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Chesapeake Beach Resort

3.5 star property
Hotel on the beach, with 2 outdoor pools

Choose dates to view prices

Chesapeake Beach Resort offers a quiet escape in Matecumbe. Start your day with a leisurely breakfast, then head to the private beach with sun loungers and kayaking. Enjoy two outdoor pools, while multilingual staff and concierge services help plan the perfect stay.

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • 24/7 front desk
  • Bar
The current price is S$278
includes taxes & fees
17 Nov - 18 Nov

Room options

Available filters for rooms
Showing 20 of 20 rooms

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

9.8 out of 10
Exceptional
(43 reviews)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Separate bedroom
  • 34 sq m
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

View all photos for Ocean View King

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King

9.4 out of 10
Exceptional
(82 reviews)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Separate bedroom
  • 34 sq m
  • Ocean view
  • Sleeps 3
  • 1 King Bed

View all photos for ADA Ocean View King Suite

Balcony

ADA Ocean View King Suite

8.0 out of 10
Very good
(3 reviews)

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 50 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed

View all photos for ADA Ocean View King

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

ADA Ocean View King

8.6 out of 10
Excellent
(17 reviews)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Separate bedroom
  • 34 sq m
  • Ocean view
  • Sleeps 3
  • 1 King Bed

View all photos for ADA Ocean View Queens

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

ADA Ocean View Queens

9.0 out of 10
Wonderful
(7 reviews)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout curtains
  • 34 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

View all photos for Hearing Impaired Ocean View Queens

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Hearing Impaired Ocean View Queens

10.0 out of 10
Exceptional
(2 reviews)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Separate bedroom
  • 34 sq m
  • Ocean view
  • 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)

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 50 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Standard Queens

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard Queens

9.4 out of 10
Exceptional
(56 reviews)

Highlights

Deck/patio
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Separate bedroom
  • 29 sq m
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard Doubles

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard Doubles

9.2 out of 10
Wonderful
(92 reviews)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Separate bedroom
  • 25 sq m
  • Sleeps 4
  • 2 Double Beds

View all photos for Standard King with Sleeper Sofa

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard King with Sleeper Sofa

9.0 out of 10
Wonderful
(21 reviews)

Highlights

Deck/patio
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Separate bedroom
  • 29 sq m
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard King

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard King

9.4 out of 10
Exceptional
(30 reviews)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Separate bedroom
  • 25 sq m
  • Sleeps 3
  • 1 King Bed

View all photos for Ocean View King Suite

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King Suite

9.4 out of 10
Exceptional
(16 reviews)

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 49 sq m
  • 1 bedroom
  • Ocean view
  • 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

8.8 out of 10
Excellent
(9 reviews)

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
  • 60 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 6
  • 2 Queen Beds

View all photos for 2-Bedroom Villa

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

2-Bedroom Villa

10.0 out of 10
Exceptional
(1 review)

Highlights

Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dishwasher
HDTV
Hypo-allergenic bedding
  • 60 sq m
  • 2 bedrooms
  • Resort view
  • Sleeps 6
  • 1 King Bed, 1 Double Bed and 1 Double Sofa Bed

View all photos for Standard King Villa

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard King Villa

Highlights

Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout curtains
  • 30 sq m
  • 1 bedroom
  • Resort view
  • Sleeps 3
  • 1 King Bed

View all photos for King Efficiency Villa

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

King Efficiency Villa

10.0 out of 10
Exceptional
(2 reviews)

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
Dishwasher
  • 48 sq m
  • 1 bedroom
  • Resort view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for ADA King Efficiency Villa

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

ADA King Efficiency Villa

Highlights

Separate dining area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
HDTV
Hypo-allergenic bedding
  • 48 sq m
  • 1 bedroom
  • Resort view
  • Sleeps 3
  • 1 King Bed

View all photos for Premium 1-Bedroom Ocean View Villa

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Premium 1-Bedroom Ocean View Villa

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
Dishwasher
  • 65 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 6
  • 2 Double Beds and 1 Double Sofa Bed

View all photos for Premium Ocean View King Villa

Living area

Premium Ocean View King Villa

Highlights

Patio
Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
  • 77 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

Ocean View King Efficiency Villa

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dishwasher
HDTV
  • 48 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

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Exterior

Fisher Inn Resort & Marina

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  • On private beach
  • Pool
  • Breakfast included
  • Pet-friendly
8.2 out of 10, Very good, 1,002 reviews
The price is S$206
includes taxes & fees
4 Dec - 5 Dec
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About the area

Map
83409 Overseas Hwy, Islamorada, FL, 33036

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
  • Theater of the Sea - 2 min drive - 2.4 km
  • Islamorada Brewery & Distillery - 3 min drive - 2.7 km
  • Bud n' Mary's Dive Center - 10 min drive - 7.6 km

