Property building in Chesapeake Beach Resort

Chesapeake Beach Resort

Hotel Highlights

Welcome to Chesapeake Beach Resort, a charming 3-star resort located in Islamorada, Florida. Our resort is situated right on the beautiful beachfront, offering stunning ocean views and a private beach area for our guests to enjoy. With a total of 918 reviews, our resort is highly rated by fellow travelers for its exceptional service and amenities.

Conveniently located just 1.2mi from the city center, Chesapeake Beach Resort provides easy access to all the attractions and activities that Islamorada has to offer. Whether you want to relax on the beach, take a dip in the outdoor swimming pool, or soak in the hot tub, our resort has something for everyone. Our pet-friendly policy allows you to bring your furry friends along for an extra charge.

Bedroom, Bed in Chesapeake Beach Resort
Living room in Chesapeake Beach Resort

Rooms

Show 7 photos

1 King Size Bed

/

0 sqft

Efficiency Villa, Accessible

Kitchenette

Microwave

Flat-screen TV

Refrigerator

Featuring a private entrance, this air-conditioned villa is consisted of of 1 living room, 1 separate bedroom and 1 bathroom with a walk-in shower and a hairdryer. The well-equipped kitchenette has a stovetop, a refrigerator, a dishwasher and kitchenware. This wheelchair accessible villa features a coffee machine, a seating area with a flat-screen TV and a roll-in shower. The unit offers 1 bed.

Show 8 photos

1 King Size Bed

1 Sofa Bed

/

595 sqft

Suite, Accessible, Ocean View

Balcony

Microwave

Flat-screen TV

Refrigerator

This spacious suite is consisted of of 1 living room, 1 separate bedroom and 1 bathroom with a walk-in shower and free toiletries. The air-conditioned suite offers a flat-screen TV with cable channels, a private entrance, a coffee machine, a seating area as well as sea views. The unit offers 2 beds.

Ocean View King in Chesapeake Beach Resort

Show 11 photos

1 King Size Bed

/

345 sqft

King Room, Ocean View

Private Bathroom

Balcony

Private entrance

Microwave

Ocean View King (1 King Bed) is 366 square feet and includes balcony, satellite tv , cable tv, hairdryer, tea and coffee making facilities , ironing set, and safe.

Discover More

Each room at Chesapeake Beach Resort is equipped with modern amenities such as air conditioning, a private bathroom, and a kitchenette with kitchenware. For your convenience, we offer free WiFi and private parking. Other amenities include a 24-hour front desk, a convenience store on-site, and daily housekeeping services.

With its prime location, excellent reviews, and a range of amenities, Chesapeake Beach Resort is the perfect choice for a relaxing and enjoyable stay in Islamorada, Florida. Prices start from $687, so book your stay with us today and experience the best of beachfront living.

View (from property/room) in Chesapeake Beach Resort
View (from property/room), Bed in Chesapeake Beach Resort

Experience the Best

At Chesapeake Beach Resort, we know that pets are part of the family too, which is why we are delighted to welcome your furry friends. Our pet-friendly policy allows you to bring your beloved pets along for an additional charge. So, no need to leave them behind while you enjoy the sun, sand, and ocean breeze. Let them explore the beautiful beachfront with you and create unforgettable memories together.

Living room in Chesapeake Beach Resort
Living room in Chesapeake Beach Resort

Plan Your Stay

When it's time to cool off and have a splash, we have not one but two outdoor pools available exclusively for adults. Our pools are heated, ensuring a comfortable swim no matter the season. Take a dip in the refreshing water or lounge by the poolside and soak up the rays. With shallow ends and stunning views of the ocean, our pools provide the perfect setting for relaxation and rejuvenation. So grab your favorite book, find a cozy spot, and let the worries of everyday life melt away.

