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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
Balcony
Hypo-allergenic bedding, pillowtop beds, laptop workspace
Water view
Aerial view

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Bar
  • 24/7 front desk
  • Pet friendly

Explore the area

Map
83409 Overseas Hwy, Islamorada, FL, 33036
  • History of Diving Museum
    ‪11 min walk‬
  • Theater of the Sea
    ‪2 min drive‬
  • Windley Key Fossil Reef Geological State Park
    ‪2 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 | 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 | 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 | 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 | 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

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 | 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 | 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

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 | 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 | 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 | 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 | 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

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

Hotel in Matecumbe
At Chesapeake Beach Resort, relax by one of the 2 outdoor swimming pools or spend the day at the private white sand beach where you can enjoy kayaking.
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. 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.

2 outdoor swimming pools are on site along with a private beach.

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 summer activities like kayaking.

A total renovation of this property was completed in January 2020.

Chesapeake Beach Resort is a smoke-free property.

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: midnight
Early check-in subject to availability
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
Late check-out subject to availability
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
  • Late check-out is available for a fee (subject to availability)

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
Minimum Spring Break check-in age is 21 years old
This property accepts credit cards; cash is not accepted

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. 1030 out of 1453 reviews
Rating 8 - Good. 244 out of 1453 reviews
Rating 6 - Okay. 101 out of 1453 reviews
Rating 4 - Poor. 44 out of 1453 reviews
Rating 2 - Terrible. 34 out of 1453 reviews

9.2/10

Cleanliness

9.2/10

Staff & service

8.8/10

Amenities

9.2/10

Property conditions & facilities

8.8/10

Eco-friendliness

Reviews

10/10 Excellent

Kim

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

Fun place with excellent shoreline

The food and bar service near pool and shore line is staffed with excellent people that work hard to make our stay fun. We attended the Super bowl barbecue at the poolside and met new friends. A great place and we plan to visit again. Breakfast was included and the chefs were awesome.
Stayed 3 nights in Feb 2025

6/10 Okay

Darin

Liked: Cleanliness
Stayed 1 night in Feb 2025

10/10 Excellent

Courtney

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

10/10 Excellent

Kim

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

Great stay!

The breakfast at the shore was wonderful with friendly service and plenty of food choices.
Stayed 2 nights in Feb 2025

2/10 Terrible

Melissa

Stayed 3 nights in Feb 2025

10/10 Excellent

andrew wayne

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
Disliked: Staff & service
Fantastic views, and very quiet
Stayed 4 nights in Feb 2025

10/10 Excellent

Crystal

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything about this place was amazing. Staff was so sweet and even set up a superbowl party for all the guests. I would definitely recommend !
Stayed 3 nights in Feb 2025

8/10 Good

thomas

Traveled with partner
Liked: Staff & service, amenities, property conditions & facilities
very nice and friendly staff very accommodating would’ve been nice to have an actual bar or a place to hang out in the afternoon closes at 5 PM, which is a bit of a shame. Otherwise the Place is great very pleased and thank you very much.
Stayed 3 nights in Feb 2025

10/10 Excellent

Kathrine

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

Loved it!

The resort is very clean and the staff are amazing. We encountered many staff during our stay and they were very friendly. Chef Chris in the Sunrise room created delicious made to order omelets. Breakfast was great.
Stayed 7 nights in Jan 2025

10/10 Excellent

kristie

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
I enjoyed my stay. The breakfast was great and outdoor breakfast seating facing the ocean was a great way to start the day. Can’t beat the beach loungers scattered around the property.
Stayed 4 nights in Feb 2025

8/10 Good

Richard

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

10/10 Excellent

Omar

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 5 nights in Oct 2024

10/10 Excellent

Angel

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Beautiful place clean and enjoyable.. don’t hesitate to book in fl keys
Stayed 1 night in Jan 2025

10/10 Excellent

scott

Liked: Cleanliness, staff & service, property conditions & facilities
Great location, staff was great, complementary breakfast was very good. We definitely will stay here again.
Stayed 1 night in Jan 2025

10/10 Excellent

Deepak

Traveled with family and small children
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Expedia’s pictures don’t do justice to beauty of this property. While the room was small, Walls are thin, could hear noises from neighboring rooms. Bathroom was upgraded. However, vibe of the resort and calmness triumpj over all the petty issues. The entire resort has a wonderful vibe, and the beachfront views are breathtaking. The breakfast was fantastic, and the staff were exceptional. I only wish we could have stayed longer! There are plenty of restaurants with different kinds of cuisines in such a small area.

4/10 Poor

Mansi

Disliked: Staff & service, amenities, property conditions & facilities
Good view of the water from the property but not our room. The beds were lumpy and pretty bad for a spring mattress. The phone didn’t work, the TV didn’t work and the walls are as thin as they can be making it noisy. For the $$ we paid per night it was not worth it. The manager never responded and staff dismissed any conversation.
Stayed 1 night in Jan 2025

10/10 Excellent

Jose

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

8/10 Good

Verified traveler

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

Weeding weekend

Went to a weeding in Islamorada and the option of the hotel was ideal
Stayed 1 night in Jan 2025

10/10 Excellent

Peter

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

Island paradise

Great location, great beach, pools and staff.
Stayed 1 night in Jan 2025

8/10 Good

Kei

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
After we realized the heater didn't work in our room, we got upgraded to a villa which was really nice. We'd like to come back in the summer. It's right on the water with a pool and offers all the water sports. The breakfast that's included was really good - omelettes made to order.
Stayed 1 night in Jan 2025

10/10 Excellent

whitney

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

You won’t regret booking.

We loved it here and would definitely go back. Everything was clean. Small bar on site. Free breakfast & Made to order omelets until 11. Outside seating near pool. Outside bathroom with room keep access only adds a nice touch not having to run back to room. Definitely get a room with balcony. We had covered parking. The checkers & chess were nice to drink/chat and hang outside. Room & bathroom were clean.
Stayed 1 night in Jan 2025

10/10 Excellent

Tracy

Liked: Cleanliness, staff & service, property conditions & facilities
Friendly staff, convenient location.
Stayed 2 nights in Jan 2025

10/10 Excellent

Nelson T

Liked: Cleanliness, staff & service, property conditions & facilities
Awesome stay!
Stayed 5 nights in Jan 2025

10/10 Excellent

Laura

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff at the front desk was super helpful. Chris was very attentive and made me a wonderful omelet. The place is beautiful.
Stayed 1 night in Jan 2025

10/10 Excellent

Yuliana

Stayed 1 night in Jan 2025