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Chesapeake Beach Resort

3.5 star property

Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun-loungers, beach towels
Deluxe Ocean View Two Queen Suite | Balcony
Hypo-allergenic bedding, pillow-top beds, laptop workspace
43-inch flat-screen TV with cable channels, TV
Water view

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Free Wi-Fi
The current price is NZ$569
includes taxes & fees
14 Apr - 15 Apr

Explore the area

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

Room options

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

9.6 out of 10
Exceptional
(48 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Ocean View King

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

Ocean View King

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

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
(7 reviews)
  • Ocean view
  • 50 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed

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
(19 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for ADA Ocean View Queens

ADA Ocean View Queens

ADA Ocean View Queens

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

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
(2 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • 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)
  • Ocean view
  • 50 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Standard Queens

Standard Queens

Standard Queens

9.4 out of 10
Exceptional
(61 reviews)
  • 29 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard Doubles

Standard Doubles

Standard Doubles

9.2 out of 10
Wonderful
(99 reviews)
  • 25 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Double Beds

View all photos for Standard King with Sleeper Sofa

Standard King with Sleeper Sofa

Standard King with Sleeper Sofa

9.2 out of 10
Wonderful
(24 reviews)
  • 29 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard King

Standard King

Standard King

9.4 out of 10
Exceptional
(36 reviews)
  • 25 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for Ocean View King Suite

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

Ocean View King Suite

9.0 out of 10
Wonderful
(18 reviews)
  • Ocean view
  • 49 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Deluxe Ocean View Two Queen Suite

Balcony

Deluxe Ocean View Two Queen Suite

9.0 out of 10
Wonderful
(11 reviews)
  • Ocean view
  • 60 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds

View all photos for 2-Bedroom Villa

2-Bedroom Villa

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

View all photos for Standard King Villa

Standard King Villa

Standard King Villa

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

View all photos for King Efficiency Villa

King Efficiency Villa

King Efficiency Villa

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

View all photos for ADA King Efficiency Villa

ADA King Efficiency Villa

ADA King Efficiency Villa

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

View all photos for Premium 1-Bedroom Ocean View Villa

Premium 1-Bedroom Ocean View Villa

Premium 1-Bedroom Ocean View Villa

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

View all photos for Premium Ocean View King Villa

Premium Ocean View King Villa | Living area

Premium Ocean View King Villa

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

View all photos for Ocean View King Efficiency Villa

Ocean View King Efficiency Villa

Ocean View King Efficiency Villa

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

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About the area

Islamorada

At Chesapeake Beach Resort you'll be within a 15-minute walk of History of Diving Museum and 1.8 km (1.1 mi) from Windley Key Fossil Reef Geological State Park. Highlights at this beachfront hotel include 2 outdoor swimming pools, a private beach and a marina. .Tiki Bar is the hotel's own bar. Enjoy the pool loungers along with access to boat tours and kayaking. Added amenities include free Wi-Fi in public areas, coffee/tea in a common area and free use of bicycles. Free continental breakfast is available daily between 6:00 AM and 10:00 AM. .With a stay at this 3.5-property class Matecumbe hotel, you'll be 2 km (1.2 mi) from Islamorada Brewery & Distillery and 2.7 km (1.7 mi) from Keys History & Discovery Center.

What's nearby

  • History of Diving Museum - 12 min walk - 1.1 km
  • Windley Key Fossil Reef Geological State Park - 2 min drive - 2.0 km
  • Islamorada Brewery & Distillery - 2 min drive - 2.4 km
  • Theater of the Sea - 2 min drive - 2.4 km
  • Bud n' Mary's Dive Center - 5 min drive - 7.3 km

Getting around

  • Miami International Airport (MIA) - 91 min drive

Restaurants

  • ‪Tiki Bar - ‬13 min walk
  • ‪Wahoo's Bar & Grill - ‬2 min walk
  • ‪Lorelei Restaurant & Cabana Bar - ‬3 min drive
  • ‪Hog Heaven - ‬3 min drive
  • ‪Wendy's - ‬2 min drive

About this property

Chesapeake Beach Resort

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.

  • 60 guestrooms or units
  • 2 levels
  • 9 buildings
  • Built in 2020
  • Continental breakfast (free)
  • Beach lounge chairs
  • Towels for the beach
  • Poolside lounge chairs
  • Coffee in lobby
  • Front desk (24 hours)
  • Staff members are multilingual
  • Concierge
  • Computer for guest use
  • No smoking on site
  • Bar or lounge
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.

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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 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

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

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
Charges for extra guests may apply and vary according to property policy.
A credit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    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 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. This property accepts Visa, Mastercard, American Express and Discover. Cash is not accepted. For guests' safety, the property includes a fire extinguisher in all accommodation.

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

Frequently asked questions

What is the cancellation policy at Chesapeake Beach Resort?

