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Chesapeake Beach Resort

Property class: 3.5
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 hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the beach through the window.
A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.
A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.
A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

Reviews

9.4 out of 10
Exceptional

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
(55 reviews)
  • Ocean view
  • 366 sq ft
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

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
(112 reviews)
  • Ocean view
  • 364 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

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

8.4 out of 10
Very good
(9 reviews)
  • Ocean view
  • 540 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed

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
(23 reviews)
  • Ocean view
  • 364 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

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

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
(4 reviews)
  • Ocean view
  • 366 sq ft
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

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

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
(77 reviews)
  • 307 sq ft
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

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
(117 reviews)
  • 272 sq ft
  • 1 bedroom
  • Sleeps 4
  • 2 Double Beds

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
(30 reviews)
  • 307 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

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
(44 reviews)
  • 272 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

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

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
(14 reviews)
  • Ocean view
  • 650 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds

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

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

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

8.8 out of 10
Excellent
(6 reviews)
  • Resort view
  • 517 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

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

View all photos for 2 Full Beds, 1-Bedroom Villa

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

2 Full Beds, 1-Bedroom 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

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

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

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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 - 16 min drive - 12.8 miles

Getting around

  • Miami Intl. Airport (MIA) - 100 min drive

Restaurants

  • ‪Hog Heaven - ‬3 min drive
  • ‪Lorelei Restaurant & Cabana Bar - ‬3 min drive
  • ‪Wahoo's Bar & Grill - ‬2 min walk
  • ‪Wendy's - ‬2 min drive
  • ‪Starbucks - ‬15 min walk

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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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

  • American Express
  • Discover
  • Mastercard
  • Visa

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 77.7 mi (100-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 Oct 19, 2026, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on Nov 4, 2026 start from $194, 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

9.4

Exceptional

Rating 10 - Excellent. 1351 out of 1799 reviews
Rating 8 - Good. 281 out of 1799 reviews
Rating 6 - Okay. 95 out of 1799 reviews
Rating 4 - Poor. 43 out of 1799 reviews
Rating 2 - Terrible. 29 out of 1799 reviews

9.6/10

Cleanliness

9.4/10

Staff & service

9.2/10

Amenities

9.4/10

Property conditions & facilities

Reviews

Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was great.
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The place was lovely. Great staff and breakfast! The pools on the beach were fantastic!
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Love the place very clean and peaceful
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very attentive service great breakfast and beautiful room.
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It’s always a great stay here! We were able to bring our dog who enjoyed his time in Islamorada. The included breakfast was a nice surprise.
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was perfect for what we needed
Stayed 4 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Awesome staff. Great location. Nice property.
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very nice rooms, very important for us is having a good AC in the room and it was perfect. 2nd time I had stay in this hotel and I will stay again.
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Great breakfast and very friendly staff
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Resort is amazing. Gets better every year. Beach, 2 pools, water sports place is amazing.
Stayed 5 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness
Very good location the rooms are Amazing
Stayed 1 night in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The villa we stayed at was ideal for our family traveling with our dog for a 2N stay 4th or July weekend. The property and location exceeded our expectations and the staff was exceptionally friendly. We recommend this place.
Stayed 1 night in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This place is perfect
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent staff. Property was beautiful and well maintained. Room was beautiful.
Stayed 2 nights in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful resort, amazing views, fantastic breakfast!
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful place enjoyed every moment of it, breakfast was not good that's th3 only issue otherwise
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The hotel has a fabulous location on the beach the staff were very friendly and we were welcomed with a glass of fizz. Breakfast had a good choice the rooms were spotless you get 2 hours free water sports per day would definitely recommend
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
the place is great for R&R
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We had a fabulous stay and would definitely return.
Stayed 6 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The property is great. You can walk out from the beach and snorkel.
Stayed 1 night in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The breakfast was wonderful!
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Perfect place to stay and a super friendly and helpful staff...definitely staying here again
Stayed 1 night in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was perfect for our family. The pools were great. The views were awesome. Breakfast was delicious and very quick. I would 100% stay here again and when we make our yearly trip to the keys, this is the first place to book on the list.
Stayed 4 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Kayak, pools and breakfast were awesome
Stayed 1 night in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nice resort with great views and a nice beach area. The breakfast was awesome
Stayed 1 night in May 2026

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