At the Islamorada Resort

The Castaway II

87395 Old Highway, Islamorada, FL 33036

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.

Check availability 305-240-1851

The Castaway II at the Islamorada Resort, Islamorada, Florida Keys Primary bedroom at The Castaway II, Islamorada, Florida Keys Bedroom dressing area at The Castaway II, Islamorada, Florida Keys Coffee and wet bar at The Castaway II, Islamorada, Florida Keys Coastal living room at The Castaway II, Islamorada, Florida Keys Blue sofa living area at The Castaway II, Islamorada, Florida Keys Main living room at The Castaway II, Islamorada, Florida Keys White kitchen at The Castaway II, Islamorada, Florida Keys Kitchen and barn door at The Castaway II, Islamorada, Florida Keys Bathroom at The Castaway II, Islamorada, Florida Keys Walk-in shower at The Castaway II, Islamorada, Florida Keys Resort pool and waterfront at The Castaway II, Islamorada, Florida Keys Oceanside fire pit at The Castaway II, Islamorada, Florida Keys The Castaway II vacation rental in Islamorada, Florida Keys – additional photo 1 The Castaway II vacation rental in Islamorada, Florida Keys – additional photo 2 The Castaway II vacation rental in Islamorada, Florida Keys – additional photo 3 The Castaway II vacation rental in Islamorada, Florida Keys – additional photo 4 The Castaway II vacation rental in Islamorada, Florida Keys – additional photo 5 The Castaway II vacation rental in Islamorada, Florida Keys – additional photo 6 The Castaway II vacation rental in Islamorada, Florida Keys – additional photo 7 Resort pool with poolside cabanas Sunning beach with loungers On-site marina with boat slips Oceanside fire pit at sunset Game pavilion with ping pong, foosball and a pool table On-site gym Resort store

Ocean-view executive residence

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 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.

  • Full ocean-view lanai
  • Exquisitely furnished
  • New high-end appliances
  • Elevator
  • Mobility lift chair
  • Golf cart for use within the resort
  • In-home washer and dryer
  • Two fishing poles with bridge net
  • Beach equipment
  • Yeti ice chest for your Keys road trips
  • Dedicated executive workspace with monitor
  • High-speed Wi-Fi for work and streaming
  • Pet-friendly accommodations
  • Dockage availability

At the Islamorada Resort — includes every resort amenity listed above.

Contact us for availability →

Location one

The Islamorada Resort

87395 Old Highway, Islamorada, FL 33036

Home to four of our five rentals — The Castaway II, High Tide Hideaway, Island Vibes Villa and Aqua Paradise. Each is a complete single-family home, not a condominium, set inside a waterfront resort community whose amenities are shared by every guest staying here. The Original Castaway Bungalow is not at this resort and has its own grounds and amenities.

01

Resort Pool & Cabanas

Relax poolside with shaded cabanas and tropical surroundings.

02

Private Sunning Beach

Unwind on loungers beside the water and soak in the Florida sunshine.

03

Kayaks & Paddleboards

Complimentary daily use makes exploring the water effortless.

04

On-Site Marina with Boat Slips

Convenient marina access with available boat slips for an additional charge.

05

Oceanside Fire Pits

Gather by the water for relaxed evenings under the stars.

06

Fitness & Recreation

Stay active with an on-site gym and a gaming lawn.

Included with every home at the Islamorada Resort

  • Pool
  • Poolside cabanas rentals available at the office
  • Marina fee for use
  • Guest fishing allowed in the marina
  • Sunning beach with loungers
  • On-site gym
  • Complimentary daily kayak use
  • Complimentary daily stand-up paddleboard use
  • Oceanside fire pits
  • Pool table
  • Ping pong
  • Foosball
  • Corn hole
  • Weekly live music
  • Daily resort activities
  • On-site food truck with bar service
See the residences →

Guest reviews

What guests say about The Castaway II

★★★★★

“The Castaway II made our extended stay incredibly easy. The elevator was a major convenience, and having the golf cart for getting around the resort made trips to the pool, beach and marina feel effortless.”

★★★★★

“This was one of the best homes we have found for working remotely in the Keys. The dedicated workstation, monitor and fast Wi-Fi made workdays comfortable, while the ocean-view lanai gave us the perfect place to disconnect afterward.”

★★★★★

“The 600-square-foot primary suite felt more like a private retreat than a bedroom. The home was beautifully furnished, spacious and thoughtfully designed for guests who are staying longer than a typical vacation.”

★★★★★

“The extra equipment made our stay feel especially thoughtful. We used the fishing poles, bridge net, beach gear and Yeti cooler constantly, and the golf cart quickly became something we wondered how we had ever vacationed without.”

★★★★★

“We loved that The Castaway II was pet friendly and offered the practical comforts of home along with full resort access. Between the ocean-view lanai, dockage options and easy mobility features, it suited our family perfectly.”

Check availability

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.

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.

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.

Call or email to check availability

Reserve your stay

Your Islamorada escape begins here.

Contact Castaway Vacation Rentals of the Florida Keys directly for availability, rates and personalized assistance.

Call to Book

305-240-1851

Email to Book