Chesapeake Beach Resort

Hotel on the beach, with 2 outdoor pools

Choose dates to view prices

Where to?

Dates

October 2025

November 2025

Private beach, white sand, sun loungers, beach towels

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

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

Bar
24/7 front desk

P11,284 total

includes taxes & fees

Oct 2 - Oct 3

Room options

Check availability for these dates

Tonight

Sep 30 - Oct 1

Tomorrow

Oct 1 - Oct 2

All rooms

1 bed

2 beds

3+ beds

Showing 20 of 20 rooms

2-Bedroom Villa

Exceptional

Highlights

Separate sitting area

Air conditioning

Free cribs/infant beds

Kitchenette

Full-sized refrigerator/freezer

Dishwasher

HDTV

Hypo-allergenic bedding

60 sq m
2 bedrooms
Resort view
Sleeps 6
1 King Bed, 1 Double 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

Blackout drapes/curtains

25 sq m
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

48 sq m
1 bedroom
Resort view
Sleeps 4
1 King Bed and 1 Double Sofa Bed

Standard Doubles

Wonderful

Highlights

Balcony

Air conditioning

Free cribs/infant beds

Mini-fridge

HDTV

Hypo-allergenic bedding

Renovated in 2020

Blackout drapes/curtains

25 sq m
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 - double

29 sq m
Sleeps 4
1 King Bed and 1 Double Sofa Bed

Hearing Impaired Ocean View Queens

Exceptional

Highlights

Balcony

Air conditioning

Free cribs/infant beds

Mini-fridge

HDTV

Hypo-allergenic bedding

Renovated in 2020

Blackout drapes/curtains

34 sq m
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

50 sq m
1 bedroom
Ocean view
Sleeps 4
1 King Bed and 1 Queen 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

48 sq m
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

65 sq m
1 bedroom
Ocean view
Sleeps 6
2 Double Beds and 1 Double 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

60 sq m
1 bedroom
Ocean view
Sleeps 6
2 Queen Beds

Ocean View King

Exceptional

Highlights

Balcony

Air conditioning

Free cribs/infant beds

Mini-fridge

HDTV

Hypo-allergenic bedding

Renovated in 2020

Sofa bed - double

34 sq m
Ocean view
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

49 sq m
1 bedroom
Ocean view
Sleeps 4
1 King Bed and 1 Queen Sofa Bed

Ocean View Queens

Exceptional

Highlights

Balcony

Air conditioning

Free cribs/infant beds

Mini-fridge

HDTV

Hypo-allergenic bedding

Renovated in 2020

Blackout drapes/curtains

34 sq m
Ocean view
Sleeps 4
2 Queen Beds

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

48 sq m
1 bedroom
Ocean view
Sleeps 4
1 King Bed and 1 Double Sofa Bed

Standard Queens

Exceptional

Highlights

Deck/patio

Air conditioning

Free cribs/infant beds

Mini-fridge

HDTV

Hypo-allergenic bedding

Renovated in 2020

Blackout drapes/curtains

29 sq m
Sleeps 4
2 Queen Beds

Standard King Villa

Highlights

Air conditioning

Free cribs/infant beds

Kitchenette

Full-sized refrigerator/freezer

HDTV

Hypo-allergenic bedding

Renovated in 2020

Separate bedroom

30 sq m
1 bedroom
Resort view
Sleeps 3
1 King 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

77 sq m
1 bedroom
Ocean view
Sleeps 4
1 King Bed and 1 Double Sofa 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

34 sq m
1 bedroom
Ocean view
Sleeps 4
2 Queen Beds

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

50 sq m
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

Blackout drapes/curtains

34 sq m
Ocean view
Sleeps 3
1 King Bed

About the neighborhood

Located on a private beach, Chesapeake Beach Resort is in Matecumbe, a neighborhood in Islamorada. Hurricane Monument and Indian Key Historic State Park are local landmarks, and some of the area's activities can be experienced at Islamorada Brewery & Distillery and Florida Keys Brewing Co.. With jet skiing and snorkeling nearby, you'll find plenty of adventures in the water.

Visit our Islamorada travel guide

83409 Overseas Hwy, Islamorada, FL, 33036

What's nearby

History of Diving Museum - 12 min walk - 1.1 km
Windley Key Fossil Reef Geological State Park - 2 min drive - 2.0 km
Theater of the Sea - 2 min drive - 2.4 km
Islamorada Brewery & Distillery - 2 min drive - 2.4 km
Florida Keys Brewing Co. - 4 min drive - 4.0 km

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
‪Starbucks - ‬15 min walk
‪Whale Harbor Buffet - ‬2 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, a computer station, and concierge services
A 24-hour front desk, beach towels, and coffee/tea in the lobby
Multilingual staff and smoke-free premises
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

P12,643 total

includes taxes & fees

Oct 5 - Oct 6

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

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

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 Sep 30, 2025, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on Oct 2, 2025 start from P 7,123.95, 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).