Chesapeake Beach Resort

★★★★★
  • 83409 Overseas Highway

    Islamorada, FL 33036

    Map & Directions
  • 305-664-4662

About Chesapeake Beach Resort

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Hotels & Travel

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Schloss Pichlarn

Zimmer & Suiten

Jedes Hotelzimmer und jede Suite im Romantik Hotel Schloss Pichlarn garantieren Entspannung und Wohlbefinden. Die einzelnen Zimmer verfügen über exquisite Details, die den einzigartigen historischen Charme des Hotels aufgreifen. Die Gäste können einen traumhaften Ausblick und luxuriöse Annehmlichkeiten genießen, während sie in einem der besten Luxushotels Österreichs entspannen.

    Restaurants & Bars

    Genießen Sie österreichische Kulinarik abgestimmt mit dem besten aus dem Internationalen während Ihres Luxusaufenthalts in den österreichischen Bergen mit und ohne Übernachtung im Schloss.
      5 50
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      .

      Stayed in a room with 2 double beds and a balcony with a great ocean view. We had a four night stay and didn't want to leave. It's in a good location for exploring further up and down the Keys. Desk staff were friendly and knowledgeable -

      3
      ★★★★★

      Stayed in a room with 2 double beds and a balcony with a great ocean view. We had a four night stay and didn't want to leave. It's in a good location for exploring further up and down the Keys. Desk staff were friendly and knowledgeable -

      .

      Had a great time staying at the resort. The rooms are huge and we had a balcony that faced the ocean. It was nice that the bikes, kayaks and paddle boats are included in the price. We had fun riding around the island

      3
      ★★★★★

      Had a great time staying at the resort. The rooms are huge and we had a balcony that faced the ocean. It was nice that the bikes, kayaks and paddle boats are included in the price. We had fun riding around the island

      .

      Enroute to our Key West condominium my wife and I often reserve a suite for a week in the Chesapeake Beach Resort.We take one of the upper level suites. Our suite, which has a jacuzzi, was well decorated, furnished and equipped. Suites

      3
      ★★★★★

      Enroute to our Key West condominium my wife and I often reserve a suite for a week in the Chesapeake Beach Resort.We take one of the upper level suites. Our suite, which has a jacuzzi, was well decorated, furnished and equipped. Suites

      .

      If you are looking for peace and quiet. This is it! Just perfect, It is an older hotel, but every thing has been redone. We loved it!!!! The view from our room was stunning. It was exactly what we were looking for

      3
      ★★★★★

      If you are looking for peace and quiet. This is it! Just perfect, It is an older hotel, but every thing has been redone. We loved it!!!! The view from our room was stunning. It was exactly what we were looking for

      .

      We had so much fun relaxing in this peaceful setting. My grandchildren said they were having the best time of their lives, kayaking, barbecuing on the beach overlooking the magnificent sunset, swimming in the heated pools at night and just

      3
      ★★★★★

      We had so much fun relaxing in this peaceful setting. My grandchildren said they were having the best time of their lives, kayaking, barbecuing on the beach overlooking the magnificent sunset, swimming in the heated pools at night and just

      .

      I call the Chesapeake Beach Resort my personal paradise. This is the place I return to, to connect to nature and to my soul. This year I am back for 2 weeks and I am enjoying every day. Included in the price of the room they supply kajaks,

      3
      ★★★★★

      I call the Chesapeake Beach Resort my personal paradise. This is the place I return to, to connect to nature and to my soul. This year I am back for 2 weeks and I am enjoying every day. Included in the price of the room they supply kajaks,

      .

      We checked in early afternoon into a garden view room. This was our home base for a two-day fishing trip, so we weren't looking for an ocean view room. It was clean, functional, close to restaurants and next door to our charter boat's

      3
      ★★★★★

      We checked in early afternoon into a garden view room. This was our home base for a two-day fishing trip, so we weren't looking for an ocean view room. It was clean, functional, close to restaurants and next door to our charter boat's

      .

      Check in was friendly. Room was very nice. We enjoyed kayaking on the beach and the grounds surrounding hotel were nice & well kept. We used one of the pools, enjoyed the breakfast and had a great dinner experience at the Lorelei and the

      3
      ★★★★★

      Check in was friendly. Room was very nice. We enjoyed kayaking on the beach and the grounds surrounding hotel were nice & well kept. We used one of the pools, enjoyed the breakfast and had a great dinner experience at the Lorelei and the

      .

      The Resort is Awesome. Fish and snorkle right in front of the Resort. There are no real beaches in the Keys. It's mostly rock. We like laid back relaxing places.\r
      And that's what you get at the Chesapeake. The views are so beautiful.

