Chesapeake Beach Resort

3.5 star property
Beach hotel with 2 outdoor pools and marina

Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun-loungers, beach towels
Water view
1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace
Outdoor spa tub
Balcony

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Bar
  • 24/7 front desk
The current price is NZ$338
includes taxes & fees
3 Nov - 4 Nov

Explore the area

View map
83409 Overseas Hwy, Islamorada, FL, 33036
  • Place, Windley Key Fossil Reef Geological State Park
    ‪2 min drive‬
  • Place, Theater of the Sea
    ‪2 min drive‬
  • Place, Florida Keys Brewing Co.
    ‪5 min drive‬

Room options

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

Ocean View King

9.4 out of 10
Exceptional
(81 reviews)

Highlights

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

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

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

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
Separate bedroom
  • 34 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

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

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

Standard Queens

9.4 out of 10
Exceptional
(55 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

Standard Doubles

9.2 out of 10
Wonderful
(88 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

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
Sofa bed
  • 29 sq m
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

Standard King

9.4 out of 10
Exceptional
(29 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

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

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

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

Standard King Villa

Highlights

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

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

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

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

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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About the area

Islamorada

At Chesapeake Beach Resort you'll be within a 15-minute walk of History of Diving Museum and 1.8 km (1.1 mi) from Windley Key Fossil Reef Geological State Park. Highlights at this beachfront hotel include 2 outdoor swimming pools, a private beach and a marina. .Tiki Bar is the hotel's own bar. Enjoy the pool loungers along with access to boat tours and kayaking. Added amenities include free Wi-Fi in public areas, coffee/tea in a common area and free use of bicycles. Free continental breakfast is available daily between 6:00 AM and 10:00 AM. .With a stay at this 3.5-property class Matecumbe hotel, you'll be 2 km (1.2 mi) from Islamorada Brewery & Distillery and 2.7 km (1.7 mi) from Keys History & Discovery Center.

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 - 2 min drive - 2.4 km
  • Florida Keys Brewing Co. - 4 min drive - 4.0 km

Getting around

  • Miami International Airport (MIA) - 91 min drive

Restaurants

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

About this property

Chesapeake Beach Resort

Beach hotel with 2 outdoor pools and marina
Simply walk outside to smell the salty 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 such as 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. A complete renovation of Chesapeake Beach Resort was completed in January 2020.

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 members are 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 features coffee/tea makers and designer toiletries. Beds feature pillowtop mattresses. 43-inch flat-screen televisions come with cable channels. Bathrooms include a shower, complimentary toiletries and hairdryers.

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 telephones along with free local calls (restrictions may apply). Additionally, rooms include an iron/ironing board and a ceiling fan. Housekeeping is offered on a daily basis and hypo-allergenic bedding can be requested.

Similar properties

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: USD 50.00 per accommodation, per night, plus a deposit of USD 50.00 per stay
  • Maximum 2 (weight limit: 50 lb 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

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
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
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 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. This property accepts Visa, Mastercard, American Express and Discover. Cash is not accepted. 

We should mention

  • Pool access available from 7:00 AM to 10:30 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

Frequently asked questions

What is the cancellation policy at Chesapeake Beach Resort?

Chesapeake Beach Resort offers free cancellation on select room rates. Check out the cancellation policy for more info.

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

As of 1 Nov 2025, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on 3 Nov 2025 start from NZ$338.15, 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.

Are there any beaches close to Chesapeake Beach Resort?

The closest beach to Chesapeake Beach Resort is Anne's Beach (16.1 km).

Does Chesapeake Beach Resort have a pool?

Yep, and guests love it! Chesapeake Beach Resort has 2 outdoor swimming pools. Grab your bathers and lounge poolside while enjoying on a lounger. The pool is open 7:00 AM to 10:30 PM.

What makes Chesapeake Beach Resort a romantic place to stay?

A private beach and a lounge bar, as well as pillowtop beds in the guestrooms, all help set the scene for a romantic weekend at Chesapeake Beach Resort.

Does Chesapeake Beach Resort serve breakfast?

Yep, guests give top marks to the free continental breakfast here! Available daily from 6:00 AM to 10:00 AM, this is the perfect place to fuel up for a big day full of adventure.

Is there a free airport shuttle available at Chesapeake Beach Resort?

No, Chesapeake Beach Resort does not offer an airport shuttle service.

What time are check-in & check-out at Chesapeake Beach Resort?

Check-in begins at 4:00 PM. Check-out time is 11 AM.

