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.

Oceanfront Mangrove Manor at SeaGlass Cove FL Keys

Mangrove Manor at SeaGlass Cove is a luxury oceanfront retreat in Marathon, Florida. This modern five-bedroom home features panoramic Atlantic views, refined coastal interiors, and seamless indoor-outdoor living. Sleeps twelve with a chef’s kitchen, ocean-view terrace, and access to resort-style amenities including a pool and pickleball courts. Located near marinas, dining, boating, fishing, and snorkeling, with concierge services for charters and private chefs. Perfect for relaxed Keys escapes.

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.

Oceanfront + Resort Perks | 4BR Villa (Sleeps 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

4 Bedroom Oceanfront Accessible Villa – Capacity 8

Spacious and fully accessible, this 3,100+ sq ft villa spans three stories with elevator access and ADA-compliant features. Three en-suite king bedrooms plus a twin room sleep up to eight. A full kitchen, dining room, and ground-floor loggia set a relaxed pace, while private balconies, laundry, and a two-car garage round out the experience. *A 5% Monroe county tourism tax will be collected at check in, as Airbnb does not include this tax in their bookings*

Oceanview 4BR Family Villa + Resort Perks | Bunks

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*

Oceanfront + Resort Perks | 4BR Villa with Bunks (

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*

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.

The Vaca House

This exquisite custom-designed home in exclusive Yacht Harbor Island is the perfect VIP retreat. Each of the five gorgeous bedrooms has a private bathroom, making it easy to relax and recharge. The outdoor living space is complete with a lavish cabana.