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Chesapeake Beach Resort

3.5 star property
3.5-star beachfront hotel with 2 outdoor pools

Choose dates to view prices

Photo gallery for Chesapeake Beach Resort

A beach with palm trees and lounge chairs.
A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.
A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the beach through the window.
A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.
A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Free WiFi

Explore the area

View in a map
83409 Overseas Hwy, Islamorada, FL, 33036
  • Place, History of Diving Museum
    ‪12 min walk‬
  • Place, Theater of the Sea
    ‪2 min drive‬
  • Place, Islamorada Brewery & Distillery
    ‪2 min drive‬

Room options

View all photos for Ocean View Queens

A balcony with two blue chairs and a small table, overlooking a beach with palm trees and the ocean.

Ocean View Queens

9.6 out of 10
Exceptional
(52 reviews)
  • Ocean view
  • 366 sq ft
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds
  • Free WiFi

View all photos for Ocean View King

A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the outdoors through a sliding glass door.

Ocean View King

9.6 out of 10
Exceptional
(103 reviews)
  • Ocean view
  • 364 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free WiFi

View all photos for ADA Ocean View King Suite

A balcony with a view of the ocean and palm trees, featuring a chair, a small table, and a bench.

ADA Ocean View King Suite

8.6 out of 10
Excellent
(8 reviews)
  • Ocean view
  • 540 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed
  • Free WiFi

View all photos for ADA Ocean View King

A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the outdoors through a sliding glass door.

ADA Ocean View King

9.0 out of 10
Wonderful
(22 reviews)
  • Ocean view
  • 364 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free WiFi

View all photos for ADA Ocean View Queens

A hotel room with two beds, a ceiling fan, a large window with a view of palm trees, and a balcony with a chair.

ADA Ocean View Queens

9.0 out of 10
Wonderful
(7 reviews)
  • Ocean view
  • 366 sq ft
  • Sleeps 4
  • 2 Queen Beds
  • Free WiFi

View all photos for Hearing Impaired Ocean View Queens

A hotel room with two beds, a desk, a TV, and a balcony with a view of palm trees.

Hearing Impaired Ocean View Queens

10.0 out of 10
Exceptional
(3 reviews)
  • Ocean view
  • 366 sq ft
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds
  • Free WiFi

View all photos for Hearing Impaired Ocean View King Suite

A modern living room with a grey sofa, wooden chairs, a round coffee table, and a large TV on the wall.

Hearing Impaired Ocean View King Suite

8.8 out of 10
Excellent
(5 reviews)
  • Ocean view
  • 540 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed
  • Free WiFi

View all photos for Standard Queens

A hotel room with two beds, a desk, a chair, a TV, and a ceiling fan.

Standard Queens

9.4 out of 10
Exceptional
(73 reviews)
  • 307 sq ft
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds
  • Free WiFi

View all photos for Standard Doubles

A hotel room with two beds, a ceiling fan, an air conditioning unit, a TV, a desk with a chair, and a view of greenery through the windows.

Standard Doubles

9.2 out of 10
Wonderful
(109 reviews)
  • 272 sq ft
  • 1 bedroom
  • Sleeps 4
  • 2 Double Beds
  • Free WiFi

View all photos for Standard King with Sleeper Sofa

A hotel room with a large bed, a ceiling fan, an air conditioning unit, a bedside table with a lamp, and a view of the outside through large windows.

Standard King with Sleeper Sofa

9.2 out of 10
Wonderful
(26 reviews)
  • 307 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Free WiFi

View all photos for Standard King

A hotel room with a large bed, a desk with a chair, a ceiling fan, and an air conditioning unit.

Standard King

9.4 out of 10
Exceptional
(41 reviews)
  • 272 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free WiFi

View all photos for Ocean View King Suite

A modern bedroom with a large bed, a ceiling fan, bedside lamps, a bench, and a view through a sliding door.

Ocean View King Suite

9.4 out of 10
Exceptional
(24 reviews)
  • Ocean view
  • 527 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed
  • Free WiFi

View all photos for Deluxe Ocean View Two Queen Suite

A wooden balcony overlooking a beach with palm trees and a sunset.

