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

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

2-Bedroom Villa | Private kitchenette | Microwave, coffee/tea maker

2-Bedroom Villa

  • 646 sq ft
  • 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

  • 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

  • 517 sq ft
  • 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

  • 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

  • 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

  • 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

  • 540 sq ft
  • 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
  • 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
  • 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

  • 650 sq ft
  • 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

  • 364 sq ft
  • Ocean view
  • Sleeps 3
  • 1 King Bed

View all photos for Ocean View King Suite

Ocean View King Suite | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King Suite

  • 527 sq ft
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

  • 366 sq ft
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

Ocean View King Efficiency Villa

  • 517 sq ft
  • 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

  • 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
  • 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
  • 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

  • 366 sq ft
  • 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

  • 540 sq ft
  • 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

  • 364 sq ft
  • Ocean view
  • Sleeps 3
  • 1 King Bed

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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.

Languages

English, Spanish

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
  • Smoke-free property
  • Traditional architecture

Room amenities

Bedroom

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

Bathroom

  • Designer toiletries
  • Hair dryer
  • Private bathroom
  • 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. 1054 out of 1472 reviews
Rating 8 - Good. 244 out of 1472 reviews
Rating 6 - Okay. 95 out of 1472 reviews
Rating 4 - Poor. 44 out of 1472 reviews
Rating 2 - Terrible. 35 out of 1472 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

8/10 Good

Robert

Liked: Cleanliness, staff & service, property conditions & facilities
Nice people, quiet resort.
Stayed 3 nights in Mar 2025

10/10 Excellent

max

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great stay, clean room!
Stayed 2 nights in Mar 2025

10/10 Excellent

Gladys

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities
Secluded quiet, excellent to relax
Stayed 1 night in Mar 2025

10/10 Excellent

Tracy

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff are super friendly. Our room was clean and well laid out. Make sure to use the 2 hours free paddle boarding that comes with your reservation, we seen sharks, manatees and lots of fish and hermit crabs. The breakfast in the morning is fresh and a great selection.
Stayed 2 nights in Mar 2025

10/10 Excellent

Rebecca, Okeechobee

Liked: Cleanliness, staff & service, property conditions & facilities
I love this place! Lovely maintained grounds, very clean and modern rooms. The sunrises are amazing. Front desk, cleaning staff, breakfast staff and bar staff were friendly and very accommodating. I am going to miss the great cooked to order omelets and drinks by the pool and beach. I would recommend this resort to anyone with families or adults only. We enjoyed the beautiful grounds which are lush and well maintained. The chess, checkers and kayak rentals plus the tiki boat rentals to the sandbar are an added bonus. This was betterthan an all inclusive resort in the Caribbean for us. Paradise in the Keys- close to shopping and great restaurants. Better than traveling south where it gets a little crazy for us. We plan to come back as often as we can.
Stayed 3 nights in Mar 2025

8/10 Good

Darlis

Stayed 2 nights in Feb 2025

10/10 Excellent

Sue Ellen

Liked: Cleanliness, staff & service, property conditions & facilities
We asked for & received early check-in. The staff was friendly & helpful & everything was immaculate! Wonderful breakfast included! Nice beach area with lots to do. We will definitely stay here again!
Stayed 1 night in Mar 2025

10/10 Excellent

Derick

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Most amazing views
Stayed 2 nights in Feb 2025

10/10 Excellent

Patrick

Liked: Cleanliness, amenities
Love this place
Stayed 2 nights in Feb 2025

10/10 Excellent

Tammy

Traveled with partner
Liked: Cleanliness, staff & service, property conditions & facilities
We found our perfect peaceful and quiet getaway! We started each day with waffles or omelets. We loved the private beach with plenty of shade. It was nice to hear the water and birds instead of music or people. The bar was just steps away from the beach or pool. We walked to dinner at Wahoo's every night. I highly recommend Chesapeake for a low key, quiet stay.
Stayed 6 nights in Feb 2025

10/10 Excellent

Dale

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean well designed and convenient. Nice staff as well
Stayed 1 night in Feb 2025

10/10 Excellent

Nancy

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Only 60 rooms. Not crowded. Lovely grounds and great staff.
Stayed 2 nights in Feb 2025

10/10 Excellent

Dignarys

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Muy buen servicio alienate muy limpio
Stayed 1 night in Mar 2025

10/10 Excellent

Avery

Traveled with partner, Traveled with pets, Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent location for family trip or fishing. Clean friendly hotel lovely custom made free breakfast by Mr Chris. Also pet friendly
Stayed 2 nights in Feb 2025

10/10 Excellent

Diane

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great staff, beautiful grounds, very nice stay.
Stayed 1 night in Feb 2025

10/10 Excellent

Carol

Traveled with partner
Liked: Cleanliness, staff & service, property conditions & facilities
Never disappointing. Wonderful Stay
Stayed 2 nights in Feb 2025

10/10 Excellent

Verified traveler

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

10/10 Excellent

Marc Ressler

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This small resort hotel was recently renovated and is very well run. The location is perfect right on the ocean and is meticulously maintained. We stayed in an ocean view villa and it was very clean, new, and well appointed. There is a $50 per day resort fee that was disclosed which includes a nice made to order omelet and waffle breakfast with fruit, bagels, yogurt, etc. They also have a small bar with drinks available throughout the day. The resort fee also includes use of water sports like kayaks and paddle boards. Even though the resort is right on the ocean, the water was remarkably calm with no waves which helped add a laid back feel to this property. The staff was great, especially Dereck at the front desk who checked me in and also reached out to me each day to see if we needed anything. The daily housekeeping was nice as many hotels have cut back on this. I will definitely stay at this resort again as I pass through the Keys.
Stayed 3 nights in Feb 2025

10/10 Excellent

Courtney

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Feb 2025

8/10 Good

Cory

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Little expensive a nice property
Stayed 1 night in Feb 2025

10/10 Excellent

Paul

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Feb 2025

8/10 Good

diana

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Our one night stay at this property was pleasant except for the noise from the cars which bothered my husband during the night but not me and our daughter. The receptionist could have said welcome and put on a smile but he didn’t. When I asked him why he didn’t offer us the welcome drinks he said he didn’t think we wanted them because we looked tired… However our ocean view from the room was beautiful and the beach is gorgeous!
Stayed 1 night in Feb 2025

10/10 Excellent

Yoav

Stayed 2 nights in Dec 2024

8/10 Good

Verified traveler

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

Would stay again-loved the place!

Everything was great-we did have an issue with our a/c but we were only there two nights so we didn't worry with having them look at it. Just reported as we left the property. Loved the place overall!
Stayed 2 nights in Feb 2025

10/10 Excellent

kathy

Stayed 3 nights in Feb 2025