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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

Relax on the beach with a tranquil ocean view and comfortable sun loungers.
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.
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.

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Bar
  • 24/7 front desk

Explore the area

Map
83409 Overseas Hwy, Islamorada, FL, 33036
  • Windley Key Fossil Reef Geological State Park
    ‪2 min drive‬
  • Theater of the Sea
    ‪2 min drive‬
  • Florida Keys Brewing Co.
    ‪4 min drive‬

Room options

View all photos for 2-Bedroom Villa

Relax in a spacious room with a large bed, flat-screen TV, and wardrobe.

2-Bedroom Villa

10.0 out of 10
Exceptional
(1 review)
  • 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

Relax in a spacious room with a large bed, nightstand, and comfortable chair, featuring a ceiling fan and air conditioning unit.

Standard King

9.4 out of 10
Exceptional
(29 reviews)
  • 25 sq m
  • Sleeps 3
  • 1 King Bed

View all photos for King Efficiency Villa

Relax in a spacious room with a large bed, nightstand, and wicker chair.

King Efficiency Villa

10.0 out of 10
Exceptional
(2 reviews)
  • 48 sq m
  • 1 bedroom
  • Resort view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard Doubles

Two large beds with white linens, a flat-screen TV, and a wooden bench await in this stylish room.

Standard Doubles

9.2 out of 10
Wonderful
(86 reviews)
  • 25 sq m
  • Sleeps 4
  • 2 Double Beds

View all photos for Standard King with Sleeper Sofa

Relax in a spacious room with a large bed, nightstand, and ceiling fan, offering a view of the outside through sheer curtains.

Standard King with Sleeper Sofa

9.0 out of 10
Wonderful
(18 reviews)
  • 29 sq m
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Hearing Impaired Ocean View Queens

Enjoy a comfortable stay with a large bed, desk, and seating area, plus a window offering a view of the outdoors.

Hearing Impaired Ocean View Queens

10.0 out of 10
Exceptional
(2 reviews)
  • 34 sq m
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

View all photos for Hearing Impaired Ocean View King Suite

Relax in this stylish living room with a sofa, coffee table, and chairs, featuring a large window with a view of palm trees and the ocean.

Hearing Impaired Ocean View King Suite

8.6 out of 10
Excellent
(4 reviews)
  • 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

Relax in a spacious room with a large bed, dark sofa, and flat-screen TV.

ADA King Efficiency Villa

  • 48 sq m
  • 1 bedroom
  • Resort view
  • Sleeps 3
  • 1 King Bed

View all photos for Premium 1-Bedroom Ocean View Villa

Two large beds with white linens and a view of palm trees.

Premium 1-Bedroom Ocean View Villa

  • 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

Enjoy breathtaking ocean views from this balcony overlooking the beach.

Deluxe Ocean View Two Queen Suite

8.8 out of 10
Excellent
(9 reviews)
  • 60 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 6
  • 2 Queen Beds

View all photos for Ocean View King

Relax in a spacious room with a large bed, nightstand, and sliding glass door leading to an outdoor area with a view of palm trees.

Ocean View King

9.6 out of 10
Exceptional
(78 reviews)
  • 34 sq m
  • Ocean view
  • Sleeps 3
  • 1 King Bed

View all photos for Ocean View King Suite

Relax in comfort with a large bed, bedside tables, and a ceiling fan above.

Ocean View King Suite

9.4 out of 10
Exceptional
(13 reviews)
  • 49 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Ocean View Queens

Enjoy the ocean view from this balcony with a pair of lounge chairs and a small table.

Ocean View Queens

9.8 out of 10
Exceptional
(43 reviews)
  • 34 sq m
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

Ocean View King Efficiency Villa

  • 48 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard Queens

Enjoy a comfortable stay in this stylish room featuring two single beds, a flat-screen TV, and a desk area.

Standard Queens

9.4 out of 10
Exceptional
(53 reviews)
  • 29 sq m
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard King Villa

Relax in a spacious room with a large bed and two bedside tables, each with a lamp.

Standard King Villa

  • 30 sq m
  • 1 bedroom
  • Resort view
  • Sleeps 3
  • 1 King Bed

View all photos for Premium Ocean View King Villa

Enjoy meals at the large dining table surrounded by six chairs, with breathtaking ocean views from the expansive balcony.

Premium Ocean View King Villa

  • 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

Enjoy ocean views from the large window, relax in the seating area with a striped ottoman, and unwind in this stylish room with two single beds.

ADA Ocean View Queens

9.0 out of 10
Wonderful
(7 reviews)
  • 34 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

View all photos for ADA Ocean View King Suite

Enjoy the ocean view from this balcony with a pair of chairs and a table.

ADA Ocean View King Suite

8.0 out of 10
Very good
(3 reviews)
  • 50 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed

View all photos for ADA Ocean View King

Relax in a spacious room with a large bed, nightstand, and sliding glass door leading to an outdoor area with a view of palm trees.

