About Chesapeake Beach Resort

Chesapeake Beach Resort offers a serene oceanfront escape in the heart of Islamorada, blending modern comfort with tropical charm. Surrounded by swaying palms and crystal-clear waters, this resort is perfect for both relaxation and adventure. Guests can enjoy private beach access, water sports, and breathtaking sunrise views over the Atlantic. Private beach and lush tropical landscaping Outdoor pools and sun deck for relaxation Complimentary use of kayaks and paddleboards Close to local dining, shopping, and attractions

Amenities at Chesapeake Beach Resort

Chesapeake Beach Resort offers Coffee/tea in common areas, Coffee/tea in common areas, Elevator/lift, 24-hour front desk, Beach sun loungers, Pool sun loungers, Smoke-free property, Computer station, On private beach, 24-hour business center, Spa tub, Spa tub (surcharge), Beach towels, Multilingual staff, Air conditioning, Refrigerator, Hypo-allergenic bedding available, Phone, Microwave, Towels provided, Free local calls, Pillowtop mattress, Linens provided, Private bathroom, Private bathroom (not in room), Free toiletries, Hair dryer, Hair dryer (on request), Iron/ironing board, Iron/ironing board (on request), Television, Television (surcharge), Cable TV service, Flat-panel TV, HDTV, Free WiFi, Free WiFi (limited) device count, Free WiFi (limited) duration, Free WiFi (limited) time, Access via exterior corridors, Blackout drapes/curtains, Designer toiletries, Heating, Shower only, Balcony, Balcony or patio, Down comforter.

Location

Chesapeake Beach Resort is located at 83409 Overseas Hwy, Islamorada.

Reviews and ratings

Chesapeake Beach Resort has an average rating of 4.1 out of 5 based on 1114 guest reviews. It holds a 2.5-star Stars rating.

Rooms and accommodations at Chesapeake Beach Resort

  • Garden View Doubles

    2 Double Beds

    Garden View Doubles

  • ADA Ocean View King Suite

    1 King Bed

    ADA Ocean View King Suite

  • ADA Ocean View King

    1 King Bed

    ADA Ocean View King

  • Ocean View Queens

    2 Queen Beds

    Ocean View Queens

  • ADA Ocean View Queens

    2 Queen Beds

    ADA Ocean View Queens

  • Hearing Impaired Ocean View King Suite

    1 King Bed and 1 Queen Sofa Bed

    Hearing Impaired Ocean View King Suite

  • Ocean View King Suite

    1 King Bed and 1 Queen Sofa Bed

    Ocean View King Suite

  • Garden View King with Sleeper Sofa

    1 King Bed and 1 Double Sofa Bed

    Garden View King with Sleeper Sofa

  • Deluxe Ocean View Two Queen Suite

    2 Queen Beds

    Deluxe Ocean View Two Queen Suite

  • Ocean View King

    1 King Bed

    Ocean View King

  • Garden View King

    1 King Bed

    Garden View King

  • Hearing Impaired Ocean View Queens

    2 Queen Beds

    Hearing Impaired Ocean View Queens

  • Garden View Queens

    2 Queen Beds

    Garden View Queens

Image of Chesapeake Beach Resort
Image of Chesapeake Beach Resort
Image of Chesapeake Beach Resort
Image of Chesapeake Beach Resort

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Image of Chesapeake Beach Resort

Rooms

Property Overview

Chesapeake Beach Resort offers a serene oceanfront escape in the heart of Islamorada, blending modern comfort with tropical charm. Surrounded by swaying palms and crystal-clear waters, this resort is perfect for both relaxation and adventure. Guests can enjoy private beach access, water sports, and breathtaking sunrise views over the Atlantic.

  • Private beach and lush tropical landscaping
  • Outdoor pools and sun deck for relaxation
  • Complimentary use of kayaks and paddleboards
  • Close to local dining, shopping, and attractions

Amenities

Food and drink

  • Coffee/tea in common areas
  • Refrigerator
  • Microwave

Property services

  • Coffee/tea in common areas
  • Elevator/lift
  • 24-hour front desk
  • Beach sun loungers
  • Pool sun loungers
  • Smoke-free property
  • Beach towels
  • Multilingual staff

Business services

  • Computer station
  • 24-hour business center

Activities

  • On private beach
  • Spa tub
  • Spa tub (surcharge)

Features

  • Air conditioning
  • Private bathroom
  • Private bathroom (not in room)
  • Hair dryer (on request)
  • Iron/ironing board
  • Iron/ironing board (on request)
  • Access via exterior corridors
  • Blackout drapes/curtains
  • Heating
  • Shower only
  • Balcony
  • Balcony or patio

Bedding and linens

  • Hypo-allergenic bedding available
  • Pillowtop mattress
  • Linens provided
  • Down comforter

Media and electronics

  • Phone
  • Free local calls
  • Television
  • Television (surcharge)
  • Cable TV service
  • Flat-panel TV
  • HDTV

Bathroom

  • Towels provided
  • Free toiletries
  • Hair dryer
  • Designer toiletries

Internet access in public areas

  • Free WiFi
  • Free WiFi (limited) device count
  • Free WiFi (limited) duration
  • Free WiFi (limited) time

Reviews

4.1
1114
Reviews

Guests rave about this intimate resort's direct oceanfront views, pristine beach access, and exceptional, made-to-order breakfast service. While most visitors praise the private, clean atmosphere and friendly staff, a few recent complaints highlight issues with room bugs, lack of elevators in certain buildings, and the poor condition of recreational equipment.

