Anna Maria, FL

Sweet Caroline

4 bedrooms 0 beds 5 baths 8 guests New

About the property

Sweet Caroline by Exclusive Vacations 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.

Sweet Caroline by Exclusive Vacations 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.

Availability & Pricing

For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
May 19, 2026$824Not Available2
May 20, 2026$842.54Not Available2
May 21, 2026$884.77Not Available2
May 22, 2026$1,214.37Not Available2
May 23, 2026$1,591.35Available4
May 24, 2026$1,377.11Not Available4
May 25, 2026$1,219.52Not Available4
May 26, 2026$1,223.64Not Available4
May 27, 2026$1,231.88Not Available4
May 28, 2026$1,327.67Not Available4
May 29, 2026$1,586.20Not Available4
May 30, 2026$1,351.36Not Available7
May 31, 2026$1,116.52Not Available7
Jun 1, 2026$1,147.42Not Available7
Jun 2, 2026$1,281.32Not Available7
Jun 3, 2026$1,301.92Not Available7
Jun 4, 2026$1,350.33Not Available7
Jun 5, 2026$1,515.13Not Available7
Jun 6, 2026$1,484.23Not Available7
Jun 7, 2026$1,330.76Not Available7
Jun 8, 2026$1,296.77Not Available7
Jun 9, 2026$1,275.14Not Available7
Jun 10, 2026$1,290.59Not Available7
Jun 11, 2026$1,345.18Not Available7
Jun 12, 2026$1,516.16Not Available7
Jun 13, 2026$1,505.86Available4
Jun 14, 2026$1,378.14Not Available4
Jun 15, 2026$1,354.45Not Available4
Jun 16, 2026$1,399.77Not Available4
Jun 17, 2026$1,377.11Not Available4
Jun 18, 2026$1,610.92Not Available5
Jun 19, 2026$1,855.03Not Available5
Jun 20, 2026$1,628.43Not Available5
Jun 21, 2026$1,631.52Not Available5
Jun 22, 2026$1,643.88Not Available4
Jun 23, 2026$1,697.44Not Available3
Jun 24, 2026$1,697.44Not Available3
Jun 25, 2026$1,710.83Not Available3
Jun 26, 2026$1,637.70Not Available4
Jun 27, 2026$1,950.82Not Available5
Jun 28, 2026$1,901.38Not Available5
Jun 29, 2026$1,894.17Not Available4
Jun 30, 2026$1,983.78Not Available3
Jul 1, 2026$2,006.44Not Available3
Jul 2, 2026$2,058.97Not Available3
Jul 3, 2026$1,969.36Not Available7
Jul 4, 2026$2,316.47Not Available7
Jul 5, 2026$1,976.57Not Available7
Jul 6, 2026$2,229.95Not Available7
Jul 7, 2026$2,229.95Not Available7
Jul 8, 2026$2,229.95Not Available7
Jul 9, 2026$2,185.66Not Available7
Jul 10, 2026$1,457.45Available7
Jul 11, 2026$1,800.44Not Available7
Jul 12, 2026$1,588.26Not Available7
Jul 13, 2026$1,599.59Not Available7
Jul 14, 2026$1,593.41Not Available7
Jul 15, 2026$1,602.68Not Available7
Jul 16, 2026$1,599.59Not Available7
Jul 17, 2026$1,802.50Not Available7
Jul 18, 2026$2,020.86Not Available4
Jul 19, 2026$1,990.99Not Available7
Jul 20, 2026$1,995.11Not Available5
Jul 21, 2026$1,989.96Not Available5
Jul 22, 2026$1,996.14Not Available4
Jul 23, 2026$2,003.35Not Available4
Jul 24, 2026$2,029.10Not Available4
Jul 25, 2026$2,317.50Available4
Jul 26, 2026$1,798.38Not Available5
Jul 27, 2026$1,720.10Not Available5
Jul 28, 2026$1,740.70Not Available5
Jul 29, 2026$1,759.24Not Available5
Jul 30, 2026$1,796.32Not Available5
Jul 31, 2026$1,978.63Not Available5
Aug 1, 2026$1,452.30Not Available5
Aug 2, 2026$1,250.42Not Available5
Aug 3, 2026$1,217.46Not Available5
Aug 4, 2026$1,193.77Not Available5
Aug 5, 2026$1,172.14Not Available5
Aug 6, 2026$1,244.24Not Available5
Aug 7, 2026$1,397.71Not Available5
Aug 8, 2026$1,362.69Not Available5
Aug 9, 2026$1,161.84Available4
Aug 10, 2026$1,042.36Available4
Aug 11, 2026$1,023.82Available4
Aug 12, 2026$1,002.19Available4
Aug 13, 2026$967.17Available4
Aug 14, 2026$1,228.79Available4
Aug 15, 2026$1,218.49Available4
Aug 16, 2026$952.75Available4
Aug 17, 2026$973.35Available4

Where you'll sleep

Amenities

Ocean view
Beach access
Pool outdoor
Hot tub
Gym
Putting green
BBQ Area
Patio

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Where you'll be

Anna Maria, FL, 34216, US

Things to know

Cancellation policy

Property rules

Children welcome (2–12 years).
Infants welcome (under 2).
Pets allowed.
No parties or events.

Safety & security

Check-in after 4:00 PM.
Check-out before 10:00 AM.
Maximum 8 guests.