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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
43-inch flat-screen TV with cable channels, TV
Water view
Deluxe Ocean View Two Queen Suite | Balcony
ADA Ocean View King Suite | Hypo-allergenic bedding, pillow-top beds, laptop workspace

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Breakfast included
  • Free Wi-Fi

Explore the area

View in a map
83409 Overseas Hwy, Islamorada, FL, 33036
  • Place, History of Diving Museum
    ‪12 min walk‬
  • Place, Theater of the Sea
    ‪2 min drive‬
  • Place, Islamorada Brewery & Distillery
    ‪2 min drive‬

Room options

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

9.6 out of 10
Exceptional
(52 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds
  • Free Wi-Fi

View all photos for Ocean View King

Hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King

9.6 out of 10
Exceptional
(101 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free Wi-Fi

View all photos for ADA Ocean View King Suite

ADA Ocean View King Suite | Balcony

ADA Ocean View King Suite

8.6 out of 10
Excellent
(8 reviews)
  • Ocean view
  • 50 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed
  • Free Wi-Fi

View all photos for ADA Ocean View King

Hypo-allergenic bedding, pillow-top beds, laptop workspace

ADA Ocean View King

8.8 out of 10
Excellent
(21 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free Wi-Fi

View all photos for ADA Ocean View Queens

ADA Ocean View Queens | Hypo-allergenic bedding, pillow-top beds, laptop workspace

ADA Ocean View Queens

9.0 out of 10
Wonderful
(7 reviews)
  • Ocean view
  • 34 sq m
  • Sleeps 4
  • 2 Queen Beds
  • Free Wi-Fi

View all photos for Hearing Impaired Ocean View Queens

Hypo-allergenic bedding, pillow-top beds, laptop workspace

Hearing Impaired Ocean View Queens

10.0 out of 10
Exceptional
(3 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds
  • Free Wi-Fi

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

8.8 out of 10
Excellent
(5 reviews)
  • Ocean view
  • 50 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed
  • Free Wi-Fi

View all photos for Standard Queens

Standard Queens | Hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard Queens

9.4 out of 10
Exceptional
(67 reviews)
  • 29 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds
  • Free Wi-Fi

View all photos for Standard Doubles

Standard Doubles | Hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard Doubles

9.2 out of 10
Wonderful
(102 reviews)
  • 25 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Double Beds
  • Free Wi-Fi

View all photos for Standard King with Sleeper Sofa

Standard King with Sleeper Sofa | Hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard King with Sleeper Sofa

9.2 out of 10
Wonderful
(25 reviews)
  • 29 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Free Wi-Fi

View all photos for Standard King

Standard King | Hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard King

9.4 out of 10
Exceptional
(40 reviews)
  • 25 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free Wi-Fi

View all photos for Ocean View King Suite

Hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King Suite

9.2 out of 10
Wonderful
(21 reviews)
  • Ocean view
  • 49 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed
  • Free Wi-Fi

View all photos for Deluxe Ocean View Two Queen Suite

Balcony

Deluxe Ocean View Two Queen Suite

9.0 out of 10
Wonderful
(12 reviews)
  • Ocean view
  • 60 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds
  • Free Wi-Fi

View all photos for 2-Bedroom Villa

2-Bedroom Villa | Hypo-allergenic bedding, pillow-top beds, laptop workspace

2-Bedroom Villa

10.0 out of 10
Exceptional
(1 review)
  • Resort view
  • 60 sq m
  • 2 bedrooms
  • Sleeps 6
  • 1 King Bed, 1 Double Bed and 1 Double Sofa Bed
  • Free Wi-Fi

View all photos for Standard King Villa

Standard King Villa | Hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard King Villa

  • Resort view
  • 30 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free Wi-Fi

View all photos for King Efficiency Villa

King Efficiency Villa | Hypo-allergenic bedding, pillow-top beds, laptop workspace

King Efficiency Villa

9.6 out of 10
Exceptional
(4 reviews)
  • Resort view
  • 48 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Free Wi-Fi

View all photos for ADA King Efficiency Villa

ADA King Efficiency Villa | Hypo-allergenic bedding, pillow-top beds, laptop workspace

ADA King Efficiency Villa

10.0 out of 10
Exceptional
(1 review)
  • Resort view
  • 48 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free Wi-Fi

View all photos for Premium 1-Bedroom Ocean View Villa

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

Premium 1-Bedroom Ocean View Villa

7.0 out of 10
Good
(2 reviews)
  • Ocean view
  • 65 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Double Beds and 1 Double Sofa Bed
  • Free Wi-Fi

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

  • Ocean view
  • 77 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Free Wi-Fi

View all photos for Ocean View King Efficiency Villa

Ocean View King Efficiency Villa | Hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King Efficiency Villa

10.0 out of 10
Exceptional
(2 reviews)
  • Ocean view
  • 48 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Free Wi-Fi

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About this property

Chesapeake Beach Resort

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.

