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Chesapeake Beach Resort

3.5 star property
Islamorada beachfront hotel with 2 outdoor pools and bar/lounge

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Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun loungers, beach towels
Water view
1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace
Outdoor spa tub
Balcony
In the heart of Matecumbe, Chesapeake Beach Resort offers a tranquil escape. Enjoy a leisurely breakfast, relax on the private beach with sun loungers and kayaking options or take a refreshing dip in one of the 2 outdoor pools. With multilingual staff and concierge services available to help plan your stay.

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Bar
  • 24/7 front desk
  • Pet friendly
  • Air conditioning

Main amenities (12)

  • Daily housekeeping
  • On a private beach
  • Marina
  • 2 outdoor pools
  • Free use of bicycles
  • Beach sun loungers
  • Beach towels
  • Bar/lounge
  • 24-hour front desk
  • Coffee/tea in a common area
  • Air conditioning
  • Computer station

Feel at home (6)

  • Microwave
  • Private bathroom
  • Cable/satellite TV service
  • Daily housekeeping
  • Coffee/tea maker
  • Blackout drapes/curtains
$236 nightly
The total price is $266
Jun 9 - Jun 10
Total includes taxes and fees

Room options

Available filters for rooms
Showing 20 of 20 rooms

View all photos for 2-Bedroom Villa

2-Bedroom Villa | Private kitchenette | Microwave, coffee/tea maker

2-Bedroom Villa

Highlights

Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
Dishwasher
HDTV
Hypo-allergenic bedding
  • Resort view
  • 646 sq ft
  • Sleeps 6
  • 1 King Bed, 1 Double Bed and 1 Double Sofa Bed

View all photos for Standard King

Standard King | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillowtop bed
  • 272 sq ft
  • Sleeps 3
  • 1 King Bed

View all photos for King Efficiency Villa

King Efficiency Villa | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

King Efficiency Villa

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
Dining table
Dishwasher
  • Resort view
  • 517 sq ft
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard Doubles

Standard Doubles | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard Doubles

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillowtop bed
  • 272 sq ft
  • Sleeps 4
  • 2 Double Beds

View all photos for Standard King with Sleeper Sofa

Standard King with Sleeper Sofa | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King with Sleeper Sofa

Highlights

Deck/patio
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 307 sq ft
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Hearing Impaired Ocean View Queens

1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Hearing Impaired Ocean View Queens

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillowtop bed
  • Ocean view
  • 366 sq ft
  • 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

Highlights

Balcony
Separate sitting area
Air conditioning
Free cribs/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • Ocean view
  • 540 sq ft
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for ADA King Efficiency Villa

ADA King Efficiency Villa | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA King Efficiency Villa

Highlights

Separate dining area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
Dining table
HDTV
Hypo-allergenic bedding
  • Resort view
  • 517 sq ft
  • Sleeps 3
  • 1 King Bed

View all photos for Premium 1-Bedroom Ocean View Villa

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

Premium 1-Bedroom Ocean View Villa

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
Dining table
Dishwasher
  • Ocean view
  • 700 sq ft
  • 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

Highlights

Balcony
Separate sitting area
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
  • Ocean view
  • 650 sq ft
  • Sleeps 6
  • 2 Queen Beds

View all photos for Ocean View King

1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • Ocean view
  • 364 sq ft
  • Sleeps 3
  • 1 King Bed

View all photos for Ocean View King Suite

Ocean View King Suite | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King Suite

Highlights

Balcony
Separate sitting area
Air conditioning
Free cribs/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • Ocean view
  • 527 sq ft
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillowtop bed
  • Ocean view
  • 366 sq ft
  • Sleeps 4
  • 2 Queen Beds

Ocean View King Efficiency Villa

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
Dishwasher
HDTV
  • Ocean view
  • 517 sq ft
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard Queens

Standard Queens | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard Queens

Highlights

Deck/patio
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillowtop bed
  • 307 sq ft
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard King Villa

Standard King Villa | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King Villa

Highlights

Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • Resort view
  • 323 sq ft
  • Sleeps 3
  • 1 King 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

Highlights

Patio
Separate dining area
Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
Dining table
  • Ocean view
  • 829 sq ft
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for ADA Ocean View Queens

ADA Ocean View Queens | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA Ocean View Queens

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • Ocean view
  • 366 sq ft
  • 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

Highlights

Balcony
Separate sitting area
Air conditioning
Free cribs/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • Ocean view
  • 540 sq ft
  • Sleeps 4
  • 1 King Bed

View all photos for ADA Ocean View King

1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA Ocean View King

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillowtop bed
  • Ocean view
  • 364 sq ft
  • Sleeps 3
  • 1 King Bed

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The price is $282
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$282 total
Total includes taxes and fees
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About the neighborhood

Map
83409 Overseas Hwy, Islamorada, FL, 33036

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
  • Founders Park - 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

A great choice for a stay in Islamorada, Chesapeake Beach Resort features a marina. After splashing around at the 2 outdoor pools, you can unwind with a drink at the bar/lounge. Fellow travelers say great things about the pool and helpful staff.

