See all properties

Chesapeake Beach Resort

3.5 star property

Choose dates to view prices

Photo gallery for Chesapeake Beach Resort

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

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Free WiFi
The current price is $269
$239 nightly
$269 total
Total with taxes and fees
Jun 8 - Jun 9

Explore the area

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

Room options

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

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

View all photos for Ocean View King

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King

9.6 out of 10
Exceptional
(102 reviews)
  • Ocean view
  • 364 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free WiFi

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
  • Free WiFi

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
(21 reviews)
  • Ocean view
  • 364 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

View all photos for Standard Queens

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

Standard Queens

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

View all photos for Standard Doubles

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

Standard Doubles

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

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
  • Free WiFi

View all photos for Standard King

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

Standard King

9.4 out of 10
Exceptional
(41 reviews)
  • 272 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free WiFi

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
(22 reviews)
  • Ocean view
  • 527 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed
  • Free WiFi

View all photos for Deluxe Ocean View Two Queen Suite

Balcony

Deluxe Ocean View Two Queen Suite

9.2 out of 10
Wonderful
(13 reviews)
  • Ocean view
  • 650 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

View all photos for ADA King Efficiency Villa

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

ADA King Efficiency Villa

10.0 out of 10
Exceptional
(1 review)
  • Resort view
  • 517 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free WiFi

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

7.0 out of 10
Good
(2 reviews)
  • Ocean view
  • 700 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Double Beds and 1 Double Sofa Bed
  • Free WiFi

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
  • Free WiFi

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
(2 reviews)
  • Ocean view
  • 517 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Free WiFi

Similar properties

Room, 1 King Bed with Sofa bed, Oceanfront (Alligator Reef, Lanai) | View from room
Amara Cay Resort
Matecumbe
  • On private beach
  • Pool
  • Pet friendly
  • Restaurant
4.4 out of 5, Excellent, 1,295 reviews
$274 nightly
The price is $309
Jul 6 - Jul 7
Total with taxes and fees
Amara Cay 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
  • Theater of the Sea - 2 min drive - 1.5 miles
  • Islamorada Brewery & Distillery - 2 min drive - 1.5 miles
  • beach near Islamorada - 2 min drive - 1.7 miles

Getting around

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

Restaurants

  • ‪Wahoo's Bar & Grill - ‬2 min walk
  • ‪Hog Heaven - ‬3 min drive
  • ‪Lorelei Restaurant & Cabana Bar - ‬3 min drive
  • ‪Wendy's - ‬2 min drive
  • ‪Starbucks - ‬15 min walk

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. 1297 out of 1742 reviews
Rating 8 - Good. 277 out of 1742 reviews
Rating 6 - Okay. 95 out of 1742 reviews
Rating 4 - Poor. 42 out of 1742 reviews
Rating 2 - Terrible. 31 out of 1742 reviews

9.4/10

Cleanliness

9.4/10

Staff & service

9.2/10

Amenities

9.2/10

Property conditions & facilities

Reviews

Verified

10/10 Excellent

Steven

Liked: Cleanliness, amenities, property conditions & facilities
Great modern resort, very clean, very friendly.
Stayed 2 nights in Feb 2026
Verified

8/10 Good

Mariola

warm pool, beautiful view at the beach, pleasant front desk and breakfast staff
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

Roger

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful ocean view from our room staff was very helpful very clean room
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

dian

Liked: Cleanliness, staff & service, amenities
Great room, wonderful staff and good location
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Doug or Lois

Liked: Cleanliness, staff & service, amenities
Nice stay
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

Keely

Liked: Cleanliness, staff & service, amenities
Clean rooms, beautiful scenery, gorgeous sunrise, delicious breakfast. Loved this place.
Stayed 4 nights in Feb 2026
Verified

10/10 Excellent

Vickki

Liked: Cleanliness, amenities, property conditions & facilities
Great vibe….very clean rooms. Wahoo next door is also fun and good food.
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

Daniel

Liked: Cleanliness, amenities, property conditions & facilities
Awesome place!!
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Melissa

Liked: Cleanliness, amenities, property conditions & facilities
The view and location were great.
Stayed 3 nights in Jan 2026
Verified

10/10 Excellent

Jason

Liked: Cleanliness, amenities, property conditions & facilities
Awesome place, nice beach! Friendly staff.
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

James

Liked: Cleanliness, amenities, property conditions & facilities
Extremely clean hotel. Breakfast was very good and staff very helpful.
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

Judy

Liked: Cleanliness, amenities, property conditions & facilities
Gorgeous view, very pleasant staff, clean room
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Mat

Liked: Cleanliness, amenities, property conditions & facilities
The entire resort was wonderful.
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Melanie

Liked: Cleanliness, staff & service, amenities
Staff great, room very nice, beach and facilities were great
Stayed 1 night in Jan 2026
Verified

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
Verified

10/10 Excellent

Matthew

Liked: Cleanliness, amenities, property conditions & facilities
Great staff, especially front desk and breakfast chefs!!! Beautiful facilty-laid back vibe just as it should be on the Keys!!!
Stayed 2 nights in Jan 2026
Verified

8/10 Good

Rosalie

Liked: Cleanliness, amenities, property conditions & facilities
Room was clean, lovely beach and lagoon with plenty of lounge chairs. Resort offers a good breakfast and there are a few nice places to eat within walking distance.
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Jim

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great property but the bar area was not opened during our stay. The staff was great and the beach and pool were great to relax to
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

Gary

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great breakfast, great location, friendly staff, nice extras.
Stayed 1 night in Dec 2025
Verified

10/10 Excellent

MARY KAY

Liked: Cleanliness, amenities, property conditions & facilities
The staff was amazing! The pool/beach were delightful. Great location
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Harry

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

8/10 Good

Nancy

Liked: Cleanliness, amenities, property conditions & facilities
The hotel is in a perfect location, and offers so much on premise
Stayed 3 nights in Jan 2026
Verified

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
Verified

10/10 Excellent

Devon

Liked: Cleanliness, amenities, property conditions & facilities
Clean, gorgeous view, amazing free breakfast, loved the robes!
Stayed 4 nights in Jan 2026
Verified

10/10 Excellent

Laura

Liked: Cleanliness, amenities, property conditions & facilities
Clean, great helpful staff, great breakfast. Lovely facility
Stayed 3 nights in Jan 2026