Anna Maria, FL

Sail Away

6 bedrooms 0 beds 7 baths 8 guests New

About the property

Sail Away by AMI Locals VR19-000048 Welcome to Sail Away, a spectacular six bedroom, six and a half bath canal-front luxury home in the heart of Anna Maria Island. With a private dock, a resort style pool with a swim up bar, and a rooftop deck showcasing stunning island views, this vacation rental is designed for unforgettable gatherings with family and friends. Just a short walk from the beautiful beaches of Anna Maria and Pine Avenue’s boutique shops and waterfront dining, Sail Away offers the perfect blend of relaxation and island adventure. Highlights • Canal front with private dock (fits up to 19ft boat) • 8-minute walk to Anna Maria beach • 6 Bedroom / 6.5 Bath • 5 King beds, 1 Twin-over-Twin bunk bed • Private pool with in-ground spa and swim-up bar • Rooftop deck with sweeping island views • Game room with pool, ping pong, and foosball tables • Elevator access • BBQ grill and outdoor shower • 4 Parking spaces The backyard is an island oasis with a sparkling pool featuring a sun shelf and swim up bar, a relaxing spa, and a sunken fire pit perfect for evening gatherings. Lounge in the Florida sunshine, fire up the BBQ grill for outdoor dining, or catch the big game on the outdoor bar’s mounted TV. Boaters will love the private dock, able to accommodate boats up to 19 ft, while the rooftop deck offers panoramic views of Anna Maria Island’s turquoise waters and vibrant sunsets. Inside, the open concept living room invites you to unwind with plush seating, a large TV, and an elegant electric fireplace. A decorative wine cellar adds a touch of sophistication, while the gourmet kitchen is equipped with a six burner stove, double ovens, premium appliances, and a massive island that makes group cooking a breeze. The dining area offers a spacious setup for group meals and additional seating at the bar for larger gatherings, providing flexible dining options for everyone. Upstairs, a second living space with a wine fridge, TV, and access to the rooftop deck provides an additional spot to relax and entertain. The third-floor primary suite is a showstopper, complete with balcony access, a spacious walk-in closet, and a spa-like ensuite bathroom featuring a soaking tub, walk-in shower, and double vanity. The second suite, also on the third floor, offers a king bed, balcony views, and a luxurious ensuite bathroom. Three more king bedrooms on the second floor each feature their own ensuite baths and balconies, while the bunk room is a nautical retreat with twin-over-twin beds and a shower/tub combo. Room Details • Primary Bedroom, 3rd floor: King bed, balcony, walk-in closet, ensuite bathroom with soaking tub and walk-in shower • Second Bedroom, 3rd floor: King bed, balcony, ensuite bathroom with walk-in shower • Third Bedroom, 2nd floor: King bed, balcony, ensuite bathroom with walk-in shower • Fourth Bedroom, 2nd floor: King bed, balcony, ensuite bathroom with walk-in shower • Fifth Bedroom, 2nd floor: King bed, ensuite bathroom with walk-in shower • Sixth Bedroom, 2nd floor: Twin-over-Twin bunk bed, ensuite bathroom with shower/tub combo For added convenience, Sail Away includes an elevator, washer and dryer, and a game room with a pool table, foosball, and ping pong. Beach days are a breeze with easy access to Anna Maria’s beach, and nearby Pine Avenue offers charming shops, restaurants, and ice cream stops to enjoy after a day in the sun. Sail Away is the ultimate island retreat for families, groups, or travelers seeking luxury, space, and fun. Reserve your stay today and start planning your perfect getaway! - No pets are allowed in this property. 4 cars maximum are able to park at this home. One of the garages is locked as owner’s storage. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. This home is managed by AMI Locals, an Anna Maria Island property management company. These premises are monitored by video surveillance in select exterior areas. 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.

