Chesapeake Beach Resort

Hotel on the beach, with 2 outdoor pools

Choose dates to view prices

Where to?

Dates

June 2025

July 2025

Private beach, white sand, sun loungers, beach towels

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

Overview
Rooms
Location
Policies

Wonderful

Popular amenities

Bar
24/7 front desk

Explore the area

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

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Room options

2-Bedroom Villa

646 sq ft
Resort view
Sleeps 6
1 King Bed, 1 Double Bed and 1 Double Sofa Bed

Standard King

272 sq ft
Sleeps 3
1 King Bed

King Efficiency Villa

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

Standard Doubles

272 sq ft
Sleeps 4
2 Double Beds

Standard King with Sleeper Sofa

307 sq ft
Sleeps 4
1 King Bed and 1 Double Sofa Bed

Hearing Impaired Ocean View Queens

366 sq ft
Ocean view
Sleeps 4
2 Queen Beds

43-inch flat-screen TV with cable channels, TV

Hearing Impaired Ocean View King Suite

540 sq ft
Ocean view
Sleeps 4
1 King Bed and 1 Queen Sofa Bed

ADA King Efficiency Villa

517 sq ft
Resort view
Sleeps 3
1 King Bed

Premium 1-Bedroom Ocean View Villa

700 sq ft
Ocean view
Sleeps 6
2 Double Beds and 1 Double Sofa Bed

Deluxe Ocean View Two Queen Suite

650 sq ft
Ocean view
Sleeps 6
2 Queen Beds

Ocean View King

364 sq ft
Ocean view
Sleeps 3
1 King Bed

Ocean View King Suite

527 sq ft
Ocean view
Sleeps 4
1 King Bed and 1 Queen Sofa Bed

Ocean View Queens

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

Standard Queens

307 sq ft
Sleeps 4
2 Queen Beds

Standard King Villa

323 sq ft
Resort view
Sleeps 3
1 King Bed

Premium Ocean View King Villa

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

ADA Ocean View Queens

366 sq ft
Ocean view
Sleeps 4
2 Queen Beds

ADA Ocean View King Suite

540 sq ft
Ocean view
Sleeps 4
1 King Bed

ADA Ocean View King

364 sq ft
Ocean view
Sleeps 3
1 King Bed

About the neighborhood

Islamorada

Located in Matecumbe within a short walk of History of Diving Museum, Chesapeake Beach Resort is within a mile (2 km) of Windley Key Fossil Reef Geological State Park. This 60-room, 3.5-star hotel has 2 outdoor pools along with a private beach and a marina.

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
Founders Park - 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

Hotel on the beach, with 2 outdoor pools

Chesapeake Beach Resort features a private beach, a marina, and 2 outdoor pools. The 24-hour front desk has multilingual staff ready to help with concierge services, and answer any questions about the area. Other amenities at this beach hotel include free WiFi in public areas, coffee/tea in a common area, and free use of bicycles.

43-inch flat-screen TVs come with cable channels, and guests can stay connected with free WiFi. Pillowtop beds grant a restful night's sleep, and bathrooms offer hair dryers and designer toiletries. Other standard amenities include microwaves, coffee makers, and free local calls.

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

Children 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.

Languages

English, Spanish

Similar properties

On private beach
Pool
Pet friendly
Restaurant

$238 nightly

Jul 6 - Jul 7

Total includes taxes and fees

3 outdoor pools, a heated pool, pool umbrellas, sun loungers

On private beach
Pool
Pet friendly
Free WiFi

$313 nightly

Jun 18 - Jun 19

Total includes taxes and fees

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

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
Private bathroom
Shampoo
Shower
Soap
Toilet paper
Towels provided

Entertainment

43-inch flat-screen TV with cable channels

Food and drink

Coffee/tea maker
Microwave

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

This property welcomes pets for USD 50.00 per accommodation, per night, plus a deposit of USD 50.00 per stay
2 total (50 lbs is the maximum weight per pet)
Restrictions apply
For more information, guests can reach out to the property at the number on the booking confirmation
Service animals exempt from fees

Property payment types

Important information

Optional extras

These fees and deposits will be charged at check-in, check-out, or the time of service.

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 list may not be comprehensive. Fees and deposits might 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

Check-in: 4:00 PM
Check-out: 11 AM
Minimum check-in age: 18

The front desk is open 24 hours a day.

