Chesapeake Beach Resort

Hotel on the beach, with 2 outdoor pools

Choose dates to view prices

Where to?

Dates

November 2025

December 2025

Private beach, white sand, sun loungers, beach towels

Chesapeake Beach Resort offers a quiet escape in Matecumbe. Start your day with a leisurely breakfast, then head to the private beach with sun loungers and kayaking. Enjoy two outdoor pools, while multilingual staff and concierge services help plan the perfect stay.

Wonderful

Popular amenities

24/7 front desk
Bar
Breakfast included

Room options

Check availability for these dates

Tonight

Oct 28 - Oct 29

Tomorrow

Oct 29 - Oct 30

All rooms

1 bed

2 beds

3+ beds

Showing 20 of 20 rooms

Ocean View Queens

Exceptional

Highlights

Balcony

Air conditioning

Free cribs/infant beds

Mini-fridge

HDTV

Hypo-allergenic bedding

Renovated in 2020

Separate bedroom

366 sq ft
Ocean view
Sleeps 4
2 Queen Beds

1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King

Exceptional

Highlights

Balcony

Air conditioning

Free cribs/infant beds

Mini-fridge

HDTV

Hypo-allergenic bedding

Renovated in 2020

Sofa bed

364 sq ft
Ocean view
Sleeps 3
1 King Bed

ADA Ocean View King Suite

Very good

Highlights

Balcony

Separate sitting area

Air conditioning

Free cribs/infant beds

Mini-fridge

Dining table

HDTV

Hypo-allergenic bedding

540 sq ft
1 bedroom
Ocean view
Sleeps 4
1 King Bed

ADA Ocean View King

Excellent

Highlights

Balcony

Air conditioning

Free cribs/infant beds

Mini-fridge

HDTV

Hypo-allergenic bedding

Renovated in 2020

Separate bedroom

364 sq ft
Ocean view
Sleeps 3
1 King Bed

ADA Ocean View Queens

Wonderful

Highlights

Balcony

Air conditioning

Free cribs/infant beds

Mini-fridge

HDTV

Hypo-allergenic bedding

Renovated in 2020

Separate bedroom

366 sq ft
1 bedroom
Ocean view
Sleeps 4
2 Queen Beds

Hearing Impaired Ocean View Queens

Exceptional

Highlights

Balcony

Air conditioning

Free cribs/infant beds

Mini-fridge

HDTV

Hypo-allergenic bedding

Renovated in 2020

Separate bedroom

366 sq ft
Ocean view
Sleeps 4
2 Queen Beds

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

Hearing Impaired Ocean View King Suite

Excellent

Highlights

Balcony

Separate sitting area

Air conditioning

Free cribs/infant beds

Mini-fridge

Dining table

HDTV

Hypo-allergenic bedding

540 sq ft
1 bedroom
Ocean view
Sleeps 4
1 King Bed and 1 Queen Sofa Bed

Standard Queens

Exceptional

Highlights

Deck/patio

Air conditioning

Free cribs/infant beds

Mini-fridge

HDTV

Hypo-allergenic bedding

Renovated in 2020

Separate bedroom

307 sq ft
Sleeps 4
2 Queen Beds

Standard Doubles

Wonderful

Highlights

Balcony

Air conditioning

Free cribs/infant beds

Mini-fridge

HDTV

Hypo-allergenic bedding

Renovated in 2020

Separate bedroom

272 sq ft
Sleeps 4
2 Double Beds

Standard King with Sleeper Sofa

Wonderful

Highlights

Deck/patio

Air conditioning

Free cribs/infant beds

Mini-fridge

HDTV

Hypo-allergenic bedding

Renovated in 2020

Sofa bed

307 sq ft
Sleeps 4
1 King Bed and 1 Double Sofa Bed

Standard King

Exceptional

Highlights

Balcony

Air conditioning

Free cribs/infant beds

Mini-fridge

HDTV

Hypo-allergenic bedding

Renovated in 2020

Separate bedroom

272 sq ft
Sleeps 3
1 King Bed

Ocean View King Suite

Exceptional

Highlights

Balcony

Separate sitting area

Air conditioning

Free cribs/infant beds

Mini-fridge

Dining table

HDTV

Hypo-allergenic bedding

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

Deluxe Ocean View Two Queen Suite

Excellent

Highlights

Balcony

Separate sitting area

Air conditioning

Free cribs/infant beds

Mini-fridge

HDTV

Hypo-allergenic bedding

Renovated in 2020

650 sq ft
1 bedroom
Ocean view
Sleeps 6
2 Queen Beds

2-Bedroom Villa

Exceptional

Highlights

Separate sitting area

Air conditioning

Free cribs/infant beds

Kitchenette

Full-sized refrigerator/freezer

Dishwasher

HDTV

Hypo-allergenic bedding

646 sq ft
2 bedrooms
Resort view
Sleeps 6
1 King Bed, 1 Double Bed and 1 Double Sofa Bed

