6 bedrooms
•
6 beds
•
6.5 bathrooms
•
8 guests
•
New
•
4439 sq. ft.
Luxury
Elevated properties with standout design
Operated by a Wander partner
Trusted operators, vetted by Wander
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!
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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.
Exterior
1 full bed
Pool
1 full bed
Balcony
1 full bed
Dining Room
1 full bed
Game Room 1
1 full bed
Bedroom 1
1 full bed
Bedroom 3
1 king bed
Bedroom 4
1 king bed
Bedroom 5
1 king bed
Bedroom 6
2 twin beds
Exterior
1 full bed
Pool
1 full bed
Balcony
1 full bed
Dining Room
1 full bed
Game Room 1
1 full bed
Bedroom 1
1 full bed
Bedroom 3
1 king bed
Bedroom 4
1 king bed
Bedroom 5
1 king bed
Bedroom 6
2 twin beds
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Anna Maria, FL 34216, US
Anna Maria, FL, USNestled on Anna Maria Island across from the beach, Wicked Cantina serves up bold Austin-style Tex Mex tacos, sizzling fajitas, and award-winning margaritas in a lively Gulf-view patio vibe with live music daily.
Nestled in historic Cortez Fishing Village, Tide Tables serves the freshest dockside seafood like blackened Corvina fish tacos amid stunning Intracoastal Waterway views, dolphin sightings, and a laid-back tiki bar vibe. Dock your boat at marker 48 and savor Old Florida charm.
Savor fresh Gulf-to-table seafood like chargrilled octopus and grouper at Sandbar Seafood + Spirits, Anna Maria Island's iconic beachfront gem. Dine toes-in-the-sand with breathtaking sunsets, rustic charm, and sustainable flavors in a refreshed coastal haven.
Nestled in Holmes Beach on Anna Maria Island, The Ugly Grouper is a lively outdoor haven for fresh seafood like crispy grouper tacos, epic frozen drinks, and live music that keeps the island vibes flowing. Play games, dine under cover, and savor the fun with family or friends.
Savor all-you-can-eat pancakes and sausage, fresh seafood platters, and juicy half-pound burgers at Anna Maria Island Beach Cafe, your gulf-front haven with casual patio dining, live music, and island-sized drinks at the bamboo beach bar.[1][2][3]
Nestled on Historic Bridge Street Pier with stunning Intracoastal Waterway views, Anna Maria Oyster Bar on the Pier serves fresh Gulf oysters nine ways, seafood favorites like grouper and shrimp, and casual Florida vibes at great value.[1][2][4]
Beach House Waterfront Restaurant is a casual waterfront dining destination on Anna Maria Island featuring fresh seafood and cocktails with stunning 650-foot Gulf of Mexico views, perfect for enjoying signature island sunsets from the climate-friendly outdoor deck or toes-in-the-sand seating.
Nestled along the serene Bayou DeSiard in a historic 1930s building, The Waterfront Grill offers upscale American and seafood dishes like grilled Black Angus steaks and Catfish DeSiard, paired with relaxing waterfront views and laid-back Louisiana charm.[1][2][4][6]
Ginny's & Jane E's is a charming cafe and boutique on Anna Maria Island that serves fresh breakfast and lunch featuring house-baked cinnamon rolls and quality ingredients, all while doubling as an eclectic gift shop filled with local art, handmade jewelry, and quirky coastal treasures that capture the laid-back island spirit.
Discover the pristine white sands and turquoise waters of Manatee Public Beach, where shell-hunting, volleyball, playground fun, and lifeguard safety create a perfect family day out. Ideal for energetic families and groups seeking memorable Anna Maria Island adventures.[1][4][5]
Unwind on Anna Maria Island Beach's pristine white sands, where turquoise waters invite swimming, kayaking, and dolphin spotting amid stunning sunsets. Perfect for families, nature lovers, and anyone craving Old Florida's serene, adventure-filled escape.
Step back in time at De Soto National Memorial, where ranger-led kayak tours glide through coastal ecosystems, living history reenactments bring 16th-century explorers to life, and short trails reveal bird-filled shores and native villages. History buffs, families, and nature lovers will relish this free, uncrowded gem blending adventure and heritage.
Discover Robinson Preserve's maze of shaded boardwalks, mangrove tunnels, and serene waterways perfect for kayaking, birdwatching, or hiking to a stunning observation tower. Nature lovers, families, and adventure seekers will love this lush 600-acre Florida wildlife haven.[1][2][4][5][6]
Discover Bean Point Beach Access, Anna Maria Island's secluded northern tip where powdery white sands meet turquoise Gulf waters and stunning Sunshine Skyway Bridge views. Nature lovers and serenity seekers will cherish this uncrowded oasis, perfect for tranquil strolls and shelling.
Unleash your furry friend at Fort De Soto's exclusive off-leash dog beach—the only one in Pinellas County—where they can romp on soft white sands, splash in turquoise waters, and play in adjacent fenced parks with showers. Dog-loving adventurers and their pups will adore this pet paradise amid nature trails and wildlife.
Discover Anna Maria Island's pristine sugar-white beaches and kayak through serene mangroves teeming with wildlife, all explorable by free trolley, bike, or golf cart in this Old Florida paradise. Families, beach lovers, and adventure seekers will cherish its relaxed charm and stunning sunsets.
