Anna Maria, FL

Sail Away

6 bedrooms6 beds6.5 baths8 guestsNew

About the property

Sail Away by AMI Locals
Vacation Rental License #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
Vacation Rental License #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.

DatePrice (USD, excl. fees and taxes)AvailabilityMin Stay (nights)
Jul 17, 2026$1,395.65Available3
Jul 18, 2026$1,701.56Not Available7
Jul 19, 2026$1,301.92Not Available7
Jul 20, 2026$1,263.81Not Available7
Jul 21, 2026$1,251.45Not Available7
Jul 22, 2026$1,347.24Not Available7
Jul 23, 2026$1,410.07Not Available7
Jul 24, 2026$1,766.45Not Available7
Jul 25, 2026$2,006.44Not Available4
Jul 26, 2026$1,653.15Not Available4
Jul 27, 2026$1,595.47Not Available4
Jul 28, 2026$1,617.10Not Available4
Jul 29, 2026$1,573.84Not Available4
Jul 30, 2026$1,623.28Not Available4
Jul 31, 2026$2,026.01Not Available4
Aug 1, 2026$1,727.31Available3
Aug 2, 2026$1,339Available3
Aug 3, 2026$1,287.50Available3
Aug 4, 2026$1,290.59Available3
Aug 5, 2026$1,251.45Available3
Aug 6, 2026$1,299.86Available3
Aug 7, 2026$1,658.30Not Available3
Aug 8, 2026$1,552.21Not Available3
Aug 9, 2026$1,159.78Not Available3
Aug 10, 2026$1,048.54Available3
Aug 11, 2026$979.53Available3
Aug 12, 2026$953.78Available3
Aug 13, 2026$973.35Available3
Aug 14, 2026$1,584.14Available3
Aug 15, 2026$1,445.09Available3
Aug 16, 2026$1,259.69Available3
Aug 17, 2026$1,210.25Available3
Aug 18, 2026$1,168.02Available3
Aug 19, 2026$1,182.44Available3
Aug 20, 2026$1,260.72Available3
Aug 21, 2026$1,191.71Not Available4
Aug 22, 2026$1,290.59Not Available4
Aug 23, 2026$1,071.20Not Available4
Aug 24, 2026$1,051.63Not Available4
Aug 25, 2026$1,048.54Not Available4
Aug 26, 2026$1,051.63Not Available4
Aug 27, 2026$1,024.85Not Available4
Aug 28, 2026$1,220.55Not Available4
Aug 29, 2026$1,198.92Not Available4
Aug 30, 2026$967.17Not Available4
Aug 31, 2026$968.20Not Available4
Sep 1, 2026$824Not Available4
Sep 2, 2026$824Not Available4
Sep 3, 2026$1,014.55Not Available4
Sep 4, 2026$1,362.69Not Available4
Sep 5, 2026$1,443.03Not Available4
Sep 6, 2026$1,286.47Not Available4
Sep 7, 2026$1,024.85Not Available4
Sep 8, 2026$965.11Available4
Sep 9, 2026$945.54Available4
Sep 10, 2026$972.32Available4
Sep 11, 2026$989.83Available4
Sep 12, 2026$1,031.03Available4
Sep 13, 2026$771.47Not Available4
Sep 14, 2026$724.09Not Available4
Sep 15, 2026$721Not Available4
Sep 16, 2026$747.78Not Available4
Sep 17, 2026$941.42Available4
Sep 18, 2026$1,049.57Available4
Sep 19, 2026$1,035.15Available4
Sep 20, 2026$806.49Available4
Sep 21, 2026$763.23Available4
Sep 22, 2026$761.17Available4
Sep 23, 2026$763.23Available4
Sep 24, 2026$880.65Available4
Sep 25, 2026$998.07Available4
Sep 26, 2026$998.07Available4
Sep 27, 2026$799.28Available4
Sep 28, 2026$748.81Available4
Sep 29, 2026$721Available4
Sep 30, 2026$736.45Available4
Oct 1, 2026$875.50Available4
Oct 2, 2026$1,080.47Available4
Oct 3, 2026$1,196.86Available4
Oct 4, 2026$1,204.07Available4
Oct 5, 2026$1,169.05Available4
Oct 6, 2026$1,133Available4
Oct 7, 2026$1,190.68Available4
Oct 8, 2026$1,162.87Not Available5
Oct 9, 2026$1,298.83Not Available5
Oct 10, 2026$1,375.05Not Available5
Oct 11, 2026$1,192.74Not Available5
Oct 12, 2026$1,502.77Not Available5
Oct 13, 2026$1,199.95Not Available5
Oct 14, 2026$1,199.95Not Available5
Oct 15, 2026$1,213.34Not Available5

Amenities

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

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Where you'll be

Anna Maria, FL, 34216, US

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

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.