Anna Maria, FL

Sweet Caroline

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8 guests
4 bedrooms
5 bathrooms
2500 sqft

Sweet Caroline by Exclusive Vacations

  • Balcony
  • Outdoor seating
  • Bath linens
8 guests
4 bedrooms
5 bathrooms
2500 sqft

  • Flexible check-in & out

    Check-in after 4:00 PM • Check-out before 10:00 AM

  • Easy cancellation


About this property

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! - 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.

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! - 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.

Availability & Pricing

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
Feb 16, 2026$695Available3
Feb 17, 2026$695Available3
Feb 18, 2026$695Available3
Feb 19, 2026$695Not Available3
Feb 20, 2026$695Not Available3
Feb 21, 2026$695Not Available3
Feb 22, 2026$695Not Available3
Feb 23, 2026$695Available3
Feb 24, 2026$695Available3
Feb 25, 2026$695Available3
Feb 26, 2026$695Available3
Feb 27, 2026$695Available3
Feb 28, 2026$695Available3
Mar 1, 2026$695Available3
Mar 2, 2026$695Available3
Mar 3, 2026$695Available3
Mar 4, 2026$695Available3
Mar 5, 2026$695Available3
Mar 6, 2026$695Available3
Mar 7, 2026$695Not Available3
Mar 8, 2026$695Not Available3
Mar 9, 2026$695Not Available3
Mar 10, 2026$695Not Available3
Mar 11, 2026$695Not Available3
Mar 12, 2026$695Not Available3
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Mar 19, 2026$695Not Available3
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Mar 26, 2026$695Not Available3
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Mar 28, 2026$695Not Available3
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Mar 31, 2026$695Not Available3
Apr 1, 2026$695Not Available3
Apr 2, 2026$695Not Available3
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Apr 5, 2026$695Available3
Apr 6, 2026$695Available3
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Apr 9, 2026$695Available3
Apr 10, 2026$695Available3
Apr 11, 2026$695Available3
Apr 12, 2026$695Available3
Apr 13, 2026$695Not Available3
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Apr 16, 2026$695Not Available3
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Apr 26, 2026$695Not Available3
Apr 27, 2026$695Not Available3
Apr 28, 2026$695Not Available3
Apr 29, 2026$695Not Available3
Apr 30, 2026$695Not Available3
May 1, 2026$695Not Available3
May 2, 2026$695Not Available3
May 3, 2026$695Not Available3
May 4, 2026$695Not Available3
May 5, 2026$695Not Available3
May 6, 2026$695Not Available3
May 7, 2026$695Not Available3
May 8, 2026$695Available3
May 9, 2026$695Available3
May 10, 2026$695Available3
May 11, 2026$695Available3
May 12, 2026$695Available3
May 13, 2026$695Available3
May 14, 2026$695Available3
May 15, 2026$695Available3
May 16, 2026$695Available3
May 17, 2026$695Available3

Top notch amenities

GUEST FAVORITES

Patio
Balcony
Outdoor seating
Bath linens
Bed linens
Body soap
Conditioner
Shampoo
Air conditioning

Where you'll sleep



Explore Anna Maria, FL

Discover the laid-back luxury of Anna Maria, a coastal paradise where the rhythm of the tides dictates the pace of life. Spend sun-soaked afternoons at the nearby Anna Maria Island Beach or Manatee Public Beach, with easy access to local provisions at the Publix Super Market at Holmes Beach. A short drive reveals the ecological wonders of Robinson Preserve, while a visit to Tide Tables Restaurant and Marina offers an

Things to know

Here are some things which you should know before booking Sweet Caroline

House rules

Check-in after 4:00 PM
Check-out before 10:00 AM
8 guests maximum
Pets not allowed
No smoking - fees will apply
Events not permitted
Commercial photography requires approval

Cancellation policy

This property follows Prime Vacations - Anna Maria’s standard cancellation policy.