House - Rating 5 (19)

Oar House


Bedroom 6 bedrooms
Bathroom 6 baths
Half Bathroom 1 half baths
Guests 8 guests
Pets Not Allowed Pets Not Allowed

  • Address: 421 Pine Ave
  • Location: Anna Maria
  • Type: House

Location Location

Description Description
Oar House by AMI Locals

Welcome to Oar House, a new 6-bedroom, 7-bath luxury home right on Pine Avenue on the north end of Anna Maria Island. It is made for easy group getaways, with a private heated pool, a large spa, and a rooftop deck with wide water views. You will also find plenty of fun, resort-style amenities. Step out the door to Pine Avenue cafes and boutiques, stroll to Bayfront Park, and reach the Gulf beaches in minutes for a relaxed Anna Maria Island vacation.

Highlights
-10-minute walk to Anna Maria Beach
-6 Bedrooms / 7 Bathrooms
-5 Kings, 1 Full-over-Full bunk and 1Queen sleeper sofa
-Private pool with in-ground spa and basketball hoop
-Rooftop deck with panoramic views
-Putting green
-Outdoor games (Tetris, ping pong, connect four, cornhole)
-Outdoor bar, covered dining and loungers
-BBQ grill
-Front and rear balconies
-4 Parking spots
-On Pine Avenue: walk to shops and restaurants.

Days drift easily between the sun-shelf pool (with in-water loungers and a basketball hoop) and the large spa under palm-framed skies. Perfect your short game on the private putting green, challenge the crew to ping pong, connect four, cornhole, or a round of giant outdoor Tetris. Then mix evening refreshments at the outdoor bar and grill dinner before gathering at the covered dining area. Head up to the rooftop deck for golden-hour views that sweep from the Bay toward the Gulf.

Soaring, lofted ceilings and high-end finishes define the open great room, styled in modern coastal hues with plush seating for movie nights. The chef’s kitchen features new stainless appliances, generous counter space for prepping, and all the culinary essentials for effortless group meals. With access to front and back balconies, enjoy views overlooking the pool and tropical landscaping.

All six bedrooms feature ensuite bathrooms, luxe bedding, TVs, and thoughtful storage. On the second floor, three king suites each include an ensuite with a walk-in shower. On the third floor, two additional king suites offer spa-like baths (one with a separate tub and shower). The sixth bedroom is a full-over-full bunk suite with a shower-tub combo, a favorite for kids. A seventh full bath adds convenience across the living spaces, and a loft provides a queen sleeper sofa for flexible lounge or overflow sleeping as permitted.

Room Details
-Primary Bedroom (2nd floor): King; ensuite with walk-in shower
-Second Bedroom (2nd floor): King; ensuite with walk-in shower
-Third Bedroom (2nd floor): King; ensuite with walk-in shower
-Fourth Bedroom (3rd floor): King; ensuite with walk-in shower
-Fifth Bedroom (3rd floor): King; ensuite with walk-in shower and separate tub
-Sixth Bedroom (3rd floor): Full-over-Full bunk; ensuite with shower-tub combo
-Loft (3rd floor): Queen sleeper sofa

Enjoy a quiet backyard finished with turf and lush landscaping, multiple balconies, and the convenience of Pine Avenue right outside your door for morning coffee, boutique shopping, and dinner reservations. Stroll to Bayfront Park for sunrise over the pier or make your way to nearby Gulf beach access for soft sands and emerald water. Explore the island car-free via the trolley, bikes, or on foot; easy island living for large group stays seeking luxury beach homes with private pools and spas.

With a rooftop deck of postcard-worthy views, a resort-style pool and spa, putting green, and a prime spot on Pine Avenue, Oar House by AMI Locals delivers the elevated, family-friendly island escape you have been searching for. Book your stay at Oar House today!

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This home is managed by AMI Locals, an Anna Maria Island property management company.

There are no pets allowed in this home.

4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.

This property has an active Ring doorbell at the main entrance.

We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our AMI Locals Rental Policies for full details.

Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

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Swipe Swipe for Availability

