Resort Pool & Cabanas
Relax poolside with shaded cabanas and tropical surroundings.
Location one
The Islamorada Resort
87395 Old Highway, Islamorada, FL 33036
Home to four of our five rentals. Each is a complete single-family home inside a waterfront resort community whose pool, beach, marina, gym and activities are shared by every guest staying here. The Original Castaway Bungalow is not at this resort.
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.
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
Four homes at this address
Monthly rentals at the Islamorada Resort
Each is a complete, private single-family home — not a condominium — with a monthly minimum stay and full access to every resort amenity above.
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.
View this home →
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.
View this home →
04
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 →Guest reviews
Our Guests Say It Best
A little slice of heaven in the Florida Keys. The best way to describe a stay at Castaway Vacation Rentals isn’t through our words—it’s through the experiences of the guests who’ve made our homes part of their Islamorada memories.
Whether you’re escaping the winter, working remotely, planning a family vacation, or simply searching for a quieter pace of life, we’re honored to have welcomed guests from across the country. Here’s what they have to say.
★★★★★
“Our favorite Islamorada rental”
“We’ve stayed in Islamorada several times, and this was by far our favorite rental. You can tell it’s locally owned and genuinely cared for. The home was spotless, beautifully maintained, and communication was exceptional from the day we booked until checkout. We loved starting each morning with coffee on the beach and ending our evenings around the waterfront fire pits. We’re already looking at dates for next year.”
★★★★★
“A month that truly felt like home”
“We spent over a month here and truly felt at home. Having access to the resort pool, private beach, complimentary kayaks and paddleboards made every day feel like vacation. The owners were incredibly responsive and offered fantastic local recommendations that helped us discover places we never would have found on our own.”
★★★★★
“The location couldn’t have been better”
“The location couldn’t have been better. Everything we wanted to do in Islamorada was just minutes away, yet the property itself felt peaceful and secluded. Watching the sunset from the beach every evening became our favorite tradition.”
★★★★★
“Resort amenities made the difference”
“The resort amenities are what really separate this property from other vacation rentals. We used the pool almost daily, took the paddleboards out several times, and loved relaxing around the fire pits after dinner. It felt like having all the perks of a luxury resort while still enjoying the privacy of our own home.”
★★★★★
“Exceptionally clean and well managed”
“We’ve rented homes throughout the Florida Keys, and this was one of the cleanest and best-managed properties we’ve ever experienced. The owners clearly take pride in providing an exceptional guest experience, and it shows in every detail.”
★★★★★
“Perfect for an extended stay”
“Perfect for our extended stay. Reliable internet made working remotely easy, while the beach, marina, and beautiful grounds made it equally easy to disconnect once the workday was over. We couldn’t have asked for a better balance.”
★★★★★
“Even better than the photos”
“Everything looked exactly like the photos—if not better. Comfortable furnishings, thoughtful touches throughout the home, and a wonderful sense of peace the moment we arrived. We immediately felt like we belonged here.”
★★★★★
“Hospitality that felt personal”
“This wasn’t just another vacation rental—it felt like staying at a friend’s beautiful Keys home. The owners made us feel genuinely welcome, and every recommendation they gave us—from restaurants to fishing charters—was spot on.”
★★★★★
“Quiet mornings on the private beach”
“The private beach was our favorite place to spend the mornings, while afternoons were usually at the pool or exploring the water with the complimentary kayaks. We loved that we could enjoy resort-style amenities without ever feeling crowded.”
★★★★★
“We can’t wait to come back”
“We’ve already recommended Castaway Vacation Rentals to friends and family. Beautiful homes, outstanding hospitality, an unbeatable Islamorada location, and resort amenities that make every day feel special. We can’t wait to come back.”
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.
Reserve your stay
Your Islamorada escape begins here.
Contact Castaway Vacation Rentals of the Florida Keys directly for availability, rates and personalized assistance.