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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
summertime120SAINT PAUL, MINNESOTA
Verified booking
Family
Standard Room
Stayed in Mar 19, 2026

"Great spring break stay!"

8.0

We were here for a quick spring break getaway. We loved the low key vibe of the hotel. We stayed in a villa, which was nice for our family of four. I did not realize when I booked it that it was two double beds and a pullout sofa. That made for a few nights of uncomfortable sleep for my husband and I. The bed was tiny! Rooms were very clean though. We loved the kitchenette and the bathroom was nice and large. My only complaint there is that the water in the shower never got hot, only warm. The water pressure was terrible too. I have lots of hair and didn’t wash it during our stay because of this. Check in was great and there were tons of lounge chairs around the property looking out to the water. I loved sitting and looking at the ocean each afternoon. The two pools were nice. One seemed much quieter and less used than the other. The hot tub was nice too. We used our two hours of daily stuff by fishing and kayaking. That was a nice amenity to have. My husband enjoyed the breakfast each morning too. The rest of us preferred to sleep in. I would definitely recommend this property.

Helpful?
M
MichaelcaCA
Verified booking
solo_traveller
Standard Room
Stayed in Mar 19, 2026

"Overall wonderful!"

10.0

The entire property was very clean. Well maintained. Great front staff.

The beach was nice but can’t really swim much due to seaweed.

Helpful?
P
plasenciausUS
Verified booking
couple
Standard Room
Stayed in Mar 18, 2026

"Exceptional"

10.0

Jose, Chris and Dilicis. Sorry for not spelling her name right. All three were amazing and so helpful. I didn't have to ask for help, they reached out to me and offered help. The food was great and the service that they offer is above and beyond. Dilicis (sp?) even brought my meal to my room. I appreciated the assistance so much. They are a great asset to the resort.

Having to leave.

Helpful?
M
mtf232026SOUTH BEND, INDIANA
Verified booking
NONE
Standard Room
Stayed in Mar 17, 2026

"Fantastic Resort"

10.0

I have stayed at several resorts throughout the country and this resort fit in the top for cleanliness. The resort in whole was either recently renovated or kept up very well.

Helpful?
G
gailsU6110CU
Verified booking
Couples
Standard Room
Stayed in Mar 16, 2026

"Relaxing"

10.0

Stayed for 10 days. Cleanliness top notch. Friendly, available staff. We loved it

Helpful?
S
SarausUS
Verified booking
family_with_children
Standard Room
Stayed in Mar 16, 2026

"I had a good time"

10.0

Beach

The breakfast area is very small and the kitchen exhaust fans are directed towards the area where you sit down to eat breakfast.

Helpful?
L
LisausUS
Verified booking
family_with_children
Standard Room
Stayed in Mar 15, 2026

"Relaxing stay in Islamorada"

7.0

The staff was very friendly and responsive. They offered a great breakfast. Our unit was nicely decorated and clean. The resort property was well maintained and clean. It was a pretty location.

The unit we had, cottage #5, was right by the main road. It was a little loud with the cars driving by constantly. The unit could use a little more kitchen accessories. The toaster did not work and there were not enough dishes.

Helpful?
M
MeganusUS
Verified booking
couple
Standard Room
Stayed in Mar 13, 2026

"Exceptional"

10.0
Helpful?
S
StephaniefrFR
Verified booking
couple
Standard Room
Stayed in Mar 12, 2026

"Une étape de passage mais cher"

6.0

L’accueil

Le bruit, au bord de la route ( pour les chambre qui ne donnent pas sur la mer)

Helpful?
S
Seaside63996590783
Verified booking
Family
Standard Room
Stayed in Mar 10, 2026

"10/10"

10.0

The whole experience was amazing from manatees, paddleboarding to fine dining and breakfast made fresh. Balcony view was a blessing along with the superb staff, particularly Jazmin was very sweet and helpful.

Helpful?