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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
Balcony
Outdoor spa tub
1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Bar
  • 24/7 front desk
  • Pet friendly
  • Pool
$201
includes taxes & fees
Sep 8 - Sep 9

Explore the area

View in a 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

2-Bedroom Villa | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

2-Bedroom Villa

10.0 out of 10
Exceptional
(1 review)
  • 646 sq ft
  • 2 bedrooms
  • 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

9.4 out of 10
Exceptional
(29 reviews)
  • 272 sq ft
  • 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
(2 reviews)
  • 517 sq ft
  • 1 bedroom
  • 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
(87 reviews)
  • 272 sq ft
  • 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
(19 reviews)
  • 307 sq ft
  • 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)
  • 366 sq ft
  • 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)
  • 540 sq ft
  • 1 bedroom
  • 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

  • 517 sq ft
  • 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 | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Premium 1-Bedroom Ocean View Villa

  • 700 sq ft
  • 1 bedroom
  • 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
(9 reviews)
  • 650 sq ft
  • 1 bedroom
  • 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

9.4 out of 10
Exceptional
(80 reviews)
  • 364 sq ft
  • 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
(15 reviews)
  • 527 sq ft
  • 1 bedroom
  • 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
(43 reviews)
  • 366 sq ft
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

Ocean View King Efficiency Villa

  • 517 sq ft
  • 1 bedroom
  • 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
(54 reviews)
  • 307 sq ft
  • 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

  • 323 sq ft
  • 1 bedroom
  • 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

  • 829 sq ft
  • 1 bedroom
  • 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)
  • 366 sq ft
  • 1 bedroom
  • 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

8.0 out of 10
Very good
(3 reviews)
  • 540 sq ft
  • 1 bedroom
  • 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
(17 reviews)
  • 364 sq ft
  • Ocean view
  • Sleeps 3
  • 1 King Bed

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Exterior

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  • Restaurant
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Amara Cay Resort

About this property

Chesapeake Beach Resort

3.5-star hotel in Matecumbe
At Chesapeake Beach Resort, you can relax at one of the 2 outdoor swimming pools, play on the private white sand beach, or spend the day at a marina.
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.

A private beach, a marina, and complimentary bicycles are featured at the hotel. 2 outdoor swimming pools are on site.

Children under 16 years old are not allowed in the swimming pool without adult supervision.

The recreational activities listed below are available either on site or nearby; fees may apply.

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.

A complimentary breakfast is offered each morning. A bar/lounge is on site where guests can unwind with a drink. A computer station is located on site and wireless Internet access is complimentary. A total renovation of this property was completed in January 2020.

Chesapeake Beach Resort is a smoke-free property.

A complimentary continental breakfast is served each morning between 6:00 AM and 10:00 AM.
Tiki Bar - Onsite bar.

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
  • Smoking not allowed
  • 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

Chesapeake Beach Resort Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 1098 out of 1516 reviews
Rating 8 - Good. 256 out of 1516 reviews
Rating 6 - Okay. 92 out of 1516 reviews
Rating 4 - Poor. 39 out of 1516 reviews
Rating 2 - Terrible. 31 out of 1516 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

10/10 Excellent

Dailen

Traveled with group, Business traveler, Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Excepcional
Stayed 3 nights in Jun 2025

10/10 Excellent

James, HOLLYWOOD

Stayed 2 nights in Jun 2025

8/10 Good

Isbet

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
In general, was fine, just not all staff was nice
Stayed 1 night in Jun 2025

6/10 Okay

Amanda

Liked: Cleanliness, property conditions & facilities
Disliked: Staff & service, room comfort
Honestly was expecting this place to be great given the price; however, that wasn’t true. Each room has a mini split for AC which did not cool our room very well given the Florida heat. Upon check in, we were told a room wasn’t ready yet and asked if we could use the kayaks in the meantime while waiting and the front desk attendant didn’t know the answer. Thankfully our room was ready minutes later. Overall, not very many amenities very available for the price paid.
Stayed 1 night in Jun 2025

10/10 Excellent

Katie

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Great stay!

