4 bedrooms
•
4 beds
•
4.5 bathrooms
•
8 guests
•
New
•
2500 sq. ft.
Luxury
Elevated properties with standout design
Operated by a Wander partner
Trusted operators, vetted by Wander
Sweet Caroline by Exclusive Vacations
Vacation Rental License #VR23-000009
Welcome to Sweet Caroline, part of our Exclusive Collection. This luxury four bedroom, four and a half bath Anna Maria Island vacation home just one small block from the Gulf beaches. This coastal retreat blends refined design, resort-style amenities, and a relaxed island vibe. Guests can enjoy a private pool and spa, rooftop deck with bay views, and outdoor living and kitchen areas; all within walking distance of the Pine Avenue shops and restaurants. With dog-friendly accommodation and a prime beach-block location, Sweet Caroline offers everything you need for an unforgettable island escape.
Highlights
• 2-minute walk to the beach
• 4 Bedrooms / 4.5 Bathrooms
• 3 King beds, 1 Full-over-Queen bunk bed
• Private pool and spa with tanning deck
• Rooftop deck with panoramic bay views
• Elevator for guest convenience
• Dog friendly with approval and additional fee
• Putting green and ping pong table for family fun
• 3 parking spaces
• Walking distance to Pine Avenue shops and restaurants
Exclusive Amenities:
• 6-Seat Club Car Cru Golf Cart for guest use
• Luxury beach bikes for guest use
• Luxury beach chairs and beach cart for guest use
• Upgraded bed and bath linens and toiletries
• Portable Pack and Play
Step outside to your private backyard oasis, where a resort-style pool and spa glisten under swaying palms. The tanning deck invites you to lounge in the Florida sunshine, while a putting green and ping pong table add a playful touch for guests of all ages. Fire up the outdoor kitchen and grill and dine beneath the shaded covered patio with plush seating and a large dining table. Ride the golf cart to the nearby beach, then return to unwind on the rooftop deck, where panoramic views set the perfect island mood. The elevator makes every level easily accessible, and with exclusive AMI Locals Collection upgrades, your stay feels effortless from check-in to checkout.
Inside, the open concept great room welcomes you with coastal decor, a comfortable seating area, and a TV for streaming your favorite shows. Sliding glass doors open to a balcony overlooking the pool, creating a seamless indoor-outdoor connection. The modern kitchen features stainless appliances, custom cabinetry, and a large island with bar seating. A family-sized dining table nearby brings everyone together for shared meals and laughter.
Each bedroom is thoughtfully designed for relaxation, blending premium comfort with chic coastal style. The primary suite features a king bed, private furnished balcony, and a spa-inspired ensuite with dual vanities, a walk-in shower, and a stand-alone soaking tub behind glass doors. Two additional king guest rooms each include private balconies and ensuite baths with walk-in showers. The bunk room, complete with a Full-over-Queen bunk bed and ensuite with a shower/tub combo, is a hit with younger guests.
Room Details
• Primary Bedroom (3rd floor): King bed, private balcony, ensuite with walk-in shower and tub
• Second Bedroom (3rd floor): King bed, balcony, ensuite with walk-in shower
• Third Bedroom (2nd floor): King bed, balcony, ensuite with walk-in shower
• Fourth Bedroom (2nd floor): Full-over-Queen bunk, ensuite with shower/tub combo
Located in the heart of Anna Maria, Sweet Caroline is steps from Anna Maria Beach and just a short stroll from the boutique shops and waterfront restaurants along Pine Avenue. Explore the island by bike or golf cart, paddleboard through tranquil bays, or book a sunset cruise for a classic Gulf Coast experience. This home accommodates three vehicles and is dog-friendly with prior approval and a pet fee.
From its rooftop bay views to its private pool and spa, Sweet Caroline delivers the perfect blend of modern luxury and island ease. Designed for families and groups seeking style, comfort, and convenience, every detail invites relaxation and connection.
Book your stay today and enjoy the best of Anna Maria Island living in this stunning luxury beach home!
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This home is managed by AMI Locals, an Anna Maria Island property management company.
With host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Rental Policies for full details.
3 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.
Use of the provided golf cart requires the driver to maintain a current U.S. automobile insurance. Proof of insurance is required upon request.
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.
Bedroom 1
1 king bed
Bedroom 2
1 king bed
Bedroom 3
1 king bed
Bedroom 4
1 full bunk bed
Bedroom 1
1 king bed
Bedroom 2
1 king bed
Bedroom 3
1 king bed
Bedroom 4
1 full bunk bed
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Anna Maria, FL 34216, US
Anna Maria, FL, USNestled in historic Cortez Fishing Village, Tide Tables Restaurant and Marina serves the freshest dockside seafood with stunning Intracoastal Waterway views, dolphin sightings, and a laid-back tiki bar vibe. Dock your boat at marker 48 and savor fish tacos or grouper bites on pet-friendly picnic tables.
