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Traveler's Palm - Studio Near Duval Street

Get ready to dive into the vibrant energy of Key West at Traveler's Palm! This recently updated, spacious second story studio puts you right in the heart of Old Town, just one block from the legendary Duval Street. Perfect for couples or friends seeking adventure and unforgettable experiences, this studio is your gateway to the best of the island. Explore iconic attractions like Fort Zachary Taylor Beach and Park, the Ernest Hemingway Home and Museum, and charming local shops. As night falls, s

Luna Light ~ Waterfront ~ Pool ~ Dock ~ Views!

Bring your family to the stylish 4BR 4.5Bath home in a tranquil waterfront area, and enjoy an unforgettable stay with your loved ones. Explore nearby attractions from this prime location, or spend the day soaking up the sun by the pool, fishing from the dock, savoring tasty BBQs, and much more! ✔ 4 Comfortable BRs ✔ Open Design Living ✔ Full Kitchen ✔ Outdoors (Heated Pool, Lounges, Dining, Games) ✔ Dock ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking (4 Cars + Trailer) ✔ Ev Charger See more bel

Rose Key Cottage - Private Pool & Near Duval

Escape to paradise with this luxurious Key West retreat, perfect for families and groups looking to unwind in style. Nestled in a serene neighborhood, this home boasts two bedrooms, a loft bedroom, and not one, but two fully-equipped kitchens, ensuring plenty of room for everyone to relax and enjoy. Just steps from Duval enjoy downtown Key West or hang back and relax by the private pool. Experience a slice of paradise at this charming historic retreat in Key West, ideal for families and groups s

The Sanchez House Room #2

There is no better welcome to Key West than staying in local and famous folk artist Mario Sanchez's birth home. This home was built in the 1860's in the heart of the historic Gato and Merrero cigar factory villages. Featuring original Dade County pine construction, and located right on historic Duval Street, the Sanchez House is guaranteed to offer the historic atmosphere and living a part of Key West many visitors want to experience. Sit on the balcony and enjoy the trade winds & Ocean Breeze.

The Sanchez House Room #1

There is no better welcome to Key West than staying in local and famous folk artist Mario Sanchez's birth home. This home was built in the 1860's in the heart of the historic Gato and Merrero cigar factory villages. Featuring original Dade County pine construction, and located right on historic Duval Street, the Sanchez House is guaranteed to offer the historic atmosphere and living a part of Key West many visitors want to experience. Sit on the balcony and enjoy the trade winds & Ocean Breeze.

Mermaid Manor ~ Waterfront Haven w/ Hot Tub & Dock

Discover waterfront luxury at Mermaid Manor, a stunning 4BR retreat in Marathon. Built in 2019, this elevated home features power-adjustable Tempur-Pedic beds, 6-person LED-lit spa, and a new 50ft dock with deep water access. Enjoy the outdoor kitchen, cantina bar, paddleboards, and multiple entertainment areas. Perfect for boating enthusiasts with quick access to both Atlantic and Gulf waters. Modern amenities include 500Mbps WiFi, smart TVs, and gourmet kitchen with specialty cookware.

Coconut Palm - Steps from Duval with Private Pool

Step into the heart of Key West at Coconut Palm! Just one block from Duval Street, this tropical gem features a private pool and offers unbeatable value with easy access to top attractions like Fort Zachary Taylor Beach, the Ernest Hemingway Home, and local shops. With Duval’s bars, restaurants, and nightlife just around the corner, Coconut Palm is perfect for couples or friends seeking adventure, relaxation, and unforgettable experiences in the vibrant spirit of Key West!"

Easy Breezy Family Complex 5BR 3BTH 100ft Dock, Po

This stunning 5-bedroom waterfront home in Marathon, Florida, offers the perfect getaway with a private pool, dock, and breathtaking ocean views. Located near Sombrero Beach, it features spacious living areas, a fully equipped kitchen, and modern amenities for a comfortable stay. Ideal for families and groups, enjoy fishing, boating, and the best of the Florida Keys. Close to top attractions, restaurants, and shopping, this vacation rental is a paradise retreat.

Villa Serenity At Sombrero Private Pool Spa Dock

Relax and unwind at Serenity at Sombrero! This cozy canal front vacation home is perfect for a secluded and relaxing Florida Keys getaway! The three bedroom two bathroom, newer build stilt home comes fully apportioned with a 30' concrete dock with space for up to a 45' boat, optionally heated pool and spa, and large industrial sized ice machine! Centrally located and just minutes from Sombrero Beach and all major shopping and tourist attractions!

Azul Paradise ~ Waterfront ~ Games ~ Pool ~ Dock

Experience modern coastal luxury at Azul Paradise, a stunning 3BR 2BA waterfront haven in Marathon, FL with heated pool, game room, private dock, and chic beach design. ✔ 3 Elegant Bedrooms ✔ Chef Kitchen ✔ NEW! Game Room (Foosball, Air Hockey, Arcade, Dominoes) ✔ Heated Lap Pool ✔ Outdoor Entertainment (Turf, Cornhole) ✔ 50ft Private Dock & Fish Station ✔ Smart TVs ✔ High-Speed WiFi (500+ Mbps) ✔ Parking (4 Cars + Trailer)

Green Room at the Grand Maloney

The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red brick, historical home on Caroline Street has been lovingly restored with a brand-new heated dipping pool on its private patio. With undeniable character, the two-story house stands out from the traditional cottages of Key West in the same way the Grand Maloney stands out from other boutique hotels in the area.

Sunset Harbor ~ Waterfront ~ Dock ~ Cabana Club

Step into this 3BR 2Bath waterfront getaway in the tranquil area of Key Colony Beach! Escape the crowds and relax on the screened lanai or private dock with kayaks, then enjoy Cabana Club membership with private beach, heated/cooled pool, tiki bar & tennis. ✔ 3 Comfortable BRs (King Suite + 2 Queens + Air Mattress) ✔ Open Design Living with Harbor Views ✔ Full Kitchen & BBQ Patio ✔ Private Dock + Kayaks