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Chesapeake Beach Resort

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

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Photo gallery for Chesapeake Beach Resort

Relax on the beach with a tranquil ocean view and comfortable sun loungers.
Overlooking the calm waters, this hotel offers stunning views of the surrounding landscape and palm trees.
Enjoy breathtaking ocean views from this balcony overlooking the beach.
Relax by the pool, surrounded by palm trees and a hot tub.
Enjoy a comfortable stay with a large bed, desk, and seating area, plus a window offering a view of the outdoors.
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
  • Air conditioning

Main amenities (12)

  • Daily housekeeping
  • On a private beach
  • Marina
  • 2 outdoor pools
  • Free use of bicycles
  • Beach sunloungers
  • 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 curtains
  • 2 outdoor pools
The current price is S$292
includes taxes & fees
10 Aug - 11 Aug

Room options

Available filters for rooms
Showing 20 of 20 rooms

View all photos for 2-Bedroom Villa

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

2-Bedroom Villa

10.0 out of 10
Exceptional
(1 review)

Highlights

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

View all photos for Standard King

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard King

9.4 out of 10
Exceptional
(29 reviews)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillow-top bed
  • 25 sq m
  • Sleeps 3
  • 1 King Bed

View all photos for King Efficiency Villa

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

King Efficiency Villa

10.0 out of 10
Exceptional
(2 reviews)

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
Dishwasher
  • 48 sq m
  • Resort view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard Doubles

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard Doubles

9.2 out of 10
Wonderful
(85 reviews)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillow-top bed
  • 25 sq m
  • Sleeps 4
  • 2 Double Beds

View all photos for Standard King with Sleeper Sofa

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard King with Sleeper Sofa

9.0 out of 10
Wonderful
(18 reviews)

Highlights

Deck/patio
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillow-top bed
  • 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)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillow-top bed
  • 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)

Highlights

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

View all photos for ADA King Efficiency Villa

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

ADA King Efficiency Villa

Highlights

Separate dining area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
HDTV
Hypo-allergenic bedding
  • 48 sq m
  • Resort view
  • Sleeps 3
  • 1 King Bed

View all photos for Premium 1-Bedroom Ocean View Villa

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Premium 1-Bedroom Ocean View Villa

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
Dishwasher
  • 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)

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
  • 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)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillow-top bed
  • 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)

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 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)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillow-top bed
  • 34 sq m
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

Ocean View King Efficiency Villa

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dishwasher
HDTV
  • 48 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard Queens

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard Queens

9.4 out of 10
Exceptional
(53 reviews)

Highlights

Deck/patio
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillow-top bed
  • 29 sq m
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard King Villa

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard King Villa

Highlights

Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillow-top bed
  • 30 sq m
  • Resort view
  • Sleeps 3
  • 1 King Bed

View all photos for Premium Ocean View King Villa

Living area

Premium Ocean View King Villa

Highlights

Patio
Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
  • 77 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for ADA Ocean View Queens

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

ADA Ocean View Queens

9.0 out of 10
Wonderful
(7 reviews)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillow-top bed
  • 34 sq m
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

View all photos for 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 cots/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 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)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillow-top bed
  • 34 sq m
  • Ocean view
  • Sleeps 3
  • 1 King Bed

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Exterior

Amara Cay Resort

  • Pool
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  • Restaurant
  • Air conditioning
8.8 out of 10, Excellent, 1,236 reviews
The price is S$330
includes taxes & fees
1 Sept - 2 Sept
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About the area

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 International 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 travellers 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 and check-out are available
    • Late check-in subject to availability
    • Minimum check-in age – 18
    • Check-out time is 11 AM
    • Contactless check-out
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 23 kg per pet)*
    • Service animals welcome
    • Restrictions apply*
WIFI

Internet

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

Parking

    • Wheelchair-accessible parking on site
    • On-site 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

