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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
Balcony
1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace
Water view
Outdoor spa tub

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.
    ‪5 min drive‬

Room options

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

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
(81 reviews)
  • 34 sq m
  • Ocean view
  • Sleeps 3
  • 1 King Bed

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

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 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 Standard Queens

Standard Queens

Standard Queens

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

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
(21 reviews)
  • 29 sq m
  • Sleeps 4
  • 1 King 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 Ocean View King Suite

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

Ocean View King Suite

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

Standard King Villa

Standard King Villa

  • 30 sq m
  • 1 bedroom
  • Resort view
  • 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 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 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

Ocean View King Efficiency Villa

  • 48 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa 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 - 3 min drive - 2.7 km
  • Florida Keys Brewing Co. - 5 min drive - 4.3 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
  • ‪Wahoo's Bar & Grill - ‬2 min walk
  • ‪Starbucks - ‬15 min walk

About this property

Chesapeake Beach Resort

Beach hotel with 2 outdoor pools and a marina
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. 1129 out of 1550 reviews
Rating 8 - Good. 259 out of 1550 reviews
Rating 6 - Okay. 93 out of 1550 reviews
Rating 4 - Poor. 40 out of 1550 reviews
Rating 2 - Terrible. 29 out of 1550 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

Collin

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 6 nights in Jul 2025

10/10 Excellent

Collin

Travelled with family and small children
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean and comfortable with breakfast on site. Close activities and a few restaurants within walking distance
Stayed 6 nights in Jul 2025

10/10 Excellent

David

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Breakfast selections were very good, including made to order omelettes and waffles. Loved the 2 pools, free beach chairs, umbrellas, towels, kayaks. Beach and water had tons of sea weed but staff did best to keep paths open. Beautiful setting, well kept
Stayed 2 nights in Jul 2025

10/10 Excellent

Ryan

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Aug 2025

10/10 Excellent

Brian

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

8/10 Good

Luz

Travelled with family
Liked: Cleanliness, staff & service, amenities
I've stayed at this property before and have always enjoyed it..it has everything and perfect for kids. The only thing I would suggest is to exterminate the rooms and facilities.
Stayed 1 night in Aug 2025

4/10 Poor

Philip

Travelled with family
Liked: Cleanliness, property conditions & facilities, room comfort
Disliked: Staff & service

Great location and rooms - service not so!

Stayed 2 nights in Jul 2025

10/10 Excellent

Josephine

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 3 nights in Jul 2025

8/10 Good

Kirsten, Thousand Oaks

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Would prefer a door or curtain so mirror is not right with the bed
Stayed 1 night in Aug 2025

10/10 Excellent

Mario

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I stayed here a long time ago prior to the renovations and I was please to find that it’s still the same great place just a lot nicer.
Stayed 1 night in Jul 2025

10/10 Excellent

Alecia

Liked: Cleanliness, staff & service, property conditions & facilities
-
Stayed 4 nights in Jul 2025

10/10 Excellent

Gary

Liked: Cleanliness, staff & service, property conditions & facilities
Loved the breakfast options! Omlets was a hit.
Stayed 4 nights in Jul 2025

10/10 Excellent

Edgardo

Liked: Amenities
It was new, loved the balcony. Beach sports were nice but needed more lifejacket sizes. Pool amenities were great. Breakfast was good.
Stayed 1 night in Jul 2025

10/10 Excellent

Francisco

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Best breakfast ever right on the ocean 😋
Stayed 1 night in Jul 2025

8/10 Good

vickie

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Ac. Was not great at all. Wish there was more of a variety for food at bar area. We were starving had to order pizza. That was one reason for picking this resort. The breakfast was wonderful tho
Stayed 1 night in Jul 2025

10/10 Excellent

Nicholas

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The hotel is wonderful
Stayed 2 nights in Jul 2025

10/10 Excellent

Adam

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We just got bk from 3 nts here: 2adults 1 child. We absolutely loved this hotel, it was clean, the staff were friendly and the rooms were very clean and the AC was perfect for escaping from the Florida heat and humidity. The breakfast offerings were plentiful, huge shout out to the chef for his waffles for the kids. The outdoor brekfast area was perfect for sitting and staring out to sea and the Islamorada lighthouse. Make sure you check out the entry to the little marina where it narrows at thebentey from the sea - looking into the crystal clear water at dawn and dusk we saw Nurse Sharks, Eels, Horseshoe crabs and so many small and media sized coloured fish. Get up early one morning to checkout the sunrise too!! So worth it! Would highly recommend and we will use again when we are next in Islamorada. A wonderful place to stay.
Stayed 3 nights in Jul 2025

10/10 Excellent

jonathan

Travelled with family, Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Front desk girl i didn't remember her name but she was very kind and proffesional and gave us a beautiful upgrade. Our second time here and will continue to come back.
Stayed 1 night in Jul 2025

10/10 Excellent

Donis

Travelled with family and small children
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Its not to close or to far
Stayed 1 night in Jul 2025

8/10 Good

Jason David

Travelled with partner
Liked: Cleanliness, staff & service, property conditions & facilities
I loved the ocean views! Awesome pool location!
Stayed 2 nights in Jul 2025

10/10 Excellent

Michael

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

Chesapeake is Amazing - Gets better every trip

We have been coming here for 5 years and the place gets better and better. Every year we come they have added new amenities. The beach and pools are amazing and the location makes it easy to go anywhere in the Keys quickly. If you are looking for a great resort for a great price in this area it is a GREAT option!
Stayed 4 nights in Jul 2025

10/10 Excellent

Liu M

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
One of my favorite places to have a relaxing trip with the family
Stayed 1 night in Jun 2025

10/10 Excellent

Rachel

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful staff. Vanessa was awesome! We will return
Stayed 2 nights in Jul 2025

6/10 Okay

Mayra

Travelled with family
Stayed 1 night in Jul 2025

10/10 Excellent

Michael

Stayed 1 night in Jul 2025