Book Sweet Caroline

4 bedrooms · 4 beds · 4.5 bathrooms · Sleeps 8

HousePet friendlyHot Tub

Where you’ll sleep

King

Bedroom 1

King

Bedroom 2

King

Bedroom 3

Full over Queen Bunk Bed

Bedroom 4

Experience ultimate island luxury at Sweet Caroline, a modern beach house featuring a rooftop deck with bay views, a resort-style backyard, and exclusive amenities, just steps from Anna Maria Beach.

–Exclusive AMI Collection luxury with premium amenities including a golf cart and beach bikes.
–Rooftop deck offering panoramic bay views and a resort-style backyard with private pool, spa, and putting green.
–Prime beach-block location, just a 2-minute walk to the Gulf beaches and Pine Avenue shops.

A modern beach house with a rooftop deck with beach views and an impressive backyard with a private pool, in-ground spa, a putting green, and covered patio. This home is part of our Exclusive AMI Collection of homes. These luxury properties provide the ultimate vacation experience for guests and include exclusive amenities such as a golf cart, four beach bikes, upgraded bed and bath linens.

About this 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!

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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.

full description

Managed by Anna Maria Vacations

Holmes Beach, FL

4.7★

4,426 reviews

Anna Maria Island vacation rentals for every traveler. Every beach vacation has a story — yours starts here.

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Guest Reviews

5.0★ · 9 reviews

★★★★★

“Deedee was a pleasure to host!”

Deedee · Sep 2025

★★★★★

“Jessica was a pleasure to host!”

Jessica · Oct 2025

★★★★★

“David was a pleasure to host Very beautiful home and thank you for everything!!! Took a trip with father and son to watch some spring baseball and it was a perfect house! Extremely clean and well kept. Thank you!”

David · Mar 2026

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Sweet Caroline

Sweet Caroline

Sweet Caroline

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Managed by Anna Maria Vacations

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