Frequently asked questions

No — there are two separate locations. The Castaway II, High Tide Hideaway, Island Vibes Villa and Aqua Paradise are all at the Islamorada Resort, 87395 Old Highway, Islamorada, FL 33036, and share that resort’s pool, sunning beach, marina, gym and activities. The Original Castaway Bungalow is a stand-alone home at 76777 Overseas Highway, Islamorada, FL 33036, several miles away. It has its own private amenities and does not include access to the Islamorada Resort.

The four homes at the Islamorada Resort — The Castaway II, High Tide Hideaway, Island Vibes Villa and Aqua Paradise — are monthly rentals with a 28 to 30 day minimum depending on the home. The Original Castaway Bungalow, at its own separate address, has a three-night minimum.

They are built for it. Fully furnished homes, linens and kitchenware provided, in-home laundry, high-speed Wi-Fi and monthly minimums mean you arrive with a suitcase and nothing else. Many guests stay for a full winter season, and month-to-month arrangements are worth discussing.

Several of our homes are pet friendly, including The Castaway II and Island Vibes Villa. A pet deposit may apply. Tell us about your dog when you inquire and we will point you to the right home.

Utilities are included on select homes — Island Vibes Villa, for example, includes them in the monthly rate. Ask us for the specific home you are considering and we will give you the full picture before you commit.

At the Islamorada Resort, every home includes the pool, poolside cabanas, sunning beach with loungers, on-site gym, oceanside fire pits, complimentary daily kayak and stand-up paddleboard use, pool table, ping pong, foosball, corn hole, weekly live music, daily resort activities and an on-site food truck with bar service. The marina is available for a fee and guest fishing is permitted there. The Bungalow Resort is separate and has its own amenities: a private jacuzzi, tiki bar, fire pit, hammock, two kayaks, two paddleboards and a pool shared with only a few neighbouring bungalow homes.

There is an on-site marina with boat slips available for an additional charge, and dockage availability can be arranged for some homes. Because slips are limited, ask about availability at the same time you ask about the home.

Yes. High-speed Wi-Fi runs throughout, and The Castaway II includes a dedicated executive workstation with a monitor, which makes it a strong fit for remote work and extended business stays.

Islamorada sits roughly ninety minutes to two hours south of Miami International Airport along the Overseas Highway, and a comparable drive north of Key West. Key Largo is about thirty minutes north and Marathon about forty minutes south.

November through April is high season, with dry mild weather and the strongest demand for winter and seasonal rentals — book well ahead for those months. Summer and early autumn are quieter, warmer and better value, and excellent for fishing and diving.

Only at The Original Castaway Bungalow on Overseas Highway, which carries a three-night minimum and is our option for romantic getaways, fishing trips and long weekends. The four homes at the Islamorada Resort are monthly rentals.

Booking direct removes the platform’s guest service fee, puts you in direct contact with the owner rather than a support queue, and makes flexible arrangements possible — longer stays, unusual arrival dates, month-to-month extensions.

Call 305-240-1851 or email us with your dates and the home you have in mind. We will confirm availability, walk you through the rate and any fees, and hold your dates while you decide.