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Chesapeake Beach Resort

3.5 star property

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Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun-loungers, beach towels
Water view
Deluxe Ocean View Two Queen Suite | Balcony
Hypo-allergenic bedding, pillow-top beds, laptop workspace
43-inch flat-screen TV with cable channels, TV

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Free Wi-Fi

Explore the area

View in a map
83409 Overseas Hwy, Islamorada, FL, 33036
  • Place, History of Diving Museum
    ‪12 min walk‬
  • Place, Islamorada Brewery & Distillery
    ‪2 min drive‬
  • Place, Theater of the Sea
    ‪2 min drive‬

Room options

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

9.6 out of 10
Exceptional
(51 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds
  • Free Wi-Fi

View all photos for Ocean View King

Hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King

9.6 out of 10
Exceptional
(99 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free Wi-Fi

View all photos for ADA Ocean View King Suite

ADA Ocean View King Suite | Balcony

ADA Ocean View King Suite

8.6 out of 10
Excellent
(8 reviews)
  • Ocean view
  • 50 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed
  • Free Wi-Fi

View all photos for ADA Ocean View King

Hypo-allergenic bedding, pillow-top beds, laptop workspace

ADA Ocean View King

8.8 out of 10
Excellent
(20 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free Wi-Fi

View all photos for ADA Ocean View Queens

ADA Ocean View Queens

ADA Ocean View Queens

9.0 out of 10
Wonderful
(7 reviews)
  • Ocean view
  • 34 sq m
  • Sleeps 4
  • 2 Queen Beds
  • Free Wi-Fi

View all photos for Hearing Impaired Ocean View Queens

Hypo-allergenic bedding, pillow-top beds, laptop workspace

Hearing Impaired Ocean View Queens

10.0 out of 10
Exceptional
(3 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds
  • Free Wi-Fi

View all photos for Hearing Impaired Ocean View King Suite

43-inch flat-screen TV with cable channels, TV

Hearing Impaired Ocean View King Suite

8.8 out of 10
Excellent
(5 reviews)
  • Ocean view
  • 50 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed
  • Free Wi-Fi

View all photos for Standard Queens

Standard Queens

Standard Queens

9.4 out of 10
Exceptional
(65 reviews)
  • 29 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds
  • Free Wi-Fi

View all photos for Standard Doubles

Standard Doubles

Standard Doubles

9.2 out of 10
Wonderful
(102 reviews)
  • 25 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Double Beds
  • Free Wi-Fi

View all photos for Standard King with Sleeper Sofa

Standard King with Sleeper Sofa

Standard King with Sleeper Sofa

9.2 out of 10
Wonderful
(25 reviews)
  • 29 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Free Wi-Fi

View all photos for Standard King

Standard King

Standard King

9.4 out of 10
Exceptional
(40 reviews)
  • 25 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free Wi-Fi

View all photos for Ocean View King Suite

Hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King Suite

9.2 out of 10
Wonderful
(19 reviews)
  • Ocean view
  • 49 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed
  • Free Wi-Fi

View all photos for Deluxe Ocean View Two Queen Suite

Balcony

Deluxe Ocean View Two Queen Suite

9.0 out of 10
Wonderful
(11 reviews)
  • Ocean view
  • 60 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds
  • Free Wi-Fi

View all photos for 2-Bedroom Villa

2-Bedroom Villa

2-Bedroom Villa

10.0 out of 10
Exceptional
(1 review)
  • Resort view
  • 60 sq m
  • 2 bedrooms
  • Sleeps 6
  • 1 King Bed, 1 Double Bed and 1 Double Sofa Bed
  • Free Wi-Fi

View all photos for Standard King Villa

Standard King Villa

Standard King Villa

  • Resort view
  • 30 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free Wi-Fi

View all photos for King Efficiency Villa

King Efficiency Villa

King Efficiency Villa

9.6 out of 10
Exceptional
(4 reviews)
  • Resort view
  • 48 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Free Wi-Fi

View all photos for ADA King Efficiency Villa

ADA King Efficiency Villa

ADA King Efficiency Villa

10.0 out of 10
Exceptional
(1 review)
  • Resort view
  • 48 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free Wi-Fi

