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Chesapeake Beach Resort

3.5 star property

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Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun-loungers, beach towels
Balcony
1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace
Outdoor spa tub
Water view

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

Room options

View all photos for 2-Bedroom Villa

2-Bedroom Villa | Private kitchenette | Microwave, coffee/tea maker

2-Bedroom Villa

  • 60 sq m
  • Resort view
  • Sleeps 6
  • 1 King Bed, 1 Double Bed and 1 Double Sofa Bed

View all photos for Standard King

Standard King | 1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard King

  • 25 sq m
  • Sleeps 3
  • 1 King Bed

View all photos for King Efficiency Villa

King Efficiency Villa | 1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

King Efficiency Villa

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

View all photos for Standard Doubles

Standard Doubles | 1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard Doubles

  • 25 sq m
  • Sleeps 4
  • 2 Double Beds

View all photos for Standard King with Sleeper Sofa

Standard King with Sleeper Sofa | 1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard King with Sleeper Sofa

  • 29 sq m
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Hearing Impaired Ocean View Queens

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Hearing Impaired Ocean View Queens

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

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

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

View all photos for ADA King Efficiency Villa

ADA King Efficiency Villa | 1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

ADA King Efficiency Villa

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

View all photos for Premium 1-Bedroom Ocean View Villa

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

Premium 1-Bedroom Ocean View Villa

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

View all photos for Deluxe Ocean View Two Queen Suite

Balcony

Deluxe Ocean View Two Queen Suite

  • 60 sq m
  • Ocean view
  • Sleeps 6
  • 2 Queen Beds

View all photos for Ocean View King

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King

  • 34 sq m
  • Ocean view
  • Sleeps 3
  • 1 King Bed

View all photos for Ocean View King Suite

Ocean View King Suite | 1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King Suite

  • 49 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

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

Ocean View King Efficiency Villa

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

View all photos for Standard Queens

Standard Queens | 1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard Queens

  • 29 sq m
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard King Villa

Standard King Villa | 1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard King Villa

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

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

View all photos for ADA Ocean View Queens

ADA Ocean View Queens | 1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

ADA Ocean View Queens

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

View all photos for ADA Ocean View King Suite

ADA Ocean View King Suite | Balcony

ADA Ocean View King Suite

  • 50 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed

View all photos for ADA Ocean View King

1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

ADA Ocean View King

  • 34 sq m
  • Ocean view
  • Sleeps 3
  • 1 King Bed

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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. A complete renovation of Chesapeake Beach Resort was completed in January 2020.

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.

Languages

English, Spanish

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
  • 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

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

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. 1052 out of 1468 reviews
Rating 8 - Good. 243 out of 1468 reviews
Rating 6 - Okay. 95 out of 1468 reviews
Rating 4 - Poor. 43 out of 1468 reviews
Rating 2 - Terrible. 35 out of 1468 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

Robert

Liked: Cleanliness, staff & service, property conditions & facilities
Nice people, quiet resort.
Stayed 3 nights in Mar 2025

10/10 Excellent

max

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great stay, clean room!
Stayed 2 nights in Mar 2025

10/10 Excellent

Gladys

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities
Secluded quiet, excellent to relax
Stayed 1 night in Mar 2025

10/10 Excellent

Tracy

Travelled with partner
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

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

Stayed 2 nights in Feb 2025

10/10 Excellent

Sue Ellen

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

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Most amazing views
Stayed 2 nights in Feb 2025

10/10 Excellent

Patrick

Liked: Cleanliness, amenities
Love this place
Stayed 2 nights in Feb 2025

10/10 Excellent

Tammy

Travelled with partner
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

Travelled with family
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

Travelled with partner
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

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Muy buen servicio alienate muy limpio
Stayed 1 night in Mar 2025

10/10 Excellent

Avery

Travelled with family, Travelled with pets, Travelled with partner
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

Travelled with partner
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

Travelled with partner
Liked: Cleanliness, staff & service, property conditions & facilities
Never disappointing. Wonderful Stay
Stayed 2 nights in Feb 2025

10/10 Excellent

Verified traveller

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Feb 2025

10/10 Excellent

Marc Ressler

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

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Feb 2025

8/10 Good

Cory

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Little expensive a nice property
Stayed 1 night in Feb 2025

10/10 Excellent

Paul

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Feb 2025

8/10 Good

diana

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

Stayed 2 nights in Dec 2024

8/10 Good

Verified traveller

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

10/10 Excellent

kathy

Stayed 3 nights in Feb 2025

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