Anna Maria, FL
Sweet Caroline
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!
-
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.
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.
| Date | Price (USD, excl. fees and taxes) | Availability | Min Stay (nights) |
|---|---|---|---|
| Jul 17, 2026 | $1,444.06 | Not Available | 7 |
| Jul 18, 2026 | $1,308.10 | Available | 4 |
| Jul 19, 2026 | $1,001.16 | Not Available | 7 |
| Jul 20, 2026 | $971.29 | Not Available | 5 |
| Jul 21, 2026 | $962.02 | Not Available | 5 |
| Jul 22, 2026 | $1,036.18 | Not Available | 4 |
| Jul 23, 2026 | $1,084.59 | Not Available | 4 |
| Jul 24, 2026 | $1,358.57 | Not Available | 4 |
| Jul 25, 2026 | $2,146.52 | Not Available | 4 |
| Jul 26, 2026 | $1,548.09 | Not Available | 5 |
| Jul 27, 2026 | $1,495.56 | Not Available | 5 |
| Jul 28, 2026 | $1,514.10 | Not Available | 5 |
| Jul 29, 2026 | $1,473.93 | Not Available | 5 |
| Jul 30, 2026 | $1,519.25 | Not Available | 5 |
| Jul 31, 2026 | $1,897.26 | Not Available | 5 |
| Aug 1, 2026 | $1,537.79 | Not Available | 5 |
| Aug 2, 2026 | $1,192.74 | Not Available | 5 |
| Aug 3, 2026 | $1,145.36 | Not Available | 5 |
| Aug 4, 2026 | $1,149.48 | Not Available | 5 |
| Aug 5, 2026 | $1,114.46 | Not Available | 5 |
| Aug 6, 2026 | $1,157.72 | Not Available | 5 |
| Aug 7, 2026 | $1,475.99 | Not Available | 5 |
| Aug 8, 2026 | $1,310.16 | Not Available | 5 |
| Aug 9, 2026 | $978.50 | Available | 2 |
| Aug 10, 2026 | $952.75 | Available | 2 |
| Aug 11, 2026 | $952.75 | Available | 2 |
| Aug 12, 2026 | $952.75 | Not Available | 4 |
| Aug 13, 2026 | $952.75 | Not Available | 4 |
| Aug 14, 2026 | $1,206.13 | Not Available | 4 |
| Aug 15, 2026 | $1,157.72 | Not Available | 4 |
| Aug 16, 2026 | $952.75 | Available | 4 |
| Aug 17, 2026 | $973.35 | Available | 4 |
| Aug 18, 2026 | $973.35 | Available | 4 |
| Aug 19, 2026 | $973.35 | Available | 4 |
| Aug 20, 2026 | $973.35 | Available | 4 |
| Aug 21, 2026 | $1,156.69 | Available | 4 |
| Aug 22, 2026 | $1,151.54 | Not Available | 4 |
| Aug 23, 2026 | $952.75 | Not Available | 4 |
| Aug 24, 2026 | $952.75 | Not Available | 4 |
| Aug 25, 2026 | $952.75 | Not Available | 4 |
| Aug 26, 2026 | $952.75 | Not Available | 4 |
| Aug 27, 2026 | $952.75 | Not Available | 4 |
| Aug 28, 2026 | $1,069.14 | Not Available | 4 |
| Aug 29, 2026 | $1,096.95 | Not Available | 4 |
| Aug 30, 2026 | $952.75 | Available | 4 |
| Aug 31, 2026 | $952.75 | Available | 4 |
| Sep 1, 2026 | $952.75 | Available | 4 |
| Sep 2, 2026 | $1,081.50 | Available | 4 |
| Sep 3, 2026 | $1,081.50 | Available | 4 |
| Sep 4, 2026 | $1,081.50 | Available | 4 |
| Sep 5, 2026 | $1,027.94 | Not Available | 4 |
| Sep 6, 2026 | $913.61 | Not Available | 4 |
| Sep 7, 2026 | $824 | Not Available | 4 |
| Sep 8, 2026 | $824 | Not Available | 4 |
| Sep 9, 2026 | $824 | Not Available | 4 |
| Sep 10, 2026 | $824 | Not Available | 4 |
| Sep 11, 2026 | $824 | Not Available | 4 |
| Sep 12, 2026 | $1,081.50 | Available | 4 |
| Sep 13, 2026 | $875.50 | Available | 4 |
| Sep 14, 2026 | $875.50 | Available | 4 |
| Sep 15, 2026 | $875.50 | Available | 4 |
| Sep 16, 2026 | $875.50 | Available | 4 |
| Sep 17, 2026 | $875.50 | Available | 4 |
| Sep 18, 2026 | $938.33 | Available | 4 |
| Sep 19, 2026 | $920.82 | Available | 4 |
| Sep 20, 2026 | $824 | Available | 4 |
| Sep 21, 2026 | $824 | Available | 4 |
| Sep 22, 2026 | $824 | Available | 4 |
| Sep 23, 2026 | $824 | Available | 4 |
| Sep 24, 2026 | $824 | Available | 4 |
| Sep 25, 2026 | $994.98 | Available | 4 |
| Sep 26, 2026 | $871.38 | Available | 4 |
| Sep 27, 2026 | $849.75 | Not Available | 4 |
| Sep 28, 2026 | $849.75 | Not Available | 4 |
| Sep 29, 2026 | $849.75 | Not Available | 4 |
| Sep 30, 2026 | $849.75 | Not Available | 4 |
| Oct 1, 2026 | $849.75 | Not Available | 5 |
| Oct 2, 2026 | $944.51 | Available | 5 |
| Oct 3, 2026 | $1,189.65 | Available | 5 |
| Oct 4, 2026 | $1,249.39 | Available | 5 |
| Oct 5, 2026 | $1,249.39 | Available | 5 |
| Oct 6, 2026 | $1,124.76 | Available | 5 |
| Oct 7, 2026 | $1,121.67 | Available | 5 |
| Oct 8, 2026 | $978.50 | Available | 5 |
| Oct 9, 2026 | $1,147.42 | Available | 5 |
| Oct 10, 2026 | $1,113.43 | Available | 5 |
| Oct 11, 2026 | $1,037.21 | Available | 5 |
| Oct 12, 2026 | $978.50 | Available | 5 |
| Oct 13, 2026 | $978.50 | Available | 5 |
| Oct 14, 2026 | $978.50 | Available | 5 |
| Oct 15, 2026 | $978.50 | Available | 5 |
Amenities
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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
You'll save $3,000+ booking direct!
Direct
Best price
$12,500
Airbnb
$18,500
Vrbo
$15,500
Booking.com
$18,500
Lower prices, every time
Pay less than you would anywhere else. No middlemen or platform fees.
Direct line, real care
Book with the team that actually runs the property. Faster answers, better service, real accountability.
Not just a transaction
We go further for direct guests. We're building a relationship, not closing a booking.