Local Guide

SIESTA KEY
SARASOTA
BEYOND SARASOTA

Point of Rocks puts you steps from the sand — but there's a whole island (and a whole coast) worth exploring.

Here are our favorite spots, gathered over 20 years of calling this place home.

Our Idea of the Perfect Day

If you're looking to experience Siesta Key like a local, here's our idea of the perfect day.

Start your morning with a walk to Toasted Mango Café for breakfast. It's one of our favorite spots on the island and the perfect way to begin a relaxing day.

After breakfast, head to Siesta Beach and enjoy the powder-soft white sand and crystal-clear Gulf water. If you're feeling adventurous, make your way down to Point of Rocks for some of the best snorkeling on the island; you'll often spot tropical fish, other marine life, and shells.

When you're ready for lunch, grab a bike or take a leisurely walk over to Anna's Deli. On your way back, be sure to stop at Meaney's Mini Donuts. Their hot, made-to-order mini donuts are an island tradition and well worth the stop.

Spend the afternoon relaxing on the beach, taking a swim, or simply soaking up the Florida sunshine.

As the day winds down, find a spot on the sand to watch one of Siesta Key's unforgettable sunsets; there's truly nothing like it.

Finish your evening by dressing up for dinner at Ophelia's on the Bay, where waterfront views, incredible food, and a beautiful atmosphere make for the perfect end to a perfect day.

View from a wooden balcony overlooking a tropical beach with palm trees, sandy shore, and blue ocean under a partly cloudy sky.
View from inside a kitchen looking out to a backyard through an open window. The countertop has a blue kettle, a vase with red flowers, a cookbook, and kitchen utensils. The backyard features a wooden deck with two red chairs, green plants, trees, and a yellow house with a black garage door.
Covered outdoor porch with chairs, a sofa, potted plant, and views of trees and greenery outside.
Sign for Siesta Beach in Sarasota, Florida, highlighting it as the number one beach in the USA, with a background of sandy pathway, palm trees, and a clear blue sky.

Siesta Key

    • South Village (3 blocks) — A quieter side of Siesta Key with local coffee shops, restaurants, beach rentals, and easy access to Crescent Beach.

    • Siesta Beach — Consistently ranked one of the best beaches in the country for its powder-soft white quartz sand and crystal-clear water. Stick around for sunset — and if you're here on a Sunday, don't miss the famous Drum Circle.

    • Siesta Key Village (2.5 miles) — The heart of the island. Wander local boutiques, grab an ice cream, catch some live music, and spend the evening hopping between the island's best restaurants and bars.

    • Turtle Beach — A local favorite for shelling, kayaking, fishing, and quieter beach days — also one of the best spots to launch a paddleboard or kayak.

    • Boat & Jet Ski Rentals — Spend the day cruising Sarasota Bay, anchoring at the sandbars, or exploring hidden beaches.

    • Bike & Beach Rentals — Several shops in South Village rent bikes, e-bikes, and beach gear by the day or the week, and most will deliver right to the house. Worth doing at least once, since the island is flat and everything is close.

      Sunset E-Bike Ride — One of our favorite ways to see the island. Cruise around Siesta Key before stopping to watch an unforgettable Gulf Coast sunset.

    • Paddleboards & Kayaks — Explore the mangrove tunnels and calm waters surrounding the island.

    • Parasailing — See Siesta Key from hundreds of feet in the air. You won't regret the view.

    • Ophelia's on the Bay (fun fact: we got married here!)

    • Clayton's Siesta Grille

    • Siesta Key Oyster Bar (SKOB)

    • The Cottage

    • Summer House Steak & Seafood

    • Toasted Mango Café (breakfast favorite!)

    • Sun Garden Café

    • Plaza de México

    • Spearfish Grille

    • Star Thai & Sushi

    • Lenny's Pizza & Island Bar

    • Anna's Deli (perfect beach sandwiches)

    • Meaney's Mini Donuts

Getting Around Siesta

The free Siesta Key Trolley runs the length of the island with a stop near the house, roughly every twenty to thirty minutes. Between the trolley and a short walk, most guests park the car when they arrive and don't think about it again until checkout.

Skyline of modern high-rise buildings along a waterfront with boats, at sunset with colorful sky.

Sarasota

    • St. Armands Circle — A beautiful shopping district filled with boutiques, restaurants, ice cream shops, and outdoor cafés. Perfect for an afternoon or evening.

    • The Ringling Museum — Art, history, circus exhibits, beautiful gardens, and the famous Ca' d'Zan Mansion, all in one place.

    • Mote SEA Aquarium — A great family activity featuring sharks, sea turtles, manatees, otters, and interactive exhibits.

    • Marie Selby Botanical Gardens — A peaceful waterfront garden filled with orchids, tropical plants, and beautiful walking paths.

