Welcome to Islamorada, the enchanting gem of the Florida Keys, where the pace of life slows down, and the beauty of nature takes center stage. From its world-renowned fishing spots and vibrant coral reefs to its charming local culture, Islamorada offers a perfect blend of adventure and relaxation. To truly immerse yourself in this island paradise, choosing the right accommodation is key. Islamorada vacation rentals provide a variety of unique and inviting options, ensuring you find the perfect home away from home.

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The Top Islamorada Vacation Rentals

1. Last Resort Too – 6 Bedroom Vacation Rental
2. Villa Marlin – 3 Bedroom Vacation Rental
3. Oceanfront Estate – 5 Bedroom Vacation Rental
4. Waterfront 33 – 3 Bedroom Vacation Rental
5. Casa Rio – 1 Bedroom Vacation Rental
6. Canalfront Home in Gated Community – 5 Bedroom Vacation Rental
7. Atlantic Ocean Condo – 3 Bedroom Vacation Rental

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1. Last Resort Too- Islamorada, Florida

Welcome to Last Resort Too, a hidden gem on two prime oceanfront acres in Islamorada. This private retreat features a sandy beach and lush grounds shaded by coconut palms. The main home offers five bedrooms, including three king ensuites and a bunk room, plus a private master suite with ocean views. Enjoy open-concept living with an upscale kitchen and stunning vistas. A separate poolside guest cottage has a wrap-around porch. Relax by the pool just steps from the ocean, or explore with provided kayaks and bikes. Perfect for large families or friend getaways, this retreat blends luxury and adventure in paradise.

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2. Villa Marlin- Islamorada, Florida

Explore Villa Marlin in Islamorada, a boat-friendly vacation rental ideal for unforgettable family getaways. This three-bedroom, two-bath private home boasts a new 70-foot dock and easy access to both the bay and ocean. Enjoy exclusive amenities such as a private sandy beach, outdoor shower, hammocks, and a well-equipped kitchen with a BBQ. With complimentary access to kayaks, paddle boards, and fishing gear, every day brings new adventures on the water or exploring nearby attractions like downtown Islamorada and the Theater of the Sea. Perfect for families seeking comfort, convenience, and lasting memories in the heart of the Florida Keys.

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3. Oceanfront Estate – Islamorada, Florida

Escape to an unparalleled oceanfront estate nestled on 3.5 private acres in the heart of Islamorada. This remarkable retreat features a private boat basin with extensive deep water dockage, a boat ramp, and a fishing pier. Relax in the expansive saltwater pool and hot tub, or unwind in the third-floor master suite with an office, master bathroom, and private balcony offering breathtaking ocean views. With five large bedrooms, five baths, and multiple patios overlooking the Atlantic, this tropical oasis provides the ultimate luxury experience in the world-renowned fishing capital.

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4. Waterfront 33 – Islamorada, Florida

Experience the perfect family retreat at this spacious two-story bay-side waterfront home on Lower Matecumbe Key. Featuring 3 bedrooms and 3 baths, including a separate downstairs suite, it offers ample space and comfort. The great room with an HD TV and panoramic views of Hurricane Creek is ideal for entertaining or relaxing. Step out onto the balcony overlooking the park and partial bay view, or head down to the 96-foot dock for fishing and boating. Located near Islamorada’s dining and shopping, and just minutes from ocean access via Channel 2 and 5, this home is your gateway to a memorable Florida Keys getaway.

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5. Casa Rio – Islamorada, Florida

Immerse yourself in island bliss at Casa Rio, a secluded waterfront apartment in Islamorada. Nestled on a half-acre with a private dock and Tiki hut, this master suite offers panoramic views of a serene lagoon. Enjoy easy access to the Florida Bay and Atlantic Ocean, just minutes away via Channel 2 and 5 bridges. Fully furnished with a king-sized bed, kitchenette, and amenities like a kayak and bicycles, Casa Rio invites you to unwind and explore the vibrant marine life and dining delights of Islamorada, the ‘Sportfishing Capital of the World’.

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6. Canalfront Home in Gated Community – Islamorada, Florida

This spacious home offers the perfect blend of comfort and convenience, with ample space for dining and entertaining overlooking the tranquil canal. Enjoy the luxury of a master bedroom and bath on the upper level, complete with an additional seating area and TV. Relax on the wrap-around porches on both levels to soak in views of the waterway. Walk to fantastic restaurants and grocery stores, or enjoy community amenities like the pool, beach, and tennis courts at the nearby gated park. With dock space for up to a 40-foot boat, plus kayaks and bikes for exploring, this home is ideal for families or groups of up to 12.

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7. Atlantic Ocean Condo – Islamorada, Florida

Coastal living at its finest in this 1800n sqft condo on the Atlantic Ocean. This single-level gem features an elevator, four parking stalls, and ample room for your boat trailer. Enjoy immediate access to the Atlantic and a quick boat ride to Florida Bay. The master suite boasts a jetted tub and walk-in shower, while the second bath is newly remodeled. The gorgeous kitchen is fully equipped, and Xfinity WiFi and cable keep you connected. Relax by the heated pool, use the walk-in freezer and fish cleaning station, or head across the street to the full-service marina with live bait and a boat launch.

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Whether you’re seeking luxury, charm, family-friendly accommodations, or a unique stay, Islamorada vacation rentals offer something for everyone. With its stunning natural beauty and inviting atmosphere, Islamorada is the perfect destination for your next getaway. Start planning your trip today and discover the best places to stay in this idyllic island paradise.

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