Bedding Bedding
User User
Bedroom 1
Sleeps: 2
1 King

Attached Bathroom

User User
Bedroom 2
Sleeps: 2
1 King

Attached Bathroom

User User
Bedroom 3
Sleeps: 2
1 King

Attached Bathroom

User User
Bedroom 4
Sleeps: 2
1 King

Attached Bathroom

User User
Bedroom 5
Sleeps: 2
1 King

Attached Bathroom

User User User User
Bedroom 6
Sleeps: 4
1 Full over Full Bunk Bed

Attached Bathroom


Amenities 82 Amenities
Essentials
  • Air Conditioning
  • Beach Chairs Provided
  • Beach Towels Included
  • Bed Linens
  • Dryer
  • Free Wifi
  • Hair Dryer
  • Heating
  • Hospital Close By
  • Hot Water
  • Iron and Ironing Board
  • Long Term Stays Allowed
  • No Pets Allowed
  • Pack 'n Play
  • Private Entrance
  • Required Stairs
  • Towels
  • Washer
  • Wifi
Exterior
  • Backyard
  • Balcony
  • BBQ Area
  • BBQ Grill
  • Covered Deck
  • Fenced Yard
  • Heated Pool
  • Hot Tub or Spa
  • Outdoor Dining Area
  • Outdoor Seating
  • Outdoor Shower
  • Outdoor TV
  • Patio
  • Private Pool
  • Rooftop Deck
  • Sun Loungers
Fun and Entertainment
  • Cornhole
  • Game Room
  • Games
  • Ping Pong Table
  • Putting Green
  • Smart TV
  • TV
  • TV with Cable
Home Safety
  • Active Ring Doorbell
  • Carbon Monoxide Detector
  • Contactless Check-In
  • Deadbolt Lock
  • Fire Extinguisher
  • Keyless Lock
  • Outdoor Lighting
  • Security Camera Present
  • Smoke Detector
Interior
  • Bathtub
  • Ceiling Fans
  • Clothes Hangers
  • Clothing Storage
  • Full Kitchen
  • Living Room
  • Second Fridge
Kitchen
  • Baking Sheet
  • BBQ Utensils
  • Coffee Maker
  • Dining table
  • Dishes and Utensils
  • Dishwasher
  • Freezer
  • Ice Maker
  • Kitchen Island
  • Microwave
  • Oven
  • Pots and Pans
  • Refrigerator
  • Stove
  • Toaster
  • Wine Glasses
Location
  • 10-minute walk to the beach
  • Anna Maria
  • Anna Maria Island
  • Beach Access Nearby
  • Residential Street
  • Walking Distance to Beach
Parking
  • Four (4) Parking Spaces