Travelling with children

  • Pool gate
  • Outlet covers
  • Fence around the pool

What to do

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

Working away

  • Computer station

Services

  • 24-hour front desk
  • Concierge services
  • Multilingual staff
  • Free bike hire
  • Beach sunloungers
  • 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 bathroom
  • Wheelchair-accessible pool
  • Visual alarms in hallways
  • Handrails in hallways
  • Handrails in stairwells
  • 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 curtains
  • Pillow-top mattress
  • Bed sheets provided

Freshen up

  • Shower only
  • Designer toiletries
  • Hairdryer
  • Towels
  • Toilet paper

Stay connected

  • Laptop-friendly workspace
  • Complimentary wireless Internet access (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 – On-site 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 neighbouring building and there may be noise disturbance from the construction work.
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children. If you have any concerns, we recommend contacting the property prior to your arrival to confirm that 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 lifts.
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 that you 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 23 kg 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 social distancing and check-out are available.

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

Have fun with on-site activities such as 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. Travellers 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
Ocean

What guests liked

  • The private beach area was lovely, with plenty of shade, beautiful views, and various activities available. (141 reviews)
  • Breakfast was consistently delicious, made to order with options including custom omelets and waffles. (100 reviews)
  • The pools were great, beautiful, and well-maintained, offering a perfect blend of luxury and tranquility. (89 reviews)
AI Sparkle IconFrom real guest reviews summarized by AI.

Reviews

10/10 Exceptional

Nice place to stay.
Katya, 2-night trip

10/10 Exceptional

One of my favorite places to have a relaxing trip with the family
Liu M, 1-night trip

10/10 Exceptional

Great location and rooms.
Salim, 2-night trip

10/10 Exceptional

Chesapeake is Amazing - Gets better every trip

We have been coming here for 5 years and the place gets better and better. Every year we come they have added new amenities. The beach and pools are amazing and the location makes it easy to go anywhere in the Keys quickly. If you are looking for a great resort for a great price in this area it is a GREAT option!
Michael, 4-night trip

10/10 Exceptional

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

10/10 Exceptional

Worth every penny.

It was excellent. Beautiful location, friendly and helpful staff, amazing views.
Pablo, 1-night trip

10/10 Exceptional

Wonderful hotel, always great to be in the Florida Keys.
Mauricio, 1-night trip

10/10 Exceptional

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.
Kevin, 1-night trip

10/10 Exceptional

Great place!
Sandra, 2-night trip

10/10 Exceptional

This place is amazing the rooms are beautiful and the view is breathtaking.
Jada, 3-night trip

10/10 Exceptional

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

10/10 Exceptional

very nice hotel
phil, 2-night trip

10/10 Exceptional

Great place with a great staff.
David, 4-night trip

10/10 Exceptional

Very friendly staff that was extra accommodating to us! Clean, quiet, beautiful grounds! Would definitely stay again!
Cory, 1-night trip

8/10 Very good

Very nice location and grounds.
Scot, 2-night trip

10/10 Exceptional

Such a nice hidden gem in the keys! Lots of beach space, 2 pools, breakfast included was a nice bonus.
Pamela, 1-night trip

8/10 Very good

Nice people, quiet resort.
Robert, 3-night trip

10/10 Exceptional

Relaxing place
Rhett Jan, 2-night trip

10/10 Exceptional

Beautiful property, comfy, and clean room and excellent service!
Jessica, 1-night trip

8/10 Very good

Good for the price and convenient for fishing trips. No frills, clean rooms good location.
Adam, 3-night trip

10/10 Exceptional

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!
Alena, 2-night trip

10/10 Exceptional

Great property exceeded our expectations.
Peter, 2-night trip

10/10 Exceptional

Great stay
Christopher, 3-night trip

10/10 Exceptional

Amazing doesnt give this place justice. The staff here are great. Super friendly and helpful. The rooms are super clean, bright and perfect for our stay. The resort grounds were clean and tidy. Breakfast was good and the omelet guy was super cool. The only bad was we had to leave. This is definitely our spot every time we visit❤️
Joshua, 1-night trip

10/10 Exceptional

Love this place
Patrick, 2-night trip