Deluxe Ocean View Two Queen Suite

9.2 out of 10
Wonderful
(13 reviews)
  • Ocean view
  • 650 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds
  • Free WiFi

View all photos for 2-Bedroom Villa

A bedroom with a bed, bedside table, lamp, and a dresser with a mirror.

2-Bedroom Villa

10.0 out of 10
Exceptional
(1 review)
  • Resort view
  • 646 sq ft
  • 2 bedrooms
  • Sleeps 6
  • 1 King Bed, 1 Double Bed and 1 Double Sofa Bed
  • Free WiFi

View all photos for Standard King Villa

A neatly made bed in a hotel room with a wooden headboard, two bedside tables with lamps, and a door to the right.

Standard King Villa

  • Resort view
  • 323 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free WiFi

View all photos for King Efficiency Villa

A neatly arranged hotel room with a large bed, a bedside table with a lamp, a chair, and a mirror.

King Efficiency Villa

8.4 out of 10
Very good
(5 reviews)
  • Resort view
  • 517 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Free WiFi

View all photos for ADA King Efficiency Villa

A bedroom with a bed, a sofa, a dresser, a TV, and a ceiling fan.

ADA King Efficiency Villa

10.0 out of 10
Exceptional
(1 review)
  • Resort view
  • 517 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free WiFi

View all photos for Premium 1-Bedroom Ocean View Villa

A hotel room with two beds, a large window with a view, and a ceiling with exposed beams.

Premium 1-Bedroom Ocean View Villa

7.0 out of 10
Good
(2 reviews)
  • Ocean view
  • 700 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Double Beds and 1 Double Sofa Bed
  • Free WiFi

View all photos for Premium Ocean View King Villa

A spacious room with large windows offering a view of the beach and ocean.

Premium Ocean View King Villa

  • Ocean view
  • 829 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Free WiFi

View all photos for Ocean View King Efficiency Villa

A modern kitchen with white cabinets, stainless steel appliances, and a tiled backsplash.

Ocean View King Efficiency Villa

10.0 out of 10
Exceptional
(2 reviews)
  • Ocean view
  • 517 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Free WiFi

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La Siesta Resort & Villas

Matecumbe
  • On private beach
  • Pool
  • Pet friendly
  • Air conditioning
8.6 out of 10, Excellent, 1,001 reviews
$252 nightly
The price is $283
Aug 16 - Aug 17
Total with taxes and fees
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About the neighborhood

Islamorada

On the beach.With a stay at this Matecumbe hotel, you'll be within half a mile (1 km) of History of Diving Museum and 2 miles (3 km) of Windley Key Fossil Reef Geological State Park. Islamorada Brewery & Distillery and Lorelei Restaurant & Cabana Bar are also within 2 miles (3 km).

What's nearby

  • History of Diving Museum - 12 min walk - 0.7 miles
  • Windley Key Fossil Reef Geological State Park - 2 min drive - 1.3 miles
  • Theater of the Sea - 2 min drive - 1.5 miles
  • Islamorada Brewery & Distillery - 2 min drive - 1.7 miles
  • Anne's Beach - 15 min drive - 12.8 miles

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
  • ‪Wendy's - ‬2 min drive
  • ‪The Oceanview Inn & Sports Pub - ‬2 min drive

About this property

Chesapeake Beach Resort

3.5-star beachfront hotel with 2 outdoor pools
Simply walk outside to smell the salt air and watch the ocean waves from the white sand beach. Cool off in one of the 2 outdoor swimming pools at Chesapeake Beach Resort, and enjoy amenities like a marina and complimentary bicycles.

Free breakfast is available daily. You can enjoy a drink at the bar/lounge. A computer station is on site and WiFi is free in public spaces.

This 3.5-star Islamorada hotel is smoke free.

