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Chesapeake Beach Resort

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

Choose dates to view prices

Photo gallery for Chesapeake Beach Resort

Relax on the beach with a tranquil ocean view and comfortable sun loungers.
Enjoy a comfortable stay with a large bed, desk, and seating area, plus a window offering a view of the outdoors.
Enjoy breathtaking ocean views from this balcony overlooking the beach.
Relax by the pool, surrounded by palm trees and a hot tub.
Overlooking the calm waters, this hotel offers stunning views of the surrounding landscape and palm trees.

Popular amenities

  • Bar
  • 24/7 front desk

Explore the area

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

Room options

View all photos for 2-Bedroom Villa

2-Bedroom Villa | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

2-Bedroom Villa

10.0 out of 10
Exceptional
(1 review)
  • 646 sq ft
  • Resort view
  • Sleeps 6
  • 1 King Bed, 1 Double Bed and 1 Double Sofa Bed

View all photos for Standard King

Standard King | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King

9.4 out of 10
Exceptional
(28 reviews)
  • 272 sq ft
  • Sleeps 3
  • 1 King Bed

View all photos for King Efficiency Villa

King Efficiency Villa | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

King Efficiency Villa

10.0 out of 10
Exceptional
(1 review)
  • 517 sq ft
  • Resort view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard Doubles

Standard Doubles | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard Doubles

9.2 out of 10
Wonderful
(82 reviews)
  • 272 sq ft
  • Sleeps 4
  • 2 Double Beds

View all photos for Standard King with Sleeper Sofa

Standard King with Sleeper Sofa | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King with Sleeper Sofa

9.0 out of 10
Wonderful
(18 reviews)
  • 307 sq ft
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Hearing Impaired Ocean View Queens

1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Hearing Impaired Ocean View Queens

10.0 out of 10
Exceptional
(2 reviews)
  • 366 sq ft
  • 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)
  • 540 sq ft
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for ADA King Efficiency Villa

ADA King Efficiency Villa | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA King Efficiency Villa

  • 517 sq ft
  • Resort view
  • Sleeps 3
  • 1 King Bed

View all photos for Premium 1-Bedroom Ocean View Villa

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

Premium 1-Bedroom Ocean View Villa

  • 700 sq ft
  • Ocean view
  • Sleeps 6
  • 2 Double Beds and 1 Double 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)
  • 650 sq ft
  • Ocean view
  • Sleeps 6
  • 2 Queen Beds

View all photos for Ocean View King

1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King

9.6 out of 10
Exceptional
(77 reviews)
  • 364 sq ft
  • Ocean view
  • Sleeps 3
  • 1 King Bed

View all photos for Ocean View King Suite

1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King Suite

9.4 out of 10
Exceptional
(13 reviews)
  • 527 sq ft
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

9.8 out of 10
Exceptional
(43 reviews)
  • 366 sq ft
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

Ocean View King Efficiency Villa

  • 517 sq ft
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard Queens

Standard Queens | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard Queens

9.4 out of 10
Exceptional
(52 reviews)
  • 307 sq ft
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard King Villa

Standard King Villa | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King Villa

  • 323 sq ft
  • Resort view
  • Sleeps 3
  • 1 King 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

  • 829 sq ft
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for ADA Ocean View Queens

ADA Ocean View Queens | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA Ocean View Queens

9.0 out of 10
Wonderful
(7 reviews)
  • 366 sq ft
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

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)
  • 540 sq ft
  • Ocean view
  • Sleeps 4
  • 1 King Bed

View all photos for ADA Ocean View King

1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA Ocean View King

8.6 out of 10
Excellent
(16 reviews)
  • 364 sq ft
  • Ocean view
  • Sleeps 3
  • 1 King Bed

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Relax by the oceanfront pool surrounded by palm trees and lounge chairs.

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Islamorada
  • On private beach
  • Pool
  • Pet friendly
  • Free WiFi
4.5 out of 5, Wonderful, 48 reviews
$210 nightly
The price is $237
Aug 19 - Aug 20
Total includes taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

About the neighborhood

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 - 0.7 miles
  • Windley Key Fossil Reef Geological State Park - 2 min drive - 1.3 miles
  • Theater of the Sea - 2 min drive - 1.5 miles
  • Florida Keys Brewing Co. - 4 min drive - 2.5 miles
  • Bud n' Mary's Dive Center - 7 min drive - 4.6 miles

Getting around

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

Restaurants

  • ‪Lorelei Restaurant & Cabana Bar - ‬3 min drive
  • ‪Hog Heaven - ‬3 min drive
  • ‪Wahoo's Bar & Grill - ‬2 min walk
  • ‪Florida Keys Brewing Co. - ‬3 min drive
  • ‪Whale Harbor Restaurant Marina - ‬2 min walk

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. 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 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.

Languages

English, Spanish

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Relax in a serene outdoor seating area with Adirondack chairs around a central fire pit, surrounded by palm trees and ocean views.

Amara Cay Resort

  • On private beach
  • Pool
  • Pet friendly
  • Restaurant
4.4 out of 5, Excellent, 1,243 reviews
$224 nightly
The price is $253
Aug 13 - Aug 14
Total includes taxes and fees
Amara Cay Resort

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

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
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. 

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

How close is Chesapeake Beach Resort to the airport?

Chesapeake Beach Resort is 77.5 mi (91-min drive) away from the Miami Intl. Airport (MIA) airport, the closest popular airport to the property.