Chesapeake Beach Resort offers free cancellation on select room rates. Check out the cancellation policy for more info.

How much does it cost to stay at Chesapeake Beach Resort?

As of 17 Mar 2026, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on 14 Apr 2026 start from NZ$569, including 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.

Are there any beaches close to Chesapeake Beach Resort?

The closest beach to Chesapeake Beach Resort is Anne's Beach (16.1 km).

Does Chesapeake Beach Resort have a pool?

Yep, and guests love it! Chesapeake Beach Resort has 2 outdoor swimming pools. Grab your bathers and lounge poolside while enjoying on a lounger. The pool is open 7:00 AM to 10:30 PM.

What makes Chesapeake Beach Resort a romantic place to stay?

A private beach and a lounge bar, as well as pillowtop beds in the guestrooms, all help set the scene for a romantic weekend at Chesapeake Beach Resort.

Does Chesapeake Beach Resort serve breakfast?

Yep, guests give top marks to the free continental breakfast here! Available daily from 6:00 AM to 10:00 AM, this is the perfect place to fuel up for a big day full of adventure.

Is there a free airport shuttle available at Chesapeake Beach Resort?

No, Chesapeake Beach Resort does not offer an airport shuttle service.

What time are check-in & check-out at Chesapeake Beach Resort?

Check-in begins at 4:00 PM. Check-out time is 11 AM.

Chesapeake Beach Resort Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 1234 out of 1671 reviews
Rating 8 - Good. 265 out of 1671 reviews
Rating 6 - Okay. 98 out of 1671 reviews
Rating 4 - Poor. 43 out of 1671 reviews
Rating 2 - Terrible. 31 out of 1671 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

9.0/10

Amenities

9.2/10

Property conditions & facilities

Reviews

10/10 Excellent

FRANK

Stayed 2 nights in Dec 2025

8/10 Good

Nafeeza

Stayed 2 nights in Dec 2025

10/10 Excellent

Yuli

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Idyllic beautiful beach setting, clean comfortable rooms, lovely setting.
Stayed 1 night in Dec 2025

10/10 Excellent

Kevin

Liked: Cleanliness, amenities, property conditions & facilities
Excellent !!!!!
Stayed 3 nights in Dec 2025

10/10 Excellent

Rafael

Stayed 2 nights in Dec 2025

10/10 Excellent

Sheila

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
The room extremely clean and staff were amazing. The grounds were well kept. The location was great the scenery was perfect AND the omelettes in the Sunrise room were off the chain delicious. 1000% recommend and will definitely be returning.
Stayed 4 nights in Dec 2025

10/10 Excellent

Suzanne

Liked: Cleanliness, amenities, property conditions & facilities
Wonderful place!
Stayed 1 night in Dec 2025

10/10 Excellent

Natasa Maria

Stayed 2 nights in Dec 2025

10/10 Excellent

Mahmoud

Stayed 2 nights in Dec 2025

10/10 Excellent

Jeff

Liked: Cleanliness, amenities, property conditions & facilities
Room was great. Staff was awesome views amazing !!!!!
View outside our room
Stayed 7 nights in Dec 2025

6/10 Okay

Kevin

Travelled with family
Liked: Staff & service
The room has ants that we had to deal with.
Stayed 2 nights in Dec 2025

8/10 Good

Kenneth

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities
Breakfast was great every day. Chef Chris was so friendly and made us feel welcome.
Stayed 4 nights in Dec 2025

10/10 Excellent

Melanie

Stayed 2 nights in Dec 2025

10/10 Excellent

Michael

Stayed 1 night in Dec 2025

10/10 Excellent

Michael

Stayed 1 night in Nov 2025

10/10 Excellent

Gary

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great breakfast, great location, friendly staff, nice extras.
Stayed 1 night in Dec 2025

8/10 Good

Miurel

Stayed 2 nights in Dec 2025

8/10 Good

Rita

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Just a painted up old hotel, was fine though.
Stayed 2 nights in Dec 2025

10/10 Excellent

Kara

Stayed 1 night in Dec 2025

10/10 Excellent

Stanley

Stayed 1 night in Dec 2025

10/10 Excellent

Ranae

Stayed 1 night in Nov 2025

10/10 Excellent

Jesus

Liked: Cleanliness, property conditions & facilities, room comfort
Great place
Stayed 2 nights in Sep 2025

4/10 Poor

John

Travelled with partner
Liked: Cleanliness, property conditions & facilities
Great location but not a good value for the cost. The road noise was horrible all night . The room was nice but the thin walls unfortunately let enjoy your neighbors conversation. The breakfast included with the room cost was very good however.
Stayed 1 night in Nov 2025

10/10 Excellent

BRIAN

Liked: Property conditions & facilities
Stayed 1 night in Nov 2025

8/10 Good

cody, Ben Wheeler

Stayed 2 nights in Nov 2025