Breakfast in Chesapeake Beach Resort
Balcony/Terrace in Chesapeake Beach Resort

Amenities

Beachfront

Private beach area

Outdoor swimming pool

Free Private Parking

Free wifi

Beach

Air conditioning

Private entrance

Bathroom in Chesapeake Beach Resort
Bathroom in Chesapeake Beach Resort

Pool

Outdoor, Adults only

All season, Heated, Shallow end, With view

Swimming pool in Chesapeake Beach Resort
Swimming pool in Chesapeake Beach Resort
Beach in Chesapeake Beach Resort
Breakfast included and good 👍 you can walk next door for two restaurants and an all you can eat seafood buffet. I went with myself and two adult children. The food was good at restaurants. For 3 with cocktails lunch or dinner all meals were with tip $80 to $100 . Just expect that . Drinks pricey though hotel has happy hour drinks for $7. Free kyacking ,paddle boards, you can fish on the property. 1 hour 45 in early am to key west . Great location . Very impressed by all staff at the hotel and restaurants. I was upgraded to a villa . We loved it . Full fridge, stove top, microwave , sink , dishes and silverware. Fishing charters all around the area . We did a charter at Robbie’s a really cool spot to hang out at .

Maddalone

There is a private beach at the resort that is absolutely beautiful. You can swim at the ocean, there is a clear space from the seaweeds, it's so beautiful. You can have 2 hours / day to use the kayaks and the stand up paddle, which is pretty convenient. If you take the ocean view room, the view is amazing. The room is also very comfortable. Parking is super easy. They don't have a restaurant at the property, but walking less than 2 minutes there is an amazing all you can eat seafood restaurant. You can also take the car and 2-3 minutes away you'll find amazing restaurants. The lady who was in the front desk welcoming the guests was adorable, very polite and kind.

Paula

This is our place to go when my wife and I need to take a break from our stressful routine. We land in key west, rent a car (buy some wine and other groceries) and drive to our favorite refuge. We always get the ocean view room. Rooms are clean, beds very comfy and cozy, the view from the balcony is stunning and refreshing! The resort is quiet and peaceful with a relaxed vibe, two pools, a hot tub and a private beach. All you have to do is enjoy the sun and forget about the rest of the world!

Giovanni

The room was beautiful and ocean front. Vey comfortable beds! The balcony was spacious as was the bathroom. The beachfront was stunning and the pools were a lot of fun! Complimentary water sports was such a wonderful bonus and the breakfast was great with many options and open for such a long span of time. Oh and at check in they offered you champagne. The staff was exceptional the whole time checking in on our needs and it was a very busy week as we stayed over the holiday.

Megan

The rooms were very comfortable and clean. The staff serving breakfast was super friendly and helpful. Actually all the staff (office, chamber maid) was very accommodating. Beach was very nice and we had plenty of sitting. Was nice that there were paddleboards and kayaks to use. Pool/spa was perfect and we enjoyed both! We enjoyed our stay enough that my friend is going to bring her family back. We all would stay here again!

Bonnie

Breakfast included and good 👍 you can walk next door for two restaurants and an all you can eat seafood buffet. I went with myself and two adult children. The food was good at restaurants. For 3 with cocktails lunch or dinner all meals were with tip $80 to $100 . Just expect that . Drinks pricey though hotel has happy hour drinks for $7. Free kyacking ,paddle boards, you can fish on the property. 1 hour 45 in early am to key west . Great location . Very impressed by all staff at the hotel and restaurants. I was upgraded to a villa . We loved it . Full fridge, stove top, microwave , sink , dishes and silverware. Fishing charters all around the area . We did a charter at Robbie’s a really cool spot to hang out at .

Maddalone

There is a private beach at the resort that is absolutely beautiful. You can swim at the ocean, there is a clear space from the seaweeds, it's so beautiful. You can have 2 hours / day to use the kayaks and the stand up paddle, which is pretty convenient. If you take the ocean view room, the view is amazing. The room is also very comfortable. Parking is super easy. They don't have a restaurant at the property, but walking less than 2 minutes there is an amazing all you can eat seafood restaurant. You can also take the car and 2-3 minutes away you'll find amazing restaurants. The lady who was in the front desk welcoming the guests was adorable, very polite and kind.

