Luxury rentals in Islamorada

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.

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.

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

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.

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

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.

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*

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*

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*

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.