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Chesapeake Beach Resort

3.5 star property
3.5-star beachfront hotel with 2 outdoor pools

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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, pillowtop beds, laptop workspace
43-inch flat-screen TV with cable channels, TV

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Free WiFi

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
(49 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Ocean View King

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King

9.6 out of 10
Exceptional
(98 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

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

View all photos for ADA Ocean View King

Hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA Ocean View King

8.8 out of 10
Excellent
(19 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

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

View all photos for Hearing Impaired Ocean View Queens

Hypo-allergenic bedding, pillowtop 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

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

8.6 out of 10
Excellent
(4 reviews)
  • Ocean view
  • 50 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Standard Queens

Standard Queens

Standard Queens

9.4 out of 10
Exceptional
(62 reviews)
  • 29 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard Doubles

Standard Doubles

Standard Doubles

9.2 out of 10
Wonderful
(100 reviews)
  • 25 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Double Beds

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

View all photos for Standard King

Standard King

Standard King

9.6 out of 10
Exceptional
(37 reviews)
  • 25 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for Ocean View King Suite

Hypo-allergenic bedding, pillowtop 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

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

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

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

View all photos for King Efficiency Villa

King Efficiency Villa

King Efficiency Villa

9.4 out of 10
Exceptional
(3 reviews)
  • Resort view
  • 48 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for ADA King Efficiency Villa

ADA King Efficiency Villa

ADA King Efficiency Villa

  • Resort view
  • 48 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for Premium 1-Bedroom Ocean View Villa

Premium 1-Bedroom Ocean View Villa

Premium 1-Bedroom Ocean View Villa

  • Ocean view
  • 65 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Double Beds and 1 Double Sofa Bed

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

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

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About the area

Islamorada

On the beach.With a stay at this Matecumbe hotel, you'll be within half a mile (1 km) of History of Diving Museum and 2 miles (3 km) of Windley Key Fossil Reef Geological State Park. Islamorada Brewery & Distillery and Keys History & Discovery Center are also within 2 miles (3 km).

What's nearby

  • History of Diving Museum - 12 min walk - 1.1 km
  • Windley Key Fossil Reef Geological State Park - 2 min drive - 2.0 km
  • Islamorada Brewery & Distillery - 2 min drive - 2.4 km
  • Theater of the Sea - 2 min drive - 2.4 km
  • Bud n' Mary's Dive Center - 5 min drive - 7.3 km

Getting around

  • Miami Intl. Airport (MIA) - 91 min drive

Restaurants

  • ‪Wahoo's Bar & Grill - ‬2 min walk
  • ‪Hog Heaven - ‬3 min drive
  • ‪Tiki Bar - ‬13 min walk
  • ‪Wendy's - ‬2 min drive
  • ‪Lorelei Restaurant & Cabana Bar - ‬3 min drive

About this property

Chesapeake Beach Resort

3.5-star beachfront hotel with 2 outdoor pools
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.

  • 60 guestrooms or units
  • 2 levels
  • 9 buildings
  • Built in 2020
  • Continental breakfast (free)
  • Beach lounge chairs
  • Towels for the beach
  • Poolside lounge chairs
  • Coffee in lobby
  • Front desk (24 hours)
  • Staff is multilingual
  • Concierge
  • Computer for guest use
  • No smoking on site
  • Bar or lounge
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.

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Property amenities

Family friendly

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

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 transportation

  • 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

Things to do

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

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 washroom

Room amenities

Entertainment

  • 43-inch flat-screen TV with cable channels

Bedroom

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

Bathroom

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

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 stay
  • 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.

Property payment types

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 stay
  • 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

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
Charges for extra guests may apply and vary according to property policy.
A credit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. 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. This property accepts Visa, Mastercard, American Express, and Discover. Cash is not accepted. For guests' safety, the property includes a fire extinguisher in each accommodation.

