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9 / 10 Guest Rating

Chesapeake Beach Resort

83409 Overseas Highway, Islamorada, us

Chesapeake Beach Resort - main view

About the Property

Oceanfront Resort with Free WiFi

Luxurious Rooms with Balconies
Indulge in comfort with a 37-inch flat-screen TV and a small refrigerator in each room. Upgrade to a suite for a private balcony overlooking the ocean.

Outdoor Pool with Ocean View
Relax and unwind by the outdoor pool while enjoying the breathtaking ocean view.

Nearby Attractions
Explore the History of Diving Museum just a 3-minute walk away or catch a show at the Theater of the Sea, only a 4-minute drive from the resort.

Experience the ultimate blend of luxury and convenience at Chesapeake Beach Resort. Book now for an unforgettable stay!

Facilities & Amenities

WiFi available
Free WiFi
Parking
Free Parking
Non-smoking rooms
Air conditioning
Swimming pool
24-hour front desk
Heating
Pets allowed

Important Information

Check-in & Out

Check-in
Check-out11:00 AM

Property Notes

You must show a valid photo ID and credit card upon check-in. Please note that all special requests cannot be guaranteed and are subject to availability upon check-in. Additional charges may apply. If you expect to arrive outside check in hours, please inform the property in advance. Please note, due to previous hurricanes some amenities are limited. Please contact the property for more details. Please note that the property is currently undergoing restoration. Limited amenities may be available.Guests are required to show a photo ID and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply. A deposit may be required at the property.

Check Room Availability

1 night · 2 adults

Available Rooms

Ocean View King  - Photo 1
Ocean View King  - Photo 2
Ocean View King  - Photo 3
Ocean View King  - Photo 4
Ocean View King  - Photo 5
Ocean View King  - Photo 6
Ocean View King  - Photo 7
Ocean View King  - Photo 8
Ocean View King  - Photo 9
Ocean View King  - Photo 10
Ocean View King  - Photo 11
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Ocean View King

This room features a balcony with a pool view. A small refrigerator and flat-screen cable TV are also included.

32 sqm
Sleeps 4
1 Extra-large double bed (Super-king size) (181-210 cm wide)
Amenities
ShowerTVTelephoneAir conditioningHair dryerRefrigerator

Ocean View King

Non-refundable
Breakfast Included
20% OFF$582.73

$466.18

Includes taxes & fees
ADA Ocean View King - Photo 1
ADA Ocean View King - Photo 2
ADA Ocean View King - Photo 3
ADA Ocean View King - Photo 4
ADA Ocean View King - Photo 5
ADA Ocean View King - Photo 6
1/6

ADA Ocean View King

This room features an ocean view, 37-inch flat-screen cable TV, and small refrigerator. Coffee-making facilities are also included.

34 sqm
Sleeps 4
1 Extra-large double bed (Super-king size) (181-210 cm wide)
Amenities
ShowerTVTelephoneAir conditioningHair dryerRefrigerator

ADA Ocean View King

Non-refundable
Breakfast Included
20% OFF$582.73

$466.18

Includes taxes & fees
Standard Double Room - Photo 1
Standard Double Room - Photo 2
Standard Double Room - Photo 3
Standard Double Room - Photo 4
Standard Double Room - Photo 5
Standard Double Room - Photo 6
Standard Double Room - Photo 7
Standard Double Room - Photo 8
1/8

Standard Double Room

The spacious double room features air conditioning, a private entrance, as well as a private bathroom boasting a walk-in shower and a hairdryer. Featuring a balcony, this double room also provides a coffee machine, a wardrobe and a flat-screen TV with cable channels. The unit has 2 beds.