  • 60 guestrooms or units
  • 2 levels
  • 9 buildings
  • Built in 2020
  • Continental breakfast (free)
  • Beach lounge chairs
  • Towels for the beach
  • Poolside lounge chairs
  • Coffee in lobby
  • Front desk (24 hours)
  • Staff is multilingual
  • Concierge
  • Computer for guest use
  • No smoking on site
  • Bar or lounge
Chesapeake Beach Resort offers 60 air-conditioned accommodations, which are accessible via exterior corridors and feature coffee/tea makers and designer toiletries. Beds feature pillowtop mattresses. 43-inch flat-screen televisions come with cable channels. Bathrooms include showers, complimentary toiletries, and hair dryers.

This Islamorada hotel provides complimentary wireless Internet access, with a speed of 100+ Mbps (good for 1–2 people or up to 6 devices). Business-friendly amenities include phones along with free local calls (restrictions may apply). Additionally, rooms include irons/ironing boards and ceiling fans. Housekeeping is offered daily and hypo-allergenic bedding can be requested.

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  • On private beach
  • Pool
  • Pet friendly
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4.4 out of 5, Excellent, 1,286 reviews
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Aug 16 - Aug 17
Total with taxes and fees
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Property amenities

Family friendly

  • 2 outdoor pools
  • Fenced pool
  • In-room microwave
  • Pool gate

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

Things to do

  • 2 outdoor pools
  • Boat tours
  • Fishing
  • Free bicycle rentals
  • Kayaking

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

Room amenities

Entertainment

  • 43-inch flat-screen TV with cable channels

Bedroom

  • Bedsheets provided
  • Blackout drapes
  • Hypo-allergenic bedding
  • Pillowtop mattress

Bathroom

  • Designer toiletries
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

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
Information provided by the property may be translated using automated translation tools

Access methods

Staffed front desk

Pets

  • Pets: USD 50.00 per accommodation, per night, plus a deposit of USD 50.00 per night
  • Maximum 2 (weight limit: 50 lbs per pet)
  • Restrictions apply
  • For more information, you can reach out to the property at the number on the booking confirmation
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.
  • Rollaway/extra beds are not available.

Property payment types

Important information

Optional extras

The fees and deposits listed below will be charged at the time of service, check-in, or check-out.

  • Pet deposit: USD 50.00 per night
  • Pet fee: USD 50.00 per accommodation, per night
  • Service animals are exempt from fees
  • A late check-out fee will be charged

This may not be a comprehensive list. Fees and deposits are subject to change and might not include tax.

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
Safety features at this property include a fire extinguisher
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
Charges for extra guests may apply and vary according to property policy.
A credit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. 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. This property accepts Visa, Mastercard, American Express, and Discover. Cash is not accepted. For guests' safety, the property includes a fire extinguisher in each accommodation.

We should mention

  • Pool access available from 8:00 AM to 6:00 PM.
  • Certain facilities might have restricted access. For details, you can contact the property at the number on the booking confirmation.
  • Guests may experience noise disturbance due to nearby construction work.
  • To make arrangements to bring your pet, contact the property directly at the number on your booking confirmation (please see the Fees section for related charges).

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

How close is Chesapeake Beach Resort to the airport?

Chesapeake Beach Resort is 77.5 mi (91-min drive) away from the Miami Intl. Airport (MIA) airport, the closest popular airport to the property.

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

As of Jul 19, 2026, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on Aug 16, 2026 start from $221, 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.

Does Chesapeake Beach Resort have an airport shuttle?

Airport shuttle services are not available at Chesapeake Beach Resort.

How close is Chesapeake Beach Resort to the beach?

This hotel is on a private beach. Don't forget your sunscreen!

Does Chesapeake Beach Resort offer free breakfast?

Chesapeake Beach Resort offers free continental breakfast every day from 6:00 AM to 10:00 AM.

Is there a casino at Chesapeake Beach Resort?

No, there is no casino at this hotel.

What time is check-in at Chesapeake Beach Resort?

Check-in start time: 4:00 PM; Check-in end time: 3:00 AM.

Is there free parking at Chesapeake Beach Resort?

Free parking is not available at this hotel.

Does Chesapeake Beach Resort have a pool?

Chesapeake Beach Resort features 2 outdoor pools. Guests can enjoy pool access from 8:00 AM to 6:00 PM.

Does Chesapeake Beach Resort have a spa?

There are no spa services available at this hotel.