      3
      ★★★★★

      The Resort is Awesome. Fish and snorkle right in front of the Resort. There are no real beaches in the Keys. It's mostly rock. We like laid back relaxing places.\r
      And that's what you get at the Chesapeake. The views are so beautiful.

      .

      For the past couple years me and my fiance have been traveling to Islamorada and we always stay here. It is very peaceful, nice pools and a beautiful relaxing view. the location is fantastic Whale harbor has great food. Brazalaina great

      3
      ★★★★★

      For the past couple years me and my fiance have been traveling to Islamorada and we always stay here. It is very peaceful, nice pools and a beautiful relaxing view. the location is fantastic Whale harbor has great food. Brazalaina great

      .

      We pulled into Islamorada for a surprise fishing trip for our turning-21 son. Chesapeake rep, Will welcomed us back and made sure our room rate reflected all discounts. After fishing all day 20 miles out in the Atlantic, Will suggested we

      3
      ★★★★★

      We pulled into Islamorada for a surprise fishing trip for our turning-21 son. Chesapeake rep, Will welcomed us back and made sure our room rate reflected all discounts. After fishing all day 20 miles out in the Atlantic, Will suggested we

      .

      It was an awesome vacation. We consisted of two adults and two teenagers. I can not say enough about the grounds of the Resort. They were amazing! It's a great location right on the water with plenty to do. There is a restaurant next door

      3
      ★★★★★

      It was an awesome vacation. We consisted of two adults and two teenagers. I can not say enough about the grounds of the Resort. They were amazing! It's a great location right on the water with plenty to do. There is a restaurant next door

      .

      I stayed here during a trying time for the locals, Bartenders Bash, but we all loved our stay at the Chesapeake. My wife and I shared a villa with a friend and everything was clean and working properly. 24 hour security patrolling around

      3
      ★★★★★

      I stayed here during a trying time for the locals, Bartenders Bash, but we all loved our stay at the Chesapeake. My wife and I shared a villa with a friend and everything was clean and working properly. 24 hour security patrolling around

      .

      Loved, loved it. All the employees were friendly, extremely helpful...I needed AA batteries, went to the front counter...the lady offered me two batteries. They were so helpful with directions, activity ideas around the keys, etc. Free

      3
      ★★★★★

      Loved, loved it. All the employees were friendly, extremely helpful...I needed AA batteries, went to the front counter...the lady offered me two batteries. They were so helpful with directions, activity ideas around the keys, etc. Free

      .

      We came upon this hotel when we thought we'd run out of luck as 4 othr hotels we had called at were ful. (Turned out to be a holiday weekend!) The room we had was on the 2nd floor and, though it didn't look over the bay, it had a great

      3
      ★★★★★

      We came upon this hotel when we thought we'd run out of luck as 4 othr hotels we had called at were ful. (Turned out to be a holiday weekend!) The room we had was on the 2nd floor and, though it didn't look over the bay, it had a great

      .

      We stayed here for three nights in early November. We really enjoyed it. The resort is by no means fancy, but it was much nicer than we expected. We stayed in an ocean view room and loved it. There was plenty of space, the view was

      3
      ★★★★★

      We stayed here for three nights in early November. We really enjoyed it. The resort is by no means fancy, but it was much nicer than we expected. We stayed in an ocean view room and loved it. There was plenty of space, the view was

      .

      We love this resort! This was our second stay at the Chesapeake, as it has become our "go-to" place in Islamorada. The polite staff, spotless accommodations and serene surroundings made our vacation even more enjoyable.

      3
      ★★★★★

      We love this resort! This was our second stay at the Chesapeake, as it has become our "go-to" place in Islamorada. The polite staff, spotless accommodations and serene surroundings made our vacation even more enjoyable.

      .

      I really enjoyed the place. There was nothing unpleasant throughout my 3 night stay. We paid $384 per night for this place 2/08/2013 and shared that with 5 people in the villa. We chose the ocean front view villas too. This is an

      3
      ★★★★★

      I really enjoyed the place. There was nothing unpleasant throughout my 3 night stay. We paid $384 per night for this place 2/08/2013 and shared that with 5 people in the villa. We chose the ocean front view villas too. This is an

      .

      Our family of 4 just came back from an excellent stay in a suite at the Chesapeake. Last year, we stayed in a Lanai room at Hawks Cay Resort but found it very expensive for what was provided. We are so pleased that we found the Chesapeake

      3
      ★★★★★

      Our family of 4 just came back from an excellent stay in a suite at the Chesapeake. Last year, we stayed in a Lanai room at Hawks Cay Resort but found it very expensive for what was provided. We are so pleased that we found the Chesapeake

      .

