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Chesapeake Beach Resort

3.5 star property

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Photo gallery for Chesapeake Beach Resort

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

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Bar
  • 24/7 front desk

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
  • 60 sq m
  • 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

9.6 out of 10
Exceptional
(25 reviews)

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 25 sq m
  • 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
(1 review)

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/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

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

Standard Doubles

9.2 out of 10
Wonderful
(78 reviews)

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 25 sq m
  • 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
Ceiling fan
  • 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, 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
Ceiling fan
  • 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 cribs/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

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
  • 48 sq m
  • 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
  • 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
(8 reviews)

Highlights

Balcony
Separate sitting area
Air conditioning
Free cribs/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, pillowtop beds, laptop workspace

Ocean View King

9.6 out of 10
Exceptional
(77 reviews)

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 34 sq m
  • 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
(13 reviews)

Highlights

Balcony
Separate sitting area
Air conditioning
Free cribs/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
(41 reviews)

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 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 cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
Dishwasher
HDTV
  • 48 sq m
  • 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
(49 reviews)

Highlights

Deck/patio
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 29 sq m
  • 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
  • 30 sq m
  • 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
  • 77 sq m
  • 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
Ceiling fan
  • 34 sq m
  • 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

10.0 out of 10
Exceptional
(2 reviews)

Highlights

Balcony
Separate sitting area
Air conditioning
Free cribs/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, pillowtop beds, laptop workspace

ADA Ocean View King

8.6 out of 10
Excellent
(16 reviews)

Highlights

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

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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
  • Islamorada Brewery & Distillery - 2 min drive - 2.4 km
  • Florida Keys Brewing Co. - 4 min drive - 4.0 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

Remodeled 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, sun loungers, and fishing, this hotel is the perfect place to soak up some sun. Enjoy onsite activities like kayaking and boat tours. Stay connected with free in-room WiFi.
You'll also enjoy the following perks during your stay:
  • 2 outdoor pools with sun loungers
  • Free bicycle rentals, coffee/tea in the lobby, and a computer station
  • Multilingual staff, a 24-hour front desk, and smoke-free premises
  • Beach towels and concierge services
  • 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 like free WiFi. Guest reviews speak positively of the clean, spacious rooms at the property.
More amenities include:
  • Hypo-allergenic bedding and pillowtop mattresses
  • Designer toiletries, showers, and hair dryers
  • 43-inch HDTVs with cable channels
  • Wardrobes/closets, microwaves, and coffee/tea makers

Languages

English, Spanish

Similar properties

Exterior

Amara Cay Resort

  • On private beach
  • Pool
  • Pet friendly
  • Restaurant
8.8 out of 10, Excellent, 1,222 reviews
The price is SAR 672
SAR 1,005 total
includes taxes & fees
6 Jul - 7 Jul
Amara Cay Resort

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
  • 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 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

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 stay
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 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, 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 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 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

Frequently asked questions

Does Chesapeake Beach Resort have a pool?

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

Is Chesapeake Beach Resort pet-friendly?

Yes, this property allows pets (limit 2 total) with a maximum weight of up to 50 lbs 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?

Check-out is at 11 AM. Late check-out 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 mi (3 km).

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Chesapeake Beach Resort Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 1059 out of 1475 reviews
Rating 8 - Good. 245 out of 1475 reviews
Rating 6 - Okay. 93 out of 1475 reviews
Rating 4 - Poor. 44 out of 1475 reviews
Rating 2 - Terrible. 34 out of 1475 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

This was a great place to stay.
Stayed 3 nights in Jun 2025

10/10

The property is the best for family vacation and the staff is awesome
Stayed 1 night in Jun 2025

10/10

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

10/10

We really enjoyed our stay here was very nice and quiet
Stayed 4 nights in May 2025

8/10

The pools are amazing
Stayed 1 night in Jun 2025

8/10

We loved the pool areas and little beach area. Comfortable beds with robe and slippers in the room. Super cute place on our trip back to Miami.
Stayed 1 night in May 2025

10/10

Perfect place to stay!
Stayed 1 night in Mar 2025

10/10

Great stay and fantastic staffs.
Stayed 1 night in Apr 2025

10/10

Very accommodating staff.
Stayed 2 nights in Jun 2025

10/10

Great location and rooms.
Stayed 2 nights in Apr 2025

10/10

We love coming the resort. We stay at least twice each summer and the staff is so friendly and helpful.
Stayed 4 nights in May 2025

10/10

An absolute dream! This place is absolutely amazing. Price point was great too. I can’t wait to come back!
Stayed 2 nights in Jun 2025

10/10

Great location and very clean safe property.
Stayed 1 night in May 2025

10/10

great staff, made my stay very enjoyable
Stayed 2 nights in Apr 2025

10/10

Beautiful resort! Great breakfast!
Stayed 2 nights in May 2025

10/10

Great hotel close to the beach b Wonderful costumer service Close to 3 different restaurants
Stayed 2 nights in May 2025

10/10

Everything was amazing
Stayed 2 nights in May 2025

10/10

We lived our staying here. The rooms were very clean and comfortable. The breakfast was delicious and the staff was very friendly . Love the amenities.
Stayed 2 nights in May 2025

10/10

We enjoyed all things involved. Pool breakfast room. Everything was wonderful
Stayed 2 nights in Jun 2025

10/10

Beautiful and extremely clean property. The grounds were perfect and our room was stunning!
Stayed 1 night in May 2025

10/10

Excellent stay for my family of 4 over a long weekend trip. Kids loved the water sport rentals. Staff was all very kind and helpful
Stayed 3 nights in May 2025

10/10

This place is amazing the rooms are beautiful and the view is breathtaking.
Stayed 3 nights in Apr 2025

10/10

We loved this hotel. The lady at the check in was so kind and accommodating to our needs. My kids loved the deeper pool and the fact that there were two pools helped adults at the hotel still enjoy relaxing instead of being splashed by kids. We loved the rentals and yard games, as well. Our room was clean and just what we needed after many poor experiences elsewhere in the keys. Thank you for a great stay!
Stayed 1 night in Jun 2025

10/10

Great place!
Stayed 2 nights in Dec 2024

10/10

Great weekend at the resort
Stayed 2 nights in May 2025