Chesapeake Beach Resort Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 1129 out of 1550 reviews
Rating 8 - Good. 259 out of 1550 reviews
Rating 6 - Okay. 93 out of 1550 reviews
Rating 4 - Poor. 40 out of 1550 reviews
Rating 2 - Terrible. 29 out of 1550 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

9.0/10

Amenities

9.2/10

Property conditions & facilities

9.0/10

Eco-friendliness

Reviews

10/10 Excellent

David

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Breakfast selections were very good, including made to order omelettes and waffles. Loved the 2 pools, free beach chairs, umbrellas, towels, kayaks. Beach and water had tons of sea weed but staff did best to keep paths open. Beautiful setting, well kept
Stayed 2 nights in Jul 2025

10/10 Excellent

Ryan

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Aug 2025

10/10 Excellent

Brian

Liked: Cleanliness, staff & service, property conditions & facilities
Everything
Stayed 1 night in May 2025

8/10 Good

Luz

Travelled with family
Liked: Cleanliness, staff & service, amenities
I've stayed at this property before and have always enjoyed it..it has everything and perfect for kids. The only thing I would suggest is to exterminate the rooms and facilities.
Stayed 1 night in Aug 2025

4/10 Poor

Philip

Travelled with family
Liked: Cleanliness, property conditions & facilities, room comfort
Disliked: Staff & service

Great location and rooms - service not so!

Stayed 2 nights in Jul 2025

10/10 Excellent

Josephine

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 3 nights in Jul 2025

8/10 Good

Kirsten, Thousand Oaks

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Would prefer a door or curtain so mirror is not right with the bed
Stayed 1 night in Aug 2025

10/10 Excellent

Mario

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I stayed here a long time ago prior to the renovations and I was please to find that it’s still the same great place just a lot nicer.
Stayed 1 night in Jul 2025

10/10 Excellent

Alecia

Liked: Cleanliness, staff & service, property conditions & facilities
-
Stayed 4 nights in Jul 2025

10/10 Excellent

Gary

Liked: Cleanliness, staff & service, property conditions & facilities
Loved the breakfast options! Omlets was a hit.
Stayed 4 nights in Jul 2025

10/10 Excellent

Edgardo

Liked: Amenities
It was new, loved the balcony. Beach sports were nice but needed more lifejacket sizes. Pool amenities were great. Breakfast was good.
Stayed 1 night in Jul 2025

10/10 Excellent

Francisco

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

8/10 Good

vickie

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Ac. Was not great at all. Wish there was more of a variety for food at bar area. We were starving had to order pizza. That was one reason for picking this resort. The breakfast was wonderful tho
Stayed 1 night in Jul 2025

10/10 Excellent

Nicholas

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The hotel is wonderful
Stayed 2 nights in Jul 2025

10/10 Excellent

Adam

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We just got bk from 3 nts here: 2adults 1 child. We absolutely loved this hotel, it was clean, the staff were friendly and the rooms were very clean and the AC was perfect for escaping from the Florida heat and humidity. The breakfast offerings were plentiful, huge shout out to the chef for his waffles for the kids. The outdoor brekfast area was perfect for sitting and staring out to sea and the Islamorada lighthouse. Make sure you check out the entry to the little marina where it narrows at thebentey from the sea - looking into the crystal clear water at dawn and dusk we saw Nurse Sharks, Eels, Horseshoe crabs and so many small and media sized coloured fish. Get up early one morning to checkout the sunrise too!! So worth it! Would highly recommend and we will use again when we are next in Islamorada. A wonderful place to stay.
Stayed 3 nights in Jul 2025

10/10 Excellent

jonathan

Travelled with family, Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Front desk girl i didn't remember her name but she was very kind and proffesional and gave us a beautiful upgrade. Our second time here and will continue to come back.
Stayed 1 night in Jul 2025

10/10 Excellent

Donis

Travelled with family and small children
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Its not to close or to far
Stayed 1 night in Jul 2025

8/10 Good

Jason David

Travelled with partner
Liked: Cleanliness, staff & service, property conditions & facilities
I loved the ocean views! Awesome pool location!
Stayed 2 nights in Jul 2025

10/10 Excellent

Michael

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Chesapeake is Amazing - Gets better every trip

We have been coming here for 5 years and the place gets better and better. Every year we come they have added new amenities. The beach and pools are amazing and the location makes it easy to go anywhere in the Keys quickly. If you are looking for a great resort for a great price in this area it is a GREAT option!
Stayed 4 nights in Jul 2025

10/10 Excellent

Liu M

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
One of my favorite places to have a relaxing trip with the family
Stayed 1 night in Jun 2025

10/10 Excellent

Rachel

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful staff. Vanessa was awesome! We will return
Stayed 2 nights in Jul 2025

6/10 Okay

Mayra

Travelled with family
Stayed 1 night in Jul 2025

10/10 Excellent

Michael

Stayed 1 night in Jul 2025

8/10 Good

Maria

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We were not able to enjoy the beach as it was full of algae, wild plants, and very uncomfortable
Stayed 1 night in Jul 2025

10/10 Excellent

Gabriel

Travelled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved this property. It had inclusive breakfast and watersports available
Stayed 1 night in Jul 2025