Location two

The Original Castaway Bungalow

76777 Overseas Highway, Islamorada, FL 33036

A stand-alone bungalow at its own address in Islamorada, several miles from the Islamorada Resort. Its jacuzzi, tiki bar, fire pit, kayaks and paddleboards belong to its guests alone. Three-night minimum.

Check availability 305-240-1851

The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 1 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 2 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 3 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 4 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 5 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 6 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 7 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 8 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 9 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 10 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 11 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 12 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 13 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 14 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 15 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 16 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 17 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 18 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 19 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 20 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 21 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 22 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 23 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 24 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 25 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 26 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 27 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 28 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 29 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 30 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 31 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 32 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 33 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 34 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 35 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 36 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 37 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 38 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 39 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 40 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 41 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 42 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 43 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 44 The Original Castaway Bungalow, a private Islamorada, Florida Keys rental – photo 45

VIP private tropical bungalow

Bungalow Resort · 76777 Overseas Highway2 Bedrooms1 BathSleeps 5Stand-Alone Bungalow3-Night Minimum

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 we offer. It is a stand-alone home at its own address in Islamorada, not part of the Islamorada Resort.

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
  • Two private kayaks and two paddleboards
  • Private two-person hammock
  • 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
  • Shared pool ten steps from the yard
Contact us for availability →

76777 Overseas Highway, Islamorada, FL 33036

Included with the bungalow — and only the bungalow

  • Private jacuzzi spa and deck
  • Private tiki bar two refrigerators, 55″ TV, countertop grill, bar sink, Bluetooth stereo
  • Private outdoor fire pit in a secluded tropical front garden
  • Private two-person hammock
  • Two kayaks reserved for the bungalow
  • Two stand-up paddleboards reserved for the bungalow
  • Wi-Fi
  • King master bedroom
  • Queen guest bedroom
  • Shared pool ten steps from the yard shared with only a select few bungalow homes

These amenities belong to the Bungalow Resort. The pool, beach, marina, gym and activities at the Islamorada Resort are not included with a bungalow stay.

Verified guest reviews

Our Guests Say It Best

A little slice of heaven in the Florida Keys—but don’t just take it from us. Here’s what guests have shared about their stays at The Original Castaway Bungalow.

★★★★★

“Perfect little bungalow”

“Perfect little two bedroom bungalow with everything you need. Pool and outdoor area were very nice. Host was wonderful and very accessible—even on a holiday weekend! Convenient location to great fishing and restaurants.”

Shirlene H. · May 2026 · Verified Vrbo review

★★★★★

“The private tiki area was amazing”

“We loved our time at the Tiki Bar House, and the entire experience was excellent! We will be referring our friends and family to stay when traveling to the Keys. This was private, well furnished inside and out. The private tiki area was amazing! Bar, grill, TV, fire pit, hammock, cards, chess and axe throwing, just to name a few. And the pool is 10 steps away. Rob is a fantastic host and very responsive.”

Ray D. · June 2026 · Verified Vrbo review

★★★★★

“Clean, comfortable and fun”

“We loved our stay! The house was clean and comfortable, and the tiki area was fun to hang out in.”

Carrie S. · March 2026 · Verified Vrbo review

★★★★★

“An unbelievably nice stay”

“Unbelievably nice and a great stay for our family of four. The pool and hot tub were great, and watching college football at the tiki bar was incredible. 10/10!”

Craig · December 2025 · Verified Vrbo review

★★★★★

“A fantastic host and great location”

“Rob is an amazing host! He checked in on us during our stay to make sure we were good. His communication is prompt and helpful. The property is just as described and the location is great. Our family of four had a great stay and would love to come back in the future.”

Todd C. · May 2026 · Verified Vrbo review

★★★★★

“We can’t wait to go back”

“Rob and Regina were wonderful hosts! Rob reached out to us and made sure we had everything we needed. We loved the quiet location, and all the fun amenities were perfect for us and kept our kids busy. We can’t wait to go back.”

K · October 2025 · Verified Vrbo review

★★★★★

“An amazing oasis”

“An amazing oasis. Wonderful tiki bar and pool, wonderful space and location. We enjoyed bike rides to Robbie’s! Great communication from the host and an amazing vacation for our family.”

Robert S. · April 2026 · Verified Vrbo review

★★★★★

“Cozy cottage with a wonderful outdoor space”

“Super welcoming and very helpful. We had a few minor issues with a TV not turning on and a door not closing, and Rob took care of it immediately. Such a cozy, cute cottage. Loved the outdoor space!”

Stephanie W. · February 2026 · Verified Vrbo review

★★★★★

“Perfect for a fishing trip”

“Perfect spot for a fishing trip. Thanks, Rob!”

Derek H. · April 2026 · Verified Vrbo review

★★★★★

“Outdoor paradise”

“With a tiki bar, hammock, pool access and hot tub, we spent most of our time enjoying the sunny weather. The place was super clean, very comfortable and a perfect March getaway for us. Captain Rob was attentive and offered top-notch local recommendations. Highly recommend!”

Mary O. · March 2025 · Verified Vrbo review

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