Rating 5 (12)

Sweet Caroline


Bedroom 4 bedrooms
Bathroom 4 baths
Bathroom 1 half bath
Guests 8 guests
Pets Allowed Pets Allowed

  • Address: 9306 Gulf Drive
  • Location: Anna Maria
Banner EXCLUSIVE COLLECTION


Location Location

Description Description
Sweet Caroline by Exclusive Vacations
9306 Gulf Drive, Anna Maria, FL 34216
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.

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.

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Swipe Swipe for Availability

Bedding Bedding
Bedroom 1
Bedding
1 King

Attached Bathroom

Bedroom 2
Bedding
1 King

Attached Bathroom

Bedroom 3
Bedding
1 King

Attached Bathroom

Bedroom 4
Bedding
1 Full over Queen Bunk Bed

Attached Bathroom


Amenities 66 Amenities
Essentials
  • Air Conditioning
  • Beach Chairs Provided
  • Beach Towels Included
  • Bed Linens
  • Clothes Hangers
  • Dryer
  • Hair Dryer
  • Heating
  • Hot Water
  • Iron and Ironing Board
  • Long Term Stays Allowed
  • Private Entrance
  • Towels
  • Washer
Exterior
  • Backyard
  • Balcony
  • BBQ Area
  • BBQ Grill
  • Fenced Yard
  • Heated Pool
  • Outdoor Dining Area
  • Outdoor Seating
  • Patio
  • Private Pool
  • Sun Loungers
Fun & Entertainment
  • Ping Pong Table
  • Putting Green
  • Smart TV
Highlight
  • Exclusive Collection
  • Virtual Tour
Home Safety
  • Carbon Monoxide Detector
  • Deadbolt Lock
  • Fire Extinguisher
  • Keyless Lock
  • Smoke Detector
Interior
  • Bathtub
  • Ceiling Fans
  • Dedicated Workspace
  • Living Room
Kitchen
  • Baking Sheet
  • Blender
  • Coffee Maker
  • Dining table
  • Dishwasher
  • Freezer
  • Full Kitchen
  • Hot Water Kettle
  • Keurig Coffee Maker
  • Kitchen Island
  • Microwave
  • Oven
  • Refrigerator
  • Toaster
  • Wine Fridge
  • Wine Glasses
Location
  • 2-minute walk to the beach
  • Anna Maria
  • Anna Maria Island
  • Beach View
  • On-Island Rentals
  • Residential Street
  • Water View
Must Haves
  • Elevator
  • Hot Tub or Spa
  • Rooftop Deck
Parking
  • Three (3) Parking Spaces

