Luxury rentals in Islamorada

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Top-rated luxury holiday rentals in Islamorada

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Luxe
A spacious outdoor area showcases a gleaming pool with separate hot tub, surrounded by elegant paver stones. Two covered lounge areas are present, featuring comfortable seating under shaded structures. Lush palm trees frame the scene, while a modern two-story home provides a stylish backdrop.
Home in Marathon
5 out of 5 average rating, 3 reviews

New Waterfront Luxe: Pool-Spa-Dock-Beach-Gulf View

The Gulfside Retreat is the perfect tropical luxury location to unwind in the sun, enjoy endless activities, and stay a while. This 4-bedroom, 5-bathroom 1.5 acre Gulf-front home offers the ideal private resort experience. Our home features an open layout with massive outdoor space and amazing Gulf views. You will have your own private beach, boat dockage, protected lagoon, and a long private pier to enjoy the gulf breezes. Plus, easy access to the oceanside in minutes by boat via the Vaca Cut.

Luxe
A private beach is framed by lush palm trees and vibrant foliage. The coastline is met by calm waters, with a seaplane visible in the distance. A blue surface can be seen in the foreground, suggesting recreational space, while serene skies add to the tranquil atmosphere.
Home in Islamorada

Private Beach, Pickleball Court and Tiki Bar

Hidden in the heart of Islamorada, this oceanfront villa offers an unmatched privilege of a secluded private beach—an experience few can claim. Expansive terraces stretch across both levels, framing ocean views. This haven's open design and spacious rooms blend seamlessly with serene surroundings. A lush tropical yard meets the oceanfront, where swaying palms and vibrant greenery create a private oasis, crafting a retreat as rare as it is extraordinary. Enhanced cleaning practices implemented.

Luxe
The balcony offers views of the Atlantic Ocean framed by swaying palm trees. Two wooden loungers are positioned on the tiled surface, accompanied by a small side table. Soft sunlight highlights the serene coastal scene.
Home in Islamorada

4 Bedroom Oceanfront Premium Villa – Capacity 8

Experience expansive living with breathtaking Atlantic Ocean views and blend into the natural surroundings with indoor-outdoor living. Each 3,100-square-foot Villa features three ensuite king-bed bedrooms, a twin room, a full kitchen, dining room, laundry room, and balconies. Additionally, the Villas offer a two-car garage. Please note Airbnb does not collect 5% tourism tax. This tourism tax will be charged on property at the time of check in with the credit card you provide when you arrive

Luxe
An aerial view captures the expansive tropical retreat surrounded by Florida Bay and lush mangroves. A heated pool and tiki bar are visible within the vibrant garden area, along with a dock extending towards the water, ideal for fishing or boating activities.
Home in Islamorada

Peninsula Villa | Boat Dock | Heated Pool | Sunset

This grand peninsula retreat, embraced by the Ocean and lush mangroves offering utmost privacy, has been designed for ultimate vacationing. Nestled along the tranquil shores of Florida Bay, its array of indoor & outdoor living and lounge areas, heated pool with a tiki bar, expansive sandy playgrounds, dock with ocean-access canal, gazebo boasting sunset views make this magical oasis ideal for serene escapes or vibrant family gatherings. Enhanced cleaning practices implemented.

Luxe
A serene fire pit area is set on sandy shores, surrounded by four wooden Adirondack chairs. The calm waters of the Atlantic reflect warm sunset hues, with distant palm trees visible along the shoreline.
Holiday home in Islamorada

4 Bedroom Oceanview Villa – Capacity 8

Enjoy abundant space with spectacular Atlantic Ocean views, and embrace the surrounding natural haven with indoor-outdoor living. At 3,100 SF each, the Villas include 3 in-suite king-bed bedrooms and 1 twin room, a full kitchen, dining room, laundry room, waterfront balconies, a 2-car garage. Please note Airbnb does not collect 5% tourism tax. This tourism tax will be charged on property at the time of check in with the credit card you provide when you arrive

Luxe
The outdoor area features a lagoon-style pool surrounded by lounge chairs and tropical landscaping. The two-story residence displays expansive windows reflecting evening light, while palm trees provide shade. An umbrella is positioned over the pool, and a relaxing atmosphere is enhanced by soft illumination from the house.
Flat in Islamorada

Maison Residences, 8 Bedroom oceanfront w Pool

Escape to a laid-back paradise at this 8-bedroom Islamorada residence, where two sprawling units are rented as one. The terrace boasts ocean views while soaring windows drench the interior in ribbons of natural light. Tropical palms sway in the balmy breeze as you stroll to the beach. Take a dip in the pool, try snorkeling through the coral reefs, or grab a bite to eat at a local restaurant. Copyright © Luxury Retreats. All rights reserved.

Luxe
A spacious living room features a light-colored sofa paired with a wooden armchair and a glass coffee table. Large sliding glass doors open to a balcony overlooking the Atlantic Ocean, framed by palm trees. Soft curtains enhance the natural light entering the room.
Home in Islamorada

4 Bedroom Oceanview Villa with Bunkbeds

Experience expansive living with breathtaking Atlantic Ocean views and blend into the natural surroundings with indoor-outdoor living. Each 3,100-square-foot Villa features three ensuite king-bed bedrooms, a bunk room, a full kitchen, dining room, laundry room, and balconies. Additionally, the Villas offer a two-car garage. *A 5% Monroe county tourism tax will be collected at check in, as Airbnb does not include this tax in there bookings*

Luxe
A bright living area features large glass doors leading to ocean views, with natural light illuminating the space. A comfortable sofa and an accent chair are arranged on a light-colored rug, while tropical plants add a touch of greenery.
Home in Islamorada

4 Bedroom Oceanfront Premium Villa – Capacity 10

Experience expansive living with breathtaking Atlantic Ocean views and blend into the natural surroundings with indoor-outdoor living. Each 3,100-square-foot Villa features three ensuite king-bed bedrooms, a bunk room, a full kitchen, dining room, laundry room, and balconies. Additionally, the Villas offer a two-car garage. *A 5% Monroe county tourism tax will be collected at check in, as Airbnb does not include this tax in there bookings*

Luxe
A spacious outdoor balcony features a wooden table surrounded by matching chairs, offering views of palm trees and the ocean beyond. Direct access to lush green lawns and paved pathways is visible, enhancing the inviting outdoor living space.
Villa in Islamorada
5 out of 5 average rating, 4 reviews

4 Bedroom Oceanfront Accessible Villa – Capacity 8

Enjoy abundant space with spectacular Atlantic Ocean views, and embrace the surrounding natural haven with indoor-outdoor living. At 3,100 SF each, the Villas include 3 in-suite king-bed bedrooms and 1 twin room, a full kitchen, dining room, laundry room, waterfront balconies, a 2-car garage and elevator. *A 5% Monroe county tourism tax will be collected at check in, as Airbnb does not include this tax in there bookings*

Luxe
A scenic pathway winds through lush green landscaping, leading to charming townhouses with colorful exteriors. Tall palm trees and flowering plants frame the walkways, while the bright blue sky creates a vibrant backdrop, enhancing the coastal atmosphere of the community.
Home in Islamorada

Casa Dos Hondos II

Escape to this laid-back, oceanfront townhouse in Angler’s Reef, where coastal vibes and easy living come together in the perfect Keys getaway. With three bedrooms, three baths, and plenty of charm, this spot is all about kicking back and enjoying the island life. Whether you’re here with family or friends, this laid-back spot in Angler’s Reef has all the comforts you need for a relaxing, sun-soaked escape.

Popular amenities for Islamorada luxury holiday rentals

Destinations to explore

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