    • The Candle Pour — Create your own custom candle — a fun rainy-day activity or girls' outing.

    • Smugglers Cove Mini Golf — Mini golf with waterfalls, caves, and live alligators.

    • Columbia Restaurant (St. Armands Circle)

    • Owen's Fish Camp

    • Napulé Italian Restaurant

    • Lucky 8

    • Veronica Fish & Oyster

    • Morton's Gourmet Market (grab lunch, wine, or picnic supplies for the beach)

Entrance to a tropical-themed outdoor area with a thatched-roof structure, surrounded by palm trees and lush greenery, featuring signs that say 'Welcome to Pops Sunset Grill' and 'Enter' with an arrow.

Beyond Sarasota

    • Venice Beach & Sharky's on the Pier ★

    • Casey Key

    • Anna Maria Island ★

    • Longboat Key ★

    • Myakka River State Park

    • Myakka Elephant Ranch (book in advance)

    • Disney World ★

    • Universal Orlando Resort ★

    • Busch Gardens Tampa Bay

    ★ = Great day-trip destinations

    • Casey Key Fish House | Osprey

    • Sharky’s on the Pier | Venice

    • Whitney’s | Longboat Key

    • Pop’s Sunset Grill | Nokomis

A motorboat speeding through the ocean leaving a trail of white foam behind it on a sunny day with a blue sky and some clouds.

A Day on the Water
Aboard Liberty

We're thrilled to offer our guests an unforgettable day on the water aboard our private charter, Liberty.

Experience Sarasota the way it was meant to be enjoyed — by land and by sea.

Now offering:

  • Half-Day Charters

  • Full-Day Charters

  • Sunset Cruises

As a guest of The Original Beach House, you'll receive exclusive pricing and preferred booking.

Whether you're dolphin watching, cruising the sandbars, celebrating with friends, or simply taking in another Siesta Key sunset, Liberty is the perfect way to experience the Gulf.

This isn’t just a boat ride…
It’s a front-row seat to paradise.

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INFO + AVAILABILITY
A modern motorboat on the water with residential houses and palm trees in the background.
View of a yacht's deck with white cushioned seating area overlooking blue water and residential houses with palm trees on the shoreline under a clear blue sky.
A speedboat on the water with a city skyline in the background on a sunny day.
View of a yacht's deck with beige seating, black controls, and a city skyline across a body of water under a blue sky with clouds.

Guest Notes

  • Our stay at BEACH HOUSE was phenomenal! There was more than enough space for our girls trip of 6. The house has every convenience to make it feel like home. We loved it so much, we barely left the property the entire weekend! With the beach just outside the back door, we were able to easily enjoy all hours of the renowned Siesta Key beach. There were shells to collect, walks to take, even to Siesta Key Village. My favorite part was the breathtaking sunsets. I can't wait to book our next trip to the beach house!

    Karla | TX

  • We stayed here for my birthday and it was honestly the perfect trip. Waking up steps from the beach, walking down to The Toasted Mango for coffee every morning, then spending the afternoons collecting shells and snorkeling. The public beach nearby was packed, but since the house has its own beach access, we basically had our own stretch to ourselves the whole time. We’d sit out on the balcony, play cards, and watch the sunset over the water every night, and we’re already talking about coming back.

    Larry | TN

  • We had such a special stay at The Original Beach House! The house is full of charm and character, and the hosts were incredibly responsive whenever we had a question. The layout was perfect for our family. My husband and I stayed downstairs because of his mobility issues, our niece and her baby stayed upstairs, and my sister enjoyed the guest house. Having the private beachfront lawn was such a blessing, it gave my husband a peaceful place to wheel out, enjoy the sunshine, and take in the beach without the crowds. The welcome gift baskets were such a thoughtful touch and made us feel right at home. We made wonderful memories here.

    Kathy | CA

  • We had the most wonderful stay for our family reunion. It was the perfect place for everyone to gather while still having plenty of room to spread out. The location couldn't have been better, and we loved spending our days on the beach and our evenings together watching the sunset. Even though we live in Sarasota, staying here felt like a true getaway. There's something so special about this home; it has so much character and warmth. We made memories we'll cherish for years to come and are already looking forward to our next stay. Highly recommend for families or anyone looking for a one-of-a-kind Siesta Key experience!

    Dani | FL

  • We spent the Fourth of July at The Original Beach House with our entire extended family, and it couldn't have been a better place to celebrate. One of the best parts was not having to deal with the holiday traffic coming on and off Siesta Key; we parked the car and walked everywhere. We loved being able to walk to Captain Curt's and the Crescent Club.

    Sam | FL

Room to Gather,
Room to Disappear

Five bedrooms across the main house and guest cottage sleep up to twelve, with a primary suite balcony that looks straight out at the Gulf.

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