Getting around

  • Miami International Airport (MIA) - 91 min drive

Restaurants

  • ‪Tiki Bar - ‬13 min walk
  • ‪Lorelei Restaurant & Cabana Bar - ‬3 min drive
  • ‪Wahoo's Bar & Grill - ‬2 min walk
  • ‪Wendy's - ‬2 min drive
  • ‪Starbucks - ‬15 min walk

About this property

Chesapeake Beach Resort

Remodelled hotel, renovated in 2020 and located in Matecumbe
Free continental breakfast, a marina and a bar are just a few of the amenities provided at Chesapeake Beach Resort. With a private beach, sunloungers and kayaking, this hotel is the perfect place to soak up some sun. Enjoy on-site activities, such as fishing and boat tours. Stay connected with free in-room WiFi.
You'll also enjoy the following perks during your stay:
  • 2 outdoor pools, along with sunloungers
  • Free bike hire, smoke-free property and multilingual staff
  • Concierge services, coffee/tea in reception and a 24-hour front desk
  • Beach towels and a computer station
  • Guest reviews give top marks for the breakfast, beach locale and pool
Room features
All 60 rooms offer comforts such as laptop-friendly workspaces and air conditioning, in addition to perks such as free WiFi. Guest reviews speak positively of the cleanliness, size rooms at the property.
Other amenities include:
  • Hypo-allergenic bedding and pillowtop mattresses
  • Designer toiletries, showers and hairdryers
  • 43-inch HDTVs with cable channels
  • Wardrobes/cupboards, microwaves and coffee/tea makers

Similar properties

Exterior
Amara Cay Resort
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  • Pool
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  • Restaurant
8.8 out of 10, Excellent, 1,249 reviews
The price is S$292
includes taxes & fees
30 Nov - 1 Dec
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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
  • Renovated entire property - January 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 and check-out are available
Late check-in subject to availability
Minimum check-in age - 18

Check-out

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

Special check-in instructions

Front desk staff will greet guests on arrival at the property

Access methods

Staffed front desk

Pets

Pets are allowed for an extra charge of USD 50.00, per accommodation, per night, plus a deposit of USD 50.00 per stay
Service animals are welcome, and are exempt from fees
2 total (up to 23 kg per pet)
Restrictions apply; for more information contact the property on the number on the booking confirmation

Children and extra beds

Children are welcome
Rollaway/extra beds are not available.

Payment types at the property

Important information

Optional extras

  • 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

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

We should mention

This property does not have any lifts
Pool access available from 7:00 AM to 10:30 PM
Some facilities may have restricted access; guests can contact the property for details using the contact information on the booking confirmation
Construction is underway at a neighbouring building and there may be noise disturbance from the construction work
Children under 16 years old are not allowed in the swimming pool without adult supervision

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

Frequently asked questions

Does Chesapeake Beach Resort have a pool?

Yes, this property has 2 outdoor pools. Pool access is from 7:00 AM to 10:30 PM.

How much does it cost to stay at Chesapeake Beach Resort?

As of 14 Nov, 2025, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on 17 Nov, 2025 start from S$278.33, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Chesapeake Beach Resort pet-friendly?

Yes, this property allows pets (limit 2 total) with a maximum weight of up to 23 kg per pet. There's a deposit of USD 50.00 per stay and a fee of USD 50.00 per accommodation, per night. Service animals are exempt from fees. Some restrictions may apply, so please contact the property for more details.

What time is check-in at Chesapeake Beach Resort?

Check-in start time: 4:00 PM; check-in end time: 3:00 AM. Late check-in is available during limited hours.

What time is check-out at Chesapeake Beach Resort?

Checkout is at 11 AM. Late checkout is available for a fee.

Where is Chesapeake Beach Resort located?

Nestled on the beach, this Matecumbe hotel is within 1 mi (2 km) of History of Diving Museum and Windley Key Fossil Reef Geological State Park. Islamorada Brewery & Distillery and Keys History & Discovery Center are also within 2 miles (3 km).

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Reviews

Chesapeake Beach Resort Reviews

9.2

Wonderful

9.4

Cleanliness

9.0

Amenities

9.2

Staff & service

9.0

Eco-friendliness

9.2

Property conditions & facilities
Rating 10 - Excellent. 1142 out of 1568 reviews
Rating 8 - Good. 264 out of 1568 reviews
Rating 6 - Okay. 93 out of 1568 reviews
Rating 4 - Poor. 40 out of 1568 reviews
Rating 2 - Terrible. 29 out of 1568 reviews

Reviews

8/10 Good

Dwight

Liked: Cleanliness, amenities, property conditions & facilities
Clean room, friendly staff, perfect setting, good breakfast
Stayed 7 nights in Oct 2025

10/10 Excellent

Aleksandra

Liked: Cleanliness, amenities, property conditions & facilities
Great hotel and stuff
Stayed 2 nights in Oct 2025