We should mention

Details about charges, deposits, or other important information:

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.
Charges for extra guests may apply and vary depending on the property's policy.
A credit card for incidental charges and a government-issued photo ID may be required at check-in.
Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
This property accepts credit cards. Cash is not accepted.

Additional information about polices, regulations, and more:

Pool access available from 7:00 AM to 10:30 PM.
Some facilities may be restricted. For more details, contact the property. Contact information can be found on your booking confirmation.
Nearby construction work may cause some noise disturbance.
There are no elevators.
No rollaway or extra beds are available.

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

Is free cancellation available at Chesapeake Beach Resort?

Chesapeake Beach Resort offers free cancellation on select room rates. For more details, take a look at the cancellation policy on our site.

What can I see close to Chesapeake Beach Resort?

This hotel is situated in Matecumbe within a short 11-minute walk of History of Diving Museum. You'll also find Florida Keys Brewing Co. and Founders Park within a short drive.

Is parking available on site at Chesapeake Beach Resort?

Yes, there is accessible parking available.

Does Chesapeake Beach Resort include a casino at the property?

No, Chesapeake Beach Resort doesn't have a casino.

Will I find an indoor pool at Chesapeake Beach Resort?

No, this hotel doesn't have an indoor pool; however, there are 2 outdoor pools. Guests have pool access between 7:00 AM and 10:30 PM.

What amenities will couples enjoy at Chesapeake Beach Resort?

There are plenty of amenities for couples at this hotel, including a private beach, 2 outdoor pools, and a bar.

Are there hot tubs at Chesapeake Beach Resort?

No, there isn't a spa tub at this hotel.

Does Chesapeake Beach Resort have a restaurant with a breakfast menu?

Yes, Chesapeake Beach Resort serves free continental breakfast at Tiki Bar each morning.

Will Chesapeake Beach Resort allow pets to stay for free?

Although they can't stay for free, pets are welcome at Chesapeake Beach Resort for a fee of USD 50.00 per accommodation, per night. A deposit of USD 50.00 per stay is collected.

Does Chesapeake Beach Resort have connecting rooms?

No, there aren't connecting guestrooms at this hotel.

Are there rooms with balconies that I can book at Chesapeake Beach Resort?

Yes, some guestrooms at this hotel offer either a balcony or a deck where guests can enjoy ocean or garden views.

Chesapeake Beach Resort Reviews

9.2

Wonderful

9.4/10

Cleanliness

9.2/10

Staff & service

8.8/10

Amenities

9.2/10

Property conditions & facilities

9.0/10

Eco-friendliness

10/10 Excellent

Cory

Traveled with family

Apr 17, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Very friendly staff that was extra accommodating to us! Clean, quiet, beautiful grounds! Would definitely stay again!

Stayed 1 night in Apr 2025

10/10 Excellent

Mauricio

Traveled with family

Apr 6, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Wonderful hotel, always great to be in the Florida Keys.

Stayed 1 night in Apr 2025

10/10 Excellent

max

Mar 17, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Great stay, clean room!

Stayed 2 nights in Mar 2025

10/10 Excellent

Gladys

Traveled with family

Mar 16, 2025

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

Secluded quiet, excellent to relax

Stayed 1 night in Mar 2025

10/10 Excellent

Tracy

Traveled with partner

Mar 16, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

The staff are super friendly. Our room was clean and well laid out. Make sure to use the 2 hours free paddle boarding that comes with your reservation, we seen sharks, manatees and lots of fish and hermit crabs. The breakfast in the morning is fresh and a great selection.

Stayed 2 nights in Mar 2025

10/10 Excellent

Rebecca, Okeechobee

Mar 14, 2025

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

I love this place! Lovely maintained grounds, very clean and modern rooms. The sunrises are amazing. Front desk, cleaning staff, breakfast staff and bar staff were friendly and very accommodating. I am going to miss the great cooked to order omelets and drinks by the pool and beach. I would recommend this resort to anyone with families or adults only. We enjoyed the beautiful grounds which are lush and well maintained. The chess, checkers and kayak rentals plus the tiki boat rentals to the sandbar are an added bonus. This was betterthan an all inclusive resort in the Caribbean for us. Paradise in the Keys- close to shopping and great restaurants. Better than traveling south where it gets a little crazy for us. We plan to come back as often as we can.

