No platform service fees
Booking sites add a guest service fee to every reservation. Booking direct removes that layer entirely, so the rate you are quoted is the rate you pay.
Two resorts, two entirely different stays
Two Islamorada locations. Choose the one that fits.
Our rentals sit at two separate addresses in Islamorada, each with its own grounds and its own amenities. The Islamorada Resort holds four full single-family homes for monthly stays. The Islamorada Bungalow Resort is a private stand-alone bungalow several miles away, with a three-night minimum and amenities reserved for its guests alone.
Location one
The Islamorada Resort
87395 Old Highway, Islamorada, FL 33036
Three complete single-family homes inside a waterfront resort community. Guests share the pool, sunning beach, marina, gym, fire pits, kayaks, paddleboards, games, weekly live music and an on-site food truck. Monthly stays.
01
The Castaway II
Islamorada Resort · 87395 Old Highway2 Bedrooms2 Private BathsSleeps 628-Day MinimumStarting at $8,400–$12,000 Monthly
A newly built two-story ocean-view home built for a long, comfortable stay — with an elevator and mobility lift chair, a golf cart for the resort, a dedicated workstation and a 600-square-foot primary suite.
View this home →
02
High Tide Hideaway
Islamorada Resort · 87395 Old Highway2 Bedrooms2 Baths1,380 Sq. Ft.28-Day MinimumStarting at $5,650–$9,200 Monthly
A brand-new, exquisitely furnished two-story residence with a resort-view lanai, peek-a-boo ocean views and two beach cruisers waiting by the door.
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03
Island Vibes Villa
Islamorada Resort · 87395 Old Highway2 Bedrooms2 Baths1,400 Sq. Ft.Sleeps 630-Day Minimum$7,599 Monthly · Utilities Included
A brand-new ocean-view residence on a split floor plan, with a 650-square-foot king suite upstairs, its own coffee and wine bar, and utilities included in the monthly rate.
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05
Aqua Paradise
Islamorada Resort · 87395 Old Highway2 Bedrooms2 Baths1,400 Sq. Ft.30-Day Minimum$9,550 Monthly · Utilities Included
A bright ocean-view home with polished coastal interiors, a private outdoor fire pit and full access to the resort pool, beach, marina and waterfront amenities.
View this home →Location two
The Islamorada Bungalow Resort
76777 Overseas Highway, Islamorada, FL 33036
A different property at a different address, several miles from the resort above. Nothing is shared between them. The jacuzzi, tiki bar, fire pit, hammock, kayaks and paddleboards belong to the bungalow and its guests alone.
Why book with us
Book direct with the owners, not a platform
Every home here is owned and cared for by people who live and work in the Florida Keys. When you book direct you talk to them, not a call centre — and you keep the money that would otherwise disappear into booking-platform service fees.
You speak to the owner
Questions about dockage, the golf cart, whether your dog is welcome or which home suits a six-month stay get answered by the person who owns it.
Flexibility a platform cannot offer
Extended stays, arrival dates that fall outside a rigid calendar and month-to-month arrangements are all worth a conversation.
Local knowledge included
Where the fish are running, which marina to call, who to book a charter with, where to eat on a Tuesday in September. We live here.
Before you book
Frequently asked questions
Are all five rentals at the same place?
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.
What is the minimum stay?
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.
Are your rentals suitable for snowbirds and seasonal residents?
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.
Are pets allowed?
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.
Reserve your stay
Your Islamorada escape begins here.
Contact Castaway Vacation Rentals of the Florida Keys directly for availability, rates and personalized assistance.