      The deep sea fishing was as challenging and exciting as everyone has told me. While the tropical nights where romantic and leisurely spent in our clean and well maintained villa over looking the lagoon. With such helpful and courteous

      3
      ★★★★★

      The deep sea fishing was as challenging and exciting as everyone has told me. While the tropical nights where romantic and leisurely spent in our clean and well maintained villa over looking the lagoon. With such helpful and courteous

      .

      I am from Toronto, Canada and here at the Chesapeake Beach Resort for two weeks working. My room is overlooking the lagoon, there are hammocks between the palm trees, and the views are spectacular. I come every year to recharge my

      3
      ★★★★★

      I am from Toronto, Canada and here at the Chesapeake Beach Resort for two weeks working. My room is overlooking the lagoon, there are hammocks between the palm trees, and the views are spectacular. I come every year to recharge my

      .

      Decided to go to Islamorada for the weekend to surprise my son for his 13th birthday! After reading reviews here on tripadvisor, picked Chesapeake Beach Resort and what a gem. From Overseas Hwy, it looks like a small resort but it opens up

      3
      ★★★★★

      Decided to go to Islamorada for the weekend to surprise my son for his 13th birthday! After reading reviews here on tripadvisor, picked Chesapeake Beach Resort and what a gem. From Overseas Hwy, it looks like a small resort but it opens up

      .

      This property looks like an old rundown keys hotel from the road but is far from it. The rooms are very clean as is the property. It has all of the amenities and the staff is very friendly and hard working. Do not pass up on the wonderful

      3
      ★★★★★

      This property looks like an old rundown keys hotel from the road but is far from it. The rooms are very clean as is the property. It has all of the amenities and the staff is very friendly and hard working. Do not pass up on the wonderful

      .

      This was my husband and I's 2nd stay at the Chesapeake. We are locals who live just 45 min. from Islamorada but like to "get out of town" and away from the kids for a weekend alone every now and then. Both times, we have had a room with a

      3
      ★★★★★

      This was my husband and I's 2nd stay at the Chesapeake. We are locals who live just 45 min. from Islamorada but like to "get out of town" and away from the kids for a weekend alone every now and then. Both times, we have had a room with a

      .

      This place is clean, fresh, and the views are beautiful. It is reasonably priced and the staff couldn't be nicer or more helpful. You must check out the tiki hut. The breeze is refreshing the ocean view is calendar picture good. A good

      3
      ★★★★★

      This place is clean, fresh, and the views are beautiful. It is reasonably priced and the staff couldn't be nicer or more helpful. You must check out the tiki hut. The breeze is refreshing the ocean view is calendar picture good. A good

      .

      The Chesapeake Resort was exactly what we needed -- low key, comfortable, great location, friendly staff. We ended up being upgraded from a 1 bedroom ocean view villa to a 2 bedroom ocean view villa. It was huge! 1200 sq. ft. with a full

      3
      ★★★★★

      The Chesapeake Resort was exactly what we needed -- low key, comfortable, great location, friendly staff. We ended up being upgraded from a 1 bedroom ocean view villa to a 2 bedroom ocean view villa. It was huge! 1200 sq. ft. with a full

      .

      Chesapeake Beach is a great resort. This is my 3rd trip to Islamorada and I've stayed at The Hampton Inn before which is also very nice. I would rate Chesapeake above it because it feels more homey and has an old school Keys-feel. We

      3
      ★★★★★

      Chesapeake Beach is a great resort. This is my 3rd trip to Islamorada and I've stayed at The Hampton Inn before which is also very nice. I would rate Chesapeake above it because it feels more homey and has an old school Keys-feel. We

      .

      We had a great stay at the Chesapeake Beach Resort this weekend August 9th through the 12th. The front desk staff (Cesar and a girl) were very helpful and courteous. The stay got even better as we (there were 6 in our party) headed down to

      3
      ★★★★★

      We had a great stay at the Chesapeake Beach Resort this weekend August 9th through the 12th. The front desk staff (Cesar and a girl) were very helpful and courteous. The stay got even better as we (there were 6 in our party) headed down to

      .