25 sqm
Sleeps 4
2 Double bed (131-150 cm wide)
Amenities
ShowerTVTelephoneAir conditioningHair dryerRefrigerator

Standard Doubles

Non-refundable
Breakfast Included
20% OFF$374.81

$299.85

Includes taxes & fees
Hearing Impaired Ocean View King Suite - Photo 1
Hearing Impaired Ocean View King Suite - Photo 2
Hearing Impaired Ocean View King Suite - Photo 3
Hearing Impaired Ocean View King Suite - Photo 4
Hearing Impaired Ocean View King Suite - Photo 5
Hearing Impaired Ocean View King Suite - Photo 6
Hearing Impaired Ocean View King Suite - Photo 7
Hearing Impaired Ocean View King Suite - Photo 8
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Hearing Impaired Ocean View King Suite

This spacious suite is consisted of of 1 living room, 1 separate bedroom and 1 bathroom with a walk-in shower and free toiletries. The air-conditioned suite offers a flat-screen TV with cable channels, a private entrance, a coffee machine, a seating area as well as sea views. The unit offers 2 beds.

55 sqm
Sleeps 4
1 Extra-large double bed (Super-king size) (181-210 cm wide)
Amenities
ShowerTVTelephoneAir conditioningHair dryerRefrigerator

Hearing Impaired Ocean View King Suite

Non-refundable
Breakfast Included
20% OFF$652.03

$521.62

Includes taxes & fees
Hearing impaired Ocean view Two Queen Beds - Photo 1
Hearing impaired Ocean view Two Queen Beds - Photo 2
Hearing impaired Ocean view Two Queen Beds - Photo 3
Hearing impaired Ocean view Two Queen Beds - Photo 4
Hearing impaired Ocean view Two Queen Beds - Photo 5
Hearing impaired Ocean view Two Queen Beds - Photo 6
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Hearing impaired Ocean view Two Queen Beds

The spacious double room provides air conditioning, a private entrance, a balcony with sea views as well as a private bathroom featuring a walk-in shower. The unit offers 2 beds.

34 sqm
Sleeps 4
2 Queen bed (151-180 cm wide)
Amenities
ShowerTVTelephoneAir conditioningHair dryerRefrigerator

Hearing Impaired Ocean View Queens

Non-refundable
Breakfast Included
20% OFF$596.61

$477.29

Includes taxes & fees
Standard King Villa - Photo 1
Standard King Villa - Photo 2
Standard King Villa - Photo 3
Standard King Villa - Photo 4
Standard King Villa - Photo 5
1/5

Standard King Villa

Featuring a private entrance, this air-conditioned villa is consisted of of a kitchenette, 1 bedroom and 1 bathroom with a walk-in shower and a hairdryer. In the well-equipped kitchenette, guests will find a stovetop, a refrigerator, a dishwasher and kitchenware. The villa features tiled floors, a seating area with a flat-screen TV with cable channels, a coffee machine, a wardrobe, as well as a sofa. The unit offers 1 bed.

0
Sleeps 2
1 Extra-large double bed (Super-king size) (181-210 cm wide)
Amenities
ShowerTVTelephoneAir conditioningHair dryerKitchenette

Standard King Villa

Non-refundable
Breakfast Included
20% OFF$679.76

$543.81

Includes taxes & fees
King Efficiency Villa - Photo 1
King Efficiency Villa - Photo 2
King Efficiency Villa - Photo 3
King Efficiency Villa - Photo 4
King Efficiency Villa - Photo 5
King Efficiency Villa - Photo 6
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King Efficiency Villa

Boasting a private entrance, this air-conditioned villa comes with 1 living room, 1 separate bedroom and 1 bathroom with a walk-in shower and a hairdryer. In the well-equipped kitchenette, guests will find a stovetop, a refrigerator, a dishwasher and kitchenware. The villa has tiled floors, a seating area with a flat-screen TV with cable channels, a coffee machine, a wardrobe, as well as a sofa. The unit has 2 beds.