Stunning oceanfront views and private beach accessMade-to-order breakfast and welcoming staffRecently updated rooms with balconies
cleanliness4.9
location5
value4.8
service4.8
amenities4.2
C
Colby Cunningham
3 months ago

We were in awe with this place! From immaculate beach themed lobby when you check in to your room over looking the beach! It can't be beat! Super clean facility! Rooms spot on! Two pools, one salt and one fresh water with a hot tub as well. We enjoyed some beach checkers on the life-size game board as well. What makes this place truly special, and in my opinion, "takes the cake" is the made to order egg breakfast! What a differentiator! Awesome job! ? We will be back!

C
Courtney Knickerbocker
3 months ago

This place was beautiful! Super clean and updated right on the beach! We would 100% stay here again and will recommend to friends and family. The continental breakfast was way better than we expected! They have a build your own omelette bar! The pools were great and warm, we never had to call housekeeping for more towels. Each day they came when we were out and always kept everything neat in the room for us. My only complaint was one day we arrived to the room after being gone all day to our door cracked open from housekeeping and we don’t know how long our room was wide open for. Thankfully nothing seemed out of place.

A
Andrea Smith
4 months ago

I spent three nights in room 211 which is a partial ocean view king room. The rooms are fresh and updated; the large walk-in shower and balcony were my favorite parts. The fridge and microwave came in handy. I wish I had paid extra to have the full ocean view, as my room mainly looked at the heated pool and building next door. It had a slight ocean view from the corner of the balcony. The breakfast is excellent; I enjoyed an omelette each morning from the same friendly gentleman. The clear kayaks are right out front and easy to use. I enjoyed both pools and the hot tub along with the live music Saturday afternoon. I was in a real bind in my last day. Jasmine and Vanessa at the front desk went above and beyond to save the day! I am so so grateful to them! This property has a tremendous staff that understands customer service. They are to be applauded. Also, I highly recommend going out on the Morada Mermaid boat to the sandbar and enjoying their sunset cruise. I did both. It leaves from a marina 7 minutes down the road. It is only $50 a person for the month of January which is a steal. A trip to Islamorada isn’t complete unless you get out on the water. The hotel is next door to two great restaurants, Flagler Station and Wahoo’s. Flagler’s is upscale, and Wahoo’s is casual. I had great experiences at both. I will be back! Thank you again.

C
Chris O'Riordan
4 months ago

We stayed here for one night on our one week Keys trip. We knew check in was 4pm, we arrived around 1pm in hope that our room would be ready, but we were told it wasn't and to come back at 4pm. As we are travelling from Australia and doing several cruises we had heavy suitcases and asked if we could have a low floor room. We were told we were in building 2 and that there was a lift to take our bags up. We sat in the sun on the deck chairs for a while then had lunch next door at Wahoo which was great. About 3.50pm we headed back to check in to find a long line of people checking in with only 1 person on check in. After half an hour we got to the counter and were told we were in the main building on level 2, but there was no lift in this building. We struggled with our bags up 2 flights of stairs. The room was good, all that we needed. Breakfast was good too, I had pancakes, they were really good, moist and tasty. My wife had omelette and loved it.

G
George Zamora
4 months ago

The resort is good. Located around some key and iconic spots, the shoreline access is something amazing. We stayed on the waterfront rooms that face the sunrise and it was absolutely gorgeous. The room was clean and quite spacious. The staff we interacted with at breakfast were ok. Not greeted just asked what type of omelette we wanted. We left by 930. But I would recommend it is for a short stay.

R
Rajeev Guleria
5 months ago

The area was beautiful and the amenities were also nice, there were kayaks and fishing poles available for rent. The place had wonderful restaurants and fun activities nearby as well. The live breakfast bar had impeccable service and there were many options. Also, the people working there accommodated to our needs and I definitely recommend this place for families. The rooms themselves were clean and nice, also cleaned daily. Front desk was helpful as well. Would definitely stay here again.

M
Maira Weaver
5 months ago

Its not too far from home. My husband and i really enjoyed our staid.. they had an amazing breakfast.... they had everything that i liked in particular. They had healthy choices... not a big place so it didnt seem overwhelmed with options just the right amount of food. The room had an amazing ocean view i wanna come back with my whole family.

S
Stephanie Porth
6 months ago

We just loved our stay here! Made our special trip that much more enjoyable for our first time in Islamorada & The Keys. Definitely will be visiting again in the future. Staff were very welcoming and accommodating. Rooms had gorgeous views of the ocean and very clean. Love the beach decor and how comfy the beds were. Lots of great restaurants and things to do near by.

R
Randall
about 1 year ago

I looked for hours for a well priced, well maintained larger resort that didn’t have 5star prices and finally found Chesapeake Beach Resort on Islamorada. What a pleasant surprise! This place is exactly like the pictures on their website. Perfect location with breathtaking views from our room balcony that rival Maui. The extra price for a oceanfront room is worth it if you want to enjoy the stunning turquoise colored ocean views. The rooms are very clean and the price includes a delicious made to order breakfast every morning! Shoutout to Adriana for a smooth check in. Also to Chris and Shaquita at the breakfast station and Jose at the bar for their great service and hospitality. This resort does not have a full service restaurant and maybe that helps keep the prices more reasonable…don’t change a thing please!! We do not know the owners. This is a legitimate review, which I rarely do, but we would like to see this resort succeed so we can return. Thank you again!

J
Jessica Nutter
about 1 year ago

We stayed in Marathon, Key West, Islamroda, and Key Largo. Out of 4 different hotels my sister and I thought Chesapeake Beach Resort was the best. The rooms were clean and spacious. The staff were friendly and very helpful. The view was awesome and I liked that they offered fishing poles, paddle boards and scuba stuff for two hours for free. Very welcoming.

Map

Property Address
83409 Overseas Hwy
Islamorada
Property Contact
305-664-4662