Escape to Island Paradise
Your Home Away from Home!
Oceanside Islamorada
Immerse yourself in the luxury and beauty of Oceanside Resort, a brand-new gated community with 9 beachfront homes nestled in the heart of Islamorada.
Each 4 bedroom home invites you to experience modern coastal comfort while its nearly 3,000 square feet of indoor space provide ample room for family and friends. Every stylishly furnished bedroom comes complete with an en suite bathroom, and an expansive living/dining area opens directly onto a private patio & pool. Plus, savor delicious food prepared fresh from your own fully equipped kitchen or take advantage of numerous nearby restaurants, such as Morada Bay and Square Grouper, where breathtaking views meet tantalizing cuisine. Our resort, at mile marker 82, is just minutes away!
Each luxurious Oceanside home offers parking for two vehicles, a private pool, kitchen with all stainless steel appliances, large capacity washer and dryer, high-speed internet, smart TVs in every bedroom, and much more!
Weekly & Monthly Rates Available
Paradise Villa
(House 1)
8 guests • 4 bedrooms • 4.5 bathrooms
Discover a tranquil oasis where the beauty of nature seamlessly integrates with contemporary luxuries. Enter this luxurious residence that radiates a serene atmosphere, encouraging you to relax and refresh within its calm environment.
Seaside Sanctuary
(House 2)
8 guests • 4 bedrooms • 4.5 bathrooms
Experience the serenity of a blissful oasis where natural beauty harmoniously blends with modern comforts. Step into this opulent home that exudes an aura of tranquility, inviting you to unwind and rejuvenate amidst its peaceful ambiance.
Tropical Haven (House 3)
8 guests • 4 bedrooms • 4.5 bathrooms
Indulge in the enchanting hues of the sand and sea as you step into this sublimely decorated home, evoking the essence of a captivating tropical island escape. Allow yourself to be transported to a paradise of comfort and relaxation, where every detail has been carefully curated to create a truly immersive and unforgettable experience.
Coastal Retreat (House 4)
8 guests • 4 bedrooms • 4.5 bathrooms
Embodying the very essence of coastal charm, this captivating contemporary home stands as the quintessential gathering place for both family and friends. With its allure and modern design, this abode creates an inviting atmosphere that fosters shared moments and cherished connections.
What People Are Saying
Memorable family vacation
“Staying at a beautiful property, where all your needs are easily met, always makes for a sweet vacation. This home is the ideal place due to its location, the comfortable layout of the interior space, and because of the lovely outdoor pool and living areas. The host, Giovanna, is incredibly helpful and very responsive. The home is well stocked and extremely clean. We will be back!”
— Jeremy R., House 4 guest
(03/2024)
“Amazing home & great location, in the heart of Upper Matecumbe. Walking distance to a dozen + places for dinner, a mile to the Grouper. The place is spotless and very tastefully done. Giovanna was extremely responsive and helpful for anything we asked. Looking forward to our next trip to the Keys. Thanks for everything.”
— Luke, House 4 guest
(03/2024)
"We loved our time in Islamorada! We loved the house! It was exceptionally clean and organized. Giovanna was SO great to work with. Very prompt in replying and gave us great suggestions for places to see and do! We would stay here again in a heartbeat!"
— Heather B., Guest
Eat, Drink, Play and Explore
Indulge in the best Islamorada has to offer with local’s favorite restaurants and breweries. Spend the morning paddle boarding on the water and discover the native wildlife. Visit attractions and dive into the history of Islamorada.
EAT/DRINK: Morada Bay
PLAY: Beaches
Explore: Live Music at Lorelei
EAT: Chef Michael's
DRINK: Florida Keys Brewery
PLAY: Paddle board
PLAY: Fish
EXPLORE: History Museum of Diving
EAT: Bad Boy Burrito
Relax
PLAY: Boat Charter
EXPLORE: Native Wildlife
EAT: Square Grouper
PLAY: Swim
Explore: Old Gallery Road
Ride in Style:
Book a Golf Cart with Your Stay.
Move around like a local. Easily access the dozens of restaurants, local shops, cafes and mini markets all within 5 minutes from home.
Ask us for cart options, rates and availability.