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.
2nd floor: Step into a luxurious master bedroom in Florida, a sanctuary where sophisticated elegance meets relaxed coastal living.
King Bed
Balcony Access
Smart TV
Ensuite bathroom with shower
Located on the 2nd floor, enjoy ample natural light in your king bedroom, complemented by a sleek and contemporary walk-in shower in the attached bathroom.
King Bed
Balcony Access
Smart TV
Ensuite bathroom with shower
2nd floor luxurious king bedroom designed for relaxation, complete with a calming ensuite bathroom that features a spacious walk-in shower.
King Bed
Balcony Access
Smart TV
Ensuite bathroom with shower
2nd floor: A source of fun and adventure: a bunk bed with a slide! This playful build is designed to maximize both space and enjoyment, particularly for kids.
Full Bunk over a Twin Bunk
Balcony Access
Smart TV
Slide
Ensuite bathroom with bathtub and shower
Property Amenities
Essentials
Air Conditioning
Beach Towels Included
Bed Linens
Ceiling Fans
Clothes Hangers
Clothing Storage
Hair Dryer
Heating
Hot Water
Towels
Washer
Exterior Features
Backyard
Balcony
Fenced Yard
Heated Pool
Outdoor Dining Area
Outdoor Seating
Patio
Private Pool
Sun Loungers
Interior Features
Full Kitchen
Living Room
Kitchen and Dining
Blender
Coffee Maker
Dining table
Dishwasher
Freezer
Hot Water Kettle
Keurig Coffee Maker
Kitchen Island
Microwave
Oven
Refrigerator
Stove
Toaster
Wine Fridge
Wine Glasses
Safety Features
Carbon Monoxide Detector
Deadbolt Lock
Fire Extinguisher
Keyless Lock
Smoke Detector
Exclusive Amenities
Experience the perfect blend of luxury hotel amenities in the comfort of your private vacation home. Each property is meticulously equipped with premium features and services to ensure an exceptional stay.
Let our dedicated concierge team craft your perfect island experience. From private chefs to sunset cruises, we'll help you create unforgettable memories with curated activities and exclusive adventures tailored to your preferences.
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!
Greg
6/5/2026
The house was beautiful, words can’t describe it. The proximity to a nice quiet beach, perfect. The attention to detail in the house, plus the service from the concierge, if needed, made it best family trip we’ve been. We’ll be back.
High end in all aspects
Exclusive Vacations staff
Thank you for the wonderful feedback on Sweet Caroline by Exclusive Vacations, Alan. We’re delighted to hear the home delivered a truly elevated experience in every way. From the thoughtful design to the refined details throughout, Sweet Caroline was created to feel effortlessly luxurious and completely relaxing. It was a pleasure hosting you, and we’d be honored to welcome you back for another exceptional island stay.
Beautiful home with easy close access to the beach.
Exclusive Vacations staff
Hi, Rene, thank you for staying with AMI Locals at Sweet Caroline! We’re so glad you enjoyed the beautiful home and the easy access to the beach. That close to the sand is always a win on Anna Maria Island. We appreciate you choosing AMI Locals and would love to welcome you back for another island escape in the future!!
Anastasia T.
10/27/2025
The accommodation is close to the beach and Pine Ave (restaurants, shops, and the AMI pier!) Everything about the house was so lovely and loved the pool! Definitely recommend for a fun girls getaway or a family stay.
Andrea
10/27/2025
Love love love the house, everything about the location and amenities. When we contacted management, they were so quick to respond. It was one of the moat relaxing vacations I’ve ever had.
Christine C
10/27/2025
The property was better than the pictures. The pool and roof top deck were amazing. It was a short walk to the beach and had everything we needed for a beach day. Could not have asked for more for our family getaway. We will definitely be back.
Adam D.
10/27/2025
This rental was absolutely beautiful. Tastefully decorated and comfortably designed, it seems like the owner really thought through what his guests would enjoy while staying here. We all appreciated how sparkling clean this house was when we checked in, and we are crazy particular about that kind of thing! The views are incredible from the rooftop. The home is about a block away from the beach and has a private pool area that is better than any I have seen before. We really enjoyed our time here.
Caitlin
10/27/2025
Had the best time in Anna Maria Island. The house was beautiful and in the best location. Quick walk to the beach, the local restaurants and shops.
Lena
10/27/2025
This place is a lifetime experience! Gorgeous, inspiring, designed by professionals. I could write paragraph after paragraph and it would not give it justice. Move in and see for yourself - this place is all you could dream about.
House was perfect for our stay. Quick walk to the beach. Having a golf cart made getting around very easy
Exclusive Vacations staff
Thank you for the positive review, Kristen. We're glad to hear that our house was perfect for your stay and the golf cart made getting around convenient on our little island. It's great that our property's proximity to the beach was also a highlight. We look forward to welcoming you back in the future!
tdurr304
5/27/2025
This home is amazing and just as advertised. Beautifully decorated and in a great location. We enjoyed the pool and spa each and every day.Can’t say enough great things about this home.