0
Sleeps 3
1 Extra-large double bed (Super-king size) (181-210 cm wide)
Amenities
ShowerTVTelephoneAir conditioningHair dryerKitchenette

King Efficiency Villa

Non-refundable
Breakfast Included
20% OFF$652.03

$521.62

Includes taxes & fees
ADA King Efficiency Villa - Photo 1
ADA King Efficiency Villa - Photo 2
ADA King Efficiency Villa - Photo 3
ADA King Efficiency Villa - Photo 4
ADA King Efficiency Villa - Photo 5
ADA King Efficiency Villa - Photo 6
ADA King Efficiency Villa - Photo 7
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ADA King Efficiency Villa

Featuring a private entrance, this air-conditioned villa is consisted of of 1 living room, 1 separate bedroom and 1 bathroom with a walk-in shower and a hairdryer. The well-equipped kitchenette has a stovetop, a refrigerator, a dishwasher and kitchenware. This wheelchair accessible villa features a coffee machine, a seating area with a flat-screen TV and a roll-in shower. The unit offers 1 bed.

0
Sleeps 2
1 Extra-large double bed (Super-king size) (181-210 cm wide)
Amenities
ShowerTVTelephoneAir conditioningHair dryerKitchenette

ADA King Efficiency Villa

Non-refundable
Breakfast Included
20% OFF$652.03

$521.62

Includes taxes & fees
Ocean View King Suite - Photo 1
Ocean View King Suite - Photo 2
Ocean View King Suite - Photo 3
Ocean View King Suite - Photo 4
Ocean View King Suite - Photo 5
Ocean View King Suite - Photo 6
Ocean View King Suite - Photo 7
Ocean View King Suite - Photo 8
Ocean View King Suite - Photo 9
Ocean View King Suite - Photo 10
Ocean View King Suite - Photo 11
Ocean View King Suite - Photo 12
Ocean View King Suite - Photo 13
Ocean View King Suite - Photo 14
Ocean View King Suite - Photo 15
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Ocean View King Suite

1 King Bed and 1 Queen Sofa Bed527-sq-foot room, balcony with ocean views Layout - Bedroom and sitting areaInternet - Free WiFi 100+ Mbps (good for 1–2 people or up to 6 devices) Entertainment - 43-inch HDTV with cable channelsFood & Drink - Mini-fridge, microwave, coffee/tea maker, and dining tableSleep - Pillowtop bed, hypo-allergenic bedding, blackout drapes/curtains, and bed sheets Bathroom - Shower, designer toiletries, and a hair dryerPractical - Free local calls, double sofa bed, and iron/ironing board; cribs (free) available on requestComfort - Air conditioning and daily housekeepingAccessibility - Lever door handlesNon-SmokingRoom is accessed via exterior corridors

49 m2
Sleeps 4
1 King bed (151-180 cm wide)
1 Sofa bed (150-160 cm wide)
Amenities
Coffee/tea makerShowerTVTelephoneAir conditioningHair dryer

Ocean View King Suite

Non-refundable
Breakfast Included
20% OFF$652.03

$521.62

Includes taxes & fees
Deluxe Ocean View Two Queen Suite - Photo 1
Deluxe Ocean View Two Queen Suite - Photo 2
Deluxe Ocean View Two Queen Suite - Photo 3
Deluxe Ocean View Two Queen Suite - Photo 4
Deluxe Ocean View Two Queen Suite - Photo 5
Deluxe Ocean View Two Queen Suite - Photo 6
Deluxe Ocean View Two Queen Suite - Photo 7
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Deluxe Ocean View Two Queen Suite

2 Queen Beds650-sq-foot room, balcony with ocean views Layout - Bedroom and sitting areaInternet - Free WiFi 100+ Mbps (good for 1–2 people or up to 6 devices) Entertainment - 43-inch HDTV with cable channelsFood & Drink - Mini-fridge, microwave, and coffee/tea makerSleep - Pillowtop bed, hypo-allergenic bedding, blackout drapes/curtains, and bed sheets Bathroom - Shower, designer toiletries, and a hair dryerPractical - Free local calls, double sofa bed, and iron/ironing board; cribs (free) available on requestComfort - Air conditioning and daily housekeepingAccessibility - Lever door handlesNon-SmokingRoom is accessed via exterior corridors

60 m2
Sleeps 6
2 Queen Bed (150-160 cm wide)
Amenities
Coffee/tea makerShowerTVTelephoneAir conditioningHair dryer