Paula

This is our place to go when my wife and I need to take a break from our stressful routine. We land in key west, rent a car (buy some wine and other groceries) and drive to our favorite refuge. We always get the ocean view room. Rooms are clean, beds very comfy and cozy, the view from the balcony is stunning and refreshing! The resort is quiet and peaceful with a relaxed vibe, two pools, a hot tub and a private beach. All you have to do is enjoy the sun and forget about the rest of the world!

Giovanni

The room was beautiful and ocean front. Vey comfortable beds! The balcony was spacious as was the bathroom. The beachfront was stunning and the pools were a lot of fun! Complimentary water sports was such a wonderful bonus and the breakfast was great with many options and open for such a long span of time. Oh and at check in they offered you champagne. The staff was exceptional the whole time checking in on our needs and it was a very busy week as we stayed over the holiday.

Megan

The rooms were very comfortable and clean. The staff serving breakfast was super friendly and helpful. Actually all the staff (office, chamber maid) was very accommodating. Beach was very nice and we had plenty of sitting. Was nice that there were paddleboards and kayaks to use. Pool/spa was perfect and we enjoyed both! We enjoyed our stay enough that my friend is going to bring her family back. We all would stay here again!

Bonnie

Breakfast included and good 👍 you can walk next door for two restaurants and an all you can eat seafood buffet. I went with myself and two adult children. The food was good at restaurants. For 3 with cocktails lunch or dinner all meals were with tip $80 to $100 . Just expect that . Drinks pricey though hotel has happy hour drinks for $7. Free kyacking ,paddle boards, you can fish on the property. 1 hour 45 in early am to key west . Great location . Very impressed by all staff at the hotel and restaurants. I was upgraded to a villa . We loved it . Full fridge, stove top, microwave , sink , dishes and silverware. Fishing charters all around the area . We did a charter at Robbie’s a really cool spot to hang out at .

Maddalone

There is a private beach at the resort that is absolutely beautiful. You can swim at the ocean, there is a clear space from the seaweeds, it's so beautiful. You can have 2 hours / day to use the kayaks and the stand up paddle, which is pretty convenient. If you take the ocean view room, the view is amazing. The room is also very comfortable. Parking is super easy. They don't have a restaurant at the property, but walking less than 2 minutes there is an amazing all you can eat seafood restaurant. You can also take the car and 2-3 minutes away you'll find amazing restaurants. The lady who was in the front desk welcoming the guests was adorable, very polite and kind.

Paula

This is our place to go when my wife and I need to take a break from our stressful routine. We land in key west, rent a car (buy some wine and other groceries) and drive to our favorite refuge. We always get the ocean view room. Rooms are clean, beds very comfy and cozy, the view from the balcony is stunning and refreshing! The resort is quiet and peaceful with a relaxed vibe, two pools, a hot tub and a private beach. All you have to do is enjoy the sun and forget about the rest of the world!

Giovanni

The room was beautiful and ocean front. Vey comfortable beds! The balcony was spacious as was the bathroom. The beachfront was stunning and the pools were a lot of fun! Complimentary water sports was such a wonderful bonus and the breakfast was great with many options and open for such a long span of time. Oh and at check in they offered you champagne. The staff was exceptional the whole time checking in on our needs and it was a very busy week as we stayed over the holiday.

Megan

The rooms were very comfortable and clean. The staff serving breakfast was super friendly and helpful. Actually all the staff (office, chamber maid) was very accommodating. Beach was very nice and we had plenty of sitting. Was nice that there were paddleboards and kayaks to use. Pool/spa was perfect and we enjoyed both! We enjoyed our stay enough that my friend is going to bring her family back. We all would stay here again!

Bonnie

Location

83409 Overseas Highway, Islamorada, 33036, Florida, United States

Reservations:

+1 (888) 389-1929

or
Chesapeake Beach Resort