Standard King Villa

Highlights

Air conditioning

Free cribs/infant beds

Kitchenette

Full-sized refrigerator/freezer

HDTV

Hypo-allergenic bedding

Renovated in 2020

Separate bedroom

323 sq ft
1 bedroom
Resort view
Sleeps 3
1 King Bed

King Efficiency Villa

Exceptional

Highlights

Separate dining area

Separate sitting area

Air conditioning

Free cribs/infant beds

Kitchenette

Full-sized refrigerator/freezer

Dining table

Dishwasher

517 sq ft
1 bedroom
Resort view
Sleeps 4
1 King Bed and 1 Double Sofa Bed

ADA King Efficiency Villa

Highlights

Separate dining area

Air conditioning

Free cribs/infant beds

Kitchenette

Full-sized refrigerator/freezer

Dining table

HDTV

Hypo-allergenic bedding

517 sq ft
1 bedroom
Resort view
Sleeps 3
1 King Bed

Premium 1-Bedroom Ocean View Villa

Highlights

Separate dining area

Separate sitting area

Air conditioning

Free cribs/infant beds

Kitchenette

Full-sized refrigerator/freezer

Dining table

Dishwasher

700 sq ft
1 bedroom
Ocean view
Sleeps 6
2 Double Beds and 1 Double Sofa Bed

Premium Ocean View King Villa

Highlights

Patio

Separate dining area

Separate sitting area

Air conditioning

Free cribs/infant beds

Kitchenette

Full-sized refrigerator/freezer

Dining table

829 sq ft
1 bedroom
Ocean view
Sleeps 4
1 King Bed and 1 Double Sofa Bed

Ocean View King Efficiency Villa

Highlights

Separate dining area

Separate sitting area

Air conditioning

Free cribs/infant beds

Kitchenette

Full-sized refrigerator/freezer

Dishwasher

HDTV

517 sq ft
1 bedroom
Ocean view
Sleeps 4
1 King Bed and 1 Double Sofa Bed

About the neighborhood

83409 Overseas Hwy, Islamorada, FL, 33036

What's nearby

History of Diving Museum - 12 min walk - 0.7 miles
Windley Key Fossil Reef Geological State Park - 2 min drive - 1.3 miles
Theater of the Sea - 2 min drive - 1.5 miles
Islamorada Brewery & Distillery - 2 min drive - 1.5 miles
Florida Keys Brewing Co. - 4 min drive - 2.5 miles

Getting around

Miami Intl. Airport (MIA) - 91 min drive

Restaurants

‪Tiki Bar - ‬13 min walk
‪Lorelei Restaurant & Cabana Bar - ‬3 min drive
‪Wendy's - ‬2 min drive
‪Wahoo's Bar & Grill - ‬2 min walk
‪Starbucks - ‬15 min walk

About this property

Chesapeake Beach Resort

Remodeled hotel, renovated in 2020 and located in Matecumbe

Free continental breakfast, a marina, and a bar are just a few of the amenities provided at Chesapeake Beach Resort. With a private beach, sun loungers, and kayaking, this hotel is the perfect place to soak up some sun. Enjoy onsite activities like boat tours and fishing. Stay connected with free in-room WiFi.

You'll also enjoy the following perks during your stay:

2 outdoor pools along with sun loungers
Free bicycle rentals, beach towels, and a 24-hour front desk
A computer station, coffee/tea in the lobby, and multilingual staff
Smoke-free premises and concierge services
Guest reviews give top marks for the breakfast, beach locale, and pool

Room features

All 60 rooms offer comforts such as laptop-friendly workspaces and air conditioning, in addition to perks like free WiFi. Guest reviews speak positively of the clean, spacious rooms at the property.

More amenities include:

Hypo-allergenic bedding and pillowtop mattresses
Designer toiletries, showers, and hair dryers
43-inch HDTVs with cable channels
Wardrobes/closets, microwaves, and coffee/tea makers

Similar properties

On private beach
Pool
Pet friendly
Restaurant

$211 nightly

Nov 2 - Nov 3

Total with taxes and fees

Private beach, sun loungers, beach towels, scuba diving

On private beach
Pool
Pet friendly
Free WiFi

$262 nightly

Nov 3 - Nov 4

Total with taxes and fees

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

Frequently asked questions

Does Chesapeake Beach Resort have a pool?

Yes, this property has 2 outdoor pools. Pool access is from 7:00 AM–10:30 PM.

How much does it cost to stay at Chesapeake Beach Resort?

As of Oct 28, 2025, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on Oct 29, 2025 start from $111.49, excluding taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Chesapeake Beach Resort pet-friendly?

Yes, this property allows pets (limit 2 total) with a maximum weight of up to 50 lbs per pet. There's a deposit of USD 50.00 per stay and a fee of USD 50.00 per accommodation, per night. Service animals are exempt from fees. Some restrictions may apply, so please contact the property for more details.