      I booked my stay based on Tripadvisor reviews and was not disappointed! In fact, I found Chesapeake exceeded my expectations. Several posted reviews dissed the cleanliness, condition, and bedding qualities of the rooms, so I arrived with a

      3
      ★★★★★

      I booked my stay based on Tripadvisor reviews and was not disappointed! In fact, I found Chesapeake exceeded my expectations. Several posted reviews dissed the cleanliness, condition, and bedding qualities of the rooms, so I arrived with a

      .

      friends and I stayed here for a weekend wedding. very keys-ish in style, feels welcoming. free decent breakfast buffet, resort fee includes renting of kayaks, water bikes, etc. villa had 2 double bed a pull out couch full kitchen with full

      3
      ★★★★★

      friends and I stayed here for a weekend wedding. very keys-ish in style, feels welcoming. free decent breakfast buffet, resort fee includes renting of kayaks, water bikes, etc. villa had 2 double bed a pull out couch full kitchen with full

      .

      A fun, relaxing place to stay. It wasn't perfect, but I prefer "real" to the sterile perfection of a Marriott or Hilton. We rented a cabin with my mother-in-law, her sister, and our six-year-old. Plenty of room for everyone. Two pools

      3
      ★★★★★

      A fun, relaxing place to stay. It wasn't perfect, but I prefer "real" to the sterile perfection of a Marriott or Hilton. We rented a cabin with my mother-in-law, her sister, and our six-year-old. Plenty of room for everyone. Two pools

      .

      This resort is only two hours from downtown Fort Lauderdale, so closer if you are travelling from Miami. It is a very clean, beautifully positioned property on the Atlantic side of Islamorada. The rooms were nicely appointed with huge

      3
      ★★★★★

      This resort is only two hours from downtown Fort Lauderdale, so closer if you are travelling from Miami. It is a very clean, beautifully positioned property on the Atlantic side of Islamorada. The rooms were nicely appointed with huge

      .

      We first stopped at Chesapeake Resort for one night in 1981. We loved it so much we ended up staying for a week using it as our base to explore The Keys. Since then we have returned many times staying for a couple of weeks or more. So much

      3
      ★★★★★

      We first stopped at Chesapeake Resort for one night in 1981. We loved it so much we ended up staying for a week using it as our base to explore The Keys. Since then we have returned many times staying for a couple of weeks or more. So much

      .

      We stayed in room 314 which is an upstairs villa with an efficiency. It overlooks the water and a small lagoon. I really think we lucked out with this room. It's quaint and picturesque. I would definitely stay here again.

      3
      ★★★★★

      We stayed in room 314 which is an upstairs villa with an efficiency. It overlooks the water and a small lagoon. I really think we lucked out with this room. It's quaint and picturesque. I would definitely stay here again.

      .

      This is an awesome hotel with good view to sea access, morning views were amazing and it is a calm and quiet resort. The trees, plants, shades and the locations were well maintained, we stayed for a day while on the way to Key west. We

      3
      ★★★★★

      This is an awesome hotel with good view to sea access, morning views were amazing and it is a calm and quiet resort. The trees, plants, shades and the locations were well maintained, we stayed for a day while on the way to Key west. We

      .

      Would stay there agin any time

      3
      ★★★★★

      Would stay there agin any time

      .

      very good hotel, room is very clean , staff is friendly, nice and quiet , good location,close to restaurants, nice place to relax and enjoy. Views are stunning. I would definitely stay there again. You have to be there to see it.

      3
      ★★★★★

      very good hotel, room is very clean , staff is friendly, nice and quiet , good location,close to restaurants, nice place to relax and enjoy. Views are stunning. I would definitely stay there again. You have to be there to see it.

      .

      We had a wonderful time at the Cheasapeeke resort...the room was clean, the beds were comfortable, shower was great. We loved it.

      3
      ★★★★★

      We had a wonderful time at the Cheasapeeke resort...the room was clean, the beds were comfortable, shower was great. We loved it.

      .

      nice accommodations, free breakfast and nice staff.

      3
      ★★★★★

      nice accommodations, free breakfast and nice staff.

      .

      if you want a true keys atmosphere in a beautiful tropical location with clean rooms and a great staff, then this is it. We rented a pet friendly efficiency for two nights. The room was a little outdated but well kept and clean. I think

      3
      ★★★★★

      if you want a true keys atmosphere in a beautiful tropical location with clean rooms and a great staff, then this is it. We rented a pet friendly efficiency for two nights. The room was a little outdated but well kept and clean. I think

      .

      Clean, friendly, low key. Flip flops and beach attire are acceptable everywhere. The staff was extremely helpful and friendly.

      3
      ★★★★★

      Clean, friendly, low key. Flip flops and beach attire are acceptable everywhere. The staff was extremely helpful and friendly.

      .

