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

Popular amenities

  • Bar
  • 24/7 front desk

Explore the area

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
  • 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
(28 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
  • 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
(84 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
(18 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
  • 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
  • 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
  • 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
  • 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

9.6 out of 10
Exceptional
(77 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
(13 reviews)
  • 49 sq m
  • 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
  • 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
(53 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
  • 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
  • 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
  • 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
  • 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
(16 reviews)
  • 34 sq m
  • Ocean view
  • Sleeps 3
  • 1 King Bed

Similar properties

Exterior

Amara Cay Resort

  • On private beach
  • Pool
  • Pet-friendly
  • Restaurant
4.4 out of 5, Excellent, (1235)
The price is NZ$426
for 1 room
includes taxes & fees
14 Aug - 15 Aug
Amara Cay 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
  • 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

  • ‪Lorelei Restaurant & Cabana Bar - ‬3 min drive
  • ‪Hog Heaven - ‬3 min drive
  • ‪Wahoo's Bar & Grill - ‬2 min walk
  • ‪Florida Keys Brewing Co. - ‬3 min drive
  • ‪Whale Harbor Restaurant Marina - ‬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.

Languages

English, Spanish

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. 1063 out of 1477 reviews
Rating 8 - Good. 247 out of 1477 reviews
Rating 6 - Okay. 92 out of 1477 reviews
Rating 4 - Poor. 41 out of 1477 reviews
Rating 2 - Terrible. 34 out of 1477 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

8.8/10

Amenities

9.2/10

Property conditions & facilities

9.0/10

Eco-friendliness

Reviews

10/10 Excellent

Peter

Liked: Cleanliness, staff & service, property conditions & facilities
Great property exceeded our expectations.
Stayed 2 nights in Apr 2025

10/10 Excellent

Daniel, Miami

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean, nicely decorated rooms. Direct beach access. Well maintained property.
Stayed 1 night in Apr 2025

10/10 Excellent

Helen

Liked: Cleanliness, staff & service, property conditions & facilities
Amazing location.
Stayed 4 nights in Mar 2025

10/10 Excellent

Wilson

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Todo muy Exelente las habitaciones son muy buenas y limpias recomendadisimo
Stayed 1 night in Apr 2025

6/10 Okay

Patricia

Liked: Cleanliness
was told hot tub was in working order when making the reservation. Hot tub was out of order upon arrival and during stay.
Stayed 1 night in Apr 2025

8/10 Good

Edwin

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

8/10 Good

Adam

Liked: Cleanliness, property conditions & facilities
Good for the price and convenient for fishing trips. No frills, clean rooms good location.
Stayed 3 nights in Apr 2025

10/10 Excellent

Margarita

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

2/10 Terrible

PHILIP

Travelled with family
Disliked: Staff & service, property conditions & facilities
We only stayed 1 night and checked out. We are asking Expedia and Chesapeake to REFUND us for the additional 2 nights!! BKG#73084799299276 APRIL 24-27TH
Stayed 3 nights in Apr 2025

10/10 Excellent

CHASE

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Property was very nice. Staff was very nice also. We thought property had a restaurant and bar but none available yet. They did have free breakfast and great ocean front accommodations
Stayed 3 nights in Apr 2025

10/10 Excellent

monika

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

10/10 Excellent

Salim, Boca Raton

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location and rooms.
Stayed 2 nights in Apr 2025

10/10 Excellent

Jelena

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nicely remodeled (without the smell of mold) with contemporary touches. We were prepared to find out that pictures will not turn to reality but were so pleased that they reflect what the resort really is. Breakfast is included into stay (thank you to the owner for the omelet station!). Good quality coffee and tea always available at the front desk. Another pleasant surprise was that you could check out bikes/fishing rods or kayaks for a few hours to enjoy. Such a beautiful setting and we cannot wait to return, unless something changes this will be our place to stay at the Keys. Thank you for not cutting corners and making it a pleasant experience for your guests!
Stayed 4 nights in Apr 2025

10/10 Excellent

Jada

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This place is amazing the rooms are beautiful and the view is breathtaking.
Stayed 3 nights in Apr 2025

10/10 Excellent

Christopher P

Liked: Staff & service, property conditions & facilities
Stayed 1 night in Apr 2025

10/10 Excellent

david

Stayed 2 nights in Apr 2025

8/10 Good

John

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Apr 2025

10/10 Excellent

Jen

Stayed 1 night in Apr 2025

10/10 Excellent

Dianelis

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

8/10 Good

Nicole

Liked: Cleanliness, staff & service, property conditions & facilities
Beautiful view from room , breakfast included is nice due to price of room
Stayed 4 nights in Apr 2025

8/10 Good

Tom

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Apr 2025

10/10 Excellent

jamie

Stayed 2 nights in Apr 2025

10/10 Excellent

Yoxaris

Stayed 4 nights in Apr 2025

8/10 Good

Kurt, Miami

Travelled with family
We made a stop over at this place on our way from Miami to Ley West. A convienient, nice place with good restaurants near by.
Stayed 1 night in Apr 2025

10/10 Excellent

Kirstin

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Property location was good. The views were beautiful. Lots of lounge chairs and space for everyone. We went during the week and felt like we were in an exclusive place. Front desk staff were beyond excellent. Restaurant next door was fabulous. Fresh fish and great drinks. The bed in the Villa was super comfy. Plenty of towels and amenities. I give it a great recommendation .
Stayed 4 nights in Apr 2025