Reviews Rating 5 (12) Reviews
Rating 5
Charles - Posted: 11/14/2025
Rating 5
Love love love the house, everything about the location and amenities. When we contacted management, they were so quick to respond. It was one of the moat relaxing vacations I’ve ever had. Thank you for everything.
Andrea - Posted: 9/19/2025
Hi, Andrea, thanks so much for staying with AMI Locals at Sweet Caroline! We’re so happy you loved the home, location, and amenities, it’s the perfect spot for a relaxing island escape. Our team was glad to help make your stay smooth and stress-free. Hope to welcome you back to Anna Maria Island soon for another laid-back getaway!!!
Anna Maria Paradise staff
Rating 5
House was perfect for our stay. Quick walk to the beach. Having a golf cart made getting around very easy
Kristen - Posted: 8/20/2025
Thank you for the positive review, Kristen. We're glad to hear that our house was perfect for your stay and the golf cart made getting around convenient on our little island. It's great that our property's proximity to the beach was also a highlight. We look forward to welcoming you back in the future!
Anna Maria Paradise staff
Rating 5
Amazing Time / Amazing Stay
This home is amazing and just as advertised. Beautifully decorated and in a great location. We enjoyed the pool and spa each and every day.Can’t say enough great things about this home.
tdurr304 - Posted: 5/27/2025
We are so glad to hear you enjoyed the property, the pool and the spa are for sure highlights! We appreciate your review and hope to host you again in the near future!
Anna Maria Paradise staff
Rating 5
Beautiful property with amazing location. Hosts were very responsive and helpful.
Drew - Posted: 9/7/2024
Thank you for your lovely review, Drew. Come back soon for more beautiful vibes and top-notch hosting! 🌟
Anna Maria Paradise staff
Rating 5
Spectacular house! The perfect luxury stay with an amazing location. Walking distance to the beach. My only feedback is that you should give more time for check-in and check-out. But the house is straight out of a magazine. 100% recommend.
Karla - Posted: 5/26/2024
Thank you for your feedback about check-in and check-out times; we'll definitely look into that. We're delighted that our house left such a lasting impression on you. 💖
Anna Maria Paradise staff
Rating 5
Close to everything!
The accommodation is close to the beach and Pine Ave (restaurants, shops, and the AMI pier!) Everything about the house was so lovely and loved the pool! Definitely recommend for a fun girls getaway or a family stay.
Anastasia T. - Posted: 4/30/2024
Anastasia, thank you for your wonderful review! We're thrilled to hear that you enjoyed our accommodation and found it to be close to the beach and Pine Ave with its restaurants, shops, and the AMI pier. It's fantastic to hear that everything about the house was lovely and that you loved the pool as well. We appreciate your recommendation for both a fun girls getaway and a family stay. We hope to have the pleasure of hosting you again in the future! If you have any further comments or questions, please feel free to let us know.
Anna Maria Paradise staff
Rating 5
Beach perfect
The property was better than the pictures. The pool and roof top deck were amazing. It was a short walk to the beach and had everything we needed for a beach day. Could not have asked for more for our family getaway. We will definitely be back.
Christine C. - Posted: 1/27/2024
Christine, thank you for your wonderful feedback! We're thrilled to hear that the property exceeded your expectations and that you found the pool and rooftop deck amazing. It's fantastic that the location was convenient for a short walk to the beach and that the property had everything you needed for a perfect beach day. We're delighted that your family getaway was a success, and we can't wait to welcome you back again in the future. If there's anything else we can do to make your next stay even more enjoyable, please don't hesitate to let us know. We appreciate your feedback and look forward to hosting you again!
Anna Maria Paradise staff
Rating 5
Beautiful house great location
We had a great stay at this property. The location was ideal and the house was beautiful and clean. Wouldn’t change anything!
Verified traveler - Posted: 11/4/2023
Thank you for taking the time to share your wonderful experience, Elizabeth. We are glad you enjoyed your stay and hope to welcome you back soon!
Anna Maria Paradise staff
Rating 5
Had the best time in Anna Maria Island. The house was beautiful and in the best location. Quick walk to the beach, the local restaurants and shops. Highly recommend.
Caitlin - Posted: 9/24/2023
Thank you for taking the time to share your wonderful experience with us, Caitlin. We are glad you enjoyed your stay and hope to welcome you back soon!
Anna Maria Paradise staff
Rating 5
This is literary all I could dream about. This place is a lifetime experience! Gorgeous, inspiring, designed by professionals. I could write paragraph after paragraph and it would not give it justice. Move in and see by yourself - this place is all you could dream about.
Lena - Posted: 6/23/2023
Thank you for taking the time to share your wonderful experience with us, Lena. We are thrilled to hear how much you enjoyed your stay. You were terrific guests, and we hope to welcome you all back again soon!
Anna Maria Paradise staff
Rating 5
Fun place to stay
This rental was absolutely beautiful. Tastefully decorated and comfortably designed, it seems like the owner really thought through what his guests would enjoy while staying here. We all appreciated how sparkling clean this house was when we checked in, and we are crazy particular about that kind of thing! The views are incredible from the rooftop. The home is about a block away from the beach and has a private pool area that is better than any I have seen before. We really enjoyed our time here.
Adam D. - Posted: 2/21/2023
Adam, thank you for taking the time to share your experience with us. We are glad you were comfortable and enjoyed the rooftop views. We hope to have the opportunity to host you again in the future!
Anna Maria Paradise staff
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