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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
Balcony
Outdoor spa tub
Water view
1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace
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
  • Pool
  • 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
  • Cable/satellite TV service
  • Daily housekeeping
  • Coffee/tea maker
  • Blackout drapes/curtains
  • 2 outdoor pools
$195 nightly
The total price is $220
Aug 18 - Aug 19
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 | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

2-Bedroom Villa

10.0 out of 10
Exceptional
(1 review)

Highlights

Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
Dishwasher
HDTV
Hypo-allergenic bedding
  • 646 sq ft
  • 2 bedrooms
  • Resort view
  • 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

9.4 out of 10
Exceptional
(29 reviews)

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

10.0 out of 10
Exceptional
(2 reviews)

Highlights

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

9.2 out of 10
Wonderful
(86 reviews)

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

9.0 out of 10
Wonderful
(18 reviews)

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
  • 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

10.0 out of 10
Exceptional
(2 reviews)

Highlights

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

Highlights

Balcony
Separate sitting area
Air conditioning
Free cribs/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 540 sq ft
  • 1 bedroom
  • Ocean view
  • 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
  • 517 sq ft
  • 1 bedroom
  • Resort view
  • 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
  • 700 sq ft
  • 1 bedroom
  • 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)

Highlights

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

View all photos for Ocean View King

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

Ocean View King

9.6 out of 10
Exceptional
(79 reviews)

Highlights

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

View all photos for Ocean View King Suite

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

Ocean View King Suite

9.4 out of 10
Exceptional
(15 reviews)

Highlights

Balcony
Separate sitting area
Air conditioning
Free cribs/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 527 sq ft
  • 1 bedroom
  • 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)

Highlights

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

9.4 out of 10
Exceptional
(54 reviews)

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
Pillowtop bed
  • 323 sq ft
  • 1 bedroom
  • Resort view
  • 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
  • 829 sq ft
  • 1 bedroom
  • Ocean view
  • 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

9.0 out of 10
Wonderful
(7 reviews)

Highlights

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

Highlights

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

8.6 out of 10
Excellent
(17 reviews)

Highlights

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

Similar properties

Exterior

Amara Cay Resort

  • Pool
  • Pet friendly
  • Restaurant
  • Air conditioning
8.8 out of 10, Excellent, 1,236 reviews
$246 nightly
The price is $276
Sep 1 - Sep 2
Total includes taxes and fees
Amara Cay Resort
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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
  • 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
  • ‪Wendy's - ‬2 min drive
  • ‪Whale Harbor Restaurant Marina - ‬2 min walk
  • Starbucks
  • ‪Islamorada Beer Company - ‬2 min drive

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

  • 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
Amenities

What guests liked

  • Breakfast options were plentiful and delicious, with made-to-order omelets and waffles being a highlight. (109 reviews)
  • The beach area was beautiful, with loungers provided, glass bottom kayaks, and paddle-boards available for guests to enjoy. (143 reviews)
AI Sparkle IconFrom real guest reviews summarized by AI.

Reviews

10/10 Excellent

Great place to stay, safe and quiet
Ruslan, 6-night trip

10/10 Excellent

The hotel is wonderful
Nicholas, 2-night trip

10/10 Excellent

Beautiful resort, all super clean, should have a little bit better breakfast but it was still good though.
Maricela, 1-night trip

10/10 Excellent

The inlets for breakfast were a great treat!
Stacy, 3-night trip

10/10 Excellent

Great amenities
Nilda, 2-night trip

10/10 Excellent

Best breakfast ever right on the ocean 😋
Francisco, 1-night trip

10/10 Excellent

Beautiful property
Laura, 1-night trip

10/10 Excellent

Love staying here. Any issues we’ve had they’ve resolved quickly. Can’t wait to stay here again!
Judy, 1-night trip

10/10 Excellent

Nice bed. Great ocean view.
John, 2-night trip

8/10 Good

Overall it was a great resort that offered activities and a free continental breakfast. Omelette station was a pleasant surprise.
Michael, 3-night trip

10/10 Excellent

Super nice staff! Great place to stay!
Ashleigh, 3-night trip

10/10 Excellent

I stayed here a long time ago prior to the renovations and I was please to find that it’s still the same great place just a lot nicer.
Mario, 1-night trip

10/10 Excellent

Great resort with lots to do on-site, pool/kayak/paddle boards/chess/checkers. Morning omelette was delicious & breakfast with the iguanas was fun! Great spot if you’re traveling through or on a fishing trip.
Sunrise by the beach
Our patio view
EDEN, 2-night trip

10/10 Excellent

This was a great place to stay.
Mikayla, 3-night trip

10/10 Excellent

Absolutely liked everything about this hotel. From delicious breakfast options to cozy rooms with stunning views, everything exceeded my expectations.
Evelyn, 2-night trip

10/10 Excellent

Rooms are clean and spacious. There was paddleboard and kayaking on site! Staff were very friendly
TANYA, 1-night trip

10/10 Excellent

The property is the best for family vacation and the staff is awesome
Shelly, 1-night trip

8/10 Good

I loved the ocean views! Awesome pool location!
Jason David, 2-night trip

10/10 Excellent

We had a great stay with our family! Lots to do for kids and adults. Breakfast was fast and good! Boat slip and boat ramp area was convenient and well kept. Villa was very nice for our family of 4.
Shelby, 5-night trip

10/10 Excellent

Great location, friendly and helpful staff
Monte, 2-night trip

10/10 Excellent

Very very good place.
Maria, 2-night trip

8/10 Good

It was nice
Yigal, 2-night trip

10/10 Excellent

Loved the breakfast options! Omlets was a hit.
Gary, 4-night trip

10/10 Excellent

Loved this property. It had inclusive breakfast and watersports available
Gabriel, 1-night trip

10/10 Excellent

Amenities were great
Ayelet, 1-night trip