See all properties

Chesapeake Beach Resort

3.5 star property
Islamorada hotel with 2 outdoor pools and private beach

Choose dates to view prices

Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun-loungers, beach towels
Water view
Balcony
Hypo-allergenic bedding, pillow-top beds, laptop workspace
Aerial view

Reviews

9.2 out of 10
Wonderful
In the heart of Matecumbe, Chesapeake Beach Resort offers a tranquil escape. Enjoy a leisurely breakfast, relax on the private beach with sun loungers and kayaking options or take a refreshing dip in one of the 2 outdoor pools. With multilingual staff and concierge services available to help plan your stay.

Popular amenities

  • Pet-friendly
  • Bar
  • Non-smoking
  • 24/7 front desk

Main amenities (11)

  • Daily housekeeping
  • On a private beach
  • 2 outdoor pools
  • Beach sunloungers
  • Beach towels
  • 24-hour front desk
  • Air conditioning
  • Computer station
  • Multilingual staff
  • Concierge services
  • Kayaking

Feel at home (6)

  • Microwave
  • Private bathroom
  • Cable/satellite TV service
  • Daily housekeeping
  • Coffee/tea maker
  • Blackout curtains
The current price is NZ$560
includes taxes & fees
26 May - 27 May

Room options

Available filters for rooms
Showing 20 of 20 rooms

View all photos for 2-Bedroom Villa

2-Bedroom Villa | Private kitchenette

2-Bedroom Villa

Highlights

Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dishwasher
HDTV
Hypo-allergenic bedding
  • Resort view
  • 60 sq m
  • Sleeps 6
  • 1 King Bed, 1 Double Bed and 1 Double Sofa Bed

View all photos for Standard King

Standard King

Standard King

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout curtains
  • 25 sq m
  • Sleeps 3
  • 1 King Bed

View all photos for King Efficiency Villa

King Efficiency Villa

King Efficiency Villa

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
Dishwasher
  • Resort view
  • 48 sq m
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard Doubles

Standard Doubles

Standard Doubles

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout curtains
  • 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

Highlights

Deck/patio
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Sofa bed - double
  • 29 sq m
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Hearing Impaired Ocean View Queens

Hypo-allergenic bedding, pillow-top beds, laptop workspace

Hearing Impaired Ocean View Queens

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout curtains
  • Ocean view
  • 34 sq m
  • 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

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • Ocean view
  • 50 sq m
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for ADA King Efficiency Villa

ADA King Efficiency Villa

ADA King Efficiency Villa

Highlights

Separate dining area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
HDTV
Hypo-allergenic bedding
  • Resort view
  • 48 sq m
  • 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

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
Dishwasher
  • Ocean view
  • 65 sq m
  • 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

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
  • Ocean view
  • 60 sq m
  • Sleeps 6
  • 2 Queen Beds

View all photos for Ocean View King

Hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Sofa bed - double
  • Ocean view
  • 34 sq m
  • Sleeps 3
  • 1 King Bed

View all photos for Ocean View King Suite

Ocean View King Suite

Ocean View King Suite

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • Ocean view
  • 49 sq m
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout curtains
  • Ocean view
  • 34 sq m
  • Sleeps 4
  • 2 Queen Beds

Ocean View King Efficiency Villa

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dishwasher
HDTV
  • Ocean view
  • 48 sq m
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard Queens

Standard Queens

Standard Queens

Highlights

Deck/patio
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout curtains
  • 29 sq m
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard King Villa

Standard King Villa

Standard King Villa

Highlights

Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • Resort view
  • 30 sq m
  • Sleeps 3
  • 1 King Bed

View all photos for Premium Ocean View King Villa

Premium Ocean View King Villa | Living area

Premium Ocean View King Villa

Highlights

Patio
Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
  • Ocean view
  • 77 sq m
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for ADA Ocean View Queens

ADA Ocean View Queens

ADA Ocean View Queens

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • Ocean view
  • 34 sq m
  • 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

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • Ocean view
  • 50 sq m
  • Sleeps 4
  • 1 King Bed

View all photos for ADA Ocean View King

Hypo-allergenic bedding, pillow-top beds, laptop workspace

ADA Ocean View King

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout curtains
  • Ocean view
  • 34 sq m
  • Sleeps 3
  • 1 King Bed

Similar properties

Exterior

Amara Cay Resort

  • Pool
  • Pet-friendly
  • Free parking
  • Internet access
8.8 out of 10, Excellent, 1,194 reviews
The price is NZ$522
includes taxes & fees
5 May - 6 May
Amara Cay Resort
Mod logo
Sign in to view eligible discounts and perks. More rewards for more adventures!
Sign inSign up, it's free

About the area

Map
83409 Overseas Hwy, Islamorada, FL, 33036

What's nearby

  • History of Diving Museum - 11 min walk - 1.0 km
  • Theater of the Sea - 2 min drive - 1.8 km
  • Windley Key Fossil Reef Geological State Park - 2 min drive - 1.8 km
  • Florida Keys Brewing Co. - 3 min drive - 3.5 km
  • Bud n' Mary's Dive Center - 6 min drive - 6.2 km

Getting around

  • Miami International 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

Situated by the ocean, Chesapeake Beach Resort is a great choice for a stay in Islamorada. Guests can keep active with on-site kayaking. Fellow travellers say great things about the pool and helpful staff.

