See all properties
Save

Chesapeake Beach Resort

3.5 star property

Photo gallery for Chesapeake Beach Resort

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

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Breakfast included
  • Free Wi-Fi
  • Restaurant

Explore the area

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

Room options

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

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

View all photos for Ocean View King

Hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King

9.6 out of 10
Exceptional
(88 reviews)
  • Ocean view
  • 34 sq m
  • 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

8.4 out of 10
Very good
(5 reviews)
  • Ocean view
  • 50 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed

View all photos for ADA Ocean View King

Hypo-allergenic bedding, pillow-top beds, laptop workspace

ADA Ocean View King

8.6 out of 10
Excellent
(17 reviews)
  • Ocean view
  • 34 sq m
  • 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)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Hearing Impaired Ocean View Queens

Hypo-allergenic bedding, pillow-top beds, laptop workspace

Hearing Impaired Ocean View Queens

10.0 out of 10
Exceptional
(2 reviews)
  • Ocean view
  • 34 sq m
  • 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)
  • Ocean view
  • 50 sq m
  • 1 bedroom
  • 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
(60 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
(95 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

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

View all photos for Standard King

Standard King

Standard King

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

View all photos for Ocean View King Suite

Hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King Suite

9.2 out of 10
Wonderful
(17 reviews)
  • Ocean view
  • 49 sq m
  • 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
  • 60 sq m
  • 1 bedroom
  • 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)
  • Resort view
  • 60 sq m
  • 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

Standard King Villa

  • Resort view
  • 30 sq m
  • 1 bedroom
  • 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)
  • Resort view
  • 48 sq m
  • 1 bedroom
  • 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

  • Resort view
  • 48 sq m
  • 1 bedroom
  • 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

  • Ocean view
  • 65 sq m
  • 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

Premium Ocean View King Villa

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

Ocean View King Efficiency Villa

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

Similar properties

Hibiscus Waterfront 2-Bedroom, Two Bath Master Suite (Brand New) | Terrace/patio
Lime Tree Bay Resort
  • On private beach
  • Pool
  • Pet-friendly
  • Parking included
4.6 out of 5, Wonderful, 1,145 reviews
Lime Tree Bay 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
  • Theater of the Sea - 3 min drive - 2.0 km
  • Windley Key Fossil Reef Geological State Park - 3 min drive - 2.0 km
  • Islamorada Brewery & Distillery - 3 min drive - 2.7 km
  • Bud n' Mary's Dive Center - 10 min drive - 7.6 km

Getting around

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

Restaurants

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

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 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
  • 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
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 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. 1212 out of 1653 reviews
Rating 8 - Good. 271 out of 1653 reviews
Rating 6 - Okay. 98 out of 1653 reviews
Rating 4 - Poor. 42 out of 1653 reviews
Rating 2 - Terrible. 30 out of 1653 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

9.0/10

Amenities

9.2/10

Property conditions & facilities

Reviews

8/10 Good

Julio

Stayed 3 nights in Oct 2025

10/10 Excellent

William

Stayed 1 night in Oct 2025

10/10 Excellent

Sergey, Plantation

Stayed 2 nights in Oct 2025

10/10 Excellent

Michelle

Stayed 2 nights in Oct 2025

10/10 Excellent

Brian

Liked: Cleanliness, staff & service, property conditions & facilities
I was very pleased with the resort. It’s a quiet hidden gem with a friendly and helpful staff. I would love to stay here again.
Stayed 1 night in Oct 2025

10/10 Excellent

Daniel

Travelled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything was updated and clean.
Stayed 4 nights in Oct 2025

10/10 Excellent

Krzysztof, warszawa

Stayed 1 night in Oct 2025

10/10 Excellent

Raymond

Travelled with family, Business traveller
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
For just choosing a property off the internet, we hit gold!!! The staff, the room, the amenities, the view, the tw9 restaurants and bars next door were beyond belief! We almost incurred a flight change fee to stay longer! We will be back!
Stayed 1 night in Oct 2025

10/10 Excellent

Brayan

Stayed 2 nights in Oct 2025

8/10 Good

Theresa

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Great venue.
Our view.
Stayed 2 nights in Oct 2025

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The front desk lady was very pleasant upon my check-in. She answered all my questions and made me feel comfortable driving to my room where I was staying. I slept late the next day with the do not disturb sign and I received a personal text from the front desk in the early afternoon asking me to respond when I was ready for them to make up my room. I did eat breakfast at the resort each morning. The chefs were extremely friendly and I enjoyed a sunrise breakfast overlooking the water. The breakfast is complimentary as well! Other than that, I wasn’t T the resort to stay the entire time. The rest of the time I was out and about, but I looked forward to jumping in the super comfy bed each evening when I would get back. I’ll be back the next time I’m in Islamorada!!
Stayed 3 nights in Oct 2025

10/10 Excellent

Christina

Liked: Cleanliness
Stayed 3 nights in Oct 2025

10/10 Excellent

Mitzi

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

Gem!

What a CLEAN and beautiful place! Vanessa at the front desk was awesome! Only stayed one night on the way to Key West, but I would definitely stay again!! So many amenities and your own private beach. 10/10
Stayed 1 night in Oct 2025

10/10 Excellent

Alex

Stayed 1 night in Oct 2025

10/10 Excellent

Alisha

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everyone was so nice and helpful at this resort!!! I had such an amazing time and would definitely recommend to any family & friends!!!
Stayed 1 night in Oct 2025

10/10 Excellent

Lisaimy

Stayed 1 night in Oct 2025

10/10 Excellent

Cynthia

Travelled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We had a great experience at the Chesapeake!
Stayed 2 nights in Oct 2025

10/10 Excellent

garry

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Resort offered alot considering it was somewhat smaller. Excellent staff and rooms/amenities..will definitely go back.
Stayed 3 nights in Oct 2025

10/10 Excellent

Sandee

Travelled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Vanessa and Adriana made our stay excellent. Actually stayed an extra day. The morning chef was awesome!!
Stayed 1 night in Oct 2025

10/10 Excellent

JOSE

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean room | Great Outdoor pool | Amazing view
Stayed 5 nights in Oct 2025

10/10 Excellent

Rob

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
A good peaceful fishing area which is my main reason for staying there.The room was very clean and a bit on the small side.The location of this resort is great.
Stayed 2 nights in Oct 2025

10/10 Excellent

Vickie

Liked: Cleanliness, staff & service, property conditions & facilities
Love this place. Great beach/pool. Lovely room with great bathroom. Unbelievable view of the sunrise over the water from our balcony
Stayed 4 nights in Oct 2025

10/10 Excellent

Carrie

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
.
Stayed 1 night in Oct 2025

10/10 Excellent

ID

Travelled with partner
Liked: Cleanliness, staff & service, property conditions & facilities
The pools where very clean and very comfy, the place is keep very clean. Thank you.
Stayed 2 nights in Oct 2025

10/10 Excellent

Aloke

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great place, ambience, people and peacefull
Stayed 3 nights in Oct 2025