The Oar House on Anna Maria Island

10/29/2026

One of our favorite things about November on the island: sunset comes early enough to catch it before dinner.

With the clocks back, the sun goes down around 5:35 to 5:45 PM all month. Our pick is Bean Point at the north tip of the island. Grab a couple of beach chairs from the house, watch from the sand, then head back to Pine Avenue for dinner. There are no lifeguards at Bean Point and the currents there are strong, so it's a spot for watching, not swimming.

Dates at theoarhouseami.com

Erin and Greg

10/19/2026

More than just a house.

10/18/2026

Chelsea, thank you so much for such a wonderful and thoughtful review! It truly means the world to us knowing that The Oar House was such a special part of your families’ vacation. We love hearing about everyone enjoying all the things we felt would be important to have in a vacation home.

Your family picture on the beach is priceless. Definitely a framing moment! We absolutely loved it! Seeing everyone together in their Oar House hoodies put the biggest smiles on our faces. Those are the memories that make sharing our home so rewarding.

And for the record, we firmly believe you can NEVER have too many beach towels! Greg personally goes through an average of three towels every time he enjoys a little pool time, so we completely understand the importance of having a healthy supply! 😂

Be well and may you and yours family have safe and happy holidays!

08/28/2026

Imagine gathering by the pool/jacuzzi with your friends & family, making some amazing homemade pizzas- then heading up to the rooftop deck for drinks, and a warm fire, while gazing out at the ocean during sunset! Tag who’s coming with you on your next epic vacation!

08/01/2026

✨ Imagine this being your next getaway… 🌴☀️

Dolphins playing just offshore. 🐬
Sunsets that stop you in your tracks. 🌅
A private heated pool & jacuzzi waiting after a day at the beach. 💦
A charming walk down Pine Avenue filled with local boutiques, waterfront dining, ice cream, and island vibes. 🛍️🍹
Then ending the evening with homemade pizza fresh from your own outdoor pizza oven. 🍕❤️

This is what vacation memories are made of at The Oar House on Anna Maria Island.

👇 Tell us…
What’s the FIRST thing you’d do when you arrive?
🐬 Dolphin watching
🏖️ Hit the beach
💦 Jump in the pool
🍕 Fire up the pizza oven

Tag the person you’d bring, share this with someone who needs an island escape, and let us know your answer in the comments!

Ready to skip the booking fees and book direct for the best experience?
👉 https://theoarhouseami.com

07/27/2026

Can you picture yourself here? 💙

A quiet morning beneath the shade of tropical trees, gentle island breezes, and nothing on your schedule except making memories.

Whether you’re planning a romantic escape, a family vacation, or a much-needed reset, The Oar House is ready to welcome you.

✨ Now booking fall and winter stays!

06/25/2026

Two great windows just opened up this summer: the week of Aug 15-22, and Labor Day weekend (Sept 4-7)!

If you've stayed with us, you know the house. Six bedrooms, a private bath in each, heated pool, and rooftop sunsets right in the heart of Pine Ave.

New since you've been here: a pizza oven, a rooftop fire pit, and a top-to-bottom design refresh with luxury linens and towels.

Hope to see you on the island!

www.airbnb.com/h/theoarhouseami
https://www.vrbo.com/5352747
www.theoarhouseami.com

06/03/2026

🌴✨ Beach days, pool days, or both?

At The Oar House, you can have it all! ☀️

🏡 6 Bedrooms | 6.5 Bathrooms
🏊 Private pool, hot tub & putting green
🍕 Outdoor pizza oven
🛍️ Steps from the shops and restaurants of Pine Avenue
🌅 Minutes from some of Anna Maria Island’s best sunset views

👇 Who would you bring for the ultimate island getaway?

Tag them in the comments and start planning your escape! 🌴💙

05/23/2026

Big things are happening at The Oar House 👀

We’re excited to share that moving forward, we’ll officially be taking full ownership of the guest experience at The Oar House.

This next chapter is all about making the experience even better- more personal, more intentional, and focused on the little details that make a stay memorable!

Over the next few weeks, you’ll start to see:
✨ New updates and design touches throughout the home
✨ An even smoother guest experience from booking to checkout
✨ Direct booking now available through our new website with discounted rates!

What’s not changing? The laid-back coastal feel and the experience guests have come to love.

We’re incredibly excited for what’s ahead and can’t wait to share more soon!

Book direct here:
https://theoarhouseami.com

Erin & Greg

Luxury vacation rental on Pine Avenue, Anna Maria Island. Six bedrooms, six bathrooms, heated pool and spa, rooftop deck. Walk to beach, dining, and shops.

02/27/2026

HEARTFELT THANK YOU FROM
🌴The Oar House!🌴

We just wanted to take a moment to say THANK YOU to all the amazing families who stayed with us at The Oar House in 2025! Whether this was your first visit or your third year in a row, we are so grateful you chose to spend your Anna Maria Island memories with us.

Seeing your families enjoy the house and make beach memories means the world to us. We truly love sharing our little slice of paradise with you.

We can’t wait to host many of you again in 2026!

With Gratitude,
Erin & Greg