Islamorada & Florida Keys Villas | Islander Bayside Villas

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EXPERIENCE THE KEYS AS THEY WERE MEANT TO BE

Discover your home away from home in the Florida Keys at the new Bayside Villas by Islander Resort. Our townhome-style beachfront accommodations are fully renovated and reimagined. Here you'll find an idyllic escape for group getaways, family vacations, and extended stays in beautiful Islamorada. Plus, our exceptional on-site amenities including boat slips and a bay view pool, ensure that your luxury experience is second to none.

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

Find your perfect accommodation experience

Sunset Views

Discover a home by the bay in our Bayside Villas. These two-bedroom townhouse-style accommodations are ideal for families or friend groups and feature bayside pool access, water sports, rental boat slips, and full access to our oceanside resort’s amenities.

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Stay Experiences: From the Ocean to the Bay

An Oasis of Ocean Views

Rise with the sun in our Oceanside Bungalows. These new retreats offer sweeping ocean and tropical views, queen and king-bed options, and expansive indoor-outdoor living spaces.

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Stay Experiences: From the Ocean to the Bay

A Beachfront Escape

Experience comfort and luxury in our beautifully appointed suites, featuring breathtaking views and top-tier amenities.

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Islander Signature Moments 

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Islander Day Trip

Escape to the Islander Resort for an unforgettable day of sun-soaked leisure.

Sunset Cruises

This trip departs from the iconic Islander Resort and takes a comfortable boat ride to the bayside of the island.

Seaside Links

Brand New: Experience the PuttTek Putting Course at Islander Resort—where scenic design and playful spirit turn every round into lasting memories with family and friends.

Drift

Restaurants & Bars

Drift: On The Beach

Drift celebrates the pure flavors and simple joys of dining. Inspired by the culinary traditions of coastal towns, Drift's dishes are crafted using fresh, locally sourced ingredients, cooked over open flames to accentuate their intrinsic flavors. This method highlights the quality and freshness of the produce, delivering a dining experience where every element on the plate shines. The bar complements this setting with a nod to the adventurous rum-running history of the Keys, featuring carefully crafted cocktails, local beers, and an eclectic, global selection of wines.

A Table With Plates Of Food And Drinks On It

Tides Beachside Bar & Grill

Restaurants & Bars

Tides beachside Bar

Choose from freshly caught seafood, signature sandwiches and entrees, daily specials, and more. Pair it with an ice-cold beverage, including a wide selection of beer and wine, tropical cocktails, and signature drinks sure to put you on island time.

A Table With Plates Of Food And Cans Of Soda

Coccoloba

Restaurants & Bars

Coccoloba

Set against the resort’s easygoing rhythm, Coccoloba provides the perfect in-between bite—a place where flavors meet the moment. Shaded tables, the distant sound of gentle waves, and the sun's warmth create an inviting space for relaxed enjoyment. Coccoloba embodies the essence of Islander Resort—bold, fresh and effortlessly vibrant.

Discover your adventurous side

Paddle Board

Glide across the water with our guided stand-up paddleboarding experience, offering a perfect blend of adventure and tranquility while exploring the ocean from a unique perspective.

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Boating

Boating in the Florida Keys offers a unique and picturesque experience with its crystal-clear waters, abundant marine life, and vibrant coral reefs.

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Yoga

Yoga in the Florida Keys provides a tranquil and rejuvenating escape amidst stunning natural surroundings.

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PuttTek

At Islander Resort, the PuttTek Putting course is more than just a game – it’s about bringing people together. With scenic design and a playful spirit, PuttTek turns each round into cherished moments with family and friends. Come play, connect, and create lasting memories.

Seaside Sports

Snorkeling

A Person Riding A Wave On A Surfboard In The Water

Head out with our water sports guides for a private snorkeling trip along the reef and meet the colorful native creatures along the way. Your adventure includes boat transportation, lunch, and snacks.

Experiences

Bocce Ball

A Group Of Blue Balls On A Sandy Surface

Our resort's bocce ball court is nestled just steps from the pristine sand, offering a delightful blend of leisurely competition and breathtaking coastal views.

Seaside Sports

Kayaking

Paddle through the serene waters of Islamorada with our guided kayaking adventure at Islander Resort.

Seaside Sports

Biking

A Group Of People Riding Bikes On A Dirt Road

At Islander Resort, biking isn't just an activity—it's a journey through paradise. Cruise along lush tropical paths framed by swaying palms and the glimmer of the turquoise ocean.

Seaside Sports

Volleyball

Feel the sun-kissed sand between your toes as you dive for the volleyball on our brand new court, perfectly positioned just steps from the ocean's edge.

Seaside Sports

Cabanas

A Pool With Palm Trees And A Building In The Background

Unwind to the gentle sound of waves, lounge under the shade of palm trees, and enjoy direct access to the beach for swimming, sunbathing, or leisurely walks along the shore.

Experiences

Islamorada Boating Vacations at Bayside Villas

Explore Islamorada by boat from Bayside Villas. Discover boat slip rentals, trailer parking access, fishing opportunities, sandbar adventures, and spacious villa accommodations on Florida Bay, all with access to the amenities of Islander Resort.

Florida Keys Mini Lobster Season 2026 from Bayside Villas

Experience Florida Keys Mini Lobster Season 2026 from Bayside Villas in Islamorada. Enjoy spacious accommodations, convenient access to Florida Bay, trailer parking, and the ideal home base for one of the Keys' most anticipated boating and lobstering traditions.

Pets Welcome

Make memories with your whole family, furry companions included. Enjoy a relaxing getaway together at our pet-friendly resort.

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Reserve your stay

Rooms

Adults

Children

Special Rates

THE NEW BAYSIDE VILLAS BY ISLANDER RESORT

Islander Signature Moments

Restaurants & Bars

Drift: On The Beach

Restaurants & Bars

Tides beachside Bar

Restaurants & Bars

Coccoloba

Discover your adventurous side

Book Now

Reserve your stay

Rooms

Adults

Children

Special Rates

THE NEW BAYSIDE VILLAS BY ISLANDER RESORT

4th Night Free

Islander Signature Moments

Restaurants & Bars

Drift: On The Beach

Restaurants & Bars

Tides beachside Bar

Restaurants & Bars

Coccoloba

Discover your adventurous side

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Islander Signature Moments 