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Chesapeake Beach Resort

3.5 star property
Hotel on the beach, with 2 outdoor pools

Choose dates to view prices

Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun-loungers, beach towels
Water view
1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace
Outdoor spa tub
Balcony

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • 24/7 front desk
  • Bar
  • Housekeeping
  • Pet-friendly
The current price is S$290
includes taxes & fees
17 Aug - 18 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
  • 2 bedrooms
  • 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
  • 1 bedroom
  • 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
(86 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
  • 1 bedroom
  • 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
  • 1 bedroom
  • 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
  • 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 cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
  • 60 sq m
  • 1 bedroom
  • 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
(79 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
(15 reviews)

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 49 sq m
  • 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 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
  • 1 bedroom
  • 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
(54 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
  • 1 bedroom
  • 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
  • 1 bedroom
  • 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
  • 1 bedroom
  • 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
  • 1 bedroom
  • 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
(17 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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About the area

Located on a private beach, Chesapeake Beach Resort is in Matecumbe, a neighbourhood in Islamorada. Hurricane Monument and Indian Key Historic State Park are local landmarks, and some of the area's activities can be experienced at Islamorada Brewery & Distillery and Florida Keys Brewing Co.. With jet skiing and snorkelling nearby, you'll find plenty of adventures in the water.
Visit our Islamorada travel guideOpens in a new window
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
  • ‪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

Remodelled hotel, renovated in 2020 and located in Matecumbe
Free continental breakfast, a marina and a bar are just a few of the amenities provided at Chesapeake Beach Resort. With a private beach, sunloungers and kayaking, this hotel is the perfect place to soak up some sun. Enjoy on-site activities, such as fishing and boat tours. Stay connected with free in-room WiFi.
You'll also enjoy the following perks during your stay:
  • 2 outdoor pools with sunloungers
  • Free bike hire, a 24-hour front desk and smoke-free property
  • Concierge services, beach towels and a computer station
  • Coffee/tea in reception and multilingual staff
  • Guest reviews give top marks for the breakfast, beach locale and pool
Room features
All 60 rooms offer comforts such as laptop-friendly workspaces and air conditioning, in addition to perks such as free WiFi. Guest reviews speak positively of the cleanliness, size rooms at the property.
Other amenities include:
  • Hypo-allergenic bedding and pillowtop mattresses
  • Designer toiletries, showers and hairdryers
  • 43-inch HDTVs with cable channels
  • Wardrobes/cupboards, microwaves and coffee/tea makers

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 and check-out are available
Late check-in subject to availability
Minimum check-in age - 18

Check-out

Check-out before 11 AM
Contactless check-out
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 are 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 23 kg per pet)
Restrictions apply; for more information contact the property on the number on the booking confirmation

Children and extra beds

Children are welcome
Rollaway/extra beds are not available.

Payment types at the property

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 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

We should mention

This property does not have any lifts
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 neighbouring 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

Frequently asked questions

Does Chesapeake Beach Resort have a pool?

Yes, this property has 2 outdoor pools. Pool access is from 7:00 AM to 10:30 PM.

How much does it cost to stay at Chesapeake Beach Resort?

As of 15 Aug, 2025, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on 17 Aug, 2025 start from S$289.53, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Chesapeake Beach Resort pet-friendly?

Yes, this property allows pets (limit 2 total) with a maximum weight of up to 23 kg per pet. There's a deposit of USD 50.00 per stay and a fee of USD 50.00 per accommodation, per night. Service animals are exempt from fees.

What time is check-in at Chesapeake Beach Resort?

Check-in start time: 4:00 PM; check-in end time: 3:00 AM. Late check-in is available during limited hours.

What time is check-out at Chesapeake Beach Resort?

Checkout is at 11 AM. Late checkout is available for a fee.

Where is Chesapeake Beach Resort located?

