See all properties

Chesapeake Beach Resort

3.5 star property

Choose dates to view prices

Photo gallery for Chesapeake Beach Resort

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

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Bar
  • 24/7 front desk
  • Pet-friendly
  • Pool

Explore the area

View in a 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 | 1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace

2-Bedroom Villa

10.0 out of 10
Exceptional
(1 review)
  • 60 sq m
  • 2 bedrooms
  • 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

9.4 out of 10
Exceptional
(29 reviews)
  • 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

10.0 out of 10
Exceptional
(2 reviews)
  • 48 sq m
  • 1 bedroom
  • 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

9.2 out of 10
Wonderful
(87 reviews)
  • 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

9.0 out of 10
Wonderful
(19 reviews)
  • 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

10.0 out of 10
Exceptional
(2 reviews)
  • 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

8.6 out of 10
Excellent
(4 reviews)
  • 50 sq m
  • 1 bedroom
  • 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
  • 1 bedroom
  • 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
  • 1 bedroom
  • 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

8.8 out of 10
Excellent
(9 reviews)
  • 60 sq m
  • 1 bedroom
  • 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

9.6 out of 10
Exceptional
(79 reviews)
  • 34 sq m
  • Ocean view
  • Sleeps 3
  • 1 King Bed

View all photos for Ocean View King Suite

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

Ocean View King Suite

9.4 out of 10
Exceptional
(15 reviews)
  • 49 sq m
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

9.8 out of 10
Exceptional
(43 reviews)
  • 34 sq m
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

Ocean View King Efficiency Villa

  • 48 sq m
  • 1 bedroom
  • 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

9.4 out of 10
Exceptional
(54 reviews)
  • 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
  • 1 bedroom
  • 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
  • 1 bedroom
  • 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

9.0 out of 10
Wonderful
(7 reviews)
  • 34 sq m
  • 1 bedroom
  • 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

8.0 out of 10
Very good
(3 reviews)
  • 50 sq m
  • 1 bedroom
  • 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

8.6 out of 10
Excellent
(17 reviews)
  • 34 sq m
  • Ocean view
  • Sleeps 3
  • 1 King Bed

Similar properties

Exterior

Amara Cay Resort

  • On private beach
  • Pool
  • Pet-friendly
  • Restaurant
4.5 out of 5, Wonderful, 1,243 reviews
The price is CHF 205
includes taxes & fees
1 Sept - 2 Sept
Amara Cay Resort

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 spaciousness and cleanliness
  • 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.

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
  • 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. 1084 out of 1502 reviews
Rating 8 - Good. 254 out of 1502 reviews
Rating 6 - Okay. 92 out of 1502 reviews
Rating 4 - Poor. 40 out of 1502 reviews
Rating 2 - Terrible. 32 out of 1502 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

9.0/10

Amenities

9.2/10

Property conditions & facilities

9.0/10

Eco-friendliness

Reviews

2/10 Terrible

Amanda

Travelled with family
Disliked: Cleanliness, amenities, property conditions & facilities
I had a terrible experience at Chesapeake Beach Resort. I stayed for three nights, but for the first two, I couldn’t sleep because the air conditioning was leaking water directly onto the bed. I reported the problem to the front desk on the first day, and they told me they would send maintenance, but nothing was done. They also said I should call Expedia to resolve the issue, which I did, but no one helped me, and my requests were completely ignored. They finally changed my room on the last night, but the damage was already done. I also requested a refund for the first two nights, and I’m still waiting for the security deposit to be returned. This situation was handled very poorly, and I wouldn’t recommend this hotel to anyone. It was a stressful and disappointing experience.
Stayed 3 nights in May 2025

10/10 Excellent

Steven

Travelled with pets, Travelled with partner
Liked: Cleanliness, property conditions & facilities
We love coming the resort. We stay at least twice each summer and the staff is so friendly and helpful.
Stayed 4 nights in May 2025

2/10 Terrible

leslie

Travelled with family
Disliked: Cleanliness, amenities, property conditions & facilities
Dirty property not wonderful as Expedia rated . People had their dogs swimming in the pool staff did nothing about it and claimed they had no complaints . Felt like I was in a third world country not Islamorada . Shame on you Expedia for not allowing me to cancel my reservation & blaming me for contacting to late . Will never use you again or go to this disgusting hotel ! Beware is my word of caution to anyone considering this property or Expedia .
Stayed 1 night in May 2025

10/10 Excellent

BRUNO

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
Good
Stayed 3 nights in May 2025