8/10 Good

Rhonda

Liked: Cleanliness, amenities, property conditions & facilities
Nice place, good location, friendly staff, clean room, good food, beat views, easy access to pool and beach.
Stayed 3 nights in Nov 2025

10/10 Excellent

Carlos Alberto

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great place to relax.
Stayed 5 nights in Aug 2025

10/10 Excellent

Kelley

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything about the property was impressive. It was a great stay, and we would stay there again.
Stayed 2 nights in Nov 2025

10/10 Excellent

Laurie

Liked: Cleanliness, amenities, property conditions & facilities
Beautiful location. The room was very comfortable and clean. The ocean view room with a balcony was perfect. The continental breakfast was great. I would highly recommend staying here.
Stayed 5 nights in Nov 2025

10/10 Excellent

Marilyn

Liked: Cleanliness
Friendly staff clean room!!!
Stayed 1 night in Oct 2025

10/10 Excellent

Aloke

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great place, ambience, people and peacefull
Stayed 3 nights in Oct 2025

10/10 Excellent

Andrew

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location right on the beach with 2 pools. Entire place looks to have been totally renovated in the last year or two, and the rooms and fixtures all look brand new. Easy parking, nice breakfast included
Stayed 1 night in Nov 2025

8/10 Good

Darrick

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Friendly staff
Stayed 3 nights in Oct 2025

10/10 Excellent

garry

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Resort offered alot considering it was somewhat smaller. Excellent staff and rooms/amenities..will definitely go back.
Stayed 3 nights in Oct 2025

8/10 Good

Cody Douglas

Liked: Cleanliness, amenities, property conditions & facilities
Room was very clean, staff very friendly. The resort was nice and well taken care of. A very nice resort to stay without the resort up charges! My wife and I would come back again. Chef Chris, handling the breakfast in the morning is the man!
Stayed 4 nights in Nov 2025

10/10 Excellent

Yudith

Liked: Cleanliness, amenities, property conditions & facilities
Especial as always
Stayed 2 nights in Nov 2025

10/10 Excellent

Cheryl

Liked: Cleanliness, amenities, property conditions & facilities
Our room was beautiful and spotless. The staff was always polite, handling any inquiry or request. The location is ideal, located on the beach with easy access to the main road. They provide a nice breakfast from 6 to 10 every morning with a variety of options to choose from on top of 24-hour coffee.
Stayed 3 nights in Nov 2025

10/10 Excellent

Kendra

Liked: Cleanliness, property conditions & facilities
We ended up there because the Air BnB that we had booked was having the floors painted our last night. We had to find something else at the last minute. Chesapeake Beach Resort was beautiful! There was so much to do. We wish we would have stayed there our whole trip. We will definitely be staying again if we go back to the Keys!
Stayed 1 night in Nov 2025

10/10 Excellent

nancy Rioseco

Liked: Cleanliness, staff & service, property conditions & facilities
The breakfast was fresh and hot with a nice selection of fruits and drink. The staff was amazing. Would definitely recommend this resort. The pools were clean and the beach was beautiful.
Stayed 2 nights in Sep 2025

10/10 Excellent

Juan

Liked: Cleanliness, amenities, property conditions & facilities
All cleaning and organized
Stayed 1 night in Nov 2025

8/10 Good

haley

Liked: Cleanliness, amenities, property conditions & facilities
breakfast was very good, but it was totally self service clean up as well. The beach in the keys is nothing special. The kayak was included for one hour if you want a fishing rod or two hours with two people only no fishing rod.
Stayed 1 night in Nov 2025

10/10 Excellent

Alex

Liked: Cleanliness, amenities, property conditions & facilities
Feom start to finsh i have nothing but 100 stars for this place! Check in was a breeze, view was perfect. Privacy, quiet, except noise from main road but once you close the sliding door and curtains good night! The complimentary breakfast was a hit and definitely filling, you eat and can sit right next to the water and watch the fish and sunrise! Pleanty of charis on beach! Parking was perfect and covered! Bed was comphy and shower was amazing!
Stayed 3 nights in Nov 2025

10/10 Excellent

Katya

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Nice place to stay.
Stayed 2 nights in Jun 2025

10/10 Excellent

Thomas

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was welcoming and accommodating
Stayed 1 night in Aug 2025

8/10 Good

Nancy

Liked: Cleanliness, amenities, property conditions & facilities
The room is always very clean. The only thing that I always have an issue with is there is no vanity space in the bathroom for toiletries. A shelf or something would be a nice addition to store toiletries.
Stayed 2 nights in Nov 2025

10/10 Excellent

Annie

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent
Stayed 1 night in Sep 2025

10/10 Excellent

Evelin

Liked: Cleanliness, staff & service, property conditions & facilities
All is clean the service is nice 💕
Stayed 1 night in Aug 2025

10/10 Excellent

Francisco

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Best breakfast ever right on the ocean 😋
Stayed 1 night in Jul 2025