Chesapeake Beach Resort

Hotel on the beach, with 2 outdoor pools

Choose dates to view prices

Where to?

Dates

October 2025

4

November 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

Place, Windley Key Fossil Reef Geological State Park
‪2 min drive‬
Place, Theater of the Sea
‪2 min drive‬
Place, Florida Keys Brewing Co.
‪4 min drive‬

Room options

Ocean View Queens

Exceptional

366 sq ft
Ocean view
Sleeps 4
2 Queen Beds

Ocean View King

Exceptional

364 sq ft
Ocean view
Sleeps 3
1 King Bed

ADA Ocean View King Suite

Very good

540 sq ft
1 bedroom
Ocean view
Sleeps 4
1 King Bed

ADA Ocean View King

Excellent

364 sq ft
Ocean view
Sleeps 3
1 King Bed

ADA Ocean View Queens

Wonderful

366 sq ft
1 bedroom
Ocean view
Sleeps 4
2 Queen Beds

Hearing Impaired Ocean View Queens

Exceptional

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

Excellent

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

Standard Queens

Exceptional

307 sq ft
Sleeps 4
2 Queen Beds

Standard Doubles

Wonderful

272 sq ft
Sleeps 4
2 Double Beds

Standard King with Sleeper Sofa

Wonderful

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

Standard King

Exceptional

272 sq ft
Sleeps 3
1 King Bed

Ocean View King Suite

Exceptional

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

Deluxe Ocean View Two Queen Suite

Excellent

650 sq ft
1 bedroom
Ocean view
Sleeps 6
2 Queen Beds

2-Bedroom Villa

Exceptional

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

Standard King Villa

323 sq ft
1 bedroom
Resort view
Sleeps 3
1 King Bed

King Efficiency Villa

Exceptional

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

ADA King Efficiency Villa

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

Premium 1-Bedroom Ocean View Villa

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

Premium Ocean View King Villa

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

Ocean View King Efficiency Villa

517 sq ft
1 bedroom
Ocean view
Sleeps 4
1 King Bed and 1 Double Sofa 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
Islamorada Brewery & Distillery - 2 min drive - 1.5 miles
Florida Keys Brewing Co. - 4 min drive - 2.5 miles

Getting around

Miami Intl. Airport (MIA) - 91 min drive

Restaurants

‪Tiki Bar - ‬13 min walk
‪Lorelei Restaurant & Cabana Bar - ‬3 min drive
‪Wendy's - ‬2 min drive
‪Starbucks - ‬15 min walk
‪Whale Harbor Buffet - ‬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.

Similar properties

On private beach
Pool
Pet friendly
Restaurant

$208 nightly

Oct 6 - Oct 7

Total with taxes and fees

Private beach, sun loungers, beach towels, scuba diving

On private beach
Pool
Pet friendly
Free WiFi

$245 nightly

Oct 6 - Oct 7

Total with 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

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

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.

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

As of Oct 4, 2025, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on Oct 6, 2025 start from $132.05, 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.

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 Founders Park and Islamorada County 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, this hotel doesn't have a spa tub.

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, this hotel doesn't feature connecting guestrooms.

Can I book a room with a balcony 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.