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

As of Jul 24, 2025, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on Aug 5, 2025 start from $199.0, excluding 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.

Does Chesapeake Beach Resort have an airport shuttle?

Airport shuttle services are not available at Chesapeake Beach Resort.

How close is Chesapeake Beach Resort to the beach?

This hotel is on a private beach. Don't forget your sunscreen!

Does Chesapeake Beach Resort offer free breakfast?

Chesapeake Beach Resort offers free continental breakfast every day from 6:00 AM to 10:00 AM.

Is there a casino at Chesapeake Beach Resort?

No, there is no casino at this hotel.

What time is check-in at Chesapeake Beach Resort?

Check-in start time: 4:00 PM; Check-in end time: 3:00 AM.

Is there free parking at Chesapeake Beach Resort?

Free parking is not available at this hotel.

Does Chesapeake Beach Resort have a pool?

Chesapeake Beach Resort features 2 outdoor pools. Guests can enjoy pool access from 7:00 AM to 10:30 PM.

Does Chesapeake Beach Resort have a spa?

There are no spa services available at this hotel.

How close is Chesapeake Beach Resort to downtown Islamorada?

Chesapeake Beach Resort is 1.2 mi away from Islamorada.

Chesapeake Beach Resort Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 1072 out of 1490 reviews
Rating 8 - Good. 250 out of 1490 reviews
Rating 6 - Okay. 93 out of 1490 reviews
Rating 4 - Poor. 41 out of 1490 reviews
Rating 2 - Terrible. 34 out of 1490 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

8.8/10

Amenities

9.2/10

Property conditions & facilities

9.0/10

Eco-friendliness

Reviews

10/10 Excellent

Michael Joseph

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
Very clean, the staff was great. Breakfast was terrific. I would recommend staying here. I’ll definitely be going back.
The view from our room, 317 was incredible!
!!!!
Stayed 3 nights in Jul 2025

10/10 Excellent

Michelle

Stayed 2 nights in Jun 2025

10/10 Excellent

VIANA

Stayed 2 nights in May 2025

10/10 Excellent

Jada

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This place is amazing the rooms are beautiful and the view is breathtaking.
Stayed 3 nights in Apr 2025

10/10 Excellent

Christopher P

Liked: Staff & service, property conditions & facilities
Stayed 1 night in Apr 2025

10/10 Excellent

david

Stayed 2 nights in Apr 2025

8/10 Good

John

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Apr 2025

10/10 Excellent

Jen

Stayed 1 night in Apr 2025

10/10 Excellent

Dianelis

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excelent
Stayed 1 night in Mar 2025

8/10 Good

Nicole

Liked: Cleanliness, staff & service, property conditions & facilities
Beautiful view from room , breakfast included is nice due to price of room
Stayed 4 nights in Apr 2025

8/10 Good

Tom

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Apr 2025

10/10 Excellent

jamie

Stayed 2 nights in Apr 2025

10/10 Excellent

Yoxaris

Stayed 4 nights in Apr 2025

8/10 Good

Kurt, Miami

Traveled with family
We made a stop over at this place on our way from Miami to Ley West. A convienient, nice place with good restaurants near by.
Stayed 1 night in Apr 2025

10/10 Excellent

Kirstin

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Property location was good. The views were beautiful. Lots of lounge chairs and space for everyone. We went during the week and felt like we were in an exclusive place. Front desk staff were beyond excellent. Restaurant next door was fabulous. Fresh fish and great drinks. The bed in the Villa was super comfy. Plenty of towels and amenities. I give it a great recommendation .
Stayed 4 nights in Apr 2025

10/10 Excellent

Jennifer

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great views, easy beach and pool access. 2 hours of included daily use of kayaks and paddle boards. Quiet, relaxing, friendly staff. Great location between Miami and Key West.
Stayed 5 nights in Apr 2025

10/10 Excellent

Steven

Liked: Cleanliness, staff & service, property conditions & facilities
This is a wonderful spot. The staff was welcoming and our room was wonderful. We’ll be back!
Stayed 2 nights in Apr 2025

10/10 Excellent

Pamela, Dunkirk

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Such a nice hidden gem in the keys! Lots of beach space, 2 pools, breakfast included was a nice bonus.
Stayed 1 night in Apr 2025

10/10 Excellent

Jan

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Apr 2025

10/10 Excellent

WD

Stayed 1 night in Apr 2025

8/10 Good

Amy

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

Nice Resort for the Money

I was looking for a one night stay in Islamorada that wouldn't break the bank, but still be comfortable and clean. The Chesapeake Resort fit the bill! Rooms have been updated and resort was clean and quiet. It has a nice area for sunning and two pools. There isn't a restaurant or bar on site, but they do offer a very good continental breakfast with made to order eggs and a bar cart with quality liquor, beer, and wine. Also, two restaurants are within walking distance.
Stayed 1 night in Mar 2025

10/10 Excellent

Brian

Liked: Cleanliness, staff & service, property conditions & facilities
The property was clean and and everything was well maintained.
Stayed 4 nights in Apr 2025

4/10 Poor

Angelina

Disliked: Cleanliness, property conditions & facilities
Stayed 2 nights in Apr 2025

10/10 Excellent

Tammy M.

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Absolutely heaven on Earth! Gorgeous grounds beautiful room. The property was beyond exceptional in everyday!
Stayed 2 nights in Apr 2025

10/10 Excellent

Patricia

Stayed 2 nights in Apr 2025