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
  • 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

Information provided by the property may be translated using automated translation tools

Access methods

Staffed front desk

Pets

  • Pets: USD 50.00 per accommodation, per night, plus a deposit of USD 50.00 per night
  • 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 night
  • 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
Safety features at this property include a fire extinguisher
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 8:00 AM to 6:00 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. 1290 out of 1736 reviews
Rating 8 - Good. 277 out of 1736 reviews
Rating 6 - Okay. 96 out of 1736 reviews
Rating 4 - Poor. 42 out of 1736 reviews
Rating 2 - Terrible. 31 out of 1736 reviews

9.4/10

Cleanliness

9.4/10

Staff & service

9.2/10

Amenities

9.2/10

Property conditions & facilities

Reviews

10/10 Excellent

Scott

Stayed 5 nights in Feb 2026

10/10 Excellent

Charles Temple

Liked: Cleanliness, amenities, property conditions & facilities
Nice clean spacious room.Beautiful location overlooking the water.Staff was eager to please
Stayed 7 nights in Feb 2026

10/10 Excellent

Lindsey

Stayed 1 night in Feb 2026

10/10 Excellent

Scott

Liked: Cleanliness, amenities, property conditions & facilities
From check in to check out the service was great. Nice view of the ocean. Great included breakfast. Thanks for the nice time
Stayed 2 nights in Feb 2026

10/10 Excellent

Todd

Stayed 3 nights in Feb 2026

10/10 Excellent

Vickki

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Great vibe….very clean rooms. Wahoo next door is also fun and good food.
Stayed 3 nights in Feb 2026

10/10 Excellent

Gabriel, Celina

Nice
Stayed 1 night in Feb 2026

10/10 Excellent

Kathleen

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
Clean rooms, friendly staff. Liked that coffee, tea and water available 24 hours. However, we felt the cost was very expensive.
Stayed 2 nights in Feb 2026

4/10 Poor

Ryan

Stayed 3 nights in Feb 2026

10/10 Excellent

Richard

Clean room..staff qaa qond
Stayed 2 nights in Feb 2026

10/10 Excellent

Katherine

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
room was clean ,quiet. ocean view with balcony, large shower no tub.
Stayed 2 nights in Feb 2026

10/10 Excellent

Suzanne

Stayed 2 nights in Jan 2026

10/10 Excellent

Matthew

Liked: Cleanliness, amenities, property conditions & facilities
Great staff, especially front desk and breakfast chefs!!! Beautiful facilty-laid back vibe just as it should be on the Keys!!!
Stayed 2 nights in Jan 2026

10/10 Excellent

Keely

Travelled with family
Liked: Cleanliness, staff & service, amenities
Clean rooms, beautiful scenery, gorgeous sunrise, delicious breakfast. Loved this place.
Stayed 4 nights in Feb 2026

10/10 Excellent

Mrs

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Very clean and comfortable beds Lovely friendly staff Fantastic location and views And could not fault the breakfast which was included Chris the chef made everything fresh, omelettes, pancakes there was a fantastic selection The only negative were the rooms weren’t sound proof and we could hear our neighbours coughing throughout the night
Stayed 1 night in Feb 2026

10/10 Excellent

Amy Louise

Liked: Cleanliness, amenities, property conditions & facilities
Clean comfortable room, excellent staff, incredible view... Very happy with our choice!
Stayed 4 nights in Feb 2026

10/10 Excellent

Jason

Travelled with group
Liked: Cleanliness, amenities, property conditions & facilities
Awesome place, nice beach! Friendly staff.
Stayed 1 night in Feb 2026

10/10 Excellent

Cynthia

Stayed 3 nights in Jan 2026

8/10 Good

Karan

Travelled with family
Liked: Cleanliness
Beautiful view
Stayed 4 nights in Feb 2026

10/10 Excellent

Deivy

Stayed 1 night in Feb 2026

10/10 Excellent

Lina

Liked: Cleanliness, amenities, property conditions & facilities
Just perfect
Stayed 2 nights in Dec 2025

10/10 Excellent

James

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Extremely clean hotel. Breakfast was very good and staff very helpful.
Stayed 3 nights in Feb 2026

10/10 Excellent

Taylor

Stayed 1 night in Feb 2026

10/10 Excellent

Doug or Lois

Liked: Cleanliness, staff & service, amenities
Nice stay
Stayed 1 night in Feb 2026

10/10 Excellent

Jonathan

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Great property. Pictures don’t really do it justice. Wish we could have stayed longer!
Stayed 1 night in Feb 2026