ADA Ocean View King

8.6 out of 10
Excellent
(16 reviews)
  • 34 sq m
  • Ocean view
  • Sleeps 3
  • 1 King Bed

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About the area

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 Keys History & Discovery Center are also within 2 miles (3 km).

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 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

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. A complete renovation of Chesapeake Beach Resort was completed in January 2020.

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.

Languages

English, Spanish

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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

Access methods

Staffed front desk

Pets

  • Pets: USD 50.00 per accommodation, per night, plus a deposit of USD 50.00 per stay
  • 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 stay
  • 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
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. 

We should mention

  • Pool access available from 7:00 AM to 10:30 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

Chesapeake Beach Resort Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 1065 out of 1478 reviews
Rating 8 - Good. 248 out of 1478 reviews
Rating 6 - Okay. 91 out of 1478 reviews
Rating 4 - Poor. 41 out of 1478 reviews
Rating 2 - Terrible. 33 out of 1478 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

Collin

Travelled with family and small children
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean and comfortable with breakfast on site. Close activities and a few restaurants within walking distance
Stayed 6 nights in Jul 2025

10/10 Excellent

Michael Joseph

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
Very clean, the staff was great. Breakfast was terrific. I would recommend staying here. I’ll definitely be going back.
The view from our room, 317 was incredible!
!!!!
Stayed 3 nights in Jul 2025

10/10 Excellent

Michelle

Stayed 2 nights in Jun 2025

10/10 Excellent

VIANA

Stayed 2 nights in May 2025

10/10 Excellent

Rob

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I can fish at night in peace at this property.The free breakfeast is a plus.The room was very clean and on the small size.
Stayed 1 night in May 2025

10/10 Excellent

Daniel

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities
Right on the beach and also pool
Stayed 1 night in May 2025

10/10 Excellent

Kass

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

6/10 Okay

Debbie

Liked: Cleanliness, property conditions & facilities
It did have a beach was very clean.. bathroom had no counter..towels werent even in bathroom.. it was a nice clean space.cleaning people didnt no english.. probally not stay there again.. 2 queen were. p
Stayed 2 nights in Apr 2025

10/10 Excellent

HUGH

Liked: Cleanliness, staff & service, property conditions & facilities
Great weekend at the resort
Stayed 2 nights in May 2025

10/10 Excellent

Deborah

Travelled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in May 2025

10/10 Excellent

Rhett Jan, Boynton Beach

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Relaxing place
Stayed 2 nights in Apr 2025

10/10 Excellent

Anny, Medford

Travelled with family and small children
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We had a Vila and it was very nice, new and very clean. We loved all about it!
Stayed 3 nights in Apr 2025

10/10 Excellent

Peter

Liked: Cleanliness, staff & service, property conditions & facilities
Great property exceeded our expectations.
Stayed 2 nights in Apr 2025

10/10 Excellent

Daniel, Miami

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean, nicely decorated rooms. Direct beach access. Well maintained property.
Stayed 1 night in Apr 2025

10/10 Excellent

Helen

Liked: Cleanliness, staff & service, property conditions & facilities
Amazing location.
Stayed 4 nights in Mar 2025

10/10 Excellent

Wilson

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Todo muy Exelente las habitaciones son muy buenas y limpias recomendadisimo
Stayed 1 night in Apr 2025

6/10 Okay

Patricia

Liked: Cleanliness
was told hot tub was in working order when making the reservation. Hot tub was out of order upon arrival and during stay.
Stayed 1 night in Apr 2025

8/10 Good

Edwin

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Apr 2025

8/10 Good

Adam

Liked: Cleanliness, property conditions & facilities
Good for the price and convenient for fishing trips. No frills, clean rooms good location.
Stayed 3 nights in Apr 2025

10/10 Excellent

Margarita

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Apr 2025

2/10 Terrible

PHILIP

Travelled with family
Disliked: Staff & service, property conditions & facilities
We only stayed 1 night and checked out. We are asking Expedia and Chesapeake to REFUND us for the additional 2 nights!! BKG#73084799299276 APRIL 24-27TH
Stayed 3 nights in Apr 2025

10/10 Excellent

CHASE

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Property was very nice. Staff was very nice also. We thought property had a restaurant and bar but none available yet. They did have free breakfast and great ocean front accommodations
Stayed 3 nights in Apr 2025

10/10 Excellent

monika

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 3 nights in Apr 2025

10/10 Excellent

Salim, Boca Raton

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location and rooms.
Stayed 2 nights in Apr 2025

10/10 Excellent

Jelena

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nicely remodeled (without the smell of mold) with contemporary touches. We were prepared to find out that pictures will not turn to reality but were so pleased that they reflect what the resort really is. Breakfast is included into stay (thank you to the owner for the omelet station!). Good quality coffee and tea always available at the front desk. Another pleasant surprise was that you could check out bikes/fishing rods or kayaks for a few hours to enjoy. Such a beautiful setting and we cannot wait to return, unless something changes this will be our place to stay at the Keys. Thank you for not cutting corners and making it a pleasant experience for your guests!
Stayed 4 nights in Apr 2025