9 / 10 Guest Rating

Chesapeake Beach Resort

Name: Chesapeake Beach Resort
Address: 83409 Overseas Highway, Islamorada, us
Rating: 9

83409 Overseas Highway, Islamorada, us

from US$314 / night

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

Check-in

Check-out

Guests

1 night · 2 adults

Available Rooms

11 rates found

1/11

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

Room Option

Board / Meal

Price for 1 night

Ocean View King

Non-refundable

Breakfast Included

20% OFF$588.75

$471

Includes taxes & fees

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

Room Option

Board / Meal

Price for 1 night

ADA Ocean View King

Non-refundable

Breakfast Included

20% OFF$588.75

$471

Includes taxes & fees

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

Room Option

Board / Meal

Price for 1 night

Ocean View Queens

Non-refundable

Breakfast Included

20% OFF$602.8

$482.24

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

1/6

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

Room Option

Board / Meal

Price for 1 night

Hearing Impaired Ocean View Queens

Non-refundable

Breakfast Included

20% OFF$602.8

$482.24

Includes taxes & fees

1/6

Standard King 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. The unit has 1 bed.

25 sqm

Sleeps 2

1 Extra-large double bed (Super-king size) (181-210 cm wide)

Amenities

ShowerTVTelephoneAir conditioningHair dryerRefrigerator

Room Option

Board / Meal

Price for 1 night

Standard King

Non-refundable

Breakfast Included

20% OFF$392.36

$313.89

Includes taxes & fees

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.

Sleeps 2

1 Extra-large double bed (Super-king size) (181-210 cm wide)

Amenities

ShowerTVTelephoneAir conditioningHair dryerKitchenette

Room Option

Board / Meal

Price for 1 night

Standard King Villa

Non-refundable

Breakfast Included

20% OFF$686.98

$549.58

Includes taxes & fees

1/6

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.

Sleeps 3

1 Extra-large double bed (Super-king size) (181-210 cm wide)

Amenities

ShowerTVTelephoneAir conditioningHair dryerKitchenette

Room Option

Board / Meal

Price for 1 night

King Efficiency Villa

Non-refundable

Breakfast Included

20% OFF$658.91

$527.13

Includes taxes & fees

1/7

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.

Sleeps 2

1 Extra-large double bed (Super-king size) (181-210 cm wide)

Amenities

ShowerTVTelephoneAir conditioningHair dryerKitchenette

Room Option

Board / Meal

Price for 1 night

ADA King Efficiency Villa

Non-refundable

Breakfast Included

20% OFF$658.91

$527.13

Includes taxes & fees

1/15

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

Room Option

Board / Meal

Price for 1 night

Ocean View King Suite

Non-refundable

Breakfast Included

20% OFF$658.91

$527.13

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

1/7

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

Room Option

Board / Meal

Price for 1 night

Deluxe Ocean View Two Queen Suite

Non-refundable

Breakfast Included

20% OFF$672.95

$538.36

Includes taxes & fees

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

Room Option

Board / Meal

Price for 1 night

Ocean View King Efficiency Villa

Non-refundable

Breakfast Included

20% OFF$701

$560.8

Includes taxes & fees

Guest Reviews

Exceptional1138 verified reviews

AI Summary

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

Select topics to read reviews

Steven

Verified booking

couple

Standard Room

Stayed in May 18, 2026

"Would stay again in an instant."

Exceptional

9.0

All of it

Nothing

Helpful?

Nadja

Verified booking

family_with_children

Standard Room

Stayed in May 18, 2026

"Schöne Anlage mit vielen kostenlosen Aktivitäten"

Excellent

8.0

Vieles war inkl. plus die Lage direkt am Beach

Der Meerabschnitt war sehr Algenbewachsen

Helpful?

David

Verified booking

extended_group

Standard Room

Stayed in May 17, 2026

"Exceptional"

Exceptional

10.0

Helpful?

