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Chesapeake Beach Resort

3.5 star property
Travelers relax on sun-kissed beaches or take refreshing swims in outdoor pools at this peaceful Florida Keys resort with private waterfront access

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

  • Free Wi-Fi
  • Restaurant
The current price is €379
includes taxes & fees
11 Mar - 12 Mar

Room options

Available filters for rooms
Showing 20 of 20 rooms

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

9.6 out of 10
Exceptional
(48 reviews)

Highlights

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

View all photos for Ocean View King

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

Ocean View King

9.6 out of 10
Exceptional
(92 reviews)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Sofa bed
Blackout curtains
  • 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
(7 reviews)

Highlights

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

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
(18 reviews)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Ceiling fan
Separate bedroom
  • 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)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Blackout curtains
Pillow-top bed
  • Ocean view
  • 34 sq m
  • Sleeps 4
  • 2 Queen Beds

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
(2 reviews)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Ceiling fan
Separate bedroom
  • 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)

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 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
(61 reviews)

Highlights

Deck/patio
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Ceiling fan
Separate bedroom
  • 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
(98 reviews)

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Ceiling fan
Separate bedroom
  • 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
(24 reviews)

Highlights

Deck/patio
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Sofa bed
Blackout curtains
  • 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

9.4 out of 10
Exceptional
(36 reviews)

Highlights

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

View all photos for Ocean View King Suite

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

Ocean View King Suite

9.0 out of 10
Wonderful
(18 reviews)

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 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)

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Sofa bed
  • 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)

Highlights

Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dishwasher
HDTV
Hypo-allergenic bedding
  • 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

Highlights

Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
HDTV
Hypo-allergenic bedding
Ceiling fan
Separate bedroom
  • 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

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
  • 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

Highlights

Separate dining area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
HDTV
Hypo-allergenic bedding
  • 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

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
Dishwasher
  • 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

Highlights

Patio
Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
  • 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

Highlights

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

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About the area

Located on a private beach, Chesapeake Beach Resort is in Matecumbe, a neighbourhood in Islamorada. Hurricane Monument and Indian Key Historic State Park are local landmarks, and some of the area's activities can be experienced at Islamorada Brewery & Distillery and Florida Keys Brewing Co.. With jet skiing and snorkelling nearby, you'll find plenty of adventures in the water. Visit our Islamorada travel guide
Map
83409 Overseas Hwy, Islamorada, FL, 33036

What's nearby

  • History of Diving Museum
    History of Diving Museum
    12 min walk - 1.1 km
  • Windley Key Fossil Reef Geological State Park
    Windley Key Fossil Reef Geological State Park
    2 min drive - 2.0 km
  • Theater of the Sea which includes a fountain and signage
    Theater of the Sea
    2 min drive - 2.4 km
  • Islamorada_BudnMarysDiveCenter_6069243-0004
    Bud n' Mary's Dive Center
    5 min drive - 7.3 km
  • Islamorada Brewery & Distillery
    2 min drive - 2.4 km

Getting around

  • Miami International Airport (MIA)
    91 min drive

Restaurants

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

About this property

Chesapeake Beach Resort

Hotel 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 fishing, this hotel is the perfect place to soak up some sun. Enjoy on-site activities, such as kayaking 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, beach towels and a computer station
  • Concierge services, multilingual staff and smoke-free property
  • Coffee/tea in reception and a 24-hour front desk
  • 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

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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
  • 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
Information provided by the property may be translated using automated translation tools

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

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 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
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

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 9 Mar 2026, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on 11 Mar 2026 start from €379, 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

9.2

Property conditions & facilities
Rating 10 - Excellent. 1235 out of 1676 reviews
Rating 8 - Good. 269 out of 1676 reviews
Rating 6 - Okay. 99 out of 1676 reviews
Rating 4 - Poor. 43 out of 1676 reviews
Rating 2 - Terrible. 30 out of 1676 reviews

Reviews

10/10 Excellent

Melissa

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

10/10 Excellent

Judy

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

8/10 Good

Rosalie

Liked: Cleanliness, amenities, property conditions & facilities
Room was clean, lovely beach and lagoon with plenty of lounge chairs. Resort offers a good breakfast and there are a few nice places to eat within walking distance.
Stayed 2 nights in Jan 2026

10/10 Excellent

Kurt

Liked: Cleanliness, staff & service, property conditions & facilities
Wonderful breakfast with omelettes cooked to order, great pancakes, fresh fruit, etc. very pleasant staff and beautiful beach area.
Stayed 2 nights in Jan 2026

10/10 Excellent

Laura

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

10/10 Excellent

Cameron

Liked: Cleanliness, amenities, property conditions & facilities
Staff were friendly, room was a really good size. Resort was nice. Breakfast was fine.
Stayed 1 night in Feb 2026

10/10 Excellent

Stephanie

Liked: Cleanliness, amenities, property conditions & facilities
We loved this place. It’s small and easy to get around. Beautiful setting, watched the sunrise from bed, and the best hotel breakfast we’ve ever had.
View from balcony
Stayed 5 nights in Jan 2026

10/10 Excellent

Warren

Liked: Cleanliness, amenities, property conditions & facilities
Great staff, clean room, nice breakfast and convenient location. Enjoyed our week.
Stayed 6 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

8/10 Good

Nancy

Liked: Cleanliness, amenities, property conditions & facilities
The hotel is in a perfect location, and offers so much on premise
Stayed 3 nights in Jan 2026

10/10 Excellent

Devon

Liked: Cleanliness, amenities, property conditions & facilities
Clean, gorgeous view, amazing free breakfast, loved the robes!
Stayed 4 nights in Jan 2026

10/10 Excellent

Michelle Marie

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

Yuli

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Idyllic beautiful beach setting, clean comfortable rooms, lovely setting.
Stayed 1 night in Dec 2025

10/10 Excellent

Jacqueline

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

Randy

Liked: Cleanliness, amenities, property conditions & facilities
The king suite with ocean view was fantastic. The resort is in good shape with plenty of space to lounge, activities and includes nice breakfast options. Also close to many bars and restaurants.
Stayed 4 nights in Jan 2026

10/10 Excellent

Lauren

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

10/10 Excellent

Joshua

Liked: Cleanliness, property conditions & facilities
Great staff. Lovely grounds. Comfortable clean rooms.
Stayed 7 nights in Jan 2026

10/10 Excellent

Rodney

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

Tom

Liked: Cleanliness
Room was clean. Check in was fast and the staff was very friendly and welcoming.
Stayed 1 night in Jan 2026

10/10 Excellent

Julie

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

Annie

Liked: Cleanliness, amenities, property conditions & facilities
Wonderful nice and clean staff 👌 very nice special specially staff Vanessa she very helpful and sweet. Is nice place to stay we will come again. Thank you Vanessa again.
Stayed 1 night in Jan 2026

10/10 Excellent

Brittany

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The resort is a great family friendly atmosphere. The staff was extremely hospitable. The beach is clean and lots of fun activities to do. Only wish we had more time!
Stayed 1 night in Jan 2026

10/10 Excellent

Gabriel

Liked: Cleanliness, amenities, property conditions & facilities
The staff was amazing. Breakfast was awesome. This was truly a magical time for my wife and i
Stayed 2 nights in Jan 2026

10/10 Excellent

Julie

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

10/10 Excellent

Thomas

Room was clean, breakfast and staff were good
Stayed 2 nights in Nov 2025