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Chesapeake Beach Resort

3.5 star property

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Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun loungers, beach towels
Water view
Deluxe Ocean View Two Queen Suite | Balcony
Hypo-allergenic bedding, pillowtop beds, laptop workspace
43-inch flat-screen TV with cable channels, TV

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Free WiFi
$280
$249 nightly
$280 total
Total with taxes and fees
May 3 - May 4

Explore the area

View in a map
83409 Overseas Hwy, Islamorada, FL, 33036
  • Place, History of Diving Museum
    ‪12 min walk‬
  • Place, Islamorada Brewery & Distillery
    ‪2 min drive‬
  • Place, Theater of the Sea
    ‪2 min drive‬

Room options

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

9.6 out of 10
Exceptional
(49 reviews)
  • Ocean view
  • 366 sq ft
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Ocean View King

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King

9.6 out of 10
Exceptional
(99 reviews)
  • Ocean view
  • 364 sq ft
  • 1 bedroom
  • 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

8.6 out of 10
Excellent
(8 reviews)
  • Ocean view
  • 540 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed

View all photos for ADA Ocean View King

Hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA Ocean View King

8.8 out of 10
Excellent
(20 reviews)
  • Ocean view
  • 364 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for ADA Ocean View Queens

ADA Ocean View Queens | Hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA Ocean View Queens

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

View all photos for Hearing Impaired Ocean View Queens

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Hearing Impaired Ocean View Queens

10.0 out of 10
Exceptional
(3 reviews)
  • Ocean view
  • 366 sq ft
  • 1 bedroom
  • 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

8.8 out of 10
Excellent
(5 reviews)
  • Ocean view
  • 540 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Standard Queens

Standard Queens | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard Queens

9.4 out of 10
Exceptional
(65 reviews)
  • 307 sq ft
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard Doubles

Standard Doubles | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard Doubles

9.2 out of 10
Wonderful
(101 reviews)
  • 272 sq ft
  • 1 bedroom
  • Sleeps 4
  • 2 Double Beds

View all photos for Standard King with Sleeper Sofa

Standard King with Sleeper Sofa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King with Sleeper Sofa

9.2 out of 10
Wonderful
(25 reviews)
  • 307 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard King

Standard King | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King

9.6 out of 10
Exceptional
(39 reviews)
  • 272 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for Ocean View King Suite

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King Suite

9.2 out of 10
Wonderful
(19 reviews)
  • Ocean view
  • 527 sq ft
  • 1 bedroom
  • 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

9.0 out of 10
Wonderful
(11 reviews)
  • Ocean view
  • 650 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds

View all photos for 2-Bedroom Villa

2-Bedroom Villa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

2-Bedroom Villa

10.0 out of 10
Exceptional
(1 review)
  • Resort view
  • 646 sq ft
  • 2 bedrooms
  • Sleeps 6
  • 1 King Bed, 1 Double Bed and 1 Double Sofa Bed

View all photos for Standard King Villa

Standard King Villa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King Villa

  • Resort view
  • 323 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for King Efficiency Villa

King Efficiency Villa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

King Efficiency Villa

9.6 out of 10
Exceptional
(4 reviews)
  • Resort view
  • 517 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for ADA King Efficiency Villa

ADA King Efficiency Villa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA King Efficiency Villa

  • Resort view
  • 517 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for Premium 1-Bedroom Ocean View Villa

Premium 1-Bedroom Ocean View Villa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Premium 1-Bedroom Ocean View Villa

8.0 out of 10
Very good
(1 review)
  • Ocean view
  • 700 sq ft
  • 1 bedroom
  • 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 | 43-inch flat-screen TV with cable channels, TV

Premium Ocean View King Villa

  • Ocean view
  • 829 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Ocean View King Efficiency Villa

Ocean View King Efficiency Villa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King Efficiency Villa

10.0 out of 10
Exceptional
(1 review)
  • Ocean view
  • 517 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

Similar properties

Exterior
Islander Resort
Matecumbe
  • On private beach
  • Pool
  • Pet friendly
  • Parking included
4.6 out of 5, Wonderful, 1,007 reviews
$270 nightly
The price is $304
May 17 - May 18
Total with taxes and fees
Islander Resort

About the neighborhood

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 - 0.7 miles
  • Windley Key Fossil Reef Geological State Park - 2 min drive - 1.3 miles
  • Islamorada Brewery & Distillery - 2 min drive - 1.5 miles
  • Theater of the Sea - 2 min drive - 1.5 miles
  • Bud n' Mary's Dive Center - 5 min drive - 4.6 miles

Getting around

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

Restaurants

  • ‪Lorelei Restaurant & Cabana Bar - ‬3 min drive
  • ‪Wahoo's Bar & Grill - ‬2 min walk
  • ‪Hog Heaven - ‬3 min drive
  • ‪Tiki Bar - ‬13 min walk
  • ‪Wendy's - ‬2 min drive

About this property

Chesapeake Beach Resort

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 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 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

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. 1259 out of 1704 reviews
Rating 8 - Good. 276 out of 1704 reviews
Rating 6 - Okay. 96 out of 1704 reviews
Rating 4 - Poor. 42 out of 1704 reviews
Rating 2 - Terrible. 31 out of 1704 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