Claudine

Verified booking

couple

Standard Room

Stayed in May 16, 2026

"Séjour très agréable"

Exceptional

9.0

La plage et le petit déjeuner incroyable Personnel très sympathique

Helpful?

Janey

Verified booking

couple

Standard Room

Stayed in May 15, 2026

"A friendly staff, terrific breakfast and lots of beautiful views."

Exceptional

10.0

We were only steps away from pool and beach. A covered garage was a plus. Restaurant next door was great as was the free breakfast.

Helpful?

Julia

Verified booking

couple

Standard Room

Stayed in May 14, 2026

"Great room and nice ground but ruined by behaviour of other guests"

Good

6.0

Room was very good - comfortable beds - spotlessly clean

Other guests are allowed to play extremely loud music at the pool and generally take it over leaving other guests to put up with it !!

Helpful?

Manuele

Verified booking

solo_traveller

Standard Room

Stayed in May 13, 2026

"Très bien"

Exceptional

9.0

Parfait pour faire une étape vers Key West. Endroit calme et charmant. Chambre propre, bien équipée, avec jolie vue. Bon petit déjeuner.

Helpful?

bettyp867

Verified booking

Couples

Standard Room

Stayed in May 11, 2026

"Excellent resort"

Exceptional

10.0

Amazing resort can’t wait to come back awesome staff & Chef Jose & Dilcia made the best omelettes ever you guys Rock

Helpful?

aussiewanderersSYDNEY, NEW SOUTH WALES

Verified booking

Couples

Standard Room

Stayed in May 10, 2026

"Luxurious resort with wide beach frontage but some minor room shortfalls"

Exceptional

10.0

We stayed here for almost a week and enjoyed the resort very much. It is about an hour's drive from mainland Florida and 2hrs from Key West. The resort pools are very nice and the beach looks inviting but in reality is difficult to swim in because the sand is littered with coral debris. An Oceanfront room has 180 degree water views, very nice. You see moon risings in the evenings and sunrises but no sunsets. While the resort has no restaurant, a hot breakfast is provided to order each morning until 10am. Some shaded car parking is available, free. Limited use of water toys is also free. Incongruously for a resort of this level, the wardrobe, at least in the Oceanview rooms, is tiny and grossly inadequate. Also, there is no in-room safe for valuables. Overall, a great place to relax in a tropical atmosphere, or use as a base from which to see the sites of the Florida Keys.

Helpful?

Izquierdo

Verified booking

extended_group

Standard Room

Stayed in May 10, 2026

"Recomendable 100%"

Exceptional

10.0

El alojamiento en general. La limpieza espectacular. Pero quisiera resaltar la amabilidad de las muchachas de la carpeta y los muchachos del desayuno que su trato fue excelente.

Todo me gustó

Helpful?

2 3

5 6

Chesapeake Beach Resort

About the Property

Facilities & Amenities

Important Information

Check-in & Out

Property Notes

Check Room Availability

Available Rooms

Ocean View King

Amenities

ADA Ocean View King

Amenities

Standard Double Room

Amenities

Hearing impaired Ocean view Two Queen Beds

Amenities

Standard King Room

Amenities

Standard King Villa

Amenities

King Efficiency Villa

Amenities

ADA King Efficiency Villa

Amenities

Ocean View King Suite

Amenities

Deluxe Ocean View Two Queen Suite

Amenities

Ocean View King Efficiency Villa

Amenities

Guest Reviews

Categories

Select topics to read reviews

"Would stay again in an instant."

"Schöne Anlage mit vielen kostenlosen Aktivitäten"

"Exceptional"

"Séjour très agréable"

"A friendly staff, terrific breakfast and lots of beautiful views."

"Great room and nice ground but ruined by behaviour of other guests"

"Très bien"

"Excellent resort"

"Luxurious resort with wide beach frontage but some minor room shortfalls"

"Recomendable 100%"