Live Like a Local: St. Augustine Historic Home for Rent

St. Augustine Historic Home For Rent

Imagine starting the day with a cup of coffee in a sweet backyard garden of a historic home rental, before heading out to explore St. Augustine. That is the draw of a stay at Pineapple Cove, a St. Augustine historic home rental!

Exquisitely and painstakingly renovated to preserve the historic home’s history, the owners have kept the vintage feel of the property. They’ve added pops of color along with whimsical touches throughout the home, creating a delightful historic home rental in the heart of St. Augustine.

Disclosure: Our team only recommends vacation rentals they’ve experienced firsthand. All opinions are their own. 

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light green st. augustine historic home for rent with a pink porch with white chairs
The lovely entrance to Pineapple Cove, a St. Augustine historic home for rent

An Ideal St. Augustine Home Rental Choice For Larger Groups Or Families

pink vintage toaster on counter
Vintage pops of color can be seen throughout the historic home rental
magical woman on wall

The two-unit St. Augustine historic home for rent sleeps 4 per unit, and if traveling with a large family, you can rent the entire home.

Even during the busy seasons, Pineapple Cove will feel like your own private retreat.


Unique, whimsical touches throughout gives a fun, and relaxed feel to the historic home rental. The outdoor shower is refreshing after a hot day on one of the area’s beaches.

Each unit in the historic home rental features a full kitchen, with fun pops of color. The upstairs offers a balcony with seating that overlooks the front yard. The street-level unit offers a back porch overlooking the garden area. There is a firepit with chairs available to both units.

The downstairs unit gives a true 1920s feel, with ornate chandeliers and gold accents. Take advantage of the cozy back porch overlooking the yard while you sip your morning coffee, or end the day with a delightful cocktail before bed. 

There is a kingsize bed in the master, and twin beds in the second bedroom. The shower offers good pressure and is a nice size. The unit has a spacious living room and a separate dining area. There is a flat-screen television as well.

The upstairs unit is the complete opposite, offering a relaxed modern beach feel. The large porch is wonderful for morning coffee!  The master features a king-size bed, and there is a queen bed in the second bedroom. The bathroom has a waterfall shower which is amazing! You’ll feel your stress and exhaustion melt away! A nice size living room with flat screen television and a bar with plenty of seating rounds out the home.

The backyard offers a firepit and a table to seat 10 and is lit with strings of Edison lightbulbs that bring a touch of magic to the area.

The front porch has two comfortable chairs, and offers a nice street and front yard view.

Backyard table fence in background topped with greenery

The Seasons of St. Augustine

St. Augustine is located in near the far northeastern corner of Florida, along the Atlantic Ocean. Because of its location, December, January, and February can be chilly, with highs in the 50s and 60s, and reaching into the 70s on sunny days.

Spring and fall are our favorite times of the year in St. Augustine, with temperatures in the 60s to 80s.

The summer is hot and humid, but in the historic downtown, you can feel a bit of the sea breezes.

What To Do In St. Augustine

From special events to music, golf, food tours, dining, fishing, beachcombing, boating, and shopping in the downtown historic district, there is no shortage of things to do on your St. Augustine vacation. Take a food tour of historic downtown St. Augustine or St. Augustine Beach, or take a sailing tour of St. Augustine for a different perspective.

The owners of live nearby, and give this St. Augustine historic home for rent our highest recommendation!

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