Languages

English, Spanish

At a glance

DONE

Hotel size

    • 60 rooms
    • Arranged over 2 floors
DONE

Arriving/Leaving

    • 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 time is 11 AM
    • Contactless check-out available
DONE

Special check-in instructions

    • Front desk staff will greet guests on arrival at the property
DONE

Required at check-in

    • Credit card required for incidental charges
    • Government-issued photo ID may be required
    • Minimum check-in age is 18
DONE

Pets

    • Pets allowed (2 total, up to 50 lbs per pet)*
    • Service animals welcome
    • Restrictions apply*
WIFI

Internet

    • Free WiFi in public areas
    • Free WiFi in rooms (speed: 100+ Mbps (good for 1–2 people or up to 6 devices))
LOCAL_PARKING

Parking

    • Wheelchair-accessible parking on site
    • Onsite parking includes off-street options
DONE

Other information

    • Smoke-free property

Property amenities

Food and drink

  • Free continental breakfast each morning 6:00 AM–10:00 AM
  • Bar/lounge
  • Coffee/tea in a common area

Traveling with children

  • Pool gate
  • Outlet covers
  • Fence around the pool

What to do

  • On a private beach
  • Kayaking
  • Boat tours
  • Fishing
  • Jet skiing nearby
  • Snorkeling nearby

Working away

  • Computer station

Services

  • 24-hour front desk
  • Concierge services
  • Multilingual staff
  • Free bicycle rentals
  • Beach sun loungers
  • Beach towels
  • Pool loungers

Facilities

  • 9 buildings/towers
  • Built in 2020
  • 2 outdoor pools
  • Marina
  • Traditional architecture

Accessibility

  • Braille/raised signage
  • Wheelchair-accessible parking
  • Assistive listening devices available
  • Wheelchair-accessible public washroom
  • Wheelchair-accessible pool
  • Visual alarms in hallways
  • Handrails in hallways
  • Handrails in stairways
  • Closed captioned TV
  • Lever door handles
  • Upper floors accessible by stairs only
  • Well-lit path to entrance
  • Pool hoist on site

Room amenities

Be entertained

  • 43-inch flat-screen TV
  • Cable TV channels

Home comfort

  • Air conditioning
  • Ceiling fan
  • Coffee/tea maker
  • Iron/ironing board

Sleep well

  • Hypo-allergenic bedding
  • Blackout drapes/curtains
  • Pillowtop mattress
  • Bed sheets provided

Freshen up

  • Private bathroom
  • Shower only
  • Designer toiletries
  • Hair dryer
  • Towels
  • Toilet paper

Stay connected

  • Laptop-friendly workspace
  • Free WiFi (speed of 100+ Mbps (good for 1–2 people or up to 6 devices))
  • Free local calls

Food and drink

  • Microwave

More

  • Daily housekeeping
  • Access via exterior corridors

Special features

Dining

Tiki Bar - Onsite bar.

Fees & policies

Optional extras

  • Late check-out can be arranged for an extra charge

Pets

  • Service animals exempt from fees
  • Pet deposit: USD 50.00 per stay
  • Pets are allowed for an extra charge of USD 50.00 per accommodation, per night

Pool, spa, & gym (if applicable)

  • Pool access available from 7:00 AM to 10:30 PM
  • Children under 16 years old are not allowed in the swimming pool without adult supervision

Policies

Construction is underway at a neighboring building and there may be noise disturbance from the construction work.
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.
Some facilities may have restricted access. Guests can contact the property for details using the contact information on the booking confirmation.
This property does not have elevators.
This property accepts credit cards. Cash is not accepted.
Credit cards accepted: Visa, Mastercard, American Express, Discover

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

Frequently asked questions

Does Chesapeake Beach Resort offer free cancellation for a full refund?

