Anna Maria, FL
Sail Away
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.
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.
| Date | Price (USD, excl. fees and taxes) | Availability | Min Stay (nights) |
|---|---|---|---|
| Jul 17, 2026 | $1,395.65 | Available | 3 |
| Jul 18, 2026 | $1,701.56 | Not Available | 7 |
| Jul 19, 2026 | $1,301.92 | Not Available | 7 |
| Jul 20, 2026 | $1,263.81 | Not Available | 7 |
| Jul 21, 2026 | $1,251.45 | Not Available | 7 |
| Jul 22, 2026 | $1,347.24 | Not Available | 7 |
| Jul 23, 2026 | $1,410.07 | Not Available | 7 |
| Jul 24, 2026 | $1,766.45 | Not Available | 7 |
| Jul 25, 2026 | $2,006.44 | Not Available | 4 |
| Jul 26, 2026 | $1,653.15 | Not Available | 4 |
| Jul 27, 2026 | $1,595.47 | Not Available | 4 |
| Jul 28, 2026 | $1,617.10 | Not Available | 4 |
| Jul 29, 2026 | $1,573.84 | Not Available | 4 |
| Jul 30, 2026 | $1,623.28 | Not Available | 4 |
| Jul 31, 2026 | $2,026.01 | Not Available | 4 |
| Aug 1, 2026 | $1,727.31 | Available | 3 |
| Aug 2, 2026 | $1,339 | Available | 3 |
| Aug 3, 2026 | $1,287.50 | Available | 3 |
| Aug 4, 2026 | $1,290.59 | Available | 3 |
| Aug 5, 2026 | $1,251.45 | Available | 3 |
| Aug 6, 2026 | $1,299.86 | Available | 3 |
| Aug 7, 2026 | $1,658.30 | Not Available | 3 |
| Aug 8, 2026 | $1,552.21 | Not Available | 3 |
| Aug 9, 2026 | $1,159.78 | Not Available | 3 |
| Aug 10, 2026 | $1,048.54 | Available | 3 |
| Aug 11, 2026 | $979.53 | Available | 3 |
| Aug 12, 2026 | $953.78 | Available | 3 |
| Aug 13, 2026 | $973.35 | Available | 3 |
| Aug 14, 2026 | $1,584.14 | Available | 3 |
| Aug 15, 2026 | $1,445.09 | Available | 3 |
| Aug 16, 2026 | $1,259.69 | Available | 3 |
| Aug 17, 2026 | $1,210.25 | Available | 3 |
| Aug 18, 2026 | $1,168.02 | Available | 3 |
| Aug 19, 2026 | $1,182.44 | Available | 3 |
| Aug 20, 2026 | $1,260.72 | Available | 3 |
| Aug 21, 2026 | $1,191.71 | Not Available | 4 |
| Aug 22, 2026 | $1,290.59 | Not Available | 4 |
| Aug 23, 2026 | $1,071.20 | Not Available | 4 |
| Aug 24, 2026 | $1,051.63 | Not Available | 4 |
| Aug 25, 2026 | $1,048.54 | Not Available | 4 |
| Aug 26, 2026 | $1,051.63 | Not Available | 4 |
| Aug 27, 2026 | $1,024.85 | Not Available | 4 |
| Aug 28, 2026 | $1,220.55 | Not Available | 4 |
| Aug 29, 2026 | $1,198.92 | Not Available | 4 |
| Aug 30, 2026 | $967.17 | Not Available | 4 |
| Aug 31, 2026 | $968.20 | Not Available | 4 |
| Sep 1, 2026 | $824 | Not Available | 4 |
| Sep 2, 2026 | $824 | Not Available | 4 |
| Sep 3, 2026 | $1,014.55 | Not Available | 4 |
| Sep 4, 2026 | $1,362.69 | Not Available | 4 |
| Sep 5, 2026 | $1,443.03 | Not Available | 4 |
| Sep 6, 2026 | $1,286.47 | Not Available | 4 |
| Sep 7, 2026 | $1,024.85 | Not Available | 4 |
| Sep 8, 2026 | $965.11 | Available | 4 |
| Sep 9, 2026 | $945.54 | Available | 4 |
| Sep 10, 2026 | $972.32 | Available | 4 |
| Sep 11, 2026 | $989.83 | Available | 4 |
| Sep 12, 2026 | $1,031.03 | Available | 4 |
| Sep 13, 2026 | $771.47 | Not Available | 4 |
| Sep 14, 2026 | $724.09 | Not Available | 4 |
| Sep 15, 2026 | $721 | Not Available | 4 |
| Sep 16, 2026 | $747.78 | Not Available | 4 |
| Sep 17, 2026 | $941.42 | Available | 4 |
| Sep 18, 2026 | $1,049.57 | Available | 4 |
| Sep 19, 2026 | $1,035.15 | Available | 4 |
| Sep 20, 2026 | $806.49 | Available | 4 |
| Sep 21, 2026 | $763.23 | Available | 4 |
| Sep 22, 2026 | $761.17 | Available | 4 |
| Sep 23, 2026 | $763.23 | Available | 4 |
| Sep 24, 2026 | $880.65 | Available | 4 |
| Sep 25, 2026 | $998.07 | Available | 4 |
| Sep 26, 2026 | $998.07 | Available | 4 |
| Sep 27, 2026 | $799.28 | Available | 4 |
| Sep 28, 2026 | $748.81 | Available | 4 |
| Sep 29, 2026 | $721 | Available | 4 |
| Sep 30, 2026 | $736.45 | Available | 4 |
| Oct 1, 2026 | $875.50 | Available | 4 |
| Oct 2, 2026 | $1,080.47 | Available | 4 |
| Oct 3, 2026 | $1,196.86 | Available | 4 |
| Oct 4, 2026 | $1,204.07 | Available | 4 |
| Oct 5, 2026 | $1,169.05 | Available | 4 |
| Oct 6, 2026 | $1,133 | Available | 4 |
| Oct 7, 2026 | $1,190.68 | Available | 4 |
| Oct 8, 2026 | $1,162.87 | Not Available | 5 |
| Oct 9, 2026 | $1,298.83 | Not Available | 5 |
| Oct 10, 2026 | $1,375.05 | Not Available | 5 |
| Oct 11, 2026 | $1,192.74 | Not Available | 5 |
| Oct 12, 2026 | $1,502.77 | Not Available | 5 |
| Oct 13, 2026 | $1,199.95 | Not Available | 5 |
| Oct 14, 2026 | $1,199.95 | Not Available | 5 |
| Oct 15, 2026 | $1,213.34 | Not Available | 5 |
Amenities
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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
You'll save $3,000+ booking direct!
Direct
Best price
$12,500
Airbnb
$18,500
Vrbo
$15,500
Booking.com
$18,500
Lower prices, every time
Pay less than you would anywhere else. No middlemen or platform fees.
Direct line, real care
Book with the team that actually runs the property. Faster answers, better service, real accountability.
Not just a transaction
We go further for direct guests. We're building a relationship, not closing a booking.