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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.
Reviews
9.2 out of 10
Wonderful
Popular amenities
Room options
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Showing 20 of 20 rooms
View all photos for 2-Bedroom Villa

2-Bedroom Villa
10.0 out of 10
Exceptional
(1 review)
Highlights
Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
Dishwasher
HDTV
Hypo-allergenic bedding
View all photos for Standard King

Standard King
9.4 out of 10
Exceptional
(29 reviews)
Highlights
Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillowtop bed
View all photos for King Efficiency Villa

King Efficiency Villa
10.0 out of 10
Exceptional
(2 reviews)
Highlights
Separate dining area
Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
Dining table
Dishwasher
View all photos for Standard Doubles

Standard Doubles
9.2 out of 10
Wonderful
(86 reviews)
Highlights
Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillowtop bed
View all photos for Standard King with Sleeper Sofa

Standard King with Sleeper Sofa
9.0 out of 10
Wonderful
(19 reviews)
Highlights
Deck/patio
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillowtop bed
View all photos for Hearing Impaired Ocean View Queens

Hearing Impaired Ocean View Queens
10.0 out of 10
Exceptional
(2 reviews)
Highlights
Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillowtop bed
View all photos for Hearing Impaired Ocean View King Suite

Hearing Impaired Ocean View King Suite
8.6 out of 10
Excellent
(4 reviews)
Highlights
Balcony
Separate sitting area
Air conditioning
Free cribs/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
View all photos for ADA King Efficiency Villa

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
View all photos for Premium 1-Bedroom Ocean View Villa

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
View all photos for Deluxe Ocean View Two Queen Suite

Deluxe Ocean View Two Queen Suite
8.8 out of 10
Excellent
(9 reviews)
Highlights
Balcony
Separate sitting area
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
View all photos for Ocean View King

Ocean View King
9.6 out of 10
Exceptional
(79 reviews)
Highlights
Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillowtop bed
View all photos for Ocean View King Suite

Ocean View King Suite
9.4 out of 10
Exceptional
(15 reviews)
Highlights
Balcony
Separate sitting area
Air conditioning
Free cribs/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
View all photos for Ocean View Queens

Ocean View Queens
9.8 out of 10
Exceptional
(43 reviews)
Highlights
Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillowtop 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
View all photos for Standard Queens

Standard Queens
9.4 out of 10
Exceptional
(54 reviews)
Highlights
Deck/patio
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillowtop bed
View all photos for Standard King Villa

Standard King Villa
Highlights
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillowtop bed
View all photos for Premium Ocean View King Villa

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
View all photos for ADA Ocean View Queens

ADA Ocean View Queens
9.0 out of 10
Wonderful
(7 reviews)
Highlights
Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillowtop bed
View all photos for ADA Ocean View King Suite

ADA Ocean View King Suite
8.0 out of 10
Very good
(3 reviews)
Highlights
Balcony
Separate sitting area
Air conditioning
Free cribs/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
View all photos for ADA Ocean View King

ADA Ocean View King
8.6 out of 10
Excellent
(17 reviews)
Highlights
Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillowtop bed
You may also like
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Cheeca Lodge & Spa
Matecumbe
- On private beach
- Pool
- Hot tub
- Spa
9.0 out of 10, Wonderful, 1,158 reviews
The price is CA $220
CA $341 total
includes taxes & fees
Aug 24 - Aug 25
Sign in to view eligible discounts and perks. More rewards for more adventures!
About the area
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.

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
- Florida Keys Brewing Co. - 4 min drive - 4.0 km
- Bud n' Mary's Dive Center - 7 min drive - 7.3 km
Getting around
Restaurants
- Tiki Bar - 13 min walk
- Lorelei Restaurant & Cabana Bar - 3 min drive
- Wendy's - 2 min drive
- Whale Harbor Restaurant Marina - 2 min walk
- Starbucks - 15 min walk
About this property
Property amenities
Room amenities
Policies
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
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Chesapeake Beach Resort Reviews
Reviews
9.2
Wonderful
9.4/10
Cleanliness
9.2/10
Staff & service
9.0/10
Amenities
9.2/10
Property conditions & facilities
9.0/10
Eco-friendliness
Reviews
Aug 17, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Stayed 1 night in Aug 2025
10/10 Excellent
Ruslan
Aug 7, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Ruslan
Stayed 6 nights in Aug 2025
10/10 Excellent
Kai
Aug 22, 2025
Liked: Cleanliness, amenities, property conditions & facilities

Kai
Stayed 5 nights in Aug 2025
10/10 Excellent
Nicholas
Jul 28, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nicholas
Stayed 2 nights in Jul 2025
10/10 Excellent
Maricela
Aug 10, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Maricela
Stayed 1 night in Aug 2025
10/10 Excellent
Stacy
Aug 13, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Stacy
Stayed 3 nights in Aug 2025
10/10 Excellent
Nilda
Aug 10, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nilda
Stayed 2 nights in Aug 2025
10/10 Excellent
Francisco
Jul 30, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Francisco
Stayed 1 night in Jul 2025
10/10 Excellent
Laura
Aug 10, 2025
Liked: Cleanliness, staff & service, property conditions & facilities
Laura
Stayed 1 night in Aug 2025
10/10 Excellent
Judy
Aug 11, 2025
Liked: Cleanliness, staff & service
Judy
Stayed 1 night in Jul 2025
8/10 Good
Melissa
Aug 16, 2025
Liked: Cleanliness, amenities
Melissa
Stayed 4 nights in Aug 2025
10/10 Excellent
John
Aug 11, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
John
Stayed 2 nights in Aug 2025
10/10 Excellent
Ashleigh
Jul 2, 2025
Liked: Cleanliness, amenities, property conditions & facilities
Ashleigh
Stayed 3 nights in Jun 2025
8/10 Good
Michael
Aug 15, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Michael
Stayed 3 nights in Aug 2025
10/10 Excellent
Mario
Aug 1, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Mario
Stayed 1 night in Jul 2025
10/10 Excellent
Mikayla
Jun 4, 2025
Liked: Cleanliness, amenities, property conditions & facilities
Mikayla
Stayed 3 nights in Jun 2025
10/10 Excellent
EDEN
Aug 5, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities


EDEN
Stayed 2 nights in Aug 2025
10/10 Excellent
Evelyn
Jul 16, 2025
Liked: Cleanliness, amenities, property conditions & facilities
Evelyn
Stayed 2 nights in Jul 2025
10/10 Excellent
James
Aug 21, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
James
Stayed 2 nights in Aug 2025
10/10 Excellent
Shelly
Jun 16, 2025
Liked: Cleanliness, property conditions & facilities
Shelly
Stayed 1 night in Jun 2025
10/10 Excellent
TANYA
Aug 10, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
TANYA
Stayed 1 night in Aug 2025
8/10 Good
Jason David
Jul 23, 2025
Liked: Cleanliness, staff & service, property conditions & facilities
Jason David
Stayed 2 nights in Jul 2025
10/10 Excellent
Shelby
Aug 3, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Shelby
Stayed 5 nights in Jul 2025
10/10 Excellent
Monte
Jun 22, 2025
Monte
Stayed 2 nights in Jun 2025
10/10 Excellent
Maria
Jul 2, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Maria
Stayed 2 nights in Jun 2025