Yes, Chesapeake Beach Resort does have fully refundable room rates available to book on our site. If you’ve booked a fully refundable room rate, this can be cancelled up to a few days before check-in depending on the property's cancellation policy. Just make sure to check this property's cancellation policy for the exact terms and conditions.

Is there a pool at Chesapeake Beach Resort?

Yes, there are 2 outdoor pools. Guests have pool access from 7:00 AM to 10:30 PM.

Are pets allowed at Chesapeake Beach Resort?

Yes, pets are welcome, with a limit of 2 total and maximum weight of 50 lbs per pet. There's a charge of USD 50.00 per accommodation, per night, and there's also a deposit of USD 50.00 per stay. Service animals are exempt from fees.

What are the check-in and check-out times at Chesapeake Beach Resort?

Check-in start time: 4:00 PM; Check-in end time: 3:00 AM. Check-out time is 11 AM. Late check-out is available for a charge. Contactless check-in and check-out are available.

What is there to do at Chesapeake Beach Resort and nearby?

Have fun with onsite activities like kayaking, fishing, and cycling. Enjoy a swim in one of the 2 outdoor swimming pools or use the hotel's other amenities, which include a private beach.

What's the area around Chesapeake Beach Resort like?

Chesapeake Beach Resort is in Matecumbe, a short 11-minute walk from History of Diving Museum. Travelers give top marks for the hotel's prime location.

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Chesapeake Beach Resort Reviews

Reviews

9.2

Wonderful

9.4/10

Cleanliness

9.2/10

Staff & service

8.8/10

Amenities

9.2/10

Property conditions & facilities

9.0/10

Eco-friendliness

Popular mentions

Room
Service staff
View
Beach
Location
Breakfast
Restaurant
Kayaking
Bed
Hot Tub

What guests liked

  • The beach area was beautiful, private, and offered plenty of shade, loungers, and scenic views. (136 reviews)
  • Breakfast was a highlight with a great selection and made-to-order options. (92 reviews)
  • The pools were clean, convenient, and enjoyable with great water activities and a hot tub. (82 reviews)
AI Sparkle IconFrom real guest reviews summarized by AI.

Reviews

10/10

Room was clean, lots of extras, amazing views, great breakfast
1-night trip

10/10

My experience here has been amazing. The relaxing, friendly environment made my family and me love it so much that we stayed an extra night.
1-night trip

10/10

It was one of the best of my stays at the keys. I live in Downtown Miami and love escaping for the weekend with girlfriend or husband. This time we brought our dog Mini Australian shepherd Benji. We all had blast with a pet friendly ocean view property!
2-night trip

10/10

Came into town to pick up our boat.
1-night trip

10/10

Great staff, beautiful grounds, very nice stay.
1-night trip

8/10

Very nice location and grounds.
2-night trip

10/10

Great stay
3-night trip

10/10

Awesome stay!
5-night trip

10/10

Great location, staff was great, complementary breakfast was very good. We definitely will stay here again.
1-night trip

10/10

The breakfast at the shore was wonderful with friendly service and plenty of food choices.
2-night trip

10/10

Excellent location for family trip or fishing. Clean friendly hotel lovely custom made free breakfast by Mr Chris. Also pet friendly
2-night trip

10/10

Loved the location, beach area, breakfast and STAFF
4-night trip

10/10

Beautiful location, helpful friendly staff, great breakfast , comfy robes, pools, jacuzzi, kayaks and paddle boards.
1-night trip

10/10

Loved it Beach front was perfect
5-night trip

10/10

Great location nearby restaurants. Riim was very clean beds wete great as was the staff
1-night trip

10/10

Fantastic views, and very quiet
4-night trip

10/10

Lovely beach resort in Islamorada Two large pools, location is great with its own little private beach
1-night trip

10/10

Nice quiet beach area
3-night trip

10/10

Great staff, beautiful property, very welcoming and helpful
1-night trip

10/10

Beautiful place clean and enjoyable.. don’t hesitate to book in fl keys
1-night trip

10/10

Friendly staff, convenient location.
2-night trip

8/10

The grounds are great , private beach area with loungers provided . Room comfortable and clean , bathroom small but modern with good shower . Receptionist on check in appeared very bored !! Breakfast nothing special , omelettes available but very overcooked and the cook went walk about whilst making them and when she came back she was permanently on her phone . A couple of restaurants within walking distance .
2-night trip

8/10

Great beach and clean big well furnished rooms
2-night trip

10/10

Never disappointing. Wonderful Stay
2-night trip

10/10

Great location, great beach, pools and staff.
1-night trip