Resort Pool & Cabanas
Relax poolside with shaded cabanas and tropical surroundings.
Two distinctive ways to stay
Choose the Islamorada experience that fits you best.
Select from full stand-alone single-family homes set within a resort-rich waterfront community—or discover our one-of-a-kind private luxury bungalow collection with a rare 3-night minimum for a more exclusive, highly private escape.
Luxury resort-style community living
Full single-family homes in the heart of Islamorada
Enjoy the privacy, space and comfort of an entire single-family home—not a condominium—within an amenity-rich waterfront resort-style community designed for long, unhurried days in the Keys.
Private Sunning Beach
Unwind on loungers beside the water and soak in the Florida sunshine.
Kayaks & Paddleboards
Complimentary daily use makes exploring the water effortless.
On-Site Marina with Boat Slips
Convenient marina access with available boat slips for an additional charge.
Oceanside Fire Pits
Gather by the water for relaxed evenings under the stars.
Fitness & Recreation
Stay active with an on-site gym and a gaming lawn.
The Islamorada Resort Collection
Choose your full-home tropical retreat
Both residences below are complete, private single-family homes with a 28-day minimum stay and access to the shared resort amenities featured above.
Ocean-view executive residence
The Castaway II
2 Bedrooms2 Private BathsSleeps 628-Day MinimumStarting at $8,400–$12,000 Monthly
A newly built, two-story ocean-view home created for an elevated extended stay. The residence is fully furnished, pet friendly and highlighted by a generous 600-square-foot primary suite.
Inside, coastal design meets practical luxury with a dedicated workstation, high-speed Wi-Fi, a king bedroom, queen bedroom and two queen sleeper sofas. A full kitchen, washer and dryer, air conditioning and thoughtful linens and housewares make settling in simple.
- Ocean views in a private resort setting
- Dedicated executive workspace with monitor
- High-speed Wi-Fi for work and streaming
- Pet-friendly accommodations
- Dockage availability
Refined resort residence
High Tide Hideaway
2 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 and peek-a-boo ocean views. High Tide Hideaway blends polished coastal interiors with the ease of a true home away from home.
The open living level features a large modern kitchen with high-end appliances, an island, coffee bar and dining space. Upstairs are two spacious bedrooms—one king and one queen—with ample closets, while the living room includes a queen sleeper sofa and a 75-inch smart television.
- Resort-view lanai with ocean glimpses
- Modern kitchen with premium appliances
- Large-screen smart TVs throughout
- Two bicycles included
- Washer and dryer in residence
VIP private tropical bungalow
The Original Castaway Bungalow
2 Bedrooms1 BathSleeps 5Stand-Alone Bungalow
A beautifully restored stand-alone Islamorada bungalow designed as a private luxury retreat with a rare 3-night minimum. Lush tropical landscaping, thoughtful coastal interiors and expansive private outdoor spaces make this the most exclusive retreat in the Castaway II collection.
Nearly every signature amenity is reserved exclusively for bungalow guests, including the private patio jacuzzi, private tiki bar and outdoor kitchen, private fire pit, private kayaks, paddleboards and bikes. A heated community pool is also located just steps away.
- Private patio jacuzzi and lounge deck
- Private tiki bar and outdoor kitchen
- Private fire pit and tropical garden
- Private kayaks and paddleboards
- Boat ramp 100 yards away for kayak and paddleboard access to the canal and a short paddle to the ocean flats
- Private bikes for exploring Islamorada
- Heated community pool steps away
Reserve your stay
Your Islamorada escape begins here.
Contact Castaway Vacation Rentals of the Florida Keys directly for availability, rates and personalized assistance.