Anna Maria Island, Florida
Gulf Living, Elevated
Six bedrooms. Six private bathrooms. A heated pool and 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.
From the street, you see a couple of houses on either side, the island neighborhood you'd expect. But the moment you step through the back of the house, everything changes. The pool, the palms, the privacy. It is 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.
"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 to 82 degrees year-round. 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.
A 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.
The 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. This is the moment where the trip becomes something people talk about for years.
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.
Beach Supplies
Quality beach chairs, wagons, cooler bags, towels, and reef-safe sunscreen. All staged and ready to grab. Walk to the beach with everything your group needs.
The 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're 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 walk
Breakfast and coffee. The line is worth it.
The Sandbar
5-minute walk
Waterfront dining. Sunset views. Fresh seafood.
Bean Point Beach
8-minute walk
The quieter end of the island. Shells and solitude.
Pine Avenue
At your doorstep
Boutiques, 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
35 verified reviews across all platforms
"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 didn't 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've 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
Yes. Pool and spa both heated year-round, no extra charge. In-water sun shelf loungers let you relax in the shallow end without leaving the water.
Bean Point Beach is about an 8-minute walk. Beach supplies including chairs, wagons, cooler bags, towels, and reef-safe sunscreen 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 smart lock. You'll 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 pool, and Pine Avenue at the end of the driveway. The Oar House is where families come together and nobody has to manage a thing.