The Oar House on Anna Maria Island

08/28/2026

Imagine gathering by the pool/whirlpool bath 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 & whirlpool bath 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

09/24/2025

We can't believe that it has been a year, actually a year ago today that Hurricane Helen formed! Ashly and her family had to be evacuated from the house and island. Unfortunately, their vacation was cut short. We are grateful that they wanted to give it another try. They were brave enough to come during the same week as last year! Thankfully no hurricanes this year.

Hurricane Helene

Helene at peak intensity just prior to landfall in the Big Bend region of Florida on September 26

Meteorological history
Formed - September 24, 2024
Extratropical - September 27, 2024
Dissipated - September 29, 2024
Category 4 major hurricane
1-minute sustained (SSHWS/NWS)
Highest winds 140 mph (220 km/h)
Lowest pressure 939 mbar (hPa); 27.73 inHg

11/26/2024

𝐇𝐀𝐏𝐏𝐘 𝐓𝐇𝐀𝐍𝐊𝐒𝐆𝐈𝐕𝐈𝐍𝐆 𝐅𝐑𝐎𝐌 🌴 𝐓𝐡𝐞 𝐎𝐚𝐫 𝐇𝐨𝐮𝐬𝐞 🌴!

This Thanksgiving, we want to take a moment to thank all of our wonderful renters. Your 𝙠𝙞𝙣𝙙 𝙨𝙪𝙥𝙥𝙤𝙧𝙩 𝙖𝙣𝙙 𝙩𝙝𝙚 𝙘𝙝𝙚𝙧𝙞𝙨𝙝𝙚𝙙 𝙢𝙤𝙢𝙚𝙣𝙩𝙨 you’ve shared with us mean the world. Seeing your families’ happy faces enjoying time at our beach rental brings us so much joy—it’s what makes The Oar House so special.

We’re 𝙞𝙣𝙘𝙧𝙚𝙙𝙞𝙗𝙡𝙮 𝙩𝙝𝙖𝙣𝙠𝙛𝙪𝙡 for you and wish you a warm, wonderful holiday season filled with love, laughter, and cherished memories. Here's to many more happy moments to come!

𝐖𝐢𝐭𝐡 𝐆𝐫𝐚𝐭𝐢𝐭𝐮𝐝𝐞, 𝐄𝐫𝐢𝐧 & 𝐆𝐫𝐞𝐠