Stayed 3 nights in Mar 2025

8/10 Good

Darlis

Mar 13, 2025

Stayed 2 nights in Feb 2025

10/10 Excellent

Sue Ellen

Mar 11, 2025

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

We asked for & received early check-in. The staff was friendly & helpful & everything was immaculate! Wonderful breakfast included! Nice beach area with lots to do. We will definitely stay here again!

Stayed 1 night in Mar 2025

10/10 Excellent

Derick

Mar 10, 2025

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

Most amazing views

Stayed 2 nights in Feb 2025

10/10 Excellent

Patrick

Mar 9, 2025

Liked: Cleanliness, amenities

Love this place

Stayed 2 nights in Feb 2025

10/10 Excellent

Tammy

Traveled with partner

Mar 8, 2025

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

We found our perfect peaceful and quiet getaway! We started each day with waffles or omelets. We loved the private beach with plenty of shade. It was nice to hear the water and birds instead of music or people. The bar was just steps away from the beach or pool. We walked to dinner at Wahoo's every night. I highly recommend Chesapeake for a low key, quiet stay.

Stayed 6 nights in Feb 2025

10/10 Excellent

Dale

Traveled with family

Mar 6, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Clean well designed and convenient. Nice staff as well

Stayed 1 night in Feb 2025

10/10 Excellent

Nancy

Traveled with partner

Mar 5, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Only 60 rooms. Not crowded. Lovely grounds and great staff.

Stayed 2 nights in Feb 2025

10/10 Excellent

Dignarys

Mar 2, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Muy buen servicio alienate muy limpio

Stayed 1 night in Mar 2025

10/10 Excellent

Avery

Traveled with partner, Traveled with pets, Traveled with family

Mar 1, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Excellent location for family trip or fishing. Clean friendly hotel lovely custom made free breakfast by Mr Chris. Also pet friendly

Stayed 2 nights in Feb 2025

10/10 Excellent

Diane

Traveled with partner

Feb 28, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Great staff, beautiful grounds, very nice stay.

Stayed 1 night in Feb 2025

10/10 Excellent

Carol

Traveled with partner

Feb 28, 2025

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

Never disappointing. Wonderful Stay

Stayed 2 nights in Feb 2025

10/10 Excellent

Verified traveler

Traveled with family

Feb 27, 2025

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

Stayed 1 night in Feb 2025

10/10 Excellent

Marc Ressler

Feb 27, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

This small resort hotel was recently renovated and is very well run. The location is perfect right on the ocean and is meticulously maintained. We stayed in an ocean view villa and it was very clean, new, and well appointed. There is a $50 per day resort fee that was disclosed which includes a nice made to order omelet and waffle breakfast with fruit, bagels, yogurt, etc. They also have a small bar with drinks available throughout the day. The resort fee also includes use of water sports like kayaks and paddle boards. Even though the resort is right on the ocean, the water was remarkably calm with no waves which helped add a laid back feel to this property. The staff was great, especially Dereck at the front desk who checked me in and also reached out to me each day to see if we needed anything. The daily housekeeping was nice as many hotels have cut back on this. I will definitely stay at this resort again as I pass through the Keys.

Stayed 3 nights in Feb 2025

10/10 Excellent

Courtney

Feb 26, 2025

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

Stayed 1 night in Feb 2025

8/10 Good

Cory

Traveled with partner

Feb 26, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Little expensive a nice property

Stayed 1 night in Feb 2025

10/10 Excellent

Paul

Feb 25, 2025

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

Stayed 2 nights in Feb 2025

8/10 Good

diana

Feb 24, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Our one night stay at this property was pleasant except for the noise from the cars which bothered my husband during the night but not me and our daughter. The receptionist could have said welcome and put on a smile but he didn’t. When I asked him why he didn’t offer us the welcome drinks he said he didn’t think we wanted them because we looked tired… However our ocean view from the room was beautiful and the beach is gorgeous!

Stayed 1 night in Feb 2025

10/10 Excellent

Yoav

Feb 23, 2025

Stayed 2 nights in Dec 2024

8/10 Good

Verified traveler

Feb 19, 2025

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

Would stay again-loved the place!

Everything was great-we did have an issue with our a/c but we were only there two nights so we didn't worry with having them look at it. Just reported as we left the property. Loved the place overall!

Stayed 2 nights in Feb 2025