Languages

English, Spanish

At a glance

DONE

Hotel size

    • 60 rooms
    • Arranged over 2 floors
DONE

Arriving/Leaving

    • Check-in start time: 4:00 PM; check-in end time: midnight
    • Contactless check-in and check-out are available
    • Early check-in subject to availability
    • Late check-in subject to availability
    • Minimum check-in age – 18
    • Check-out time is 11 AM
    • Contactless check-out
    • Late check-out subject to availability
DONE

Special check-in instructions

    • Front desk staff will greet guests on arrival at the property
DONE

Required at check-in

    • Credit card required for incidental charges
    • Government-issued photo ID may be required
    • Minimum check-in age is 18
    • Minimum Spring Break check-in age is 21
DONE

Pets

    • Pets allowed (2 total, up to 23 kg per pet)*
    • Service animals welcome
    • Restrictions apply*
LOCAL_PARKING

Parking

    • Wheelchair-accessible parking on site
    • On-site parking includes off-street options
DONE

Other information

    • Smoke-free property

Property amenities

Travelling with children

  • Pool gate
  • Outlet covers
  • Fence around the pool

What to do

  • On a private beach
  • Kayaking
  • Jet-skiing nearby
  • Snorkelling nearby

Working away

  • Computer station

Services

  • 24-hour front desk
  • Concierge services
  • Multilingual staff
  • Beach sunloungers
  • Beach towels
  • Pool loungers

Facilities

  • 9 buildings/towers
  • Built in 2020
  • 2 outdoor pools
  • Traditional architecture

Accessibility

  • Braille/raised signage
  • Wheelchair-accessible parking
  • Assistive listening devices available
  • Wheelchair-accessible public bathroom
  • Wheelchair-accessible pool
  • Visual alarms in hallways
  • Handrails in hallways
  • Handrails in stairwells
  • Closed-captioned TV
  • Lever door handles
  • Upper floors accessible by stairs only
  • Well-lit path to entrance
  • Pool hoist on site

Room amenities

Be entertained

  • 43-inch flat-screen TV
  • Cable TV channels

Home comfort

  • Air conditioning
  • Ceiling fan
  • Coffee/tea maker
  • Iron/ironing board

Sleep well

  • Hypo-allergenic bedding
  • Blackout curtains
  • Pillow-top mattress
  • Bed sheets provided

Freshen up

  • Private bathroom
  • Shower only
  • Designer toiletries
  • Hairdryer
  • Towels
  • Toilet paper

Stay connected

  • Laptop-friendly workspace
  • Free local calls

Food and drink

  • Microwave

More

  • Daily housekeeping
  • Access via exterior corridors

Fees & policies

Optional extras

  • Late check-out can be arranged for an extra charge (subject to availability)

Pets

  • Service animals exempt from fees
  • Pet deposit: USD 50.00 per stay
  • Pets are allowed for an extra charge of USD 50.00 per accommodation, per night

Pool, spa, & gym (if applicable)

  • Pool access available from 7:00 AM to 10:30 PM
  • Children under 16 years old are not allowed in the swimming pool without adult supervision

Policies

Construction is underway at a neighbouring building and there may be noise disturbance from the construction work.
Some facilities may have restricted access. Guests can contact the property for details using the contact information on the booking confirmation.
This property does not have lifts.
This property accepts credit cards. Cash is not accepted.
Credit cards accepted: Visa, Mastercard, American Express, Discover

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

Frequently asked questions

Does Chesapeake Beach Resort offer free cancellation for a full refund?

Yes, Chesapeake Beach Resort does have fully refundable room rates available to book on our site. If you’ve booked a fully refundable room rate, this can be cancelled up to a few days before check-in, depending on the property's cancellation policy. Just make sure that you check this property's cancellation policy for the exact terms and conditions.

Is there a pool at Chesapeake Beach Resort?

Yes, there are 2 outdoor pools. Guests have pool access from 7:00 AM to 10:30 PM.

Are pets allowed at Chesapeake Beach Resort?