Deluxe Ocean View Two Queen Suite

Non-refundable
Breakfast Included
20% OFF$665.93

$532.74

Includes taxes & fees
ADA Ocean View King Suite - Photo 1
ADA Ocean View King Suite - Photo 2
ADA Ocean View King Suite - Photo 3
ADA Ocean View King Suite - Photo 4
ADA Ocean View King Suite - Photo 5
ADA Ocean View King Suite - Photo 6
ADA Ocean View King Suite - Photo 7
ADA Ocean View King Suite - Photo 8
ADA Ocean View King Suite - Photo 9
ADA Ocean View King Suite - Photo 10
ADA Ocean View King Suite - Photo 11
1/11

ADA Ocean View King Suite

1 King Bed540-sq-foot room, balcony with ocean views Layout - Bedroom and sitting areaInternet - Free WiFi 100+ Mbps (good for 1–2 people or up to 6 devices) Entertainment - 43-inch HDTV with cable channelsFood & Drink - Mini-fridge, microwave, coffee/tea maker, and dining tableSleep - Pillowtop bed, hypo-allergenic bedding, blackout drapes/curtains, and bed sheets Bathroom - Shower, designer toiletries, and a hair dryerPractical - Free local calls, double sofa bed, and iron/ironing board; cribs (free) available on requestComfort - Air conditioning and daily housekeepingAccessibility - Lever door handlesNon-SmokingRoom is accessed via exterior corridors

50 m2
Sleeps 4
1 King bed (151-180 cm wide)
Amenities
Coffee/tea makerShowerTVTelephoneAir conditioningHair dryer

ADA Ocean View King Suite

Non-refundable
Breakfast Included
20% OFF$652.03

$521.62

Includes taxes & fees
Ocean View King Efficiency Villa - Photo 1

Ocean View King Efficiency Villa

1 King Bed and 1 Double Sofa Bed517-sq-foot room, located on the ground floor, ocean viewsLayout - Bedroom, 2 living rooms, and dining areaInternet - Free WiFi 100+ Mbps (good for 1–2 people or up to 6 devices) Entertainment - 43-inch HDTV with cable channelsFood & Drink - Kitchenette with refrigerator, stovetop, microwave, and dishwasherSleep - Pillowtop bed, hypo-allergenic bedding, blackout drapes/curtains, and bed sheets Bathroom - Shower, designer toiletries, and a hair dryerPractical - Iron/ironing board, laptop workspace, and phone; cribs (free) available on requestComfort - Air conditioning and daily housekeepingAccessibility - Lever door handlesNon-SmokingRoom is accessed via exterior corridors

48 m2
Sleeps 4
1 King bed (151-180 cm wide)
1 Sofa bed (131-150 cm wide)
Amenities
Coffee/tea makerShowerTVTelephoneAir conditioningHair dryer

Ocean View King Efficiency Villa

Non-refundable
Breakfast Included
20% OFF$693.64

$554.91

Includes taxes & fees

Guest Reviews

9
Exceptional1142 verified reviews
AI Summary

Guests highly rate the great location and frequently praise the delicious breakfast.

Categories

Cleanliness8.3
Service9.1
Location9.8
Room Quality8.8
Amenities8.8
Value for Money8.3
Food and Beverage9.5
Overall Experience9.3

Select topics to read reviews

S
Sebastian Fabio AgnelloitIT
Verified booking
family_with_children
Standard Room
Stayed in Apr 27, 2026

"Very Good"

7.0

Camera

Colazione, terribile

Helpful?
G
Getaway55893863402
Verified booking
NONE
Standard Room
Stayed in Apr 26, 2026

"I'd go back in a heartbeat!"

