See all properties

Chesapeake Beach Resort

3.5 star property

Choose dates to view prices

Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun-loungers, beach towels
Hypo-allergenic bedding, pillow-top beds, laptop workspace
Water view
43-inch flat-screen TV with cable channels, TV
Deluxe Ocean View Two Queen Suite | Balcony

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Free Wi-Fi

Explore the area

View in a map
83409 Overseas Hwy, Islamorada, FL, 33036
  • Place, History of Diving Museum
    ‪12 min walk‬
  • Place, Theater of the Sea
    ‪3 min drive‬
  • Place, Islamorada Brewery & Distillery
    ‪3 min drive‬

Room options

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

9.6 out of 10
Exceptional
(45 reviews)
  • 34 sq m
  • Sleeps 4
  • 2 Queen Beds
  • Ocean view

View all photos for Ocean View King

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

Ocean View King

9.6 out of 10
Exceptional
(87 reviews)
  • 34 sq m
  • Sleeps 3
  • 1 King Bed
  • Ocean view

View all photos for ADA Ocean View King Suite

ADA Ocean View King Suite | Balcony

ADA Ocean View King Suite

8.4 out of 10
Very good
(5 reviews)
  • 50 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed
  • Ocean view

View all photos for ADA Ocean View King

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

ADA Ocean View King

8.6 out of 10
Excellent
(17 reviews)
  • 34 sq m
  • Sleeps 3
  • 1 King Bed
  • Ocean view

View all photos for ADA Ocean View Queens

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

ADA Ocean View Queens

9.0 out of 10
Wonderful
(7 reviews)
  • 34 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds
  • Ocean view

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)
  • 34 sq m
  • Sleeps 4
  • 2 Queen Beds
  • Ocean view

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)
  • 50 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed
  • Ocean view

View all photos for Standard Queens

Standard Queens | Hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard Queens

9.4 out of 10
Exceptional
(59 reviews)
  • 29 sq m
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard Doubles

Standard Doubles | Hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard Doubles

9.2 out of 10
Wonderful
(95 reviews)
  • 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, pillow-top beds, laptop workspace

Standard King with Sleeper Sofa

9.2 out of 10
Wonderful
(23 reviews)
  • 29 sq m
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard King

Standard King | Hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard King

9.6 out of 10
Exceptional
(34 reviews)
  • 25 sq m
  • 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

9.4 out of 10
Exceptional
(16 reviews)
  • 49 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed
  • Ocean view

View all photos for Deluxe Ocean View Two Queen Suite

Balcony

Deluxe Ocean View Two Queen Suite

8.8 out of 10
Excellent
(10 reviews)
  • 60 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds
  • Ocean view

View all photos for 2-Bedroom Villa

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

2-Bedroom Villa

10.0 out of 10
Exceptional
(1 review)
  • 60 sq m
  • 2 bedrooms
  • Sleeps 6
  • 1 King Bed, 1 Double Bed and 1 Double Sofa Bed
  • Resort view

View all photos for Standard King Villa

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

Standard King Villa

  • 30 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Resort view

View all photos for King Efficiency Villa

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

King Efficiency Villa

10.0 out of 10
Exceptional
(2 reviews)
  • 48 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Resort view

View all photos for ADA King Efficiency Villa

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

ADA King Efficiency Villa

  • 48 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Resort view

View all photos for Premium 1-Bedroom Ocean View Villa

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

Premium 1-Bedroom Ocean View Villa

  • 65 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Double Beds and 1 Double Sofa Bed
  • Ocean view

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

  • 77 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Ocean view

Ocean View King Efficiency Villa

  • 48 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Ocean view

Similar properties

Hibiscus Waterfront 2-Bedroom, Two Bath Master Suite (Brand New) | Terrace/patio
Lime Tree Bay Resort
  • On private beach
  • Pool
  • Pet-friendly
  • Parking included
4.6 out of 5, Wonderful, 1,139 reviews
Lime Tree Bay Resort

About this property

Chesapeake Beach Resort

Hotel on the beach, with 2 outdoor pools
At Chesapeake Beach Resort, you can relax at one of the 2 outdoor swimming pools, play on the private white sand beach or spend the day at a marina.
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.

A private beach, a marina and complimentary bicycles are featured at the hotel. 2 outdoor swimming pools are on site.

Children aged under 16 years old are not allowed in the swimming pool without adult supervision.

The recreational activities listed below are available either on-site or nearby; fees may apply.

The free breakfast at Chesapeake Beach Resort gets high marks from our customers. During your stay, you'll be within walking distance of History of Diving Museum. Enjoy features like free WiFi in public areas, plus 2 outdoor pools and a marina.
  • Free continental breakfast served daily
  • Free Wi-Fi (speed: 100+ Mbps (good for 1–2 people or up to 6 devices))
  • Enjoy drinks at the bar/lounge
  • Take a swim in the 2 outdoor pools
  • Amenities include a computer, multilingual staff and coffee/tea in a common area
  • On-site recreation includes a private beach, complimentary bicycles and kayaking
  • Guests really like the accommodation for the cleanliness and spaciousness
  • 11 minutes on foot from History of Diving Museum and a 2-minute drive from Windley Key Fossil Reef Geological State Park
  • Pets welcome for a fee (restrictions apply)
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.

This 3.5-star Islamorada hotel is smoke free.

