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Chesapeake Beach Resort

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

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Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun loungers, beach towels
Property preview
Water view
Outdoor spa tub
Hypo-allergenic bedding, pillowtop beds, laptop workspace

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
    ‪3 min drive‬
  • Place, Islamorada Brewery & Distillery
    ‪3 min drive‬

Room options

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

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

View all photos for Ocean View King

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King

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

View all photos for ADA Ocean View King Suite

ADA Ocean View King Suite | Balcony

ADA Ocean View King Suite

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

View all photos for ADA Ocean View King

Hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA Ocean View King

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

View all photos for ADA Ocean View Queens

ADA Ocean View Queens

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 Hearing Impaired Ocean View Queens

Hypo-allergenic bedding, pillowtop beds, laptop workspace

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

43-inch flat-screen TV with cable channels, TV

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 Standard Queens

Standard Queens

Standard Queens

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

View all photos for Standard Doubles

Standard Doubles

Standard Doubles

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

View all photos for Standard King with Sleeper Sofa

Standard King with Sleeper Sofa

Standard King with Sleeper Sofa

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

View all photos for Standard King

Standard King

Standard King

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

View all photos for Ocean View King Suite

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King Suite

9.4 out of 10
Exceptional
(16 reviews)
  • 49 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen 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
(10 reviews)
  • 60 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 6
  • 2 Queen Beds

View all photos for 2-Bedroom Villa

2-Bedroom Villa

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 Villa

Standard King Villa

Standard King Villa

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

View all photos for King Efficiency Villa

King Efficiency Villa

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 ADA King Efficiency Villa

ADA King Efficiency Villa

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

Premium 1-Bedroom Ocean View Villa

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 Premium Ocean View King Villa

Premium Ocean View King Villa | Living area

Premium Ocean View King Villa

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

Ocean View King Efficiency Villa

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

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
  • Theater of the Sea - 3 min drive - 2.0 km
  • Windley Key Fossil Reef Geological State Park - 3 min drive - 2.0 km
  • Islamorada Brewery & Distillery - 3 min drive - 2.7 km
  • Bud n' Mary's Dive Center - 10 min drive - 7.6 km

Getting around

  • Miami Intl. Airport (MIA) - 91 min drive

Restaurants

  • ‪Tiki Bar - ‬13 min walk
  • ‪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. 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.

Similar properties

Exterior
Lime Tree Bay Resort
  • On private beach
  • Pool
  • Hot tub
  • Pet friendly
4.6 out of 5, Wonderful, 1,122 reviews
Lime Tree Bay Resort

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 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. 1176 out of 1614 reviews
Rating 8 - Good. 269 out of 1614 reviews
Rating 6 - Okay. 98 out of 1614 reviews
Rating 4 - Poor. 42 out of 1614 reviews
Rating 2 - Terrible. 29 out of 1614 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

9.0/10

Amenities

9.2/10

Property conditions & facilities

9.0/10

Eco-friendliness

Reviews

8/10 Good

DAWNE, Tampa

Travelled with partner
Liked: Property conditions & facilities
Staff was wonderful
Stayed 3 nights in Dec 2025

10/10 Excellent

Stanley

Stayed 1 night in Dec 2025

8/10 Good

Angela

Stayed 4 nights in Oct 2025

10/10 Excellent

Kimberly

Stayed 6 nights in Nov 2025

10/10 Excellent

MATTHEW, CAVECREEK

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
Room was awesome and the amenities were great! Loved our stay!!!
Stayed 7 nights in Oct 2025

10/10 Excellent

Brian

Liked: Cleanliness, staff & service, property conditions & facilities
I was very pleased with the resort. It’s a quiet hidden gem with a friendly and helpful staff. I would love to stay here again.
Stayed 1 night in Oct 2025

10/10 Excellent

Eric Brooks

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Quiet. Peaceful. Perfect getaway for couples. Excellent customer service. This was our second stay at Chesapeake. Chesapeake and Islamorada are our new favorite destinations in the Keys. Islamorada reminds us of the Key West we fell in love with 30 years ago. Low key and peaceful. Every day is perfect when starting with Krystal's French toast. Her smile is infectious. She and the breakfast gang aim to please with their attention to detail. The private beach is lovely with shade and sun options. No talking or music. It was the perfect spot to watch the boats at the sand bar or to take a nap. Walk through the adjacent parking lot to four restaurants. We love the casual vibe outside at Wahoos. We can't wait to go back.
Stayed 7 nights in Sep 2025

10/10 Excellent

Nicole

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Our stay was short sadly, only 2 nights, but we would gladly stay here again. We had a beautiful view of the ocean from our room and the room itself was clean and comfortable. The hotel offers complimentary water activities and on Saturday morning held a beach yoga class, which was lovely. You can walk to several restaurants easily and there is a free cab service offered by the city for anywhere else locally. I recommend staying here. Our only regret was not being able to stay longer!
Stayed 2 nights in Sep 2025

10/10 Excellent

Monica

Stayed 2 nights in Sep 2025

10/10 Excellent

Hermes

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent recommendation for a small budget.
Stayed 3 nights in Sep 2025

10/10 Excellent

Annia

Travelled with family, Travelled with family and small children
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Amazing location grounds are very well maintained. Staff is beyond amazing Vanessa and Jose
Stayed 1 night in Sep 2025

8/10 Good

Britnee

Liked: Amenities
Beautiful resort with easy going staff
Stayed 1 night in Sep 2025

10/10 Excellent

Carl

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful property, breakfast was awesome
Stayed 1 night in Sep 2025

10/10 Excellent

Roger

Stayed 2 nights in Sep 2025

10/10 Excellent

francine

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The front desk and staff was very helpful, courteous, and professional. Will definitely be back. Property was beautiful. The rooms were clean, exquisite and comfortable.
Stayed 2 nights in Sep 2025

10/10 Excellent

Annie

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent
Stayed 1 night in Sep 2025

8/10 Good

Yoel

Stayed 2 nights in Sep 2025

4/10 Poor

David

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Anything extra is very expensive, especially beverages in the lobby ! Price gouging !
Stayed 2 nights in Sep 2025

10/10 Excellent

nancy Rioseco

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities
The breakfast was fresh and hot with a nice selection of fruits and drink. The staff was amazing. Would definitely recommend this resort. The pools were clean and the beach was beautiful.
Stayed 2 nights in Sep 2025

10/10 Excellent

Yvette

Travelled with partner
Liked: Staff & service, amenities, property conditions & facilities
Everything was perfect and beautiful
Stayed 1 night in Sep 2025

2/10 Terrible

Kelly

Travelled with partner
Liked: Cleanliness, staff & service, amenities
We arrived on Friday September 12, our room had no dresser to put all our clothes in which I found very strange then on Saturday around 3pm the electricity went out, we waited a couple hours then we called the front desk and the girl said it would be out for a while so I was having sinus issues plus asthma so I went to the office to speak with the receptionist and she apologized but didn’t know when the electric would be restored so do to my condition we had to go back home to Miami , we were not offered a different room first, check the office video , we would like , Saturday and Sunday nights refund back to us since we left on Saturday.
Stayed 3 nights in Sep 2025

10/10 Excellent

Shakene

Stayed 3 nights in Sep 2025

10/10 Excellent

RUBEN

Liked: Cleanliness, staff & service, property conditions & facilities
Excelent
Stayed 1 night in Sep 2025

10/10 Excellent

Deborah

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very clean property, good breakfast included and the views are spectacular!! Beautiful beach location!! Would go back anytime!!
Stayed 3 nights in Sep 2025

10/10 Excellent

Osvaldo

Stayed 2 nights in Sep 2025