Castaway Vacation Rentals Islamorada

10/14/2026

Our final property with January still open! Vellamar- Where the Ocean Meets the Sky. Available with a 28 night minimum.

Vellamar - Where the Ocean Meets the Sky Welcome to Vellamar, located behind a private and gated entry, this exclusive oceanfront sanctuary in the heart of Islamorada, where endless blue water, tropical beauty and effortless luxury come together. Newly built in 2025, this immaculate two-bedroom, two...

10/14/2026

https://islamorada-castawayvacationrentals.com/

Fully furnished monthly and seasonal rentals in Islamorada, Florida Keys. Three single-family homes at the Islamorada Resort plus a private bungalow wit.

10/13/2026

Our fall and winter season is now booked up through Apr 15th at the Castaway 2. Grab your diner months before it’s too late. We will include a free golf set for your stay and we have mobility enhancements for those that struggle with stairs.

Two story new built home exclusively decorated and furnished for the executive traveler. Elevator, mobility chair lift, golf cart included for use in the resort. Pet friendly with no pet fee. Ocean View with a 600 square foot master suite. Dedicated work station with monitor and ergonomic chair. Que...

09/09/2026

🌴 LIVE THE ISLAMORADA RESORT LIFE FOR AN ENTIRE MONTH! 🌴

Why settle for one week when a full month in one of our beautiful vacation homes can cost what many Islamorada resorts charge for just seven nights?

Choose from four luxuriously furnished vacation homes located inside a world-class waterfront resort in the Florida Keys. Each home offers the space, comfort and privacy you want—with incredible resort amenities just steps from your door:

🌊 Two heated and chilled swimming pools
🚤 Marina with 42 boat slips
🛶 Complimentary daily kayak and paddleboard use
🏋️ On-site fitness center
🎱 Pool tables and ping-pong
🎯 Outdoor lawn games
🔥 Waterside fire pits
🐾 Pet-friendly accommodations

Bring your boat, bring your pup and settle into the laid-back Islamorada lifestyle for a full month.

📩 Message Castaway Vacation Rentals today for availability, pricing and details on our four available homes!



The Following Following Following Love

09/09/2026

🌴 LIVE THE ISLAMORADA RESORT LIFE FOR AN ENTIRE MONTH! 🌴

Why settle for one week when a full month in one of our beautiful vacation homes can cost what many Islamorada resorts charge for just seven nights?

Choose from four luxuriously furnished vacation homes located inside a world-class waterfront resort in the Florida Keys. Each home offers the space, comfort and privacy you want—with incredible resort amenities just steps from your door:

🌊 Two heated and chilled swimming pools
🚤 Marina with 42 boat slips
🛶 Complimentary daily kayak and paddleboard use
🏋️ On-site fitness center
🎱 Pool tables and ping-pong
🎯 Outdoor lawn games
🔥 Waterside fire pits
🐾 Pet-friendly accommodations

Bring your boat, bring your pup and settle into the laid-back Islamorada lifestyle for a full month.

📩 Message Castaway Vacation Rentals today for availability, pricing and details on our four available homes!

PetFriendlyTravel BoatingLife FloridaKeysVacation

09/04/2026

Take $2000 off any 30 day or more booking between October 1, 2026 and January 20, 2027

08/26/2026

Welcome to the Aqua Paradise in Islamorada. This exquisitely furnished home enjoys all the same amenities as our others. Currently available Oct-Dec then February 14th through July. Available at ONE month minimum rental. This is truly a bring your suitcase and that’s it kinda home.

08/26/2026

Www.islamorada-castawayvacationrentals.com