Guests are served a free continental breakfast daily from 6:00 AM to 10:00 AM.
Tiki Bar – On-site bar.

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: 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 at the property

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

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
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
Front desk staff will greet guests on arrival at the property.

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

Chesapeake Beach Resort Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 1203 out of 1651 reviews
Rating 8 - Good. 276 out of 1651 reviews
Rating 6 - Okay. 99 out of 1651 reviews
Rating 4 - Poor. 43 out of 1651 reviews
Rating 2 - Terrible. 30 out of 1651 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

9.0/10

Amenities

9.2/10

Property conditions & facilities

Reviews

10/10 Excellent

Brayan

Stayed 2 nights in Oct 2025

8/10 Good

Theresa

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Great venue.
Our view.
Stayed 2 nights in Oct 2025

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The front desk lady was very pleasant upon my check-in. She answered all my questions and made me feel comfortable driving to my room where I was staying. I slept late the next day with the do not disturb sign and I received a personal text from the front desk in the early afternoon asking me to respond when I was ready for them to make up my room. I did eat breakfast at the resort each morning. The chefs were extremely friendly and I enjoyed a sunrise breakfast overlooking the water. The breakfast is complimentary as well! Other than that, I wasn’t T the resort to stay the entire time. The rest of the time I was out and about, but I looked forward to jumping in the super comfy bed each evening when I would get back. I’ll be back the next time I’m in Islamorada!!
Stayed 3 nights in Oct 2025

10/10 Excellent

Christina

Liked: Cleanliness
Stayed 3 nights in Oct 2025

10/10 Excellent

Mitzi

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

Gem!

What a CLEAN and beautiful place! Vanessa at the front desk was awesome! Only stayed one night on the way to Key West, but I would definitely stay again!! So many amenities and your own private beach. 10/10
Stayed 1 night in Oct 2025

10/10 Excellent

Alex

Stayed 1 night in Oct 2025

10/10 Excellent

Alisha

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everyone was so nice and helpful at this resort!!! I had such an amazing time and would definitely recommend to any family & friends!!!
Stayed 1 night in Oct 2025

10/10 Excellent

Lisaimy

Stayed 1 night in Oct 2025

10/10 Excellent

Cynthia

Travelled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We had a great experience at the Chesapeake!
Stayed 2 nights in Oct 2025

10/10 Excellent

garry

Travelled with family
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

10/10 Excellent

Sandee

Travelled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Vanessa and Adriana made our stay excellent. Actually stayed an extra day. The morning chef was awesome!!
Stayed 1 night in Oct 2025

10/10 Excellent

JOSE

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean room | Great Outdoor pool | Amazing view
Stayed 5 nights in Oct 2025

10/10 Excellent

Rob

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
A good peaceful fishing area which is my main reason for staying there.The room was very clean and a bit on the small side.The location of this resort is great.
Stayed 2 nights in Oct 2025

10/10 Excellent

Vickie

Liked: Cleanliness, staff & service, property conditions & facilities
Love this place. Great beach/pool. Lovely room with great bathroom. Unbelievable view of the sunrise over the water from our balcony
Stayed 4 nights in Oct 2025

10/10 Excellent

Carrie

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
.
Stayed 1 night in Oct 2025

10/10 Excellent

ID

Travelled with partner
Liked: Cleanliness, staff & service, property conditions & facilities
The pools where very clean and very comfy, the place is keep very clean. Thank you.
Stayed 2 nights in Oct 2025

10/10 Excellent

Aloke

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

10/10 Excellent

Melissa R

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

Beautiful views

Check in person was very friendly and included a glass of champagne! Beautiful resort location!
Stayed 1 night in Oct 2025

10/10 Excellent

Sherry

Liked: Cleanliness, staff & service, property conditions & facilities
We loved it here ..
Stayed 2 nights in Oct 2025

10/10 Excellent

Keziah

Travelled with pets
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I had a wonderful stay here with my pet! The hotel is super pet-friendly, which made our trip so easy and enjoyable. There’s plenty of parking, and the view from our room was amazing. I also loved that my favorite buffet was right in the parking lot next door — total bonus! Perfect spot for anyone who enjoys relaxing by the water and doing a little fishing too. Highly recommend!
Stayed 3 nights in Sep 2025

10/10 Excellent

Keziah

Travelled with pets
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Love that its pet friendly, breakfast is amazing and LOVE that its 4 hours, clean and right next to best seafood buffet- whale harbor.
Stayed 4 nights in Sep 2025

10/10 Excellent

Tammy

Stayed 2 nights in Oct 2025

10/10 Excellent

Jeanie

Stayed 1 night in Oct 2025

10/10 Excellent

Shogun

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

10/10 Excellent

Eric Brooks

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Quiet. Peaceful. Perfect getaway for couples. Excellent customer service. This was our second stay at Chesapeake. Chesapeake and Islamorada are our new favorite destinations in the Keys. Islamorada reminds us of the Key West we fell in love with 30 years ago. Low key and peaceful. Every day is perfect when starting with Krystal's French toast. Her smile is infectious. She and the breakfast gang aim to please with their attention to detail. The private beach is lovely with shade and sun options. No talking or music. It was the perfect spot to watch the boats at the sand bar or to take a nap. Walk through the adjacent parking lot to four restaurants. We love the casual vibe outside at Wahoos. We can't wait to go back.
Stayed 7 nights in Sep 2025