Anna Maria Island, Florida
Gulf Living,
Elevated
Six bedrooms. Six private bathrooms. A heated spa surrounded by palms. Pine Avenue at the end of the driveway. Park the car once.
The House
Built for the ones who bring everyone together
The Oar House sits at the center of Anna Maria Island, steps from Pine Avenue and everything that makes this island feel like home. Coffee in the morning. Oysters at sunset. Live music after dinner. All on foot.
Step through the back of the house and everything changes. The pool, the palms, the privacy. An oasis in the middle of everything, completely surrounded by tropical landscaping. No neighbors have line of sight into the pool, no street noise reaches the back. It is surprisingly, almost impossibly quiet.
Inside, soaring lofted ceilings and an open floor plan give your whole group room to breathe. The kitchen was designed to cook in, not just look at. Six bedrooms, each with its own private bathroom, so everyone gets their own retreat.
The Spaces
See yourself here
Wide-open interiors, a pool that stops you in your tracks, and a rooftop where the Gulf meets the bay at golden hour.
The Layout
How the house is laid out
The Oar House climbs over three floors and a rooftop. Living and gathering spaces below, bedrooms spread across two levels so every family gets its own floor, and a rooftop deck up top. Here is how it all fits together.
Main living and three king suites
Walk in to soaring lofted ceilings and an open floor plan. The kitchen, dining, and living spaces flow together, with three king suites and two decks on this level. This is where the group gathers.
Two king suites plus the bunk room
Up top, two more king suites and the full-over-full bunk room, with three full baths so nobody waits. A bonus area with a queen pull-out sofa adds flex space for a big crew.
The deck everyone talks about
The fourth-floor rooftop deck has a fire table and seating for six, with the Gulf on one side and the bay on the other. The best sunset seat on Pine Avenue.
"Built for the week your family talks about for years."
Six bedrooms. Six private bathrooms. Everyone gets their own retreat.
Five king suites with private en-suite baths. The primary opens to a private balcony. The sixth bedroom has full-over-full bunks for the kids.
Primary Suite
King bed, en-suite bath, private balcony
Second Suite
King bed, en-suite bath
Third Suite
King bed, en-suite bath
Fourth Suite
King bed, en-suite bath
Fifth Suite
King bed, en-suite bath
Bunk Room
Full-over-full bunks, en-suite bath
The Details
Everything that matters, handled
The pool is why they come. The kitchen is why they stay. The rooftop is what they talk about for years.
Pool and Spa
Heated spa available year-round with in-water sun shelf loungers, a separate spa, and poolside lounge chairs surrounded by tropical landscaping. Completely private, walled in by palms on every side.
Private, walled-in pool deckA Kitchen That Works
Not a kitchen for reheating leftovers. Full-size appliances, quality pans, a breakfast bar, and enough counter space to prep dinner for the whole crew. Open to the living room so whoever is cooking stays part of the conversation.
Coffee setup, oil, spices, and essentials stockedThe Rooftop
Gulf on one side, bay on the other, and the Sunshine Skyway Bridge changing colors in the distance. Adirondack chairs, a drink rail, and the best sunset seat on Pine Avenue. This is the photo everyone posts.
Two-horizon views: Gulf and Bay
Game Room
Ping pong, arcade games, and enough space to keep every age group occupied. Mentioned in 14 of 35 reviews. The reason parents finally get to sit by the pool in peace.
Arcade, ping pong, cornhole, basketball hoopBeach Supplies
Quality beach chairs, a wagon, cooler bags, and towels. All staged and ready to grab. Walk to the beach with everything your group needs.
Chairs, wagon, cooler, towels, all includedThe Neighborhood
Park the car once
The Oar House sits on Pine Avenue, the main street of Anna Maria Island. Turn left or right out the front door and you are in it. Coffee, restaurants, shops, ice cream, the beach. There is no reason to ever get in the car.
Ginny's & Jane E's
2-minute walkBreakfast and coffee. The line is worth it.
The Sandbar
5-minute walkWaterfront dining. Sunset views. Fresh seafood.
Bean Point Beach
8-minute walkThe quieter end of the island. Shells and solitude.
Pine Avenue
At your doorstepBoutiques, galleries, live music, ice cream. All on foot.
Location
Right in the heart of Pine Avenue
Beach to the west, canal to the east, restaurants and shops in every direction. This is the center of Anna Maria Island.
Reviews
"The house exceeded every expectation. The pool was the center of our trip, the kitchen was fully stocked, and Pine Avenue was right outside. We never moved the car."
"Immaculately clean. Every bedroom had its own bathroom, which made things so easy with multiple families. The rooftop deck at sunset was the highlight of the whole trip."
"The kids spent hours in the pool and game room. The adults finally got to relax. Beach supplies were already there, ready to grab. We did not need to bring or buy a thing."
"The personal touches made all the difference. Welcome note, wine on the counter, restaurant recommendations that were actually good. You could tell the hosts genuinely care."
"We have rented luxury homes all over Florida. This one is different. It feels like someone built it specifically for families who want to actually spend time together."
"Every detail was handled. The check-in was seamless, the mid-stay message asking if we needed anything was a nice touch, and checkout was simple. Professional from start to finish."
FAQ
Everything you want to know before you book
The spa is heated and available year-round, with controls accessible to guests. In-water sun shelf loungers let you relax in the shallow end without leaving the water. The pool stays comfortable for most of the Florida year.
Bean Point Beach is about an 8-minute walk. Beach supplies including chairs, a wagon, cooler bags, and towels are all provided and ready to grab.
Yes. All six bedrooms have private en-suite bathrooms. There is also a half bath for common areas.
Yes. Full-size appliances, sharp knives, quality pans, a breakfast bar, coffee setup, olive oil, spices, and essentials are all stocked and ready to use.
Pine Avenue is right outside the front door. Ginny's for breakfast, the Sandbar for sunset, live music on weekends. Park the car once and leave it.
Self check-in with a smart lock. You will receive a personalized welcome message with your door code, house layout, and local recommendations a few days before arrival.
The pool, game room with arcade and ping pong, cornhole, basketball hoop, and fully stocked beach supplies keep kids of all ages busy and happy.
Your family's week starts here
Six bedrooms, six private bathrooms, a heated spa, and Pine Avenue at the end of the driveway. The Oar House is where families come together and nobody has to manage a thing.