Yes, pets are welcome, with a limit of 2 total and maximum weight of 23 kg per pet. There's a charge of USD 50.00 per accommodation, per night, and there's also a deposit of USD 50.00 per stay. Service animals are exempt from fees.

What are the check-in and check-out times at Chesapeake Beach Resort?

Check-in start time: 4:00 PM; check-in end time: midnight. Check-out time is 11 AM. Late check-out is available for a charge (subject to availability). Contactless social distancing and check-out are available.

What is there to do at Chesapeake Beach Resort and nearby?

Have fun during the warmer months with activities such as kayaking. Enjoy a swim in one of the 2 outdoor swimming pools or use the hotel's other amenities, which include a private beach.

What's the area around Chesapeake Beach Resort like?

Chesapeake Beach Resort is in Matecumbe, a short 11-minute walk from History of Diving Museum. Travellers give top marks for the hotel's prime location.

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Chesapeake Beach Resort Reviews

Reviews

9.2

Wonderful

9.2/10

Cleanliness

9.2/10

Staff & service

8.8/10

Amenities

9.2/10

Property conditions & facilities

8.8/10

Eco-friendliness

Popular mentions

Room
Service staff
View
Beach
Location
Breakfast
Restaurant
Kayaking
Bed
Hot Tub

What guests liked

  • The beach area was beautiful, private, and perfect for relaxation with plenty of shade and scenic views. (132 reviews)
  • Breakfast was a highlight with a great selection, friendly service, and made-to-order options like omelets. (86 reviews)
  • The pool area was clean, convenient, and enjoyable with many guests praising its beauty and amenities. (79 reviews)
From real guest reviews summarized by AI.

Reviews

8/10 Very good

Very nice location and grounds.
Scot, 2-night trip

10/10 Exceptional

Great stay
Christopher, 3-night trip

10/10 Exceptional

Awesome stay!
Nelson T, 5-night trip

10/10 Exceptional

Great stay!

The breakfast at the shore was wonderful with friendly service and plenty of food choices.
Kim, 2-night trip

10/10 Exceptional

Loved the location, beach area, breakfast and STAFF
Jeannie, 4-night trip

10/10 Exceptional

Beautiful location, helpful friendly staff, great breakfast , comfy robes, pools, jacuzzi, kayaks and paddle boards.
Karen, 1-night trip

10/10 Exceptional

Beautiful place clean and enjoyable.. don’t hesitate to book in fl keys
Angel, 1-night trip

10/10 Exceptional

Great staff, beautiful property, very welcoming and helpful
Heather, 1-night trip

10/10 Exceptional

Lovely beach resort in Islamorada Two large pools, location is great with its own little private beach
Sandra, 1-night trip

10/10 Exceptional

Friendly staff, convenient location.
Tracy, 2-night trip

10/10 Exceptional

Most amazing views
Derick, 2-night trip

8/10 Very good

Nice Resort for the Money

I was looking for a one night stay in Islamorada that wouldn't break the bank, but still be comfortable and clean. The Chesapeake Resort fit the bill! Rooms have been updated and resort was clean and quiet. It has a nice area for sunning and two pools. There isn't a restaurant or bar on site, but they do offer a very good continental breakfast with made to order eggs and a bar cart with quality liquor, beer, and wine. Also, two restaurants are within walking distance.
Amy, 1-night trip

10/10 Exceptional

Island paradise

Great location, great beach, pools and staff.
Peter, 1-night trip

8/10 Very good

Great beach and clean big well furnished rooms
Luca, 2-night trip

10/10 Exceptional

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.
kristie, 4-night trip

10/10 Exceptional

Excellent place

I love this place, every stay is truly a wonderful experience. The staff is always helpful and friendly. The grounds are really pretty as well.
cheryl, 4-night trip

10/10 Exceptional

Awesome place to stay in islamorada. Quiet private beach for relaxation
Joseph, 2-night trip

10/10 Exceptional

So beautiful, quiet, warm pools, excellent breakfast, views, and reception was amazing! Highly recommend!
Holly, 1-night trip

10/10 Exceptional

Very nice property. Staff was nice, room was nice and clean, beach area was beautiful, pool was warm, dinning options near
Riceldys, 1-night trip

10/10 Exceptional

Good hotel
Felix, 1-night trip

10/10 Exceptional

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.
Kim, 3-night trip

10/10 Exceptional

Absolutely gorgeous, clean, friendly staff, and great location
Amy, 4-night trip

10/10 Exceptional

Absolutely great place with beach access!
mariana, 3-night trip

10/10 Exceptional

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.
Kathrine, 7-night trip

10/10 Exceptional

Beautiful place , we was satisfied , beautiful beach .
Peter, 4-night trip