Islander Bayside & Oceanside presents a serene escape where coastal elegance and tropical charm converge. Surrounded by the natural beauty of Islamorada, this refined retreat offers an elevated experience infused with island sophistication. Each detail reflects a harmonious blend of modern style and relaxed ambiance, creating the perfect backdrop for unforgettable moments. Discover the art of effortless luxury in the heart of the Florida Keys. Pets allowed with a fee Water activities On-site parking Area shuttle
Bayside Villas by Islander Resort offers Beach Access, Beach volleyball, Bicycle rentals, Events allowed, Outdoor pool, Yoga classes, Meeting rooms, Bar/lounge, Kitchen/Kitchenette, Restaurants, Wedding services, Self parking (surcharge), Accessible property, Pets allowed with a fee, Area shuttle (surcharge), Hair dryer, Sofa bed, Balcony, In-room climate (air conditioning), In-room climate control (heating), Iron/ironing board, Private entrance, Phone, Television, WiFi (surcharge).
Bayside Villas by Islander Resort is located at 81450 Overseas Highway, Islamorada.
Bayside Villas by Islander Resort has an average rating of 4.3 out of 5 based on 271 guest reviews.
2 Queen Beds and 1 Double Sofa Bed
Brand New Queen/Queen Bedroom ADA
2 King Beds and 1 Double Sofa Bed
Brand New Two King Bed Preferred
2 King Beds and 1 Double Sofa Bed
Brand New Two King Bay Front
2 King Beds and 1 Double Sofa Bed
Brand New Two King Bedroom Bay View
2 King Beds and 1 Double Sofa Bed
Brand New Two King Bed Standard




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Islander Bayside & Oceanside presents a serene escape where coastal elegance and tropical charm converge. Surrounded by the natural beauty of Islamorada, this refined retreat offers an elevated experience infused with island sophistication. Each detail reflects a harmonious blend of modern style and relaxed ambiance, creating the perfect backdrop for unforgettable moments. Discover the art of effortless luxury in the heart of the Florida Keys.
Travelers consistently praise the Bayside Villas for its stunning bay views and exceptional owner/service interaction, though some guests report issues with cleanliness and deferred maintenance. The property combines a tranquil, relaxed island vibe with convenient amenity access to the nearby Islander Resort.
Great couple day escape from Miami! We loved the room. Very peaceful right on the bay. William was great! Very friendly and even went out of his way to drive down the road after we checked out to deliver something we forgot. Thank you for a great trip!!
William took great care of us! Top tier service. We would come back just for him! The rooms are great and we enjoyed sitting out on the balcony overlooking the bay. The restaurant at the islander resort was delicious along with the other restaurants William gave as recommendations. The shuttles were extremely convenient to have. Our drivers were always very friendly.??????
We had an amazing time staying at the Bayside Villas and seeing fireworks at The Islander for New Year’s! William and Jeremy were incredibly nice and were always available to help. They had a smile every time we crossed paths. Loved the tranquility of Bayside, the sunsets, and the pool. Until next time!
William was the best! Anytime we needed assistance, he was there to help. He noticed we were trying to turn on the grill and without us having to ask, he came seemingly out of nowhere to turn it on for us. Great person to have around. The atmosphere is very chill and having the amenities at The Islander is a plus. Great stay!
?? Unforgettable Stay at Bayside Villas by Islander Resort! ?? We recently had the pleasure of staying at Bayside Villas by Islander Resort in beautiful Islamorada, Florida, and it was truly a memorable getaway! Nestled right on the water with stunning bay views and a relaxed island vibe, this place is the perfect escape for families, friends, or anyone looking for a peaceful yet fun tropical retreat. ? From the moment we arrived, we felt welcomed and well taken care of. The villas themselves are spacious, beautifully presented, and feel just like a home away from home — complete with full kitchens, comfortable living spaces, and easy access to both the bayside pool and the wider resort amenities. ? Guests here also enjoy access to the Islander Resort’s activities, beach areas, and water sports, which makes every day feel like a new adventure. ? What truly made our stay exceptional was the hospitality — especially William, whose warm attitude, professionalism, and genuine care elevated our entire experience. William went above and beyond to make sure we were comfortable, offered helpful recommendations, and always greeted us with a smile. His service was one of the highlights of our trip, and we can’t thank him enough for making our stay so special. The combination of beautiful surroundings, roomy and well-equipped villas, access to great amenities, and service from people like William makes Bayside Villas by Islander Resort a top choice if you’re planning a getaway in the Florida Keys. We already can’t wait to return! ??
The villa was spacious and offered a full kitchen and sufficient space for all of us. The price of the villa includes access to the amenities at the resort down the road. the shuttle service was very nice. William is great, and always made sure we had everything we needed. We will be back!
My wife and I stayed 5 days at the Islander Bayside Resort. Pretty good experience. I would recommend with certain caveats. The staff was great, everyone was friendly and helpful. Very pet friendly. The grounds and amenities at the oceanfront property are great. The marina slips are nice for small boats, not sure anything over 20-22 ft would fit. The exterior of the bayside property look good, but the inside has some deferred maintenance and the interior could use some updating. The bayside units are two bedroom with 1 1/2 baths, so both bedrooms share the upstairs bath / shower and can get cramped for more than two people. There are limited amenities at the bayside property, so you have to travel to the oceanside property to utilize most amenities and visit their bars, restaurants, etc. Regarding bars and restaurants, the bar was OK and the bar food was mediocre at best (limited options). Our experience at the main restaurant, Drift, was just bad. The food was bad, it took a long time to get the food, and the server (who was very nice) seemed overwhelmed (and there were only 4 tables occupied in the restaurant counting us totaling 8 people). During our stay, we had four entrees at drift, and none of them were good. The challenge is we had a daily resort credit included in our nightly rate that had to be spent daily, or it expired. So we felt obliged to go to the bar or restaurant daily. The credit could also be spent at the lobby, but the selection of items there were limited and not interesting to us. Also, if a resort credit is included in the rate, you will want to ask for a paper receipt for every purchase, as I had to address multiple discrepancies on my bill (all resolved). Overall I would recommend the oceanfront rooms over the bayside rooms, depending upon the room rate. Keep in mind the property charges a resort fee, slip fee if you have a boat, and a pet fee in addition to the nightly rate. We utilized the “near inclusive” rate structure, which included these fees plus a resort credit. But the resort credit just ended up causing us stress as we didn’t want to eat anything on property after the second day. Overall, I would give our experience at the bayside property 3 - 3.5 stars (would be 4 stars if some maintenance items were addressed and if the food situation was better).
Rooms are worn. Daily service was poor. They Couldn’t even wipe the dining table after we ate a light breakfast. Poor amenities- not even a towel in the powder bath. The kitchen was very basic. There was no garbage disposal or a big bowl for a salad. Not stocked for cooking. King bed was squeezed into small bedrooms. If you decide to stay here, please do have them send you the address. Alison was nice, but we had to go to the website to get the address. Price was high , not reflective of the value.
Great quiet location in the middle of Islamorada. They have a pool and boat dock available. We like the size of the rooms. We travel with 3 teenagers so we had plenty of room for them to roam without feeling crowded. They also provide on demand shuttle to their sister property a few blocks down the road with plenty of amenities to enjoy. Overall great experience. Pictures were taken from the poll area at sunset. Great views!!
Our trip got cut short by a family emergency unfortunately, but the staff at both the Villas (Allison) and the Islander Resort (Angie) were uncommonly understanding and accommodating. Great experience all around, will definitely return. Great family friendly resort experience