Discover Coquina Beach's pristine white sands, calm waters teeming with dolphins, manatees, and sea turtles, plus thrilling kayaking and shell-hunting adventures. Families and couples love its safe, wildlife-rich shores and sunset magic.[1][2][4]
Discover the thrill of watersports in Holmes Beach, from adrenaline-pumping jet skiing and kayaking over crystal-clear Gulf waters teeming with sea life, to serene paddleboarding at sunset. Adventure seekers and beach lovers will adore this vibrant playground on Anna Maria Island.[1]
Discover the magic of Palma Sola Botanical Park, a lush 10-acre oasis brimming with rare tropical fruits like dragon fruit and lychee, fluttering butterflies, tranquil lakes, and exotic gardens. Nature lovers, birdwatchers, and serene strollers will adore this free, frost-free haven perfect for peaceful exploration.
Free cancellation up to 14 days before check-in. No refund after that.
Pets not allowed
No smoking - fees will apply
Events not allowed
Check-in after 4:00 pm
Check-out before 10:00 am
8 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Jul 14, 2026 | $1155 | Available |
| Jul 15, 2026 | $1151 | Available |
| Jul 16, 2026 | $1191 | Available |
| Jul 17, 2026 | $1499 | Available |
| Jul 18, 2026 | $1647 | Not Available |
| Jul 19, 2026 | $1288 | Not Available |
| Jul 20, 2026 | $1310 | Not Available |
| Jul 21, 2026 | $1442 | Not Available |
| Jul 22, 2026 | $1501 | Not Available |
| Jul 23, 2026 | $1552 | Not Available |
| Jul 24, 2026 | $1750 | Not Available |
| Jul 25, 2026 | $1983 | Not Available |
| Jul 26, 2026 | $1639 | Not Available |
| Jul 27, 2026 | $1578 | Not Available |
| Jul 28, 2026 | $1796 | Not Available |
| Jul 29, 2026 | $1800 | Not Available |
| Jul 30, 2026 | $1873 | Not Available |
| Jul 31, 2026 | $2026 | Not Available |
| Aug 1, 2026 | $1813 | Available |
| Aug 2, 2026 | $1406 | Available |
| Aug 3, 2026 | $1349 | Available |
| Aug 4, 2026 | $1353 | Available |
| Aug 5, 2026 | $1311 | Available |
| Aug 6, 2026 | $1361 | Available |
| Aug 7, 2026 | $1689 | Not Available |
| Aug 8, 2026 | $1635 | Not Available |
| Aug 9, 2026 | $1217 | Not Available |
| Aug 10, 2026 | $1101 | Available |
| Aug 11, 2026 | $1029 | Available |
| Aug 12, 2026 | $1011 | Available |
| Aug 13, 2026 | $1467 | Available |
| Aug 14, 2026 | $1811 | Available |
| Aug 15, 2026 | $1445 | Available |
| Aug 16, 2026 | $1258 | Available |
| Aug 17, 2026 | $1210 | Available |
| Aug 18, 2026 | $1167 | Available |
| Aug 19, 2026 | $1172 | Available |
| Aug 20, 2026 | $1282 | Available |
| Aug 21, 2026 | $1204 | Not Available |
| Aug 22, 2026 | $1294 | Not Available |
| Aug 23, 2026 | $1075 | Not Available |
| Aug 24, 2026 | $1052 | Not Available |
| Aug 25, 2026 | $1049 | Not Available |
| Aug 26, 2026 | $1052 | Not Available |
| Aug 27, 2026 | $1025 | Not Available |
| Aug 28, 2026 | $1231 | Not Available |
| Aug 29, 2026 | $1212 | Not Available |
| Aug 30, 2026 | $982 | Not Available |
| Aug 31, 2026 | $969 | Not Available |
| Sep 1, 2026 | $824 | Not Available |
| Sep 2, 2026 | $824 | Not Available |
| Sep 3, 2026 | $1019 | Not Available |
| Sep 4, 2026 | $1375 | Not Available |
| Sep 5, 2026 | $1458 | Not Available |
| Sep 6, 2026 | $1286 | Not Available |
| Sep 7, 2026 | $1030 | Not Available |
| Sep 8, 2026 | $969 | Available |
| Sep 9, 2026 | $945 | Available |
| Sep 10, 2026 | $968 | Available |
| Sep 11, 2026 | $901 | Available |
| Sep 12, 2026 | $936 | Available |
| Sep 13, 2026 | $771 | Not Available |
| Sep 14, 2026 | $723 | Not Available |
| Sep 15, 2026 | $721 | Not Available |
| Sep 16, 2026 | $746 | Not Available |
| Sep 17, 2026 | $941 | Available |
| Sep 18, 2026 | $1050 | Available |
| Sep 19, 2026 | $1049 | Available |
| Sep 20, 2026 | $845 | Available |
| Sep 21, 2026 | $800 | Available |
| Sep 22, 2026 | $797 | Available |
| Sep 23, 2026 | $800 | Available |
| Sep 24, 2026 | $895 | Available |
| Sep 25, 2026 | $993 | Available |
| Sep 26, 2026 | $998 | Available |
| Sep 27, 2026 | $830 | Available |
| Sep 28, 2026 | $778 | Available |
| Sep 29, 2026 | $756 | Available |
| Sep 30, 2026 | $773 | Available |
| Oct 1, 2026 | $802 | Available |
| Oct 2, 2026 | $1080 | Available |
| Oct 3, 2026 | $1185 | Available |
| Oct 4, 2026 | $1201 | Available |
| Oct 5, 2026 | $1115 | Available |
| Oct 6, 2026 | $1130 | Available |
| Oct 7, 2026 | $1191 | Available |
| Oct 8, 2026 | $1163 | Not Available |
| Oct 9, 2026 | $1280 | Not Available |
| Oct 10, 2026 | $1363 | Not Available |
| Oct 11, 2026 | $1193 | Not Available |
| Oct 12, 2026 | $1503 | Not Available |