Chesapeake Beach Resort

Islamorada beachfront hotel with 2 outdoor pools and bar/lounge

Choose dates to view prices

Where to?

Dates

November 2025

December 2025

Private beach, white sand, sun loungers, beach towels

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

In the heart of Matecumbe, Chesapeake Beach Resort offers a tranquil escape. Enjoy a leisurely breakfast, relax on the private beach with sun loungers and kayaking options or take a refreshing dip in one of the 2 outdoor pools. With multilingual staff and concierge services available to help plan your stay.

Wonderful

Popular amenities

24/7 front desk
Bar
Free breakfast
Air conditioning

Main amenities (12)

Daily housekeeping
On a private beach
Marina
2 outdoor pools
Free use of bicycles
Beach sun loungers
Beach towels
Bar/lounge
24-hour front desk
Coffee/tea in a common area
Air conditioning
Computer station

Feel at home (6)

Microwave
Cable/satellite TV service
Daily housekeeping
Coffee/tea maker
Blackout drapes/curtains
2 outdoor pools

$194 total

includes taxes & fees

Oct 29 - Oct 30

Room options

Check availability for these dates

Tonight

Oct 25 - Oct 26

Tomorrow

Oct 26 - Oct 27

All rooms

1 bed

2 beds

3+ beds

Showing 20 of 20 rooms

Ocean View Queens

Exceptional

Highlights

Balcony

Air conditioning

Free cribs/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

Exceptional

Highlights

Balcony

Air conditioning

Free cribs/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

Very good

Highlights

Balcony

Separate sitting area

Air conditioning

Free cribs/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

Excellent

Highlights

Balcony

Air conditioning

Free cribs/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

Wonderful

Highlights

Balcony

Air conditioning

Free cribs/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

Exceptional

Highlights

Balcony

Air conditioning

Free cribs/infant beds

Mini-fridge

HDTV

Hypo-allergenic bedding

Renovated in 2020

Separate bedroom

34 sq m
Ocean view
Sleeps 4
2 Queen Beds

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

Hearing Impaired Ocean View King Suite

Excellent

Highlights

Balcony

Separate sitting area

Air conditioning

Free cribs/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

Exceptional

Highlights

Deck/patio

Air conditioning

Free cribs/infant beds

Mini-fridge

HDTV

Hypo-allergenic bedding

Renovated in 2020

Separate bedroom

29 sq m
Sleeps 4
2 Queen Beds

Standard Doubles

Wonderful

Highlights

Balcony

Air conditioning

Free cribs/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

Wonderful

Highlights

Deck/patio

Air conditioning

Free cribs/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

Exceptional

Highlights

Balcony

Air conditioning

Free cribs/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

Exceptional

Highlights

Balcony

Separate sitting area

Air conditioning

Free cribs/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

Excellent

Highlights

Balcony

Separate sitting area

Air conditioning

Free cribs/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

Exceptional

Highlights

Separate sitting area

Air conditioning

Free cribs/infant beds

Kitchenette

Full-sized refrigerator/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 cribs/infant beds

Kitchenette

Full-sized refrigerator/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

Exceptional

Highlights

Separate dining area

Separate sitting area

Air conditioning

Free cribs/infant beds

Kitchenette

Full-sized refrigerator/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 cribs/infant beds

Kitchenette

Full-sized refrigerator/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 cribs/infant beds

Kitchenette

Full-sized refrigerator/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 cribs/infant beds

Kitchenette

Full-sized refrigerator/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 cribs/infant beds

Kitchenette

Full-sized refrigerator/freezer

Dishwasher

HDTV

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

Similar properties

Pool
Pet friendly
Restaurant
Air conditioning

$234 total

includes taxes & fees

Oct 27 - Oct 28

Sign in to view eligible discounts and perks. More rewards for more adventures!

Sign in Sign up, it's free

About the neighborhood

83409 Overseas Hwy, Islamorada, FL, 33036

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 Intl. 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

A great choice for a stay in Islamorada, Chesapeake Beach Resort features a marina. After splashing around at the 2 outdoor pools, you can unwind with a drink at the bar/lounge. Fellow travelers say great things about the pool and helpful staff.

