Anna Maria, FL

Sweet Caroline

4 bedrooms4 beds4.5 baths8 guestsNew

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!

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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.

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.

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.

DatePrice (USD, excl. fees and taxes)AvailabilityMin Stay (nights)
Jul 17, 2026$1,444.06Not Available7
Jul 18, 2026$1,308.10Available4
Jul 19, 2026$1,001.16Not Available7
Jul 20, 2026$971.29Not Available5
Jul 21, 2026$962.02Not Available5
Jul 22, 2026$1,036.18Not Available4
Jul 23, 2026$1,084.59Not Available4
Jul 24, 2026$1,358.57Not Available4
Jul 25, 2026$2,146.52Not Available4
Jul 26, 2026$1,548.09Not Available5
Jul 27, 2026$1,495.56Not Available5
Jul 28, 2026$1,514.10Not Available5
Jul 29, 2026$1,473.93Not Available5
Jul 30, 2026$1,519.25Not Available5
Jul 31, 2026$1,897.26Not Available5
Aug 1, 2026$1,537.79Not Available5
Aug 2, 2026$1,192.74Not Available5
Aug 3, 2026$1,145.36Not Available5
Aug 4, 2026$1,149.48Not Available5
Aug 5, 2026$1,114.46Not Available5
Aug 6, 2026$1,157.72Not Available5
Aug 7, 2026$1,475.99Not Available5
Aug 8, 2026$1,310.16Not Available5
Aug 9, 2026$978.50Available2
Aug 10, 2026$952.75Available2
Aug 11, 2026$952.75Available2
Aug 12, 2026$952.75Not Available4
Aug 13, 2026$952.75Not Available4
Aug 14, 2026$1,206.13Not Available4
Aug 15, 2026$1,157.72Not Available4
Aug 16, 2026$952.75Available4
Aug 17, 2026$973.35Available4
Aug 18, 2026$973.35Available4
Aug 19, 2026$973.35Available4
Aug 20, 2026$973.35Available4
Aug 21, 2026$1,156.69Available4
Aug 22, 2026$1,151.54Not Available4
Aug 23, 2026$952.75Not Available4
Aug 24, 2026$952.75Not Available4
Aug 25, 2026$952.75Not Available4
Aug 26, 2026$952.75Not Available4
Aug 27, 2026$952.75Not Available4
Aug 28, 2026$1,069.14Not Available4
Aug 29, 2026$1,096.95Not Available4
Aug 30, 2026$952.75Available4
Aug 31, 2026$952.75Available4
Sep 1, 2026$952.75Available4
Sep 2, 2026$1,081.50Available4
Sep 3, 2026$1,081.50Available4
Sep 4, 2026$1,081.50Available4
Sep 5, 2026$1,027.94Not Available4
Sep 6, 2026$913.61Not Available4
Sep 7, 2026$824Not Available4
Sep 8, 2026$824Not Available4
Sep 9, 2026$824Not Available4
Sep 10, 2026$824Not Available4
Sep 11, 2026$824Not Available4
Sep 12, 2026$1,081.50Available4
Sep 13, 2026$875.50Available4
Sep 14, 2026$875.50Available4
Sep 15, 2026$875.50Available4
Sep 16, 2026$875.50Available4
Sep 17, 2026$875.50Available4
Sep 18, 2026$938.33Available4
Sep 19, 2026$920.82Available4
Sep 20, 2026$824Available4
Sep 21, 2026$824Available4
Sep 22, 2026$824Available4
Sep 23, 2026$824Available4
Sep 24, 2026$824Available4
Sep 25, 2026$994.98Available4
Sep 26, 2026$871.38Available4
Sep 27, 2026$849.75Not Available4
Sep 28, 2026$849.75Not Available4
Sep 29, 2026$849.75Not Available4
Sep 30, 2026$849.75Not Available4
Oct 1, 2026$849.75Not Available5
Oct 2, 2026$944.51Available5
Oct 3, 2026$1,189.65Available5
Oct 4, 2026$1,249.39Available5
Oct 5, 2026$1,249.39Available5
Oct 6, 2026$1,124.76Available5
Oct 7, 2026$1,121.67Available5
Oct 8, 2026$978.50Available5
Oct 9, 2026$1,147.42Available5
Oct 10, 2026$1,113.43Available5
Oct 11, 2026$1,037.21Available5
Oct 12, 2026$978.50Available5
Oct 13, 2026$978.50Available5
Oct 14, 2026$978.50Available5
Oct 15, 2026$978.50Available5

Amenities

Ocean view
Pool outdoor
Hot tub
Putting green
BBQ Area
Patio
Balcony
Elevator

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Where you'll be

Anna Maria, FL, 34216, US

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

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.