      My family spend a week here most years in the same period.\r
      We take a suite which is excellent value, with a small kitchen where one can prepare simple meals as required.A fridge is provided for the storage of foods, beer and white

      3
      ★★★★★

      My family spend a week here most years in the same period.\r
      We take a suite which is excellent value, with a small kitchen where one can prepare simple meals as required.A fridge is provided for the storage of foods, beer and white

      .

      one of the best views in islamorada the place was imaculate friendly staff we will definitely return we wont even consider looking for another hotel awesome relaxing vacation at the chesapeake, great location close to alot of good places

      3
      ★★★★★

      one of the best views in islamorada the place was imaculate friendly staff we will definitely return we wont even consider looking for another hotel awesome relaxing vacation at the chesapeake, great location close to alot of good places

      .

      It was a charming little properity. intimate. Perfect for a romantic weekend.

      3
      ★★★★★

      It was a charming little properity. intimate. Perfect for a romantic weekend.

      .

      We were delighted with our stay. The staff was friendly and helpful. The layout and functionality of the room was excellent and the balcony was a real plus. The room had a mini fridge, a desk, a table for dining or cards or whatever, a

      3
      ★★★★★

      We were delighted with our stay. The staff was friendly and helpful. The layout and functionality of the room was excellent and the balcony was a real plus. The room had a mini fridge, a desk, a table for dining or cards or whatever, a

      .

      The complimentary kayaks and bicycles are great if you want to be a bit active. There is coin laundry on site (you can get quarters from the front desk). The staff were friendly and made some great restaurant recommendations. Given the

      3
      ★★★★★

      The complimentary kayaks and bicycles are great if you want to be a bit active. There is coin laundry on site (you can get quarters from the front desk). The staff were friendly and made some great restaurant recommendations. Given the

      .

      My wife and I were traveling to Key West and taking our time about it so we needed an extra nights hotel room. We stopped at one of the FL Visitor centers and talked to them about a place to stay and the nice lady mentioned this Hotel as a

      3
      ★★★★★

      My wife and I were traveling to Key West and taking our time about it so we needed an extra nights hotel room. We stopped at one of the FL Visitor centers and talked to them about a place to stay and the nice lady mentioned this Hotel as a

      .

      We came here for a birthday celebration/romantic get away. The resort was recommended to us by a friend. The property is beautiful and very tropical. Our villa was very nice inside. The staff was friendly and helpful.

      3
      ★★★★★

      We came here for a birthday celebration/romantic get away. The resort was recommended to us by a friend. The property is beautiful and very tropical. Our villa was very nice inside. The staff was friendly and helpful.

      .

      The rooms are still very clean - well done house keeping!

      3
      ★★★★★

      The rooms are still very clean - well done house keeping!

      .

      We stayed in the standard room--overlooking the gardens and tennis court. Bed linens and curtains are updated, Pretty view, even though not an ocean view. Pretty spot on the beach with plenty of room to yourself for sunning. Two pools--one

      3
      ★★★★★

      We stayed in the standard room--overlooking the gardens and tennis court. Bed linens and curtains are updated, Pretty view, even though not an ocean view. Pretty spot on the beach with plenty of room to yourself for sunning. Two pools--one

      Message from Chesapeake Beach Resort

      Discover the beauty and allure of Islamorada’s legendary beach and fishing destination – the Chesapeake Beach Resort.



      Lose yourself amidst swaying palm trees, endless ocean vistas, flowering hibiscus, exotic birds, and a lush private lagoon. A 6.5-acre oceanfront property, our Islamorada hotel offers a tranquil sanctuary of sparkling white sands and tropical gardens— the perfect island getaway.

      Select one of our 65 guest rooms and suites, which feature luxurious tropical decors and amenities like complimentary Wi-Fi, private balconies with amazing views of the deep-blue waters outside and tropical gardens.



      For more than 50 years, the Chesapeake Beach Resort has welcomed generations of families, group tours, adventurers, and sport-fishing enthusiasts. It’s easy to see why when you take advantage of our recreational choices. Enjoy our two heated oceanfront pools, soaking spa, and tennis and shuffleboard court. Charter a boat for deep-sea or back-country fishing, or plan a day of snorkeling or diving.



      The friendly staff at our Islamorada hotel is here to make your stay a wonderful and memorable experience. Whether you’re planning a unique corporate gathering or group retreat, a romantic escape for two, or a fun family vacation, we’ll fit your lifestyle and needs. Anything is possible at Islamorada’s most famous beach and fishing resort. Come slip away with us.

      Yext PowerListings

       

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