At a glance

Hotel size

- 60 rooms
- Arranged over 2 floors

Arriving/Leaving

- 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 time is 11 AM
- Contactless check-out available

Special check-in instructions

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

Required at check-in

- Credit card required for incidental charges
- Government-issued photo ID may be required
- Minimum check-in age is 18

Pets

- Pets allowed (2 total, up to 50 lbs per pet)*
- Service animals welcome
- Restrictions apply*

Internet

- Free WiFi in public areas
- Free WiFi in rooms (speed: 100+ Mbps (good for 1–2 people or up to 6 devices))

Parking

- Wheelchair-accessible parking on site
- Onsite parking includes off-street options

Other information

- Smoke-free property

Property amenities

Food and drink

Free continental breakfast each morning 6:00 AM–10:00 AM
Bar/lounge
Coffee/tea in a common area

Traveling with children

Pool gate
Outlet covers
Fence around the pool

What to do

On a private beach
Kayaking
Boat tours
Fishing
Jet skiing nearby
Snorkeling nearby

Working away

Computer station

Services

24-hour front desk
Concierge services
Multilingual staff
Free bicycle rentals
Beach sun loungers
Beach towels
Pool loungers

Facilities

9 buildings/towers
Built in 2020
2 outdoor pools
Marina
Traditional architecture

Accessibility

Braille/raised signage
Wheelchair-accessible parking
Assistive listening devices available
Wheelchair-accessible public washroom
Wheelchair-accessible pool
Visual alarms in hallways
Handrails in hallways
Handrails in stairways
Closed captioned TV
Lever door handles
Upper floors accessible by stairs only
Well-lit path to entrance
Pool hoist on site

Room amenities

Be entertained

43-inch flat-screen TV
Cable TV channels

Home comfort

Air conditioning
Ceiling fan
Coffee/tea maker
Iron/ironing board

Sleep well

Hypo-allergenic bedding
Blackout drapes/curtains
Pillowtop mattress
Bed sheets provided

Freshen up

Shower only
Designer toiletries
Hair dryer
Towels
Toilet paper

Stay connected

Laptop-friendly workspace
Free WiFi (speed of 100+ Mbps (good for 1–2 people or up to 6 devices))
Free local calls

Food and drink

Microwave

More

Daily housekeeping
Access via exterior corridors

Special features

Dining

Tiki Bar - Onsite bar.

Fees & policies

Optional extras

Late check-out can be arranged for an extra charge

Pets

Service animals exempt from fees
Pet deposit: USD 50.00 per stay
Pets are allowed for an extra charge of USD 50.00 per accommodation, per night

Pool, spa, & gym (if applicable)

Pool access available from 7:00 AM to 10:30 PM
Children under 16 years old are not allowed in the swimming pool without adult supervision

Policies

Construction is underway at a neighboring building and there may be noise disturbance from the construction work.

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.

Some facilities may have restricted access. Guests can contact the property for details using the contact information on the booking confirmation.

This property does not have elevators.

This property accepts credit cards. Cash is not accepted.

Credit cards accepted: Visa, Mastercard, American Express, Discover

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

Does Chesapeake Beach Resort offer free cancellation for a full refund?

Yes, Chesapeake Beach Resort does have fully refundable room rates available to book on our site. If you’ve booked a fully refundable room rate, this can be cancelled up to a few days before check-in depending on the property's cancellation policy. Just make sure to check this property's cancellation policy for the exact terms and conditions.

Is there a pool at Chesapeake Beach Resort?

Yes, there are 2 outdoor pools. Guests have pool access from 7:00 AM to 10:30 PM.

Are pets allowed at Chesapeake Beach Resort?

Yes, pets are welcome, with a limit of 2 total and maximum weight of 50 lbs per pet. There's a charge of USD 50.00 per accommodation, per night, and there's also a deposit of USD 50.00 per stay. Service animals are exempt from fees. Some restrictions may apply, so please contact the property for more details.

What are the check-in and check-out times at Chesapeake Beach Resort?

Check-in start time: 4:00 PM; Check-in end time: 3:00 AM. Check-out time is 11 AM. Late check-out is available for a charge. Contactless check-in and check-out are available.

What is there to do at Chesapeake Beach Resort and nearby?

Have fun with onsite activities like kayaking, fishing, and cycling. Enjoy a swim in one of the 2 outdoor swimming pools or use the hotel's other amenities, which include a private beach.

What's the area around Chesapeake Beach Resort like?

Chesapeake Beach Resort is in Matecumbe, a short 11-minute walk from History of Diving Museum. Travelers give top marks for the hotel's prime location.