How close is Chesapeake Beach Resort to downtown Islamorada?

Chesapeake Beach Resort is 1.2 mi away from Islamorada.

Chesapeake Beach Resort Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 1307 out of 1745 reviews
Rating 8 - Good. 278 out of 1745 reviews
Rating 6 - Okay. 89 out of 1745 reviews
Rating 4 - Poor. 41 out of 1745 reviews
Rating 2 - Terrible. 30 out of 1745 reviews

9.6/10

Cleanliness

9.4/10

Staff & service

9.2/10

Amenities

9.4/10

Property conditions & facilities

Reviews

Verified

8/10 Good

Louis

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great and friendly staff, perfect location.
Stayed 1 night in Apr 2026
Verified

8/10 Good

Christopher

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent breakfast options, lovely setting.
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

Brittany

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very clean, amazing breakfast, lovely staff.
Stayed 4 nights in Mar 2026
Verified

10/10 Excellent

Kenneth

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Breakfast was great, views were awesome, nice little private beach (rare in the keys) perfect location with plenty of night life walking distance and near by! Would stay again for sure!
Stayed 3 nights in Apr 2026
Verified

10/10 Excellent

Jerrod

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location and beautiful beach
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

Jon

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful renovated property. Nice free breakfast with eggs, pancakes and French toast. Paddle boards and kayaks available for use, 2 pools and a nice beach area on the ocean.
Stayed 4 nights in Apr 2026
Verified

10/10 Excellent

sarah

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything was good and peaceful I definitely recommend this property
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

Philip

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great room, very clean and comfortable, pool heated and very nice area to relax. The private beach area is very nice.
Stayed 4 nights in Apr 2026
Verified

8/10 Good

Mauricio

Liked: Staff & service, amenities
Nice hotel, second time we stay there. Nice pool and jacuzzi.
Stayed 1 night in Apr 2026
Verified

10/10 Excellent

Patrick

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Awesome beachfront clean rooms walk to restaurants
Stayed 1 night in Mar 2026
Verified

10/10 Excellent

Matthew

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Breakfast was great!
Stayed 3 nights in Mar 2026
Verified

8/10 Good

Rick

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We enjoyed our stay. Amenities were goo
Stayed 2 nights in Apr 2026
Verified

10/10 Excellent

Steven

Liked: Cleanliness, amenities, property conditions & facilities
Great modern resort, very clean, very friendly.
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

Wasim

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location, access to the water front. Very nice and quiet atmosphere. Excellent made to order breakfast and other options.
Stayed 2 nights in Jan 2026
Verified

8/10 Good

Mariola

warm pool, beautiful view at the beach, pleasant front desk and breakfast staff
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We enjoyed our stay. Nice staff, nice looking property, nice room, very good breakfast which was included and the omelette chef worked very hard to accommodate us and the other guests. Walked to a restaurant for dinner at Wahoos Seafood Bar and Grill, very good, about 200 yards from the resort.
Stayed 1 night in Apr 2026
Verified

10/10 Excellent

Jordan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location. Beautiful grounds felt very private.
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

celso

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
clean-staff very friendly and helpful-place is paradise
Stayed 7 nights in Mar 2026
Verified

10/10 Excellent

dian

Liked: Cleanliness, staff & service, amenities
Great room, wonderful staff and good location
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Roger

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful ocean view from our room staff was very helpful very clean room
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

Doug or Lois

Liked: Cleanliness, staff & service, amenities
Nice stay
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

Keely

Liked: Cleanliness, staff & service, amenities
Clean rooms, beautiful scenery, gorgeous sunrise, delicious breakfast. Loved this place.
Stayed 4 nights in Feb 2026
Verified

8/10 Good

Ryan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Outdoor areas was convenient after a long day running the Keys. Very relaxing.
Stayed 5 nights in Jan 2026
Verified

8/10 Good

Beth

Liked: Cleanliness, staff & service, amenities
Nice grounds beautiful view
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

David

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Rooms are very clean. The beds are super comfortable. Plenty of loungers around the pool. Great location in Islamorada Central to bars and restaurants.
Stayed 3 nights in Apr 2026