10.0

I highly recommend Chesapeake Beach Resort in Islamorada! My husband and I visited to celebrate our wedding anniversary and they left us a nice note and bottle of champagne in our room at check in. We booked an ocean view room and what an amazing ocean view it was! The pictures on the website do not do the location justice! It was so much more beautiful in person! The colors of the water are amazing, the palm trees and the sandy beach just outside our balcony... Made it hard to want to leave the room! The room itself was very large and spacious, quite comfortable & quiet. Barely ever heard our neighbors or people outside. We had a comfortable king bed with plenty of pillows & nice linens. The room was sparsely furnished but certainly sufficient. There was a couch and a chair and small round table but we never sat inside because it was just too gorgeous outside to be in, so we spent our down time on the balcony that had two chairs and a small table. We never turned on the tv either. Was helpful to have the small fridge, coffee maker and microwave. The robe and slippers were a nice touch as well, made it comfy to walk on the tile floors. The bathroom was huge! Very spacious glass door shower, good-size sink vanity, always plenty of towels. Housekeeping was available daily if needed and they were great being there when we needed them but left us be when we had our do not disturb sign out. The breakfast really sets this place apart! Fresh made omelets, pancakes, french toast made with a smile and friendly chat by Mr. Chris, as well as other breakfast foods... cereals, toast, muffins, bagels, english muffins, yogurts, fruits, coffee, tea, juices... It was a wonderful perk and saved money & time not having to hunt down breakfast places. Two nice pools, a hot tub, "lawn" games like checkers/chess/cornhole, as well as water sports & Friday yoga made it so there was plenty to do when you wanted to be active at the resort. I loved the location being in the Middle Keys. It was our first trip to the Keys so it was a perfect spot to venture North to experience the Upper Keys as well as South to experience the Lower Keys. There are so many stores, restaurants and touristy places to visit in the area. A rental car definitely added a plus to our trip as well and there was free parking at the resort. If I'm ever fortunate enough to go back to the Florida Keys, I wouldn't take a chance at staying anywhere else knowing how perfect the Chesapeake Beach Resort is!

Helpful?
S
SvenbrBR
Verified booking
solo_traveller
Standard Room
Stayed in Apr 26, 2026

"Exceptional"

9.0
Helpful?
E
EricausUS
Verified booking
couple
Standard Room
Stayed in Apr 24, 2026

"Perfection"

10.0

Absolutely loved this stay!! Beautiful, clean, and exceptional customer service by staff. The view from our room was amazing.

NA

Helpful?
E
eddekronhg
Verified booking
NONE
Standard Room
Stayed in Apr 22, 2026

"Wedding Trip"

10.0

Loved teh hotel and my room was very spacious , excellent bed and grest bathrooom. Complimentary breakfast was delicious.

Helpful?
J
jb06333
Verified booking
NONE
Standard Room
Stayed in Apr 22, 2026

"Waterfront luxury"

10.0

This resort offers everything we hoped to find at a reasonable price. Outstanding breakfast was included.

Helpful?
D
dmlabrieBEVERLY HILLS, FLORIDA
Verified booking
NONE
Standard Room
Stayed in Apr 21, 2026

"Very Nice, but…"

8.0

We initially booked a King Balcony room, but prior to arrival I was put in a non weight bearing cast. The hotel switched us to and confirmed an ADA King Villa. It was NOT ADA compliant. Although the room had room to maneuver, the bathroom was a nightmare. The toilet had no grab rails and no space on either side. The shower was small and inaccessible. The parking for this villa was non-ADA and was two spaces away on all gravel making maneuvering next to impossible. Needless to say, we were not pleased with the accommodations we were provided. However, the resort itself seemed very nice. Breakfast was good. Views from the deck were amazing. They had what looked like a nice pool with an ADA lift. They also had many water activities available from fishing to kayaking and paddle boarding.

Helpful?
H
HannahusUS
Verified booking
solo_traveller
Standard Room
Stayed in Apr 21, 2026

"Excellent"

8.0
Helpful?
S
SusanusUS
Verified booking
extended_group
Standard Room
Stayed in Apr 20, 2026

"Excellent"

8.0
Helpful?
M
marcelo barvausUS
Verified booking
couple
Standard Room
Stayed in Apr 19, 2026

"Exceptional"

9.0
Helpful?