Nestled on Anna Maria Island's beachfront, Sandbar Seafood + Spirits serves fresh, wild-caught seafood like chargrilled octopus and grouper in a refreshed rustic-chic setting with toes-in-the-sand dining and stunning Gulf sunsets. This iconic spot blends coastal charm with vibrant flavors for unforgettable meals.[1][2][3][4][6]
Savor fresh seafood and cocktails at Beach House Waterfront Restaurant, where toes-in-the-sand dining and a 650ft Gulf of Mexico view create the ultimate beachfront sunset escape. This upscale casual gem on Anna Maria Island blends sun, fun, and sustainable flavors since 1993.
Discover The Ugly Grouper, a quirky outdoor seafood haven on Anna Maria Island, where fresh local grouper tacos and lively games meet palm-shaded seating and live music under a massive metal fish statue.[1][2][3][5]
Anna Maria Island Beach Cafe is a casual beachfront dining spot famous for its all-you-can-eat pancakes and fresh seafood, offering Gulf views, nightly live entertainment, and a laid-back island atmosphere perfect for families and sunset lovers.
Nestled on Stuart's scenic waterfront, The Waterfront delights with fresh American seafood, Asian-inspired dishes, and pub fare amid stunning river views and a vibrant, welcoming vibe. Highly rated at 4.6 stars, it's the perfect spot for casual dining with craft beers and cozy ambiance.[1]
Nestled on Historic Bridge Street Pier with stunning Intracoastal Waterway views, Anna Maria Oyster Bar on the Pier serves fresh oysters nine ways, seafood classics like coconut shrimp, and casual Florida vibes—perfect for boaters and beachgoers alike.
Savor Austin-style Tex Mex tacos, burgers, and seafood at Wicked Cantina Bradenton Beach, where Gulf views from the patio pair perfectly with live music, award-winning margaritas, and endless chips and salsa. Open daily for breakfast, lunch, and dinner with a vibrant, family-friendly island vibe.
Nestled on Anna Maria Island, Ginny's & Jane E's Cafe and Gift Store blends a cozy cafe with an eclectic boutique of local art, antiques, and beach treasures. Savor fresh-baked giant cinnamon rolls, hearty breakfasts, and gourmet coffee amid quirky charm that feels like a second home.[1][3][4][5]
Experience the thrill of horseback riding into the crystal-clear waters of Palma Sola Bay near Anna Maria Island, where you can swim alongside gentle rescue horses and spot dolphins, manatees, and stingrays in their natural habitat.
Bean Point offers a serene escape at Anna Maria Island's northern tip, where soft white sand meets turquoise waters with stunning views of the Sunshine Skyway Bridge and Tampa Bay—perfect for nature lovers seeking a quieter, less-crowded beach experience.
Discover De Soto National Memorial, a hidden gem blending 16th-century history with coastal nature trails, ranger-led kayak tours, birdwatching, and living history reenactments at Camp Uzita. History buffs, families, and outdoor adventurers will love this free, uncrowded Florida escape.[1][3][5]
Discover Robinson Preserve's mangrove mazes, canopy walkways, and kayak trails teeming with manatees and dolphins, all crowned by a 53-foot observation tower with sweeping Tampa Bay views. Nature lovers, families, and outdoor adventurers will love this coastal paradise.[1][2][3][8]
Discover the pristine sugar-white sands and Old Florida charm of Anna Maria Island, where you can kayak through mangroves, spot dolphins from a pier, or soar on a parasailing adventure. Beach lovers, families, and water enthusiasts will adore its serene turquoise waters and stunning sunsets.
Unwind on Anna Maria Island Beach's pristine, sugar-white sands, where calm turquoise waters invite swimming, kayaking, and dolphin spotting amid Old Florida charm. Beach lovers, families, and nature enthusiasts will adore this serene paradise for unforgettable relaxation and adventure.
Discover the pristine white sands and turquoise waters of Manatee Public Beach, where shell-hunting, volleyball, and playground fun meet lifeguard safety and family picnic spots. Ideal for energetic families and beach lovers seeking a perfect Anna Maria Island escape.
Discover the magic of Palma Sola Botanical Park, a 10-acre tropical haven with rare fruit trees like dragon fruit and lychee, fluttering butterflies, serene lakes, and vibrant gardens in a frost-free microclimate. Nature lovers, families, and plant enthusiasts will adore this free, serene escape.[1][2][3]
Discover Coquina Beach's pristine white sands, where families and couples thrill to kayaking, dolphin spotting, and manatee encounters amid safe, lifeguard-patrolled waters. Its uncrowded shores and vibrant wildlife make it Florida's ultimate relaxing paradise.
Discover Holmes Beach's pristine sands and thrilling watersports like jet skiing and paddleboarding on the Gulf, paired with family golf cart adventures and local art galleries. Beach lovers, thrill-seekers, and relaxed explorers will adore this serene Anna Maria Island gem.[1][2][5]
Free cancellation up to 14 days before check-in. No refund after that.