We loved this property! We actually cancelled our second night at a different hotel in Marathon to come back to this one. The pools were great, rooms were clean and beautiful, front desk employees were kind and helpful. The breakfast was delicious and I loved the option to purchase a mimosa with breakfast. We went to Wahoo’s restaurant which is in walking distance to the hotel as well as Papa Joe’s and both were fantastic. We would definitely come back here!
Stayed 1 night in May 2025

10/10 Excellent

karen

Traveled with partner, Traveled with pets
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was family oriented. Love that pets were allowed on premises. Many activities for adults and children even though we didn’t have kids it was nice to see. Staff very pleasant and helpful.
Stayed 1 night in May 2025

6/10 Okay

Albert

Liked: Cleanliness
Stayed 3 nights in Jun 2025

4/10 Poor

Fadi

Traveled with family
Liked: Amenities, property conditions & facilities
Disliked: Staff & service
Poco personal y los que están no son nada agradables y atienden horrible a los huéspedes.
Stayed 1 night in May 2025

10/10 Excellent

Ramkumar, Redmond

Traveled with family and small children, Business traveler, Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
One of the best stays I’ve experienced. The property offers stunning views—especially during sunrise, which is truly unforgettable. The infinity pool overlooking the sea creates a perfect blend of luxury and tranquility. Rooms are exceptionally spacious, well-maintained, and designed for comfort. Highly recommend for those seeking both relaxation and scenic beauty.
Stayed 1 night in Apr 2025

10/10 Excellent

Lester

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent getaway
Stayed 1 night in May 2025

10/10 Excellent

Mikayla

Liked: Cleanliness, amenities, property conditions & facilities
This was a great place to stay.
Stayed 3 nights in Jun 2025

10/10 Excellent

Alena

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
It was one of the best of my stays at the keys. I live in Downtown Miami and love escaping for the weekend with girlfriend or husband. This time we brought our dog Mini Australian shepherd Benji. We all had blast with a pet friendly ocean view property!
Stayed 2 nights in May 2025

10/10 Excellent

Peter

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

10/10 Excellent

Sergii

Liked: Cleanliness, staff & service, amenities
Everything was amazing
Stayed 2 nights in May 2025

10/10 Excellent

Yanitzia

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
Un lugar maravilloso, con una atención increíble. La habitación que da para el mar , es un expectaculo de linda. Para pareja y familia Lo recomiendo 100%
Stayed 1 night in May 2025

10/10 Excellent

Tracey

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Came into town to pick up our boat.
Stayed 1 night in May 2025

10/10 Excellent

Donna

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
The staff person who checked us in was very friendly and helpful. The room was very clean and had a really comfortable bed. Staff checked once a day to see if we needed anything. We would definitely return!
Stayed 3 nights in May 2025

10/10 Excellent

tina

Traveled with partner
Liked: Staff & service, amenities
One of the pools had a dirty diaper left on a table. The staff dropped off towels but didn't look around to clean up left over cups, used diaper, etc. Granted guests should be responsible and clean up their own trash but it would be nice if the housekeeping would watch for this since I had to point it out. Other than that it was a great location and nice hotel. Two restaurants next door to the property so you don't have to drive if you don't want. Breakfast was great, made to order custom omelet, rooms had robes and slippers, there's paddle boards, clear bottom kayaks and fishing poles to use.
Stayed 1 night in May 2025

10/10 Excellent

Kevin

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
My experience here has been amazing. The relaxing, friendly environment made my family and me love it so much that we stayed an extra night.
Stayed 1 night in May 2025

10/10 Excellent

Amy

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Room was clean, lots of extras, amazing views, great breakfast
Stayed 1 night in Apr 2025

10/10 Excellent

Joey

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in May 2025

2/10 Terrible

Amanda

Traveled with family
Disliked: Cleanliness, amenities, property conditions & facilities
I had a terrible experience at Chesapeake Beach Resort. I stayed for three nights, but for the first two, I couldn’t sleep because the air conditioning was leaking water directly onto the bed. I reported the problem to the front desk on the first day, and they told me they would send maintenance, but nothing was done. They also said I should call Expedia to resolve the issue, which I did, but no one helped me, and my requests were completely ignored. They finally changed my room on the last night, but the damage was already done. I also requested a refund for the first two nights, and I’m still waiting for the security deposit to be returned. This situation was handled very poorly, and I wouldn’t recommend this hotel to anyone. It was a stressful and disappointing experience.
Stayed 3 nights in May 2025

10/10 Excellent

Steven

Traveled with partner, Traveled with pets
Liked: Cleanliness, property conditions & facilities
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

2/10 Terrible

leslie

Traveled with family
Disliked: Cleanliness, amenities, property conditions & facilities
Dirty property not wonderful as Expedia rated . People had their dogs swimming in the pool staff did nothing about it and claimed they had no complaints . Felt like I was in a third world country not Islamorada . Shame on you Expedia for not allowing me to cancel my reservation & blaming me for contacting to late . Will never use you again or go to this disgusting hotel ! Beware is my word of caution to anyone considering this property or Expedia .
Stayed 1 night in May 2025

10/10 Excellent

BRUNO

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
Good
Stayed 3 nights in May 2025