View all photos for Premium 1-Bedroom Ocean View Villa

Premium 1-Bedroom Ocean View Villa

Premium 1-Bedroom Ocean View Villa

8.0 out of 10
Very good
(1 review)
  • Ocean view
  • 65 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Double Beds and 1 Double Sofa Bed
  • Free Wi-Fi

View all photos for Premium Ocean View King Villa

Premium Ocean View King Villa | Living area

Premium Ocean View King Villa

  • Ocean view
  • 77 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Free Wi-Fi

View all photos for Ocean View King Efficiency Villa

Ocean View King Efficiency Villa

Ocean View King Efficiency Villa

10.0 out of 10
Exceptional
(1 review)
  • Ocean view
  • 48 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Free Wi-Fi

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About this property

Chesapeake Beach Resort

At Chesapeake Beach Resort, you can relax at one of the 2 outdoor swimming pools, play on the private white sand beach, or spend the day at a marina.
Chesapeake Beach Resort offers 60 air-conditioned accommodations, which are accessible via exterior corridors and feature coffee/tea makers and designer toiletries. Beds feature pillowtop mattresses. 43-inch flat-screen televisions come with cable channels. Bathrooms include showers, complimentary toiletries, and hair dryers.

This Islamorada hotel provides complimentary wireless Internet access, with a speed of 100+ Mbps (good for 1–2 people or up to 6 devices). Business-friendly amenities include phones along with free local calls (restrictions may apply). Additionally, rooms include irons/ironing boards and ceiling fans. Housekeeping is offered daily and hypo-allergenic bedding can be requested.

A private beach, a marina, and complimentary bicycles are featured at the hotel. 2 outdoor swimming pools are on site.

Children under 16 years old are not allowed in the swimming pool without adult supervision.

The recreational activities listed below are available either on site or nearby; fees may apply.

The free breakfast at Chesapeake Beach Resort gets high marks from our customers. During your stay, you'll be within walking distance of History of Diving Museum. Enjoy features like free WiFi in public areas, plus 2 outdoor pools and a marina.
  • Free continental breakfast served daily
  • Free WiFi (speed: 100+ Mbps (good for 1–2 people or up to 6 devices))
  • Enjoy drinks at the bar/lounge
  • Take a swim in the 2 outdoor pools
  • Amenities include a computer, a multilingual staff, and coffee/tea in a common area
  • Onsite recreation includes a private beach, complimentary bicycles, and kayaking
  • Guests really like the accommodations for the cleanliness and spaciousness
  • 11 minutes by foot from History of Diving Museum and a 2-minute drive from Windley Key Fossil Reef Geological State Park
  • Pets welcome for a fee (restrictions apply)
Simply walk outside to smell the salt air and watch the ocean waves from the white sand beach. Cool off in one of the 2 outdoor swimming pools at Chesapeake Beach Resort, and enjoy amenities like a marina and complimentary bicycles.

Free breakfast is available daily. You can enjoy a drink at the bar/lounge. A computer station is on site and WiFi is free in public spaces.

This 3.5-star Islamorada hotel is smoke free.

Guests are served free continental breakfast daily from 6:00 AM to 10:00 AM.
Tiki Bar - Onsite bar.

Property amenities

Internet

  • Available in all rooms: Free WiFi
  • In-room WiFi speed: 100+ Mbps (good for 1–2 people or up to 6 devices)
  • Available in some public areas: Free WiFi

Parking and transport

  • Wheelchair-accessible parking available
  • Onsite parking includes off-street options

Food and drink

  • Free continental breakfast available daily 6:00 AM to 10:00 AM
  • A bar/lounge
  • Coffee and tea in common areas

Restaurants on site

  • Tiki Bar

Things to do

  • 2 outdoor pools
  • Boat tours
  • Fishing
  • Free bicycle rentals
  • Kayaking

Family friendly

  • 2 outdoor pools
  • Fenced pool
  • In-room microwave
  • Pool gate

Conveniences

  • 24-hour front desk

Guest services

  • Concierge services
  • Housekeeping (daily)
  • Multilingual staff

Business services

  • Computer station

Outdoors

  • Beach loungers
  • Beach towels
  • Marina
  • On a private beach
  • Pool loungers

