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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 WiFi
The current price is AED 674
AED 964 total
includes taxes & fees
6 Jan - 7 January 2026

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 cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillowtop bed
  • 34 sq m
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

View all photos for Ocean View King

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King

9.4 out of 10
Exceptional
(86 reviews)

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout drapes/curtains
  • 34 sq m
  • Ocean view
  • 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

8.0 out of 10
Very good
(3 reviews)

Highlights

Balcony
Separate sitting area
Air conditioning
Free cribs/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

Hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA Ocean View King

8.6 out of 10
Excellent
(17 reviews)

Highlights

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

View all photos for ADA Ocean View Queens

ADA Ocean View Queens | Hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA Ocean View Queens

9.0 out of 10
Wonderful
(7 reviews)

Highlights

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

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Pillowtop bed
  • 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 cribs/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

Standard Queens | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard Queens

9.4 out of 10
Exceptional
(56 reviews)

Highlights

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

View all photos for Standard Doubles

Standard Doubles | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard Doubles

9.2 out of 10
Wonderful
(92 reviews)

Highlights

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

View all photos for Standard King with Sleeper Sofa

Standard King with Sleeper Sofa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King with Sleeper Sofa

9.0 out of 10
Wonderful
(22 reviews)

Highlights

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

View all photos for Standard King

Standard King | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King

9.4 out of 10
Exceptional
(32 reviews)

Highlights

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

View all photos for Ocean View King Suite

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King Suite

9.4 out of 10
Exceptional
(16 reviews)

Highlights

Balcony
Separate sitting area
Air conditioning
Free cribs/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 cribs/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

2-Bedroom Villa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

2-Bedroom Villa

10.0 out of 10
Exceptional
(1 review)

Highlights

Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/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

Standard King Villa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King Villa

Highlights

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

View all photos for King Efficiency Villa

King Efficiency Villa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

King Efficiency Villa

10.0 out of 10
Exceptional
(2 reviews)

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/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

ADA King Efficiency Villa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA King Efficiency Villa

Highlights

Separate dining area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/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

Premium 1-Bedroom Ocean View Villa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Premium 1-Bedroom Ocean View Villa

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/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

Premium Ocean View King Villa | Living area | 43-inch flat-screen TV with cable channels, TV

Premium Ocean View King Villa

Highlights

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

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Islander Resort

Matecumbe
  • On private beach
  • Pool
  • Pet friendly
  • Parking included
9.2 out of 10, Wonderful, 1,002 reviews
The price is AED 1,619
AED 2,069 total
includes taxes & fees
9 Jan - 10 January 2026
Islander Resort

About the neighborhood

Map
83409 Overseas Hwy, Islamorada, FL, 33036

What's nearby

  • History of Diving Museum - 12 min walk - 1.1 km
  • Theater of the Sea - 3 min drive - 2.0 km
  • Windley Key Fossil Reef Geological State Park - 3 min drive - 2.0 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 Intl. 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

Remodeled 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, sun loungers, and fishing, this hotel is the perfect place to soak up some sun. Enjoy onsite activities like 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 sun loungers
  • Free bicycle rentals, multilingual staff, and a computer station
  • A 24-hour front desk, coffee/tea in the lobby, and beach towels
  • Concierge services and smoke-free premises
  • 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 like free WiFi. Guest reviews speak positively of the clean, spacious rooms at the property.
More amenities include:
  • Hypo-allergenic bedding and pillowtop mattresses
  • Designer toiletries, showers, and hair dryers
  • 43-inch HDTVs with cable channels
  • Wardrobes/closets, microwaves, and coffee/tea makers

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Lime Tree Bay Resort
  • On private beach
  • Pool
  • Hot tub
  • Pet friendly
9.2 out of 10, Wonderful, 1,109 reviews
Lime Tree Bay Resort

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 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

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 washroom

More

  • 2 floors
  • 9 buildings
  • Built in 2020
  • Renovated entire property - January 2020
  • Smoking not allowed
  • 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 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 50 lbs per pet)
Restrictions apply; for more information contact the property at the number on the booking confirmation

Children and extra beds

Children are welcome
Rollaway/extra beds are not available

Property payment types

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, 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

We should mention

This property does not have elevators
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 neighboring 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–10:30 PM.

Is Chesapeake Beach Resort pet-friendly?

Yes, this property allows pets (limit 2 total) with a maximum weight of up to 50 lbs 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?

Check-out is at 11 AM. Late check-out 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 mi (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. 1167 out of 1602 reviews
Rating 8 - Good. 268 out of 1602 reviews
Rating 6 - Okay. 96 out of 1602 reviews
Rating 4 - Poor. 42 out of 1602 reviews
Rating 2 - Terrible. 29 out of 1602 reviews

Reviews

10/10 Excellent

Mat

Liked: Cleanliness, amenities, property conditions & facilities
The entire resort was wonderful.
Stayed 3 nights in Dec 2025

10/10 Excellent

Gary

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great breakfast, great location, friendly staff, nice extras.
Stayed 1 night in Dec 2025

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

Suzanne

Liked: Cleanliness, amenities, property conditions & facilities
Wonderful place!
Stayed 1 night in Dec 2025

10/10 Excellent

ALEXANDER

Liked: Cleanliness, amenities, property conditions & facilities
Excellent hotel
Stayed 3 nights in Nov 2025

10/10 Excellent

Sue

Liked: Cleanliness, amenities, property conditions & facilities
Great chef that made breakfast to order! Resort was calming and relaxing!
Stayed 7 nights in Nov 2025

10/10 Excellent

Naima

Liked: Cleanliness, amenities, property conditions & facilities
Everything was very nice and clean
Stayed 2 nights in Dec 2025

8/10 Good

James

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great breakfast very well kept grounds
Stayed 6 nights in Nov 2025

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

10/10 Excellent

Jeff

Liked: Cleanliness, amenities, property conditions & facilities
Room was great. Staff was awesome views amazing !!!!!
View outside our room
Stayed 7 nights in Dec 2025

8/10 Good

Kenneth

Liked: Cleanliness, staff & service, property conditions & facilities
Breakfast was great every day. Chef Chris was so friendly and made us feel welcome.
Stayed 4 nights in Dec 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

Sheila

Liked: Cleanliness, amenities, property conditions & facilities
The room extremely clean and staff were amazing. The grounds were well kept. The location was great the scenery was perfect AND the omelettes in the Sunrise room were off the chain delicious. 1000% recommend and will definitely be returning.
Stayed 4 nights in Dec 2025

10/10 Excellent

Maira

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was a great breakfast.... they had everything that i liked in particular. They had healthy options.. not a big place so it didnt seem overwhelmed with options just the right amount of options. Place i staid had an amazing ocean view :)
Stayed 1 night in Dec 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

Carl

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful property, breakfast was awesome
Stayed 1 night in Sep 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

8/10 Good

Rita

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Just a painted up old hotel, was fine though.
Stayed 2 nights in Dec 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

Aloke

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

10/10 Excellent

Sarah

Liked: Cleanliness, amenities, property conditions & facilities
Beautiful resort with lots of included activities & water sports. Friendly staff. Clean rooms.
Stayed 1 night in Nov 2025

10/10 Excellent

Kevin

Liked: Cleanliness, amenities, property conditions & facilities
Excellent !!!!!
Stayed 3 nights in Dec 2025

10/10 Excellent

Marilyn

Liked: Cleanliness
Friendly staff clean room!!!
Stayed 1 night 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