Travelled with pets, Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was family oriented. Love that pets were allowed on premises. Many activities for adults and children even though we didn’t have kids it was nice to see. Staff very pleasant and helpful.
Stayed 1 night in May 2025

6/10 Okay

Albert

Liked: Cleanliness
Stayed 3 nights in Jun 2025

4/10 Poor

Fadi

Travelled with family
Liked: Amenities, property conditions & facilities
Disliked: Staff & service
Poco personal y los que están no son nada agradables y atienden horrible a los huéspedes.
Stayed 1 night in May 2025

10/10 Excellent

Ramkumar, Redmond

Travelled with family, Travelled with family and small children, Business traveller
Liked: Cleanliness, amenities, property conditions & facilities
One of the best stays I’ve experienced. The property offers stunning views—especially during sunrise, which is truly unforgettable. The infinity pool overlooking the sea creates a perfect blend of luxury and tranquility. Rooms are exceptionally spacious, well-maintained, and designed for comfort. Highly recommend for those seeking both relaxation and scenic beauty.
Stayed 1 night in Apr 2025

10/10 Excellent

Lester

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent getaway
Stayed 1 night in May 2025

10/10 Excellent

Mikayla

Liked: Cleanliness, amenities, property conditions & facilities
This was a great place to stay.
Stayed 3 nights in Jun 2025

10/10 Excellent

Alena

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
It was one of the best of my stays at the keys. I live in Downtown Miami and love escaping for the weekend with girlfriend or husband. This time we brought our dog Mini Australian shepherd Benji. We all had blast with a pet friendly ocean view property!
Stayed 2 nights in May 2025

10/10 Excellent

Peter

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Jun 2025

10/10 Excellent

Sergii

Liked: Cleanliness, staff & service, amenities
Everything was amazing
Stayed 2 nights in May 2025

10/10 Excellent

Yanitzia

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
Un lugar maravilloso, con una atención increíble. La habitación que da para el mar , es un expectaculo de linda. Para pareja y familia Lo recomiendo 100%
Stayed 1 night in May 2025

10/10 Excellent

Tracey

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Came into town to pick up our boat.
Stayed 1 night in May 2025

10/10 Excellent

Donna

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
The staff person who checked us in was very friendly and helpful. The room was very clean and had a really comfortable bed. Staff checked once a day to see if we needed anything. We would definitely return!
Stayed 3 nights in May 2025

10/10 Excellent

tina

Travelled with partner
Liked: Staff & service, amenities
One of the pools had a dirty diaper left on a table. The staff dropped off towels but didn't look around to clean up left over cups, used diaper, etc. Granted guests should be responsible and clean up their own trash but it would be nice if the housekeeping would watch for this since I had to point it out. Other than that it was a great location and nice hotel. Two restaurants next door to the property so you don't have to drive if you don't want. Breakfast was great, made to order custom omelet, rooms had robes and slippers, there's paddle boards, clear bottom kayaks and fishing poles to use.
Stayed 1 night in May 2025