See all properties

Chesapeake Beach Resort

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

Reviews

9.2 out of 10
Wonderful

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

Book today, save on your next hotel stay

It's that easy when you're a member of Orbitz Rewards. It's free to join!

Room options

View all photos for 2-Bedroom Villa

Relax in a spacious room with a large bed, flat-screen TV, and wardrobe.

2-Bedroom Villa

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

View all photos for Standard King

Relax in a spacious room with a large bed, nightstand, and comfortable chair, featuring a ceiling fan and air conditioning unit.

Standard King

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

View all photos for King Efficiency Villa

Relax in a spacious room with a large bed, nightstand, and wicker chair.

King Efficiency Villa

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

View all photos for Standard Doubles

Two large beds with white linens, a flat-screen TV, and a wooden bench await in this stylish room.

Standard Doubles

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

View all photos for Standard King with Sleeper Sofa

Relax in a spacious room with a large bed, nightstand, and ceiling fan, offering a view of the outside through sheer curtains.

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

Enjoy a comfortable stay with a large bed, desk, and seating area, plus a window offering a view of the outdoors.

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

Relax in this stylish living room with a sofa, coffee table, and chairs, featuring a large window with a view of palm trees and the ocean.

Hearing Impaired Ocean View King Suite

8.6 out of 10
Excellent
(4 reviews)
  • 540 sq ft
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for ADA King Efficiency Villa

Relax in a spacious room with a large bed, dark sofa, and flat-screen TV.

ADA King Efficiency Villa

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

View all photos for Premium 1-Bedroom Ocean View Villa

Two large beds with white linens and a view of palm trees.

Premium 1-Bedroom Ocean View Villa

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

View all photos for Deluxe Ocean View Two Queen Suite

Enjoy breathtaking ocean views from this balcony overlooking the beach.

Deluxe Ocean View Two Queen Suite

8.8 out of 10
Excellent
(9 reviews)
  • 650 sq ft
  • 1 bedroom
  • Ocean view
  • Sleeps 6
  • 2 Queen Beds

View all photos for Ocean View King

Relax in a spacious room with a large bed, nightstand, and sliding glass door leading to an outdoor area with a view of palm trees.

Ocean View King

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

View all photos for Ocean View King Suite

Relax in comfort with a large bed, bedside tables, and a ceiling fan above.

Ocean View King Suite

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

View all photos for Ocean View Queens

Enjoy the ocean view from this balcony with a pair of lounge chairs and a small table.

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

View all photos for Standard Queens

Enjoy a comfortable stay in this stylish room featuring two single beds, a flat-screen TV, and a desk area.

Standard Queens

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

View all photos for Standard King Villa

Relax in a spacious room with a large bed and two bedside tables, each with a lamp.

Standard King Villa

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

View all photos for Premium Ocean View King Villa

Enjoy meals at the large dining table surrounded by six chairs, with breathtaking ocean views from the expansive balcony.

Premium Ocean View King Villa

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

View all photos for ADA Ocean View Queens

Enjoy ocean views from the large window, relax in the seating area with a striped ottoman, and unwind in this stylish room with two single beds.

ADA Ocean View Queens

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

View all photos for ADA Ocean View King Suite

Enjoy the ocean view from this balcony with a pair of chairs and a table.

ADA Ocean View King Suite

8.0 out of 10
Very good
(3 reviews)
  • 540 sq ft
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed

View all photos for ADA Ocean View King

Relax in a spacious room with a large bed, nightstand, and sliding glass door leading to an outdoor area with a view of palm trees.

ADA Ocean View King

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

You may also like

Ad
Enjoy ocean views from the large window in this stylish living room, featuring a comfortable sofa and a potted plant.

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Key Largo
  • On private beach
  • Pool
  • Hot Tub
  • Pet friendly
8.6 out of 10, Excellent, 1,001 reviews
$303 nightly
The price is $341
Sep 3 - Sep 4
Total includes taxes and fees
Baker's Cay Resort Key Largo, Curio Collection by Hilton

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
  • 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

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

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
8.8 out of 10, Excellent, 1,239 reviews
$246 nightly
The price is $276
Sep 1 - Sep 2
Total includes taxes and fees
Amara Cay Resort

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 Aug 6, 2025, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on Aug 17, 2025 start from $151.05, 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 there parking available 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.

Is Chesapeake Beach Resort a good place to stay for couples?

