Retro Resort Review: Postcard Inn Islamorada

I have a deep love for Old Florida motels. When I see breezeblocks or a neon sign, I squeal inside.  I moved to FL when I was 6, but before my family lived here we stayed at Midcentury “Mom ‘n’ Pop” motels.  I remember thinking how cool it was that they had HBO and I did not know what “Vacancy” was.  I loved playing shuffleboard, keeping score for my sister with chalk on the court. My favorite place for hide & seek was by the ice machine, the stray motel cats (aka cheap & cute pest control) often napped under there so I could pet them as my sister took forever to find me. She honestly probably wasn’t looking.

The Flamingo Motel on Clearwater Beach became a memory when it was knocked down to build a high-rise condo. Since then, I have been chasing that nostalgic Florida beach hotel and I finally found a place that hit me in the feels: The Postcard Inn Holiday Isle. This spot is so authentically Florida and a throwback to the great American beach vacation.

The Retro Resort Concept

Holiday Isle dates back to 1951 when it was a premier Midcentury resort in the Florida Keys. It made a mark on many hearts of many Florida Keys visitors. The new millennium threatened the family friendly resort and Holiday Isle was a target. An abomination of high rises was swarming the coasts of Florida worse than lovebug season. Holiday Isle was an optimal site for, yet another luxury condo-hotel. The property was scooped up for $100 million to make it a place for the elite.

After real estate bubble burst, the luxury condo market took a nosedive in shallow water. Starwood Capital swooped in to purchase Holiday Isle for a cool $11 million in 2009. The brand had a clear concept, the Postcard Inn, a throwback to the American family beach vacation.

The Postcard Inn [PCI] brand concept had already been tested in St. Pete Beach. The brand was born out of problem resolution when St. Pete Beach residents protested Starwood’s luxury high-rise project. Locals did not want to see the 1957 Travelodge knocked down and a slice of the Suncoast history destroyed. St. Pete residents feared this project would invade the beach’s Midcentury charm. Starwood partners brainstormed over a scrapbook of vintage Americana then decided to restore the motor lodge as a surf-inspired retro resort. It accommodated all types of St. Pete visitors and became a staycation favorite to Suncoast residents while serving as a local watering hole.

The Postcard Inn Holiday Isle opened in Islamorada in 2012 meeting similar success to the St. Pete location. It became a local gathering spot and a family friendly hotel for tourists. In 2017, Hurricane Irma slammed into the Florida Keys leaving destruction along Mile Marker 84. After 14 months of tactful renovation, Postcard Inn Holiday Isle reopened in November 2018 as “Postcard Perfect Again.” Today, this 3-star resort has affordable rates to accommodate all types of travelers, from couples to families, and even your four-legged children.

A Stamp on Florida’s History

Drawing in locals, film crews and Tikiphiles alike, the Tiki Bar at Holiday Isle is truly World Famous. It was established in 1969 as the Hapi Hula Hut. In 1972 the bartender “Tiki John” was challenged by his manager to make a cocktail from extra liquor behind the bar. He blended up a frozen concoction of dark rum, blackberry brandy, banana liqueur, grenadine syrup, orange juice and pineapple juice then topped it off with Bacardi 151. This was the birth of the Rum Runner and the beginning of hangovers starting with the words, “But I only had two!” In addition to the genesis of the infamous libation, the Tiki Bar was a primary filming location for the Netflix series, Bloodline.

Play like a Kid Again

When the concierge kept listing off the amenities at check-in, I exclaimed “Seriously! You need to advertise this more on your website. I had no idea how dope this place is!” They offer free rentals on kayaks, paddleboards, snorkel gear and bicycles. If you want to lay low, they have a lagoon style pool, private beach, and second pool on property. The resort has family friendly events, during our stay they had a Dive-In Movie (Moana, you’re welcome!) and Tarpon feeding from the marina docks. If you have a boat, tow it down and tie up at the boat slips available for guests. For an additional cost you can claim a beachside cabana, rent a boat, book a SCUBA excursion or fishing trip.

Shop and Dine Like an Adult

PCI has three shops on property and “The Last Starbucks for 80 miles,” traveling South. We rented fishing poles and got bait from Abel’s Tackle Box for some impromptu fishing at Pelican Cove. There are two boutiques, Island Trendz and Island Dreams that had coastal décor, luxury beachwear and amazing sea inspired costume jewelry.

Out of the four dining options on property, we ate at two. The first night we ate at the Raw Bar that opened November 2019. The views from the deck were incredible as we noshed on clams while watching pelicans dive for a sunset catch. I ordered the Islamorada Boil, a classic seafood boil with andouille, clams, shrimp, corn on the cob and a Caribbean lobster tail.

We also dined at Ciao Hound, where pasta meets the pooch as a dog themed Italian restaurant.  The Tuscan inspired menu incorporates Keys-sourced ingredients with a laid-back vibe. They embrace the “Ruff Life” with a pup porch complete with astroturf, a leash holder, dog bowls and beds for canine comfort. I recommend the Snapper Puttanesca, a fillet with marinara, olives capers and sweet peppers.

5 Paw Resort

I find often that “dog friendly” really just means dog tolerant. This is not the case at PCI, it is a bone-a-fide 5 paw resort.  They allow two dogs per guest room (up to 40 pounds) in exchange for a $100 non-refundable pet fee. The fee and restrictions do not apply to certified service and emotional support animals.

We brought Hazel Bay, our 2-year-old Pitbull mix with us for our getaway to Islamorada. They did notify us at check-in that our room would not be serviced, but they would fetch us fresh towels and toiletries at request. Room service was very proactive and asked us in the hallway if we needed anything. The hotel staff was enamored with Hazel, providing her treats and ice water.

To start planning your Postcard Perfect stay in Paradise, check out my Florida Map to find other things to do in Islamorada.

Also check out my. post on how to “Pack Perfect for Paradise” with Bunulu.

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