Reviews Rating 5 (19) Reviews
Rating 5
Fantastic stay from start to finish. AMI Locals and the owners truly went above and beyond to make our trip memorable, from seamless communication to thoughtful attention to detail throughout our stay. The house was absolutely pristine and even more impressive in person than the photos suggest—beautifully maintained, comfortable, and perfectly suited for a relaxing Anna Maria Island getaway. Everything exceeded our expectations, and we wouldn’t hesitate to book again or recommend it to others!! Thanks SO MUCH again
Gabriella - Posted: 12/22/2025
Rating 5
We had a phenomenal visit to the Oar House. The owners truly made my bachelorette trip so special. They kindly even sent us pizzas and left us a bottle of both red and white wine. They even got us branded sweatshirts! Everything was absolutely pristine. The house is gorgeous and was so incredibly organized and aesthetically pleasing. We had everything we could ever need and more. We couldn’t be happier with our stay at Oar House and highly recommend. AMI Locals Mgmt was extremely responsive and they even allowed late checkout. Close walking distance to restaurants, pizza, rentals, ice cream- you name it! Would definitely rent again. Thank you so much, Erin, for making my bachelorette the best trip we could have ever imagined. Everyone was so happy.
Mary-Kate - Posted: 10/12/2025
Hi, Mary, wow, what an incredible review, thank you so much for celebrating with AMI Locals at Oar House! We’re thrilled your bachelorette trip was everything you hoped for and that our team (especially Erin!) could help make it extra special. Sounds like you made the most of the island, from the pool to the nearby spots! We’d love to welcome you all back for another unforgettable island getaway soon.
AMI Locals staff
Rating 5
The Oar House is perfect in every way. It's a gorgeous house smack in the middle of paradise. The location is excellent with the beach, shops, restaurants, etc all just a short walk away. The house is huge, clean and inviting. It has such a laid-back, homey feel and tons of amenities. I felt so at home during my stay. It really is an excellent place to stay.
Anonymous - Posted: 9/17/2025
Rating 5
This home was amazing and exactly as listed. Would highly recommend!
virginia - Posted: 9/2/2025
We’re so glad you loved the home and that it was everything you expected, Virginia! Thanks for the recommendation and for choosing AMI Locals, we’d be happy to host you again anytime.
AMI Locals staff
Rating 5
We will definitely be back! Great location on Pine. Convenient to everything in downtown to walk to restaurants and the beach. Short drive to grocery store. House is absolutely amazing. Clean, fully loaded, gourmet kitchen. Pool and hot tub are outstanding for relaxing on a sunny day or rainy day! Excellent house for large family gathering!! Owners did great job with rooms and decor. They really care about the house and experience for the renters. Quiet and relaxing spot. Best vacation this summer!!!
Erin - Posted: 6/27/2025
Rating 5
Our group of 11 had a wonderful time at Oar House. The house provided plenty of space, with an amazing open kitchen and family room. We spent hours on the large deck outside the kitchen, playing card games, eating meals, and enjoying the shade. Each room has its own bathroom, which is so nice. The pool area offered the perfect secluded space to relax and enjoy time together as a family. The location can’t be beat. We rented bikes on day one and rarely needed to use our rental cars. We were to restaurants, Bean Point, and the beach within a couple of minutes. You could easily walk as well. We also can’t say enough about the owners. They reached out at the beginning of our stay to welcome us and were so friendly. They bought pizza for us one night and gifted our entire group with matching sweatshirts. We’ve stayed at a number of places along the Gulf and this was easily one of our favorites. One of our favorite rental houses anywhere. Honestly, it was sad to come home.
Mike - Posted: 5/16/2025
Rating 5
Excellent Rental for Family Vacations
The property was in an ideal location. Property was very clean and everything in working order. I highly recommend this property for a vacation rental. The owner of the property reached out to ensure we were enjoying our stay and if we had any concerns. She also provided us with departing gifts for the family. We had the perfect vacation at this property
Anthony - Posted: 4/28/2025
We are delighted to hear that you enjoyed your stay at our property and found it to be in an ideal location, clean, and well-maintained. We strive to provide our guests with a comfortable and pleasant experience, and we're glad that we were able to achieve that for you and your family. We truly appreciate your kind words and recommendation. It brings us great joy to know that you had the perfect vacation at our property. Thank you for taking the time to provide this wonderful review. We look forward to welcoming you back in the future.
AMI Locals staff
Rating 5
The property was in an ideal location. Property was very clean and everything in working order. I highly recommend this property for a vacation rental. The owner of the property reached out to ensure we were enjoying our stay and if we had any concerns. She also provided us with departing gifts for the family. We had the perfect vacation at this property
Anthony - Posted: 4/28/2025
Rating 5
Anonymous - Posted: 6/21/2024
Rating 5
Anonymous - Posted: 6/8/2024
Rating 5
Perfect location, beautiful house, they thought of everything. Would definitely stay again!
Jennifer - Posted: 6/8/2024
Our team takes pride in providing a beautiful house with all the amenities you need. Thank you for choosing to stay with us, Jennifer! 💐
AMI Locals staff
Rating 5
Anonymous - Posted: 5/21/2024
Rating 5
Perfect House
My second time at the property, and still perfect!
ziggypope70 - Posted: 5/21/2024
Thank you!! We are so glad you loved the property again and cannot wait to host you again !
AMI Locals staff
Rating 5
Anonymous - Posted: 4/6/2024
Rating 5
Just the best ever at the OAR HOUSE
Our family had the most wonderful time Everything was better than we expected and I thought because it was on pine Ave it may have been loud, we were pleasantly surprised on how private it was. The pool was so refreshing and the grandchildren wore themselves out. The property manager was very responsive the homeowner was so kind and generous. We loved it, my 3 year old grand daughter said it best “ Mimi, this is awesome Mary Anne
Mary anne D. - Posted: 4/6/2024
Rating 5
Amazing Island Getaway
We had an amazing experience renting from AMI locals. We stayed at the Oar house and the property couldn't have been better! The rental agency was great about communicating with us regarding what to expect from check in to checkout. The property was just perfect and was ideally located on Pine Ave in the heart of things. The home was beautifully appointed with all the amenities you would want for your beach vacation. I highly recommend renting from AMI locals and staying at the Oar house!
Tyson C. - Posted: 11/13/2023
Thank you for taking the time to share your wonderful experience with us, Tyson. We are glad you enjoyed the home, location, and communication with our team. You were terrific guests, and we hope to welcome you all back again soon!
AMI Locals staff
Rating 5
I can't say enough about how wonderful The Oar House was. The property was beautiful and clean. They had all the amenities needed and more. Everything was in working order. My family had a wonderful stay and can't wait to go back. The only small inconvenience was there is zero flexibility on check in/check out but we worked around it.
Shelly - Posted: 1/8/2023
Shelly, thank you for taking the time to share your experience with us. We are thrilled to hear you and your family enjoyed your stay. We look forward to hosting you again in the future!
AMI Locals staff
Rating 5
The Oar House is divine! You won’t be disappointed. The location is central to many shops, cafes and restaurants. Beds were super comfy and the house is stocked with everything you need for the beach. The outdoor space is amazing, but don’t forget your bug spray. Would stay here again in a heartbeat!
Jason - Posted: 9/5/2022
Jason, thank you for taking the time to share your experience with us. We are happy to hear you enjoyed your stay, and we hope to host you again soon!
AMI Locals staff
Rating 5
Amazing Holiday Weekend at the Oar House - AMI
We had a family group getting together on AMI for Memorial Day weekend. The Oar House was exactly as represented and just a beautiful property in a perfect location. The downstairs games and pool area was so much fun but in a tranquil setting at the same time. The Beach became optional for some! The bean bags, golf green, pool, spa and plenty of furniture to go with the TV and the ping pong table. Not to mention floats and other games for the pool. They also supply everything you need for an amazing day at the beach - chairs, towels and wagons. The rest of the house was just as stunning. The huge main room and gorgeous (and well applianced ) kitchen, 6 bedrooms all with TV's and private bathroom/showers. And don't forget the sunsets on the roof deck where you can see the Gulf and the Bay! Walking distance to the best pizza, ice cream, coffee, restaurants and donuts as well! This is THE place for an AMI gathering! We can't wait to go back to the Oar House!
Ted B. - Posted: 6/1/2022
Ted, thank you for your families recent vacay here at Oar House! Thrilled to hear you had a blast and that you got to enjoy the amenities of the home from the pool to the rooftop sunsets! Hope to have the pleasure of hosting your family again. We welcome you back anytime.
AMI Locals staff
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