Chesapeake Beach Resort
Hotel on the beach, with 2 outdoor pools
Choose dates to view prices
Photo gallery for Chesapeake Beach Resort





Reviews
9.2 out of 10
Wonderful
Popular amenities
Explore the area

83409 Overseas Hwy, Islamorada, FL, 33036
- Place, Windley Key Fossil Reef Geological State Park2 min drive
- Place, Theater of the Sea2 min drive
- Place, Florida Keys Brewing Co.4 min drive
Room options
View all photos for Ocean View Queens

Ocean View Queens
9.8 out of 10
Exceptional
(43 reviews)
View all photos for Ocean View King

Ocean View King
9.4 out of 10
Exceptional
(81 reviews)
View all photos for ADA Ocean View King Suite

ADA Ocean View King Suite
8.0 out of 10
Very good
(3 reviews)
View all photos for ADA Ocean View King

ADA Ocean View King
8.6 out of 10
Excellent
(17 reviews)
View all photos for ADA Ocean View Queens

ADA Ocean View Queens
9.0 out of 10
Wonderful
(7 reviews)
View all photos for Hearing Impaired Ocean View Queens

Hearing Impaired Ocean View Queens
10.0 out of 10
Exceptional
(2 reviews)
View all photos for Hearing Impaired Ocean View King Suite

Hearing Impaired Ocean View King Suite
8.6 out of 10
Excellent
(4 reviews)
View all photos for Standard Queens

Standard Queens
9.4 out of 10
Exceptional
(55 reviews)
View all photos for Standard Doubles

Standard Doubles
9.2 out of 10
Wonderful
(88 reviews)
View all photos for Standard King with Sleeper Sofa

Standard King with Sleeper Sofa
9.0 out of 10
Wonderful
(21 reviews)
View all photos for Standard King

Standard King
9.4 out of 10
Exceptional
(29 reviews)
View all photos for Ocean View King Suite

Ocean View King Suite
9.4 out of 10
Exceptional
(16 reviews)
View all photos for Deluxe Ocean View Two Queen Suite

Deluxe Ocean View Two Queen Suite
8.8 out of 10
Excellent
(9 reviews)
View all photos for 2-Bedroom Villa

2-Bedroom Villa
10.0 out of 10
Exceptional
(1 review)
View all photos for Standard King Villa

Standard King Villa
View all photos for King Efficiency Villa

King Efficiency Villa
10.0 out of 10
Exceptional
(2 reviews)
View all photos for ADA King Efficiency Villa

ADA King Efficiency Villa
View all photos for Premium 1-Bedroom Ocean View Villa

Premium 1-Bedroom Ocean View Villa
View all photos for Premium Ocean View King Villa

Premium Ocean View King Villa
Ocean View King Efficiency Villa
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Pines & Palms Resort
Matecumbe
- On private beach
- Pool
- Parking included
- Free WiFi
9.2 out of 10, Wonderful, 1,006 reviews
$228 nightly
The price is $257
Oct 30 - Oct 31
Total with taxes and fees
About the neighborhood
About this property
Chesapeake Beach Resort
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Amara Cay Resort
Amara Cay Resort
- On private beach
- Pool
- Pet friendly
- Restaurant
8.8 out of 10, Excellent, 1,271 reviews
$211 nightly
The price is $238
Nov 2 - Nov 3
Total with taxes and fees
Property amenities
Room amenities
Policies
Important information
Frequently asked questions
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
Jul 30, 2025
Liked: Amenities
Stayed 1 night in Jul 2025
10/10 Excellent
Francisco
Traveled with family
Jul 30, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Francisco
Stayed 1 night in Jul 2025
8/10 Good
vickie
Traveled with family
Jul 28, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
vickie
Stayed 1 night in Jul 2025
10/10 Excellent
Nicholas
Traveled with family
Jul 28, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nicholas
Stayed 2 nights in Jul 2025
10/10 Excellent
Adam
Traveled with family
Jul 25, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Adam
Stayed 3 nights in Jul 2025
10/10 Excellent
jonathan
Traveled with partner, Traveled with family
Jul 25, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
jonathan
Stayed 1 night in Jul 2025
10/10 Excellent
Donis
Traveled with family and small children
Jul 23, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Donis
Stayed 1 night in Jul 2025
8/10 Good
Jason David
Traveled with partner
Jul 23, 2025
Liked: Cleanliness, staff & service, property conditions & facilities
Jason David
Stayed 2 nights in Jul 2025
10/10 Excellent
Michael
Jul 22, 2025
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Chesapeake is Amazing - Gets better every trip


Michael
Stayed 4 nights in Jul 2025
10/10 Excellent
Liu M
Traveled with family
Jul 21, 2025
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Liu M
Stayed 1 night in Jun 2025
10/10 Excellent
Rachel
Traveled with family
Jul 21, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Rachel
Stayed 2 nights in Jul 2025
6/10 Okay
Mayra
Traveled with family
Jul 20, 2025
Mayra
Stayed 1 night in Jul 2025
10/10 Excellent
Michael
Jul 20, 2025
Michael
Stayed 1 night in Jul 2025
8/10 Good
Maria
Traveled with family
Jul 20, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Maria
Stayed 1 night in Jul 2025
10/10 Excellent
Gabriel
Traveled with group
Jul 20, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Gabriel
Stayed 1 night in Jul 2025
10/10 Excellent
Robert
Jul 19, 2025
Robert
Stayed 4 nights in Jun 2025
10/10 Excellent
Cody
Jul 19, 2025
Liked: Cleanliness, staff & service, property conditions & facilities
Cody
Stayed 1 night in Jul 2025
10/10 Excellent
yumi, vancouver
Jul 19, 2025
Liked: Cleanliness, staff & service, property conditions & facilities
yumi
Stayed 2 nights in Jul 2025
10/10 Excellent
Kristine
Jul 19, 2025
Kristine
Stayed 1 night in Jul 2025
10/10 Excellent
Paco
Traveled with partner
Jul 17, 2025
Liked: Cleanliness, staff & service, property conditions & facilities
Paco
Stayed 2 nights in May 2025
8/10 Good
Luis, BRONX
Jul 17, 2025
Liked: Cleanliness, staff & service, property conditions & facilities
Luis
Stayed 2 nights in Jul 2025
10/10 Excellent
Evelyn
Traveled with family
Jul 16, 2025
Liked: Cleanliness, amenities, property conditions & facilities
Evelyn
Stayed 2 nights in Jul 2025
10/10 Excellent
ANTHONY
Jul 16, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
ANTHONY
Stayed 1 night in Jul 2025
10/10 Excellent
Mehtap
Traveled with family
Jul 15, 2025
Liked: Cleanliness, amenities, property conditions & facilities
Mehtap
Stayed 1 night in Jul 2025
10/10 Excellent
jennifer
Traveled with family
Jul 15, 2025
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Our New Favorite on the Keys
jennifer
Stayed 4 nights in Jul 2025
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