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. 1246 out of 1682 reviews
Rating 8 - Good. 267 out of 1682 reviews
Rating 6 - Okay. 96 out of 1682 reviews
Rating 4 - Poor. 42 out of 1682 reviews
Rating 2 - Terrible. 31 out of 1682 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

9.0/10

Amenities

9.2/10

Property conditions & facilities

Reviews

10/10 Excellent

STEPHEN, HAMPTON

Stayed 3 nights in Mar 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

4/10 Poor

Ximena

Noisy and breakfast was of poor quality ingredients. Service was great but walls lacked insulation and had noisy neighborsz
Stayed 1 night in Jan 2026

10/10 Excellent

Robert

Stayed 2 nights in Dec 2025

10/10 Excellent

Andre

Stayed 3 nights in Jan 2026

6/10 Okay

Briana

Liked: Cleanliness
Stayed 2 nights in Jan 2026

10/10 Excellent

Benny

Liked: Cleanliness
Stayed 2 nights in Dec 2025

10/10 Excellent

Gerta

Liked: Cleanliness, staff & service, property conditions & facilities
One of the most beautiful hotel I have ever stayed. It's on the pricey side, but worth staying it. We loved everything about it.
Stayed 2 nights in Dec 2025

10/10 Excellent

Nelly

Travelled with family
Liked: Cleanliness, staff & service, amenities
Yadira at the front desk greeted us with glass of champagne. The room attendant brought us extra towels immediately and the rooms are fantastic. Comfortable beds and huge bathrooms. The resort feels like a high end resort. Too bad we’re only staying one night!!
Stayed 1 night in Jan 2026

6/10 Okay

Brianna

Travelled with family
Liked: Cleanliness, staff & service, amenities
Pros: staff is very friendly and hardworking, the pool area was great, location was close to lots of shops and restaurants, loved the ability to rent fishing poles, kayaks/paddleboards, and bikes for up to 2 hours a day for free. Cons: the room we had only had one bed and a pullout couch which was super uncomfortable, you could feel the springs no matter where you layed. We ran out of toilet paper and lotion and had to call multiple times before someone came to restock. Very expensive for what you get.
Stayed 5 nights in Dec 2025

10/10 Excellent

Navya

Very clean room and friendly staff. They were very eager to answer our questions about the area/amenities and quick to get our sink fixed, even though it was late at night! Would definitely recommend them in you're spending a day in the area.
Stayed 1 night in Dec 2025

8/10 Good

Kory

Liked: Cleanliness, staff & service, property conditions & facilities
Good location and a nice resort all in all. However, the rooms are very noisy. You can hear everything being said in the rooms around you.
Stayed 2 nights in Dec 2025

10/10 Excellent

Shankar B

Liked: Cleanliness, amenities, property conditions & facilities
Room was spotless. Great breakfast. Amazing view of the sunrise.
From our balcony
Stayed 1 night in Jan 2026

10/10 Excellent

David

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Eggs to order fresh.
Stayed 6 nights in Dec 2025

10/10 Excellent

Donghyun

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Breakfast omr
Stayed 2 nights in Dec 2025

8/10 Good

Dionicio

Stayed 1 night in Dec 2025

10/10 Excellent

Julie

Travelled with family, Travelled with pets
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Entire resort was clean and beautiful. Quiet location with beautiful rooms. We will return.
Stayed 2 nights in Dec 2025

8/10 Good

DAWNE, Tampa

Travelled with partner
Liked: Property conditions & facilities
Staff was wonderful
Stayed 3 nights in Dec 2025

10/10 Excellent

Kunfeng

Travelled with family, Travelled with family and small children, Travelled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
They have warm swim pool and hot tub! Nice and clean.
Stayed 4 nights in Dec 2025

10/10 Excellent

Changyi

Stayed 4 nights in Dec 2025

10/10 Excellent

venkat

Travelled with family, Travelled with group
Liked: Cleanliness, amenities, property conditions & facilities
Great little place on highway 1 in Islamorada. Renovated, clean great bathrooms, balconies, 2 heated pools and a jacuzzi, wonderful breakfast excellent and friendly staff and a welcome champagne drink 😃. Wait did i forget to mention amazing ocean views with ample beach chairs and umbrellas. They have free fishing and kayaking activities. Two families of 4 stayed and had a great time. This place is a gem.
Stayed 2 nights in Dec 2025

6/10 Okay

Kait

Overall, our stay was okay!
Stayed 3 nights in Dec 2025

6/10 Okay

Pamela, West Palm Bch

We arrived at 3:15 there was no room available for us. So we got in a bad mood. We had to wait for the turtle club (slowwww)to clean it we finally were in our room 2 hours later. Check in time is 4pm it was after 5 by the time we we could get keys was very frustrating Breakfast was ok amenities were just ok.
Stayed 3 nights in Dec 2025

10/10 Excellent

Jordan

Stayed 3 nights in Dec 2025

10/10 Excellent

James

Stayed 2 nights in Dec 2025