Pets allowed with fee
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 | $1095 | Not Available |
| Jul 15, 2026 | $1091 | Not Available |
| Jul 16, 2026 | $1129 | Not Available |
| Jul 17, 2026 | $1420 | Not Available |
| Jul 18, 2026 | $1277 | Available |
| Jul 19, 2026 | $998 | Not Available |
| Jul 20, 2026 | $1016 | Not Available |
| Jul 21, 2026 | $1119 | Not Available |
| Jul 22, 2026 | $1163 | Not Available |
| Jul 23, 2026 | $1203 | Not Available |
| Jul 24, 2026 | $1357 | Not Available |
| Jul 25, 2026 | $2138 | Not Available |
| Jul 26, 2026 | $1545 | Not Available |
| Jul 27, 2026 | $1489 | Not Available |
| Jul 28, 2026 | $1694 | Not Available |
| Jul 29, 2026 | $1698 | Not Available |
| Jul 30, 2026 | $1767 | Not Available |
| Jul 31, 2026 | $1913 | Not Available |
| Aug 1, 2026 | $1550 | Not Available |
| Aug 2, 2026 | $1202 | Not Available |
| Aug 3, 2026 | $1155 | Not Available |
| Aug 4, 2026 | $1157 | Not Available |
| Aug 5, 2026 | $1121 | Not Available |
| Aug 6, 2026 | $1164 | Not Available |
| Aug 7, 2026 | $1444 | Not Available |
| Aug 8, 2026 | $1325 | Not Available |
| Aug 9, 2026 | $987 | Available |
| Aug 10, 2026 | $953 | Available |
| Aug 11, 2026 | $953 | Available |
| Aug 12, 2026 | $953 | Not Available |
| Aug 13, 2026 | $953 | Not Available |
| Aug 14, 2026 | $1174 | Not Available |
| Aug 15, 2026 | $1167 | Not Available |
| Aug 16, 2026 | $953 | Available |
| Aug 17, 2026 | $973 | Available |
| Aug 18, 2026 | $973 | Available |
| Aug 19, 2026 | $973 | Available |
| Aug 20, 2026 | $973 | Available |
| Aug 21, 2026 | $1163 | Available |
| Aug 22, 2026 | $1157 | Not Available |
| Aug 23, 2026 | $953 | Not Available |
| Aug 24, 2026 | $953 | Not Available |
| Aug 25, 2026 | $953 | Not Available |
| Aug 26, 2026 | $953 | Not Available |
| Aug 27, 2026 | $953 | Not Available |
| Aug 28, 2026 | $1087 | Not Available |
| Aug 29, 2026 | $1121 | Not Available |
| Aug 30, 2026 | $953 | Available |
| Aug 31, 2026 | $953 | Available |
| Sep 1, 2026 | $953 | Available |
| Sep 2, 2026 | $1082 | Available |
| Sep 3, 2026 | $1082 | Available |
| Sep 4, 2026 | $1082 | Available |
| Sep 5, 2026 | $1046 | Not Available |
| Sep 6, 2026 | $921 | Not Available |
| Sep 7, 2026 | $824 | Not Available |
| Sep 8, 2026 | $824 | Not Available |
| Sep 9, 2026 | $824 | Not Available |
| Sep 10, 2026 | $824 | Not Available |
| Sep 11, 2026 | $824 | Not Available |
| Sep 12, 2026 | $1082 | Available |
| Sep 13, 2026 | $876 | Available |
| Sep 14, 2026 | $876 | Available |
| Sep 15, 2026 | $876 | Available |
| Sep 16, 2026 | $876 | Available |
| Sep 17, 2026 | $876 | Available |
| Sep 18, 2026 | $939 | Available |
| Sep 19, 2026 | $923 | Available |
| Sep 20, 2026 | $824 | Available |
| Sep 21, 2026 | $824 | Available |
| Sep 22, 2026 | $824 | Available |
| Sep 23, 2026 | $824 | Available |
| Sep 24, 2026 | $824 | Available |
| Sep 25, 2026 | $995 | Available |
| Sep 26, 2026 | $880 | Available |
| Sep 27, 2026 | $850 | Not Available |
| Sep 28, 2026 | $850 | Not Available |
| Sep 29, 2026 | $850 | Not Available |
| Sep 30, 2026 | $850 | Not Available |
| Oct 1, 2026 | $850 | Not Available |
| Oct 2, 2026 | $953 | Available |
| Oct 3, 2026 | $1190 | Available |
| Oct 4, 2026 | $1249 | Available |
| Oct 5, 2026 | $1249 | Available |
| Oct 6, 2026 | $1125 | Available |
| Oct 7, 2026 | $1122 | Available |
| Oct 8, 2026 | $979 | Available |
| Oct 9, 2026 | $1142 | Available |
| Oct 10, 2026 | $1113 | Available |
| Oct 11, 2026 | $1037 | Available |
| Oct 12, 2026 | $979 | Available |