What time is check-in at Chesapeake Beach Resort?

Check-in start time: 4:00 PM; Check-in end time: 3:00 AM. Late check-in is available during limited hours.

What time is check-out at Chesapeake Beach Resort?

Check-out is at 11 AM. Late check-out is available for a fee.

Where is Chesapeake Beach Resort located?

Nestled on the beach, this Matecumbe hotel is within 1 mi (2 km) of History of Diving Museum and Windley Key Fossil Reef Geological State Park. Islamorada Brewery & Distillery and Keys History & Discovery Center are also within 2 mi (3 km).

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Chesapeake Beach Resort Reviews

9.2

Wonderful

9.4

Cleanliness

9.0

Amenities

9.2

Staff & service

9.0

Eco-friendliness

9.2

Property conditions & facilities

10/10 Excellent

Carl

Sep 28, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Wonderful property, breakfast was awesome

Stayed 1 night in Sep 2025

10/10 Excellent

Aloke

Oct 12, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Great place, ambience, people and peacefull

Stayed 3 nights in Oct 2025

10/10 Excellent

Cynthia

Oct 19, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

We had a great experience at the Chesapeake!

Stayed 2 nights in Oct 2025

10/10 Excellent

garry

Oct 18, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Resort offered alot considering it was somewhat smaller. Excellent staff and rooms/amenities..will definitely go back.

Stayed 3 nights in Oct 2025

10/10 Excellent

Keziah

Oct 9, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Love that its pet friendly, breakfast is amazing and LOVE that its 4 hours, clean and right next to best seafood buffet- whale harbor.

Stayed 4 nights in Sep 2025

10/10 Excellent

Alisha

Oct 20, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Everyone was so nice and helpful at this resort!!! I had such an amazing time and would definitely recommend to any family & friends!!!

Stayed 1 night in Oct 2025

8/10 Good

Britnee

Sep 28, 2025

Liked: Amenities

Beautiful resort with easy going staff

Stayed 1 night in Sep 2025

10/10 Excellent

Sherry

Oct 10, 2025

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

We loved it here ..

Stayed 2 nights in Oct 2025

10/10 Excellent

Rob

Oct 16, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

A good peaceful fishing area which is my main reason for staying there.The room was very clean and a bit on the small side.The location of this resort is great.

Stayed 2 nights in Oct 2025

10/10 Excellent

JOSE

Oct 17, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Clean room | Great Outdoor pool | Amazing view

Stayed 5 nights in Oct 2025

10/10 Excellent

Vickie

Oct 14, 2025

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

Love this place. Great beach/pool. Lovely room with great bathroom. Unbelievable view of the sunrise over the water from our balcony

Stayed 4 nights in Oct 2025

8/10 Good

Victoria

Sep 1, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Great location, clean rooms, great amenities and the staff is very friendly.

Stayed 3 nights in Aug 2025

10/10 Excellent

Daniel

Aug 30, 2025

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

Great place

Stayed 1 night in Aug 2025

10/10 Excellent

Annia

Sep 28, 2025

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

Summer

Sep 6, 2025

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

Clean, great staff

Stayed 1 night in Sep 2025

10/10 Excellent

nancy Rioseco

Sep 25, 2025

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

Ruslan

Aug 7, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Great place to stay, safe and quiet

Stayed 6 nights in Aug 2025

10/10 Excellent

Hermes

Sep 29, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Excellent recommendation for a small budget.

Stayed 3 nights in Sep 2025

10/10 Excellent

STANLEY

Aug 17, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Excellent location on the ocean and everything was really perfect. will stay there again

Stayed 1 night in Aug 2025

10/10 Excellent

ID

Oct 13, 2025

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

The pools where very clean and very comfy, the place is keep very clean. Thank you.

Stayed 2 nights in Oct 2025

10/10 Excellent

Raymond

Oct 25, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

For just choosing a property off the internet, we hit gold!!! The staff, the room, the amenities, the view, the tw9 restaurants and bars next door were beyond belief! We almost incurred a flight change fee to stay longer! We will be back!

Stayed 1 night in Oct 2025

8/10 Good

Gloria

Sep 2, 2025

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

Excellent view and nice people

Stayed 2 nights in Aug 2025

8/10 Good

Mayrene

Sep 4, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Nice place

Stayed 1 night in Aug 2025

10/10 Excellent

francine

Sep 27, 2025

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

Keziah

Oct 9, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

I had a wonderful stay here with my pet! The hotel is super pet-friendly, which made our trip so easy and enjoyable. There’s plenty of parking, and the view from our room was amazing. I also loved that my favorite buffet was right in the parking lot next door — total bonus! Perfect spot for anyone who enjoys relaxing by the water and doing a little fishing too. Highly recommend!