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Assistive listening devices
  • Braille/raised signage
  • Handrails in hallways
  • Handrails in stairways
  • Lever door handles
  • Pool hoist on site
  • Upper floors accessible by stairs only
  • Visual alarms in hallways
  • Well-lit path to entrance
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible parking
  • Wheelchair-accessible pool
  • Wheelchair-accessible public bathroom

More

  • 2 floors
  • 9 buildings
  • Built in 2020
  • Smoke-free property
  • Traditional architecture

Room amenities

Bedroom

  • Bedsheets provided
  • Blackout drapes
  • Hypo-allergenic bedding
  • Pillowtop mattress

Bathroom

  • Designer toiletries
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • 43-inch flat-screen TV with cable channels

Food and drink

  • Coffee/tea maker
  • Microwave

More

  • Access via exterior corridors
  • Air conditioning
  • Ceiling fan
  • Free local calls
  • Iron/ironing board
  • Laptop workspace
  • Phone

Policies

Check-in

Check-in start time: 4:00 PM; Check-in end time: 3:00 AM
Contactless check-in available
Late check-in subject to availability
Minimum check-in age: 18

Check-out

Check-out before 11 AM
Contactless check-out available
A late check-out fee will be charged

Special check-in instructions

Front desk staff will greet guests on arrival at the property
Information provided by the property may be translated using automated translation tools

Access methods

Staffed front desk

Pets

  • Pets: USD 50.00 per accommodation, per night, plus a deposit of USD 50.00 per night
  • Maximum 2 (weight limit: 50 lbs per pet)
  • Restrictions apply
  • For more information, you can reach out to the property at the number on the booking confirmation
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.
  • Rollaway/extra beds are not available.

Payment types at the property

Important information

Optional extras

The fees and deposits listed below will be charged at the time of service, check-in, or check-out.

  • Pet deposit: USD 50.00 per night
  • Pet fee: USD 50.00 per accommodation, per night
  • Service animals are exempt from fees
  • A late check-out fee will be charged

This may not be a comprehensive list. Fees and deposits are subject to change and might not include tax.

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
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
Safety features at this property include a fire extinguisher
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
Front desk staff will greet guests on arrival at the property.
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

We should mention

  • Pool access available from 8:00 AM to 6:00 PM.
  • Certain facilities might have restricted access. For details, you can contact the property at the number on the booking confirmation.
  • Guests may experience noise disturbance due to nearby construction work.
  • To make arrangements to bring your pet, contact the property directly at the number on your booking confirmation (please see the Fees section for related charges).

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

Chesapeake Beach Resort Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 1265 out of 1710 reviews
Rating 8 - Good. 274 out of 1710 reviews
Rating 6 - Okay. 97 out of 1710 reviews
Rating 4 - Poor. 42 out of 1710 reviews
Rating 2 - Terrible. 32 out of 1710 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

9.0/10

Amenities

9.2/10

Property conditions & facilities

Reviews

10/10 Excellent

David

Liked: Cleanliness, amenities, property conditions & facilities
Clean room but cold as it was 42’F in Florida that night and there is no heat in the rooms
Stayed 1 night in Feb 2026

10/10 Excellent

Barry

Liked: Cleanliness, staff & service, amenities
Clean room, staff was incredibly nice and helpful. Amenities were also very good. Enjoyed the cooked to order breakfast, kayaks, and beautiful views!
Stayed 2 nights in Jan 2026

8/10 Good

Frank

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
Housekeeping was excellent, and the staff was very friendly and efficient. We had unseasonably cold weather, and there was no heat in our room, only AC. Also, complementary breakfast was served in a room with no tables. We had to take the food back and eat in our room.
Stayed 3 nights in Jan 2026

8/10 Good

Gailmarie

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
Spacious clean room. Good linens and towels with comfortable beds. Staff very helpful. Elevator was broken but staff carried bags up,
Stayed 3 nights in Jan 2026