Exclusive Vacations staff
We are so glad to hear you enjoyed the property, the pool and the spa are for sure highlights! We appreciate your review and hope to host you again in the near future!
Anastasia T.
4/30/2024
The accommodation is close to the beach and Pine Ave (restaurants, shops, and the AMI pier!) Everything about the house was so lovely and loved the pool! Definitely recommend for a fun girls getaway or a family stay.
Exclusive Vacations staff
Anastasia, thank you for your wonderful review! We're thrilled to hear that you enjoyed our accommodation and found it to be close to the beach and Pine Ave with its restaurants, shops, and the AMI pier. It's fantastic to hear that everything about the house was lovely and that you loved the pool as well. We appreciate your recommendation for both a fun girls getaway and a family stay. We hope to have the pleasure of hosting you again in the future! If you have any further comments or questions, please feel free to let us know.
Christine C.
1/27/2024
The property was better than the pictures. The pool and roof top deck were amazing. It was a short walk to the beach and had everything we needed for a beach day. Could not have asked for more for our family getaway. We will definitely be back.
Exclusive Vacations staff
Christine, thank you for your wonderful feedback! We're thrilled to hear that the property exceeded your expectations and that you found the pool and rooftop deck amazing. It's fantastic that the location was convenient for a short walk to the beach and that the property had everything you needed for a perfect beach day. We're delighted that your family getaway was a success, and we can't wait to welcome you back again in the future. If there's anything else we can do to make your next stay even more enjoyable, please don't hesitate to let us know. We appreciate your feedback and look forward to hosting you again!
Verified traveler
11/4/2023
We had a great stay at this property. The location was ideal and the house was beautiful and clean. Wouldn’t change anything!
Exclusive Vacations staff
Thank you for taking the time to share your wonderful experience, Elizabeth. We are glad you enjoyed your stay and hope to welcome you back soon!
Mike V
10/26/2023
My family and I had an amazing Fall Break trip to Anna Maria. We usually go to Captiva, but couldn't due to Hurricane Ian. This was our first trip to Anna Maria, we hit it out of the park with Sweet Caroline! This house is top of the line luxury! I loved the outdoor space, great pool, jacuzzi, even used the putting green! The beach is just a block away, and it was so fun watching the neighbors coming and going on their boats in the canal behind the house! You can't beat the rooftop deck for sunset and drinks! The little kids loved the slide in the bunk room! This was just an amazing house for our family vacation and I can't wait to come back!
Adam D
2/21/2023
This rental was absolutely beautiful. Tastefully decorated and comfortably designed, it seems like the owner really thought through what his guests would enjoy while staying here. We all appreciated how sparkling clean this house was when we checked in, and we are crazy particular about that kind of thing! The views are incredible from the rooftop. The home is about a block away from the beach and has a private pool area that is better than any I have seen before. We really enjoyed our time here.
Adam D.
2/21/2023
This rental was absolutely beautiful. Tastefully decorated and comfortably designed, it seems like the owner really thought through what his guests would enjoy while staying here. We all appreciated how sparkling clean this house was when we checked in, and we are crazy particular about that kind of thing! The views are incredible from the rooftop. The home is about a block away from the beach and has a private pool area that is better than any I have seen before. We really enjoyed our time here.
Exclusive Vacations staff
Adam, thank you for taking the time to share your experience with us. We are glad you were comfortable and enjoyed the rooftop views. We hope to have the opportunity to host you again in the future!
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Today
Meet Tamara
Your Personal Concierge
Exclusive Experiences
Your Personal Concierge Service
From the moment you book until the day you depart, Tamara and her team are here to ensure every aspect of your stay is seamless and extraordinary. Whether you're seeking restaurant recommendations, planning special celebrations, or wanting your kitchen fully stocked upon arrival, we're here to make it happen.
Transportation
Convenient airport transfers to and from your rental
Grocery Delivery
Fully stocked groceries upon arrival
Island Adventures
Dolphin tours, sunset cruises, and sandbar excursions
Boat/Jet Ski Rentals
Chartered yachts to self captained boat rentals
Private Chef/Catering
Enjoy personalized culinary experiences in your rental
Rentals
From watersport rentals to baby gear, we have you covered
Photography
Document your memories with a beach photoshoot
Fishing Trips
Enjoy a day on the water catching incredible fish
Have a Question about Sweet Caroline?
Ask anything in reference to vacationing at this property that you would like to know
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
Posted: 6/5/2026
5
Unreal trip
The house was beautiful, words can’t describe it. The proximity to a nice quiet beach, perfect. The attention to detail in the house, plus the service from the concierge, if needed, made it best family trip we’ve been. We’ll be back.
Greg
Posted: 6/5/2026
5
High end in all aspects
Alan
Posted: 5/10/2026
Thank you for the wonderful feedback on Sweet Caroline by Exclusive Vacations, Alan. We’re delighted to hear the home delivered a truly elevated experience in every way. From the thoughtful design to the refined details throughout, Sweet Caroline was created to feel effortlessly luxurious and completely relaxing. It was a pleasure hosting you, and we’d be honored to welcome you back for another exceptional island stay.
Exclusive Vacations staff
5
Beautiful home with easy close access to the beach.
