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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
Outdoor spa tub
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

Explore the area

View map
83409 Overseas Hwy, Islamorada, FL, 33036
  • Place, Windley Key Fossil Reef Geological State Park
    ‪2 min drive‬
  • Place, Theater of the Sea
    ‪2 min drive‬
  • Place, 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

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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
(20 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
  • 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

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

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. 1114 out of 1540 reviews
Rating 8 - Good. 260 out of 1540 reviews
Rating 6 - Okay. 94 out of 1540 reviews
Rating 4 - Poor. 40 out of 1540 reviews
Rating 2 - Terrible. 32 out of 1540 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

9.0/10

Amenities

9.2/10

Property conditions & facilities

9.0/10

Eco-friendliness

Reviews

8/10 Good

Kevin

Travelled with pets, Travelled with group
Liked: Cleanliness, staff & service, amenities
Nice day , check in super fast , room ready in early time , clean pools and a beautiful beach access . The only problem was my AC , it wasn’t cooling enough in the night. But all the other Amenities and services was great.
Stayed 1 night in Jun 2025

10/10 Excellent

Lia, Miami

Liked: Cleanliness, staff & service, property conditions & facilities
We enjoyed so much staying at this property. The pool and beach area is so beautiful we did not want to go anywhere else. We were also available to use the marina which was a big plus. At check in we were greeted with a champagne glass which was on point. Vanessa at the front desk was super nice and very courteous. Jose at the bar goes above and beyond to serve good drinks. He also made us burgers and hot dogs on Sunday. At breakfast they have a chef making omelets and waffles which were amazing. 5 star! Overall was excellent, the only thing was we felt the double beds are more like twin beds. But after that excellent staff and property. We will definitely be back.
Stayed 1 night in Jun 2025

8/10 Good

mariah

Disliked: Staff & service
Could use a little more work around the property use more decor and things to do. Looks very old and outdated on the property. Room was nice and clean bed was super comfy. Staff weren’t very professional.
Stayed 1 night in Jun 2025

10/10 Excellent

Joseph

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

10/10 Excellent

Michelle

Stayed 2 nights in Jun 2025

10/10 Excellent

Osmel

Stayed 7 nights in Jun 2025

10/10 Excellent

alina

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The place is amazing ! Very clean everything is new
Stayed 1 night in Jun 2025

10/10 Excellent

Gabriela

Liked: Cleanliness, staff & service, property conditions & facilities
Excellent hotel. We love it
Stayed 1 night in Jun 2025

10/10 Excellent

Stacy

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We absolutely loved our stay here! Great pools and beach access, delicious breakfast every morning (made to order omelets!), very quiet and super short drive to anywhere we wanted to go on the island. Staff was always so helpful and checked in on us via text throughout our stay. Would absolutely recommend to others and stay again ourselves.
Stayed 6 nights in Jun 2025

10/10 Excellent

Pablo

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

Worth every penny.

It was excellent. Beautiful location, friendly and helpful staff, amazing views.
Stayed 1 night in Jun 2025

6/10 Okay

Anita

Travelled with family
Older property, rooms could have been cleaner. Beautiful view.
Stayed 1 night in Jun 2025

10/10 Excellent

Nick

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
An absolute dream! This place is absolutely amazing. Price point was great too. I can’t wait to come back!
Stayed 2 nights in Jun 2025

6/10 Okay

Romulla

Stayed 1 night in Jun 2025

8/10 Good

Heather

Liked: Cleanliness, staff & service, property conditions & facilities
We loved the pool areas and little beach area. Comfortable beds with robe and slippers in the room. Super cute place on our trip back to Miami.
Stayed 1 night in May 2025

10/10 Excellent

EDUARDO, MIAMI

Liked: Property conditions & facilities
Stayed 3 nights in Jun 2025

10/10 Excellent

Monte

Great location, friendly and helpful staff
Stayed 2 nights in Jun 2025

10/10 Excellent

Dawn

Liked: Cleanliness, amenities, property conditions & facilities
Very accommodating staff.
Stayed 2 nights in Jun 2025

10/10 Excellent

gary

Stayed 2 nights in Jun 2025

10/10 Excellent

Joshua

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Amazing doesnt give this place justice. The staff here are great. Super friendly and helpful. The rooms are super clean, bright and perfect for our stay. The resort grounds were clean and tidy. Breakfast was good and the omelet guy was super cool. The only bad was we had to leave. This is definitely our spot every time we visit❤️
Stayed 1 night in Jun 2025

10/10 Excellent

Amy

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We loved this hotel. The lady at the check in was so kind and accommodating to our needs. My kids loved the deeper pool and the fact that there were two pools helped adults at the hotel still enjoy relaxing instead of being splashed by kids. We loved the rentals and yard games, as well. Our room was clean and just what we needed after many poor experiences elsewhere in the keys. Thank you for a great stay!
Stayed 1 night in Jun 2025

10/10 Excellent

Kat

Liked: Cleanliness, amenities, property conditions & facilities
Beautiful !!! So clean. It was the
Stayed 6 nights in Jun 2025

10/10 Excellent

Eve

Stayed 1 night in Jun 2025

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