9.0/10

Amenities

9.2/10

Property conditions & facilities

Reviews

8/10 Good

Tracy

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

8/10 Good

Susan E

Traveled with family
Liked: Staff & service, property conditions & facilities
Same toothpaste smear on sink when we arrived, still there for 4 days. I cleaned around it myself just to see. Very disappointed. I chlorox wiped the whole room. Fortunately, that was the only issue. This was my second stay. I would come back and I will recommend you.
Stayed 8 nights in Jan 2026

10/10 Excellent

Kurt

Liked: Cleanliness, staff & service, property conditions & facilities
Wonderful breakfast with omelettes cooked to order, great pancakes, fresh fruit, etc. very pleasant staff and beautiful beach area.
Stayed 2 nights in Jan 2026

10/10 Excellent

Harry

Traveled with family
Liked: Cleanliness, staff & service
Staff was great room was very clean
Stayed 2 nights in Jan 2026

10/10 Excellent

Fritz

Liked: Cleanliness, amenities, property conditions & facilities
Yes and yes!
Stayed 1 night in Jan 2026

10/10 Excellent

Annie

Liked: Cleanliness, amenities, property conditions & facilities
Wonderful nice and clean staff 👌 very nice special specially staff Vanessa she very helpful and sweet. Is nice place to stay we will come again. Thank you Vanessa again.
Stayed 1 night in Jan 2026

6/10 Okay

Matthew

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Staff was courteous. We arrived late in the evening and our room was next to the lobby. The rooms are ok, nothing great. It was a colder evening in January and the room was cold. The front desk offered us extra blankets but it would have been nice to have directions on how to control the heating in the room. A decent value for the price, we were only there overnight so room was adequate.
Stayed 1 night in Jan 2026

10/10 Excellent

Victor, HIALEAH

Stayed 1 night in Jan 2026

10/10 Excellent

Debbie, Knoxville

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The breakfast was excellent with a nice variety and made to order. The room was spacious and the bed was comfortable. I really like the spacious bathroom. The only negative was the refrigerator kept freezing our food & beverages.
Stayed 6 nights in Jan 2026

10/10 Excellent

karen, Hollywood

Stayed 2 nights in Jan 2026

6/10 Okay

Kelly

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Room was clean with great views. Bathroom shower was only just OK. Breakfast was very good. Check-in information could be improved - for example was told breakfast started at 8:00, but found out that it actually was available much earlier.
Stayed 2 nights in Jan 2026

10/10 Excellent

Patrick

Stayed 3 nights in Jan 2026

10/10 Excellent

Maria

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
Everything was perfect Awesome place. Just a little bit noisy in the ice area early in the morning. And a lot of noise from the second floor.
Stayed 1 night in Jan 2026

10/10 Excellent

Ivor

Liked: Amenities, property conditions & facilities
Everything was perfect.
Stayed 3 nights in Jan 2026

10/10 Excellent

Tom

Liked: Cleanliness
Room was clean. Check in was fast and the staff was very friendly and welcoming.
Stayed 1 night in Jan 2026

8/10 Good

Chris

Stayed 1 night in Jan 2026

10/10 Excellent

Peter, Coral Gables

Traveled with group, Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities
A very nice property meticulously maintained. Breakfast omelets made to order was a big hit. Super nice place to stay and just a walk to our fishing charter at Wahoo's. We'll be back.
Looking out on the Atlantic
Stayed 4 nights in Jan 2026

10/10 Excellent

Joshua

Traveled with family and small children, Traveled with partner, Traveled with pets, Traveled with family
Liked: Cleanliness, property conditions & facilities
Great staff. Lovely grounds. Comfortable clean rooms.
Stayed 7 nights in Jan 2026

10/10 Excellent

Annie

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
It was very nice place to stay resort nice and clean the ataff Vanessa very helpful and sweet. We very happy will come back again. Thank you Vanessa again .
Stayed 1 night in Jan 2026

8/10 Good

Christine

Traveled with family
Liked: Cleanliness, staff & service, amenities
Friendly and helpful staff especially Xixi at the front desk. Rooms were clean and beds comfortable.
Stayed 2 nights in Jan 2026

10/10 Excellent

Gabriel

Liked: Cleanliness, amenities, property conditions & facilities
The staff was amazing. Breakfast was awesome. This was truly a magical time for my wife and i
Stayed 2 nights in Jan 2026

8/10 Good

dave

Liked: Cleanliness, staff & service, property conditions & facilities
Traffic noise at night
Stayed 1 night in Dec 2025

8/10 Good

Rick

Traveled with partner
Liked: Amenities
Decent place to stay. The room was typical of a hotel and nothing really special. Our room had a shared door which allowed sound through and we had to listen to our neighbors' music the first night. Someone was smoking weed below us on the balcony and despite the doors being closed, the smell permeated our room for hours. One of the sinks leaked. Staff at front desk very nice, the staff serving breakfast not so much. Coffee was never ready on time. The location was great and I suggest using some of the amenities because you are going to pay for them either way.
Stayed 2 nights in Jan 2026

10/10 Excellent

Roberta

Traveled with group
Liked: Cleanliness, amenities, property conditions & facilities
Clean room with friendly staff. The breakfast is amazing and you can eat next to the lagoon watching the sunrise. I would stay there again.
Stayed 2 nights in Jan 2026

10/10 Excellent

Warren

Liked: Cleanliness, amenities, property conditions & facilities
Great staff, clean room, nice breakfast and convenient location. Enjoyed our week.
Stayed 6 nights in Jan 2026