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 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

Reviews

9.2

Wonderful

Rating 10 - Excellent. 1076 out of 1493 reviews
Rating 8 - Good. 249 out of 1493 reviews
Rating 6 - Okay. 92 out of 1493 reviews
Rating 4 - Poor. 42 out of 1493 reviews
Rating 2 - Terrible. 34 out of 1493 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

8/10 Good

Cathy

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Staff friendliness seemed a bit forced
Stayed 2 nights in Jul 2025

10/10 Excellent

Daniel

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities
Right on the beach and also pool
Stayed 1 night in May 2025

10/10 Excellent

Kass

Liked: Cleanliness, staff & service, property conditions & facilities
Perfect place to stay!
Stayed 1 night in Mar 2025

6/10 Okay

Debbie

Liked: Cleanliness, property conditions & facilities
It did have a beach was very clean.. bathroom had no counter..towels werent even in bathroom.. it was a nice clean space.cleaning people didnt no english.. probally not stay there again.. 2 queen were. p
Stayed 2 nights in Apr 2025

10/10 Excellent

HUGH

Liked: Cleanliness, staff & service, property conditions & facilities
Great weekend at the resort
Stayed 2 nights in May 2025

10/10 Excellent

Deborah

Traveled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in May 2025

10/10 Excellent

Rhett Jan, Boynton Beach

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Relaxing place
Stayed 2 nights in Apr 2025

10/10 Excellent

Anny, Medford

Traveled with family and small children
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We had a Vila and it was very nice, new and very clean. We loved all about it!
Stayed 3 nights in Apr 2025

10/10 Excellent

Peter

Liked: Cleanliness, staff & service, property conditions & facilities
Great property exceeded our expectations.
Stayed 2 nights in Apr 2025

10/10 Excellent

Daniel, Miami

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean, nicely decorated rooms. Direct beach access. Well maintained property.
Stayed 1 night in Apr 2025

10/10 Excellent

Helen

Liked: Cleanliness, staff & service, property conditions & facilities
Amazing location.
Stayed 4 nights in Mar 2025

10/10 Excellent

Wilson

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Todo muy Exelente las habitaciones son muy buenas y limpias recomendadisimo
Stayed 1 night in Apr 2025

6/10 Okay

Patricia

Liked: Cleanliness
was told hot tub was in working order when making the reservation. Hot tub was out of order upon arrival and during stay.
Stayed 1 night in Apr 2025

8/10 Good

Edwin

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Apr 2025

8/10 Good

Adam

Liked: Cleanliness, property conditions & facilities
Good for the price and convenient for fishing trips. No frills, clean rooms good location.
Stayed 3 nights in Apr 2025

10/10 Excellent

Margarita

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Apr 2025

2/10 Terrible

PHILIP

Traveled with family
Disliked: Staff & service, property conditions & facilities
We only stayed 1 night and checked out. We are asking Expedia and Chesapeake to REFUND us for the additional 2 nights!! BKG#73084799299276 APRIL 24-27TH
Stayed 3 nights in Apr 2025

10/10 Excellent

CHASE

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Property was very nice. Staff was very nice also. We thought property had a restaurant and bar but none available yet. They did have free breakfast and great ocean front accommodations
Stayed 3 nights in Apr 2025

10/10 Excellent

monika

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 3 nights in Apr 2025

10/10 Excellent

Salim, Boca Raton

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location and rooms.
Stayed 2 nights in Apr 2025

10/10 Excellent

Jelena

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nicely remodeled (without the smell of mold) with contemporary touches. We were prepared to find out that pictures will not turn to reality but were so pleased that they reflect what the resort really is. Breakfast is included into stay (thank you to the owner for the omelet station!). Good quality coffee and tea always available at the front desk. Another pleasant surprise was that you could check out bikes/fishing rods or kayaks for a few hours to enjoy. Such a beautiful setting and we cannot wait to return, unless something changes this will be our place to stay at the Keys. Thank you for not cutting corners and making it a pleasant experience for your guests!
Stayed 4 nights in Apr 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

Hotels

Fontainebleau Miami Beach
Rooftop Resort - Clothing Optional - Adult Only
Embassy Suites by Hilton Fort Lauderdale 17th Street
1 Hotel South Beach
Casa Loma Inn
Casa Marina Key West, Curio Collection by Hilton
Hilton Cabana Miami Beach Resort
2bd Bayfront Ste Bay View w/balcony, Pool, nearby dining, beach access
Spectrum Resort Villas Orlando and Water Parks, Ascend Hotel Collection
Universal's Hard Rock Hotel
EAST Miami
Margaritaville Hollywood Beach Resort
Wyndham I-Drive Avanti Resort & Conference Center
Ocean Sky Hotel and Resort
Universal's Cabana Bay Beach Resort
Walt Disney World Dolphin
Grand Beach Hotel
Hyatt Place Boca Raton/Downtown
Best Western Plus Atlantic Beach Resort
Sagamore Hotel South Beach - An All Suite Hotel
The Godfrey Hotel & Cabanas Tampa
Hollywood Beach Hotels
Hard Rock Hotel Daytona Beach
Loews Miami Beach Hotel – South Beach
Holiday Inn Club Vacations at Orange Lake Resort by IHG
Hotel Maren Fort Lauderdale Beach, Curio Collection by Hilton
Daytona Grande Oceanfront Resort
Naples Grande Beach Resort