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Bayside Villas

Advanced Purchase

Be rewarded for planning ahead!

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Stay More, Save More

Book your stay of 3 nights or longer and we’ll give you up to 20% off our best available rate so you can live your dream.

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Activities & Adventures

Endless Fun in the Sun

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Bayside Villas by Islander Resort

Experience the Keys as They Were Meant to Be

Bayside Villas by Islander Resort is your home away from home in the Florida Keys. Our townhome-style beachfront accommodations are the ideal stay for group getaways, family vacations, and extended stays in beautiful Islamorada. Plus, our exceptional on-site amenities including boat slips and bay view pool, ensure that our experiences are second-to-none. We may be nestled in of the world’s most stunningly beautiful locations, but it’s our memorable service and welcoming touches that have our guests returning to us year after year. 

We look forward to welcoming you to our piece of paradise.

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Holiday Sale

Enjoy up to 25% off your island getaway with our best rates of the year.

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Arise refreshed from a dreamy night’s sleep and head to your kitchen for a fresh cup of coffee or enjoy a leisurely breakfast at Islander Resort's Tides Beachside Bar & Grill


Relax poolside or head out on your boat for a day of exploring.


Hop on a bike and go exploring around beautiful downtown Islamorada.


Dig into a delicious dinner featuring local seafood at Tides Beachside Bar & Grill.


Head back to your Villas to sit on your private deck or our waterside hammocks and watch the spectacular sunset.


Sink into softness and dream of the day's adventure to come.


Islander Bayside’s Villas are an exquisite waterfront escape; each is a townhouse-feel enclave that’s the ideal “home base” for exploring all the Florida Keys have to offer. 

All of our villas afford guests a roomy, well-appointed space with incredible ocean views, full kitchens, multiple beds, and room enough for up to eight — making them perfectly suited to groups and families. Guests also enjoy access to our on-site boat slips, pool, and all of the activities at our Oceanside resort. You’ll indulge in lush comfort and thoughtful amenities your entire stay. 

Choose the villa that’s right for you, and start dreaming of your serene seaside getaway!

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"Beautiful place to stay very clean kind and friendly staff
The fireplace was extremely great not to mention all the wood they supply they supply a lot more then most hotels would I also left behind something important I got in touch and they are organizing postage to return what I forgot highly recommend"

Michael B via Trip Advisor

"We arrived on a cold Winter's day, walked into our Villa accommodation and the wood fire had been lit which was most welcoming after all day traveling. Our Villa accommodation has everything you need, home away from home, clean, peaceful and relaxing, thank you :)"

Debra M via Trip Advisor

"We only stayed one night but this would be a great place to stay for a bit longer. The villa is in a great location. It is very well fitted out with all the conveniences (no wifi but no problem as we could use our mobile hotspots). Plenty of space with large rooms. Great shower. Good bed. Overall, excellent value and comfort."

OzHolly via Trip Advisor


From boating to diving, fishing to swimming, biking to snorkeling, the Keys are packed with amazing adventures.
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Prefer a more guided experience? Our on-site partner Islander Girl Tours offers incredible excursions.
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Plan your next gathering in one of our oceanside event rooms, and your guests will look forward to attending.
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There’s no more beautiful place on Earth to commit to each other than here. Say “I do” with an idyllic ocean view.
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What's Nearby

Islamorada is a vibrant artists’ village and culinary destination in the heart of the Florida Keys. Here are just some of the great places to check out during your visit.

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Whether you’re taking a look at us prior to your stay, or feeling nostalgic until your next one, we invite you to visit us on social media.

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