Anna Maria, FL

Oar House

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8 guests
6 bedrooms
7 bathrooms
3545 sqft

Oar House by AMI Locals

  • Fire place
  • Balcony
  • Bath linens
8 guests
6 bedrooms
7 bathrooms
3545 sqft

  • Flexible check-in & out

    Check-in after 4:00 PM • Check-out before 10:00 AM

  • Easy cancellation


About this property

Oar House by AMI Locals 421 Pine Ave, Anna Maria, FL 34216 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! - 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.

Oar House by AMI Locals 421 Pine Ave, Anna Maria, FL 34216 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! - 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.

Availability & Pricing

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
Feb 16, 2026$695Available3
Feb 17, 2026$695Available3
Feb 18, 2026$695Available3
Feb 19, 2026$695Available3
Feb 20, 2026$695Available3
Feb 21, 2026$695Available3
Feb 22, 2026$695Available3
Feb 23, 2026$695Available3
Feb 24, 2026$695Available3
Feb 25, 2026$695Not Available3
Feb 26, 2026$695Not Available3
Feb 27, 2026$695Not Available3
Feb 28, 2026$695Not Available3
Mar 1, 2026$695Available3
Mar 2, 2026$695Available3
Mar 3, 2026$695Available3
Mar 4, 2026$695Available3
Mar 5, 2026$695Available3
Mar 6, 2026$695Available3
Mar 7, 2026$695Not Available3
Mar 8, 2026$695Not Available3
Mar 9, 2026$695Not Available3
Mar 10, 2026$695Not Available3
Mar 11, 2026$695Not Available3
Mar 12, 2026$695Not Available3
Mar 13, 2026$695Not Available3
Mar 14, 2026$695Not Available3
Mar 15, 2026$695Not Available3
Mar 16, 2026$695Not Available3
Mar 17, 2026$695Not Available3
Mar 18, 2026$695Not Available3
Mar 19, 2026$695Not Available3
Mar 20, 2026$695Not Available3
Mar 21, 2026$695Not Available3
Mar 22, 2026$695Not Available3
Mar 23, 2026$695Not Available3
Mar 24, 2026$695Not Available3
Mar 25, 2026$695Not Available3
Mar 26, 2026$695Not Available3
Mar 27, 2026$695Not Available3
Mar 28, 2026$695Not Available3
Mar 29, 2026$695Not Available3
Mar 30, 2026$695Not Available3
Mar 31, 2026$695Not Available3
Apr 1, 2026$695Not Available3
Apr 2, 2026$695Not Available3
Apr 3, 2026$695Not Available3
Apr 4, 2026$695Not Available3
Apr 5, 2026$695Not Available3
Apr 6, 2026$695Not Available3
Apr 7, 2026$695Not Available3
Apr 8, 2026$695Not Available3
Apr 9, 2026$695Not Available3
Apr 10, 2026$695Not Available3
Apr 11, 2026$695Not Available3
Apr 12, 2026$695Not Available3
Apr 13, 2026$695Not Available3
Apr 14, 2026$695Not Available3
Apr 15, 2026$695Not Available3
Apr 16, 2026$695Not Available3
Apr 17, 2026$695Not Available3
Apr 18, 2026$695Not Available3
Apr 19, 2026$695Not Available3
Apr 20, 2026$695Not Available3
Apr 21, 2026$695Not Available3
Apr 22, 2026$695Not Available3
Apr 23, 2026$695Not Available3
Apr 24, 2026$695Not Available3
Apr 25, 2026$695Not Available3
Apr 26, 2026$695Not Available3
Apr 27, 2026$695Not Available3
Apr 28, 2026$695Not Available3
Apr 29, 2026$695Not Available3
Apr 30, 2026$695Not Available3
May 1, 2026$695Not Available3
May 2, 2026$695Available3
May 3, 2026$695Available3
May 4, 2026$695Available3
May 5, 2026$695Available3
May 6, 2026$695Available3
May 7, 2026$695Available3
May 8, 2026$695Available3
May 9, 2026$695Available3
May 10, 2026$695Available3
May 11, 2026$695Available3
May 12, 2026$695Available3
May 13, 2026$695Available3
May 14, 2026$695Available3
May 15, 2026$695Available3
May 16, 2026$695Not Available3
May 17, 2026$695Not Available3

Top notch amenities

GUEST FAVORITES

Fire place
Patio
Balcony
Bath linens
Bed linens
Body soap
Conditioner
Shampoo
Air conditioning

Where you'll sleep



Explore Anna Maria, FL


Things to know

Here are some things which you should know before booking Oar House

House rules

Check-in after 4:00 PM
Check-out before 10:00 AM
8 guests maximum
Pets not allowed
No smoking - fees will apply
Events not permitted
Commercial photography requires approval

Cancellation policy

This property follows Prime Vacations - Anna Maria’s standard cancellation policy.