$0
for 0 nights

Home in Anna Maria, FL

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

About the property

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!

-
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.

Where you’ll sleep

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

Amenities

Common Amenities

  • Wifi
  • Free parking
  • Shampoo
  • Body soap
  • Pack n play
  • Conditioner
  • First aid kit
  • Garden view
  • Gym
  • Kayaks
  • Patio
  • Elevator
  • Carbon monoxide detector
  • Smoke detector
  • Air conditioning
  • Hot water
  • Fire extinguisher
  • Kitchen
  • Hair dryer
  • Heating
  • Ocean view
  • BBQ Area
  • Ironing board
  • Toaster
  • Heated pool
  • Garden
  • Blender
  • Long term stays allowed
  • Ceiling fan
  • Baking sheet
  • Beach access
  • Rooftop

Pool

  • Outdoor pool
  • Hot tub

Patio

  • Outdoor seating
  • Putting green
  • Ping pong table

Balcony

  • Outdoor seating

Rooftop

  • Outdoor seating

Living Room

  • TV

Dining Room

  • Dining table

Kitchen

  • Kettle
  • Wine glasses
  • Oven
  • Stove
  • Microwave
  • Freezer
  • Fridge
  • Dishwasher
  • Dishes
  • Coffee maker

Bedroom 1

  • Bed linens

Ensuite Bathroom 1

  • Bathtub
  • Bath linens

Bedroom 2

  • TV
  • Bed linens

Bedroom 3

  • TV
  • Balcony
  • Outdoor seating
  • Bed linens

Bedroom 4

  • TV
  • Balcony
  • Bed linens

Bathroom 1

  • Bath linens
  • Bathtub

Bathroom 2

  • Bath linens

Bathroom 3

  • Bath linens

Half Bath

  • Bath linens

Laundry Room

  • Washer
  • Dryer

New · No reviews yet

Be the first to review this place.

Where you’ll be

Anna Maria, FL 34216, US

Anna Maria, FL, US
27.523682-82.7321222
Timezone: America/New_York

Restaurants

Tide Tables Restaurant and Marina

Nestled 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.

Sandbar Seafood + Spirits

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]

Beach House Waterfront Restaurant

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.

The Ugly Grouper

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

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.

The Waterfront Restaurant

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]

Anna Maria Oyster Bar on the Pier

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.

Wicked Cantina Bradenton Beach

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.

Ginny's & Jane E's Cafe and Gift Store

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]

Attractions

Cponies Beach Horseback Rides

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 Beach Access

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.

De Soto National Memorial

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]

Robinson Preserve

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]

Ana Maria island

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.

Anna Maria Island Beach

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.

Manatee Public Beach

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.

Palma Sola Botanical Park

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]

Coquina Beach

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.

Holmes Beach

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]

Things to know

Cancellation policy

Free cancellation up to 14 days before check-in. No refund after that.

Property rules

Pets allowed with fee

No smoking - fees will apply

Events not allowed

Safety & security

Check-in after 4:00 pm

Check-out before 10:00 am

8 guests maximum

Availability & Pricing

DatePrice (USD, excl. fees and taxes)Availability
Jul 14, 2026$1095Not Available
Jul 15, 2026$1091Not Available
Jul 16, 2026$1129Not Available
Jul 17, 2026$1420Not Available
Jul 18, 2026$1277Available
Jul 19, 2026$998Not Available
Jul 20, 2026$1016Not Available
Jul 21, 2026$1119Not Available
Jul 22, 2026$1163Not Available
Jul 23, 2026$1203Not Available
Jul 24, 2026$1357Not Available
Jul 25, 2026$2138Not Available
Jul 26, 2026$1545Not Available
Jul 27, 2026$1489Not Available
Jul 28, 2026$1694Not Available
Jul 29, 2026$1698Not Available
Jul 30, 2026$1767Not Available
Jul 31, 2026$1913Not Available
Aug 1, 2026$1550Not Available
Aug 2, 2026$1202Not Available
Aug 3, 2026$1155Not Available
Aug 4, 2026$1157Not Available
Aug 5, 2026$1121Not Available
Aug 6, 2026$1164Not Available
Aug 7, 2026$1444Not Available
Aug 8, 2026$1325Not Available
Aug 9, 2026$987Available
Aug 10, 2026$953Available
Aug 11, 2026$953Available
Aug 12, 2026$953Not Available
Aug 13, 2026$953Not Available
Aug 14, 2026$1174Not Available
Aug 15, 2026$1167Not Available
Aug 16, 2026$953Available
Aug 17, 2026$973Available
Aug 18, 2026$973Available
Aug 19, 2026$973Available
Aug 20, 2026$973Available
Aug 21, 2026$1163Available
Aug 22, 2026$1157Not Available
Aug 23, 2026$953Not Available
Aug 24, 2026$953Not Available
Aug 25, 2026$953Not Available
Aug 26, 2026$953Not Available
Aug 27, 2026$953Not Available
Aug 28, 2026$1087Not Available
Aug 29, 2026$1121Not Available
Aug 30, 2026$953Available
Aug 31, 2026$953Available
Sep 1, 2026$953Available
Sep 2, 2026$1082Available
Sep 3, 2026$1082Available
Sep 4, 2026$1082Available
Sep 5, 2026$1046Not Available
Sep 6, 2026$921Not Available
Sep 7, 2026$824Not Available
Sep 8, 2026$824Not Available
Sep 9, 2026$824Not Available
Sep 10, 2026$824Not Available
Sep 11, 2026$824Not Available
Sep 12, 2026$1082Available
Sep 13, 2026$876Available
Sep 14, 2026$876Available
Sep 15, 2026$876Available
Sep 16, 2026$876Available
Sep 17, 2026$876Available
Sep 18, 2026$939Available
Sep 19, 2026$923Available
Sep 20, 2026$824Available
Sep 21, 2026$824Available
Sep 22, 2026$824Available
Sep 23, 2026$824Available
Sep 24, 2026$824Available
Sep 25, 2026$995Available
Sep 26, 2026$880Available
Sep 27, 2026$850Not Available
Sep 28, 2026$850Not Available
Sep 29, 2026$850Not Available
Sep 30, 2026$850Not Available
Oct 1, 2026$850Not Available
Oct 2, 2026$953Available
Oct 3, 2026$1190Available
Oct 4, 2026$1249Available
Oct 5, 2026$1249Available
Oct 6, 2026$1125Available
Oct 7, 2026$1122Available
Oct 8, 2026$979Available
Oct 9, 2026$1142Available
Oct 10, 2026$1113Available
Oct 11, 2026$1037Available
Oct 12, 2026$979Available