Nestled on the beach, this Matecumbe hotel is within 1 mi (2 km) of History of Diving Museum and Windley Key Fossil Reef Geological State Park. Islamorada Brewery & Distillery and Keys History & Discovery Center are also within 2 miles (3 km).

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Chesapeake Beach Resort Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 1079 out of 1494 reviews
Rating 8 - Good. 250 out of 1494 reviews
Rating 6 - Okay. 92 out of 1494 reviews
Rating 4 - Poor. 41 out of 1494 reviews
Rating 2 - Terrible. 32 out of 1494 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

Ruslan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great place to stay, safe and quiet
Stayed 6 nights in Aug 2025

10/10 Excellent

Nicholas

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The hotel is wonderful
Stayed 2 nights in Jul 2025

10/10 Excellent

Maricela

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful resort, all super clean, should have a little bit better breakfast but it was still good though.
Stayed 1 night in Aug 2025

10/10 Excellent

Stacy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The inlets for breakfast were a great treat!
Stayed 3 nights in Aug 2025

10/10 Excellent

Nilda

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great amenities
Stayed 2 nights in Aug 2025

10/10 Excellent

Francisco

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Best breakfast ever right on the ocean 😋
Stayed 1 night in Jul 2025

10/10 Excellent

Laura

Liked: Cleanliness, staff & service, property conditions & facilities
Beautiful property
Stayed 1 night in Aug 2025

10/10 Excellent

Judy

Liked: Cleanliness, staff & service
Love staying here. Any issues we’ve had they’ve resolved quickly. Can’t wait to stay here again!
Stayed 1 night in Jul 2025

10/10 Excellent

John

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nice bed. Great ocean view.
Stayed 2 nights in Aug 2025

10/10 Excellent

Ashleigh

Liked: Cleanliness, amenities, property conditions & facilities
Super nice staff! Great place to stay!
Stayed 3 nights in Jun 2025

10/10 Excellent

Mario

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 1 night in Jul 2025

10/10 Excellent

EDEN

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

10/10 Excellent

Mikayla

Liked: Cleanliness, amenities, property conditions & facilities
This was a great place to stay.
Stayed 3 nights in Jun 2025

10/10 Excellent

Evelyn

Liked: Cleanliness, amenities, property conditions & facilities
Absolutely liked everything about this hotel. From delicious breakfast options to cozy rooms with stunning views, everything exceeded my expectations.
Stayed 2 nights in Jul 2025

10/10 Excellent

TANYA

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Rooms are clean and spacious. There was paddleboard and kayaking on site! Staff were very friendly
Stayed 1 night in Aug 2025

10/10 Excellent

Shelly

Liked: Cleanliness, property conditions & facilities
The property is the best for family vacation and the staff is awesome
Stayed 1 night in Jun 2025

8/10 Good

Jason David

Liked: Cleanliness, staff & service, property conditions & facilities
I loved the ocean views! Awesome pool location!
Stayed 2 nights in Jul 2025

10/10 Excellent

Shelby

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 5 nights in Jul 2025

10/10 Excellent

Monte

Great location, friendly and helpful staff
Stayed 2 nights in Jun 2025

10/10 Excellent

Maria

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very very good place.
Stayed 2 nights in Jun 2025

8/10 Good

Yigal

Liked: Amenities, property conditions & facilities
It was nice
Stayed 2 nights in Aug 2025

10/10 Excellent

Gary

Liked: Cleanliness, staff & service, property conditions & facilities
Loved the breakfast options! Omlets was a hit.
Stayed 4 nights in Jul 2025

10/10 Excellent

Gabriel

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved this property. It had inclusive breakfast and watersports available
Stayed 1 night in Jul 2025

10/10 Excellent

Ayelet

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Amenities were great
Stayed 1 night in Jul 2025

10/10 Excellent

Kass

Liked: Cleanliness, staff & service, property conditions & facilities
Perfect place to stay!
Stayed 1 night in Mar 2025