Chesapeake Beach Resort | Hotel in Islamorada

| 9.2 (1544 Reviews) |  1 Bathroom
Islamorada Hotel | Chesapeake Beach Resort

Chesapeake Beach Resort: Your Ideal Getaway in Islamorada, Florida

Your next idyllic escape awaits at Chesapeake Beach Resort, a stunning hotel located right on the beautiful shores of Islamorada, Florida. Here, you can unwind by one of the two outdoor swimming pools or spend your day soaking up the sun on our exclusive private white sand beach while indulging in kayaking activities.

The resort features 60 comfortable, air-conditioned accommodations that are accessible via exterior corridors. Each room is equipped with essential amenities such as coffee and tea makers and luxurious designer toiletries. You will enjoy restful nights on plush pillowtop mattresses, while entertainment options abound with 43-inch flat-screen televisions featuring cable channels.

Each bathroom is thoughtfully designed with showers, complimentary toiletries, and hair dryers for your convenience. For business travelers, amenities include direct phones with the option for free local calls (certain restrictions may apply). You will also find useful items like irons/ironing boards and ceiling fans in your room. Daily housekeeping ensures your accommodation remains pristine, and hypo-allergenic bedding is available upon request.

In addition to the two inviting outdoor swimming pools and the serene private beach, please note that children under the age of 16 must be supervised by an adult while enjoying the pool facilities.

For those seeking adventure, numerous recreational activities are available either on the premises or nearby—with some activities incurring additional fees.

Where to Stay in Islamorada: Discover the Charm of This Tropical Paradise

When considering where to stay in Islamorada, you’ll find that this enchanting village, often referred to as the "Sportfishing Capital of the World," is a jewel nestled in the Florida Keys. Known for its stunning turquoise waters and vibrant marine life, Islamorada boasts unique attractions such as the famous Theater of the Sea and the serene Morada Way Arts & Cultural District. With its laid-back atmosphere and welcoming community, the village offers a perfect escape for both adventure seekers and relaxation enthusiasts alike.

Located conveniently near top attractions, Chesapeake Beach Resort serves as an ideal base for your exploration. Enjoy a day at the resort’s private white sand beach or unwind by one of the two outdoor swimming pools. For those looking for adventure, indulge in kayaking or explore nearby diving spots that showcase the breathtaking coral reefs. With 60 comfortable, air-conditioned accommodations featuring modern amenities like pillowtop mattresses and flat-screen televisions, you will feel right at home. Additionally, take advantage of local experiences, from fishing charters to exquisite dining options, all just a stone's throw away from your tranquil retreat.

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83409 Overseas Hwy, Islamorada, 33036, USA

Amenities

Air Conditioner
Pool
TV
View
Ocean View
Accessibility
Security/Safety
Business Services
Bedding/Linens
Wellness Facilities
Bar
Toiletries
Guest Services
Breakfast
Child Friendly
Internet
Kitchen
Laundry

Policies

Check-in
Check-in start time: 4:00 pm; check-in end time: 3:00 am contactless check-in available late check-in subject to availability minimum check-in age: 18
Check-out
A late check-out fee will be charged check-out before 11 am contactless check-out available
Child Policy
Children are welcome. rollaway/extra beds are not available.
Payment Policy
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 the above list may not be comprehensive. fees and deposits may not include tax and are subject to change.
Pet Policy
2 total (up to 50 lbs per pet) pets allowed for an extra charge of usd 50.00 per accommodation, per night, plus a deposit of usd 50.00 per stay restrictions apply; for more information contact the property at the number on the booking confirmation service animals are welcome, and are exempt from fees
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, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

Reviews

Gregory
Sep 13, 2025 11:11:09 AM
Review Score:   10
Summary: Centrally located in Islamorada and spotless property. Not a piece of trash anywhere. Comfortable beds, great towels. Resort seems newly built. Beautiful oceanside pool or second more private pool. Lots of loungers and umbrellas all along the beach. Accessible by boat with private lagoon. You can see and probably paddle to the sandbar from there. Only downside to me was highway noise, and neighbor noise. Seems like no soundproofing. You hear the trucks and your neighbors clearly all night long if you are in the cheaper rooms that are non-ocean front/view up closer to the roadway. Bring earplugs. Staff everywhere cleaning and fixing things up. Lots of different room and little “house” options. Property is huge. Kayaks, paddleboards there for a fee.
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FAQ's

Is this Chesapeake Beach Resort pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Chesapeake Beach Resort have a swimming pool?

Yes, this Chesapeake Beach Resort has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Chesapeake Beach Resort?

Best-rates for the Chesapeake Beach Resort starts from $186 per night with includes Pool, TV, Business Services, Bedding/Linens, Breakfast, Air Conditioner, View, Accessibility, Security/Safety, Bar, Kitchen, Laundry, Ocean View, Wellness Facilities, Child Friendly, Internet, Toiletries, Guest Services with all other facilities. Hotala matches every traveler with their perfect hotel, resort, or rental and whether you are traveling with a group, friends, family, or pets.

Is Chesapeake Beach Resort a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this hotel 3 stars or guests have recommended them suitable for families. As reported by the owner or manager, the hotel has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Chesapeake Beach Resort wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Chesapeake Beach Resort has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Chesapeake Beach Resort?

Based on the information reported by the owner or manager, the Chesapeake Beach Resort indicates 1 day stay policy at this hotel. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Chesapeake Beach Resort?

Based on the information reported by the owner or manager, details for the cancellation policy for the Chesapeake Beach Resort are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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