Sail Away by AMI Locals VR19-000048 Welcome to Sail Away, a spectacular six bedroom, six and a half bath canal-front luxury home in the heart of Anna Maria Island. With a private dock, a resort style pool with a swim up bar, and a rooftop deck showcasing stunning island views, this vacation rental is designed for unforgettable gatherings with family and friends. Just a short walk from the beautiful beaches of Anna Maria and Pine Avenue’s boutique shops and waterfront dining, Sail Away offers the perfect blend of relaxation and island adventure. Highlights • Canal front with private dock (fits up to 19ft boat) • 8-minute walk to Anna Maria beach • 6 Bedroom / 6.5 Bath • 5 King beds, 1 Twin-over-Twin bunk bed • Private pool with in-ground spa and swim-up bar • Rooftop deck with sweeping island views • Game room with pool, ping pong, and foosball tables • Elevator access • BBQ grill and outdoor shower • 4 Parking spaces The backyard is an island oasis with a sparkling pool featuring a sun shelf and swim up bar, a relaxing spa, and a sunken fire pit perfect for evening gatherings. Lounge in the Florida sunshine, fire up the BBQ grill for outdoor dining, or catch the big game on the outdoor bar’s mounted TV. Boaters will love the private dock, able to accommodate boats up to 19 ft, while the rooftop deck offers panoramic views of Anna Maria Island’s turquoise waters and vibrant sunsets. Inside, the open concept living room invites you to unwind with plush seating, a large TV, and an elegant electric fireplace. A decorative wine cellar adds a touch of sophistication, while the gourmet kitchen is equipped with a six burner stove, double ovens, premium appliances, and a massive island that makes group cooking a breeze. The dining area offers a spacious setup for group meals and additional seating at the bar for larger gatherings, providing flexible dining options for everyone. Upstairs, a second living space with a wine fridge, TV, and access to the rooftop deck provides an additional spot to relax and entertain. The third-floor primary suite is a showstopper, complete with balcony access, a spacious walk-in closet, and a spa-like ensuite bathroom featuring a soaking tub, walk-in shower, and double vanity. The second suite, also on the third floor, offers a king bed, balcony views, and a luxurious ensuite bathroom. Three more king bedrooms on the second floor each feature their own ensuite baths and balconies, while the bunk room is a nautical retreat with twin-over-twin beds and a shower/tub combo. Room Details • Primary Bedroom, 3rd floor: King bed, balcony, walk-in closet, ensuite bathroom with soaking tub and walk-in shower • Second Bedroom, 3rd floor: King bed, balcony, ensuite bathroom with walk-in shower • Third Bedroom, 2nd floor: King bed, balcony, ensuite bathroom with walk-in shower • Fourth Bedroom, 2nd floor: King bed, balcony, ensuite bathroom with walk-in shower • Fifth Bedroom, 2nd floor: King bed, ensuite bathroom with walk-in shower • Sixth Bedroom, 2nd floor: Twin-over-Twin bunk bed, ensuite bathroom with shower/tub combo For added convenience, Sail Away includes an elevator, washer and dryer, and a game room with a pool table, foosball, and ping pong. Beach days are a breeze with easy access to Anna Maria’s beach, and nearby Pine Avenue offers charming shops, restaurants, and ice cream stops to enjoy after a day in the sun. Sail Away is the ultimate island retreat for families, groups, or travelers seeking luxury, space, and fun. Reserve your stay today and start planning your perfect getaway! - No pets are allowed in this property. 4 cars maximum are able to park at this home. One of the garages is locked as owner’s storage. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. This home is managed by AMI Locals, an Anna Maria Island property management company. These premises are monitored by video surveillance in select exterior areas. 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