10/10 Excellent

VIANA

Stayed 2 nights in May 2025

10/10 Excellent

Fuminori, Apex

Stayed 1 night in May 2025

10/10 Excellent

Pedro

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
We lived our staying here. The rooms were very clean and comfortable. The breakfast was delicious and the staff was very friendly . Love the amenities.
Stayed 2 nights in May 2025

10/10 Excellent

Chelsey

Stayed 2 nights in May 2025

10/10 Excellent

Juan J

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

8/10 Good

Robert

Travelled with group
Liked: Cleanliness, amenities, property conditions & facilities
The Toilet was very loose , but the Maintenance person who fixed it was very nice. We would recommend you replacing - refixing the toilet as it was still a little bit wobbly
Stayed 1 night in May 2025

8/10 Good

Lauren

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in May 2025

10/10 Excellent

Ann

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful and extremely clean property. The grounds were perfect and our room was stunning!
Stayed 1 night in May 2025

10/10 Excellent

ANTHONY, Burlington

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
My son & I had a Sport Fishing excursion for a few days thus stayed at the Chesapeake. People & staff were awesome, friendly & obliging from Omar to Vanessa and all others of course. Rooms were nice & clean. A little constructive criticism as follows: you need more clothing storage space, three drawers are not enough for 2 people for almost a week, including waste baskets need to be larger for sure. Thank you. Overall, an enjoyable stay. Will recommend.
Stayed 5 nights in May 2025

8/10 Good

Dennis

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 4 nights in May 2025

8/10 Good

Ashley

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Our stay at Chesapeake was absolutely phenomenal. The property itself is stunning—immaculately kept grounds, lush and peaceful, with a sense of tranquility that instantly helps you unwind. Everything was clean and thoughtfully maintained, from the pathways to the landscaping, which truly stood out. The room was comfortable and inviting. The air conditioning kept things perfectly cool, though it was a bit on the louder side during the night. One small detail we noticed was the smoke detector’s green light, which was brighter than expected and occasionally disrupted our sleep, even with the excellent blackout curtains. Still, these are minor notes in an otherwise serene experience. Check-in was smooth and friendly, though for added privacy, I personally prefer when room numbers aren’t spoken aloud. That said, the agent was warm and welcoming. Overall, Chesapeake offered an incredibly restful and beautiful experience. We deeply appreciated the peaceful atmosphere and how cared-for every inch of the property felt. We look forward to returning!
Stayed 1 night in May 2025

10/10 Excellent

Jamie, Clive

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent stay for my family of 4 over a long weekend trip. Kids loved the water sport rentals. Staff was all very kind and helpful
Stayed 3 nights in May 2025

10/10 Excellent

Sara, Crawfordsville

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
We really enjoyed our stay here was very nice and quiet
Stayed 4 nights in May 2025

10/10 Excellent

saily

Travelled with family, Travelled with family and small children
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great hotel close to the beach b Wonderful costumer service Close to 3 different restaurants
Stayed 2 nights in May 2025

10/10 Excellent

Lisa

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 5 nights in May 2025

10/10 Excellent

Ernesto

Travelled with family and small children, Travelled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything was amazing just the a/c was not cold enough it gets warm even with fan on
Stayed 2 nights in May 2025

10/10 Excellent

Mahika

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great stay and fantastic staffs.
Stayed 1 night in Apr 2025

10/10 Excellent

Cesar

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

10/10 Excellent

Toni

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Property was great . We booked the least expensive room and it was still a really nice room . Newly renovated clean comfy bed with fluffy pillows. Bathroom was small but still really nice . And it had a balcony with garden view. The complimentary Breakfast was delicious. Resort was beautiful pools were very nice beach was lovely . And they had glass bottom kayaks and paddle-board that were also included. . Hot tub was not working but didn’t really need it Staff was very nice especially Hailey at the front desk . We were very happy and would definitely go back
Stayed 1 night in May 2025

10/10 Excellent

Sheryl

Travelled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very comfortable, on beach, great breakfast made to order! Walking distance to Wahoo Grill which was the best Ley Lime Pie so far!
Stayed 1 night in May 2025

8/10 Good

Ben

Travelled with family
Liked: Cleanliness, property conditions & facilities, room comfort

Nice grounds

The grounds are great , private beach area with loungers provided . Room comfortable and clean , bathroom small but modern with good shower . Receptionist on check in appeared very bored !! Breakfast nothing special , omelettes available but very overcooked and the cook went walk about whilst making them and when she came back she was permanently on her phone . A couple of restaurants within walking distance .
Stayed 2 nights in May 2025