6/10 Okay

Alan

Liked: Cleanliness, amenities, property conditions & facilities
The room was nice and location , services and outside were very nice, staff was helpful. There were problems with noise levels. There was a buzzing coming from A/C unit in main room. I had to turn this off so it wouldn't wake me up. Also when someone moved a chair upstairs you could hear it sliding on the floor. They need to put felt bottoms on legs. Also there was a door connecting a room to mine and you could hear EVERYTHING They were saying. I would not get a connected room anymore. And then there was the fire alarms that went off twice. One during the day and one at night.
Stayed 5 nights in Jan 2026

10/10 Excellent

James

Stayed 2 nights in Jan 2026

10/10 Excellent

Julie

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
This place was amazing and I wish we would have stayed there more nights. The staff were so helpful. The ground were beautiful. The room was clean. Breakfast was phenomenal. This is definitely on our list to visit and stay longer next time!
Stayed 1 night in Jan 2026

10/10 Excellent

Laura

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
Clean, great helpful staff, great breakfast. Lovely facility
Stayed 3 nights in Jan 2026

10/10 Excellent

MARY KAY, DELRAY BEACH

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
The staff was amazing! The pool/beach were delightful. Great location
Stayed 3 nights in Dec 2025

10/10 Excellent

Daniel, Quincy

Liked: Cleanliness, amenities, property conditions & facilities
Awesome place!!
Stayed 2 nights in Jan 2026

10/10 Excellent

Judy

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
Gorgeous view, very pleasant staff, clean room
Stayed 2 nights in Jan 2026

10/10 Excellent

Melissa

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
The view and location were great.
Stayed 3 nights in Jan 2026

10/10 Excellent

Diane

Liked: Cleanliness, staff & service, amenities
I had a wonderful time Beautiful place. Great staff
Stayed 4 nights in Jan 2026

10/10 Excellent

Lauren, St. Louis

Liked: Cleanliness, amenities, property conditions & facilities
Love!!!!! The private beach, and the two polols and the personalized breakfast bar and the views were all perfect. Looking forward to stay again.
Stayed 1 night in Jan 2026

8/10 Good

Yu mi

Stayed 1 night in Jan 2026

10/10 Excellent

Rodney

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Friendly and helpful staff. Beautiful setting. Very nice breakfast included with made-to-order omelets. Great base to explore other things the Keys has to offer. Restaurants in walking distance.
Stayed 2 nights in Jan 2026

10/10 Excellent

Konrad

Stayed 1 night in Jan 2026

10/10 Excellent

Nadine

Liked: Cleanliness, staff & service, amenities
Clean room. Nice staff. Champagne on arrival. Two warm pools right on the ocean. A nice guitar guy for entertainment on Saturday. Breakfast was included. Made to order omelette, pancake, etc. watched them make a Mickey pancake for a little girl who smiled from ear to ear.
Stayed 1 night in Jan 2026

8/10 Good

ANNA

Liked: Cleanliness, staff & service, amenities
.
Stayed 1 night in Jan 2026

10/10 Excellent

dian

Liked: Cleanliness, staff & service, amenities
Great room, wonderful staff and good location
Stayed 2 nights in Jan 2026

10/10 Excellent

Alicia

Liked: Cleanliness, amenities, property conditions & facilities
Great stay clean room lots of resort amenities included. Champagne at check in was a nice touch
Stayed 2 nights in Jan 2026

10/10 Excellent

Jacqueline

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
This is our second time staying there and we really like it!! It is so cute, very clean and the location is close to many bars and restaurants. Uber/Lyft is very accessible too. The breakfast is also nice and you get a nice view of the water too.
Stayed 2 nights in Dec 2025

10/10 Excellent

Diane

Liked: Cleanliness, amenities, property conditions & facilities
Beautiful beach area. Friendly staff.
Stayed 1 night in Jan 2026

10/10 Excellent

Michelle Marie

Travelled with group
Liked: Cleanliness, amenities, property conditions & facilities
The room was clean and bright, the view was amazing, and the staff were always friendly, helpful and courteous! The breakfast with fresh made omelets was also a pleasure!
Stayed 6 nights in Jan 2026

10/10 Excellent

Nancy

Liked: Cleanliness, amenities, property conditions & facilities
Staff was very nice. Nice to use the complimentary clear bottom kayaks. Breakfast was good, Didi made a great omelette!
Stayed 2 nights in Jan 2026