For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
May 18, 2026$918.76Available3
May 19, 2026$881.68Available3
May 20, 2026$895.07Available3
May 21, 2026$939.36Available3
May 22, 2026$1,318.40Not Available3
May 23, 2026$1,588.26Not Available4
May 24, 2026$1,388.44Not Available4
May 25, 2026$1,172.14Available3
May 26, 2026$1,174.20Available3
May 27, 2026$1,169.05Available3
May 28, 2026$1,247.33Available3
May 29, 2026$1,505.86Available3
May 30, 2026$1,984.81Not Available5
May 31, 2026$1,640.79Not Available7
Jun 1, 2026$1,871.51Not Available7
Jun 2, 2026$1,881.81Not Available7
Jun 3, 2026$1,910.65Not Available7
Jun 4, 2026$1,981.72Not Available7
Jun 5, 2026$2,223.77Not Available7
Jun 6, 2026$2,006.44Available4
Jun 7, 2026$1,845.76Not Available4
Jun 8, 2026$1,796.32Not Available4
Jun 9, 2026$1,767.48Not Available4
Jun 10, 2026$1,790.14Not Available4
Jun 11, 2026$1,865.33Not Available4
Jun 12, 2026$2,049.70Not Available4
Jun 13, 2026$2,134.16Not Available7
Jun 14, 2026$1,917.86Not Available7
Jun 15, 2026$1,884.90Not Available7
Jun 16, 2026$1,946.70Not Available7
Jun 17, 2026$1,996.14Not Available7
Jun 18, 2026$2,028.07Not Available7
Jun 19, 2026$2,254.67Not Available7
Jun 20, 2026$2,323.68Not Available7
Jun 21, 2026$2,054.85Not Available7
Jun 22, 2026$2,114.59Not Available7
Jun 23, 2026$2,100.17Not Available7
Jun 24, 2026$2,102.23Not Available7
Jun 25, 2026$2,165.06Not Available7
Jun 26, 2026$2,366.94Not Available7
Jun 27, 2026$2,243.34Not Available7
Jun 28, 2026$2,535.86Not Available7
Jun 29, 2026$2,526.59Not Available7
Jun 30, 2026$2,535.86Not Available7
Jul 1, 2026$2,561.61Not Available7
Jul 2, 2026$2,658.43Not Available7
Jul 3, 2026$2,731.56Not Available7
Jul 4, 2026$2,505.99Not Available7
Jul 5, 2026$2,139.31Not Available7
Jul 6, 2026$2,389.60Not Available7
Jul 7, 2026$2,309.26Not Available7
Jul 8, 2026$2,306.17Not Available7
Jul 9, 2026$2,365.91Not Available7
Jul 10, 2026$2,635.77Not Available7
Jul 11, 2026$2,032.19Not Available7
Jul 12, 2026$1,902.41Available5
Jul 13, 2026$1,914.77Available5
Jul 14, 2026$1,908.59Available4
Jul 15, 2026$1,919.92Available4
Jul 16, 2026$1,915.80Available4
Jul 17, 2026$2,158.88Available4
Jul 18, 2026$1,813.83Not Available7
Jul 19, 2026$1,604.74Not Available7
Jul 20, 2026$1,629.46Not Available7
Jul 21, 2026$1,600.62Not Available7
Jul 22, 2026$1,637.70Not Available7
Jul 23, 2026$1,695.38Not Available7
Jul 24, 2026$1,878.72Not Available7
Jul 25, 2026$2,161.97Available5
Jul 26, 2026$1,917.86Not Available5
Jul 27, 2026$1,834.43Not Available5
Jul 28, 2026$1,857.09Not Available5
Jul 29, 2026$1,876.66Not Available5
Jul 30, 2026$1,916.83Not Available5
Jul 31, 2026$2,110.47Not Available5
Aug 1, 2026$2,304.11Available5
Aug 2, 2026$1,671.69Not Available5
Aug 3, 2026$1,671.69Not Available5
Aug 4, 2026$1,671.69Not Available5
Aug 5, 2026$1,671.69Not Available5
Aug 6, 2026$1,671.69Not Available5
Aug 7, 2026$1,727.31Not Available5
Aug 8, 2026$1,608.86Available5
Aug 9, 2026$1,532.64Not Available5
Aug 10, 2026$1,532.64Not Available5
Aug 11, 2026$1,532.64Not Available5
Aug 12, 2026$1,532.64Not Available5
Aug 13, 2026$1,532.64Not Available5
Aug 14, 2026$1,532.64Not Available5
Aug 15, 2026$1,328.70Available4
Aug 16, 2026$1,100.04Available4

Where you'll sleep

Amenities

Ocean view
Pool outdoor
Hot tub
Gym
Game Room
Fire pit
Fire place
BBQ Area

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Where you'll be

Anna Maria, FL, 34216, US

Things to know

Cancellation policy

Property rules

Children welcome (2–12 years).
Infants welcome (under 2).
No pets allowed.
No parties or events.

Safety & security

Check-in after 4:00 PM.
Check-out before 10:00 AM.
Maximum 8 guests.