Rene
Posted: 12/28/2025
Hi, Rene, thank you for staying with AMI Locals at Sweet Caroline! We’re so glad you enjoyed the beautiful home and the easy access to the beach. That close to the sand is always a win on Anna Maria Island. We appreciate you choosing AMI Locals and would love to welcome you back for another island escape in the future!!
Exclusive Vacations staff
5
Close to everything!
The accommodation is close to the beach and Pine Ave (restaurants, shops, and the AMI pier!) Everything about the house was so lovely and loved the pool! Definitely recommend for a fun girls getaway or a family stay.
Anastasia T.
Posted: 10/27/2025
5
Thank you for everything.
Love love love the house, everything about the location and amenities. When we contacted management, they were so quick to respond. It was one of the moat relaxing vacations I’ve ever had.
Andrea
Posted: 10/27/2025
5
Beach perfect
The property was better than the pictures. The pool and roof top deck were amazing. It was a short walk to the beach and had everything we needed for a beach day. Could not have asked for more for our family getaway. We will definitely be back.
Christine C
Posted: 10/27/2025
5
Fun place to stay
This rental was absolutely beautiful. Tastefully decorated and comfortably designed, it seems like the owner really thought through what his guests would enjoy while staying here. We all appreciated how sparkling clean this house was when we checked in, and we are crazy particular about that kind of thing! The views are incredible from the rooftop. The home is about a block away from the beach and has a private pool area that is better than any I have seen before. We really enjoyed our time here.
Adam D.
Posted: 10/27/2025
5
Highly recommend.
Had the best time in Anna Maria Island. The house was beautiful and in the best location. Quick walk to the beach, the local restaurants and shops.
Caitlin
Posted: 10/27/2025
5
This is literary all I could dream about!
This place is a lifetime experience! Gorgeous, inspiring, designed by professionals. I could write paragraph after paragraph and it would not give it justice. Move in and see for yourself - this place is all you could dream about.
Lena
Posted: 10/27/2025
5
House was perfect for our stay. Quick walk to the beach. Having a golf cart made getting around very easy
Kristen
Posted: 8/20/2025
Thank you for the positive review, Kristen. We're glad to hear that our house was perfect for your stay and the golf cart made getting around convenient on our little island. It's great that our property's proximity to the beach was also a highlight. We look forward to welcoming you back in the future!
Exclusive Vacations staff
5
Amazing Time / Amazing Stay
This home is amazing and just as advertised. Beautifully decorated and in a great location. We enjoyed the pool and spa each and every day.Can’t say enough great things about this home.
tdurr304
Posted: 5/27/2025
We are so glad to hear you enjoyed the property, the pool and the spa are for sure highlights! We appreciate your review and hope to host you again in the near future!
Exclusive Vacations staff
5
Close to everything!
The accommodation is close to the beach and Pine Ave (restaurants, shops, and the AMI pier!) Everything about the house was so lovely and loved the pool! Definitely recommend for a fun girls getaway or a family stay.
Anastasia T.
Posted: 4/30/2024
Anastasia, thank you for your wonderful review! We're thrilled to hear that you enjoyed our accommodation and found it to be close to the beach and Pine Ave with its restaurants, shops, and the AMI pier. It's fantastic to hear that everything about the house was lovely and that you loved the pool as well. We appreciate your recommendation for both a fun girls getaway and a family stay. We hope to have the pleasure of hosting you again in the future! If you have any further comments or questions, please feel free to let us know.
Exclusive Vacations staff
5
Beach perfect
The property was better than the pictures. The pool and roof top deck were amazing. It was a short walk to the beach and had everything we needed for a beach day. Could not have asked for more for our family getaway. We will definitely be back.
Christine C.
Posted: 1/27/2024
Christine, thank you for your wonderful feedback! We're thrilled to hear that the property exceeded your expectations and that you found the pool and rooftop deck amazing. It's fantastic that the location was convenient for a short walk to the beach and that the property had everything you needed for a perfect beach day. We're delighted that your family getaway was a success, and we can't wait to welcome you back again in the future. If there's anything else we can do to make your next stay even more enjoyable, please don't hesitate to let us know. We appreciate your feedback and look forward to hosting you again!
Exclusive Vacations staff
5
Beautiful house great location
We had a great stay at this property. The location was ideal and the house was beautiful and clean. Wouldn’t change anything!
Verified traveler
Posted: 11/4/2023
Thank you for taking the time to share your wonderful experience, Elizabeth. We are glad you enjoyed your stay and hope to welcome you back soon!
Exclusive Vacations staff
5
Sweet Caroline... good times never seemed so good!
My family and I had an amazing Fall Break trip to Anna Maria. We usually go to Captiva, but couldn't due to Hurricane Ian. This was our first trip to Anna Maria, we hit it out of the park with Sweet Caroline! This house is top of the line luxury! I loved the outdoor space, great pool, jacuzzi, even used the putting green! The beach is just a block away, and it was so fun watching the neighbors coming and going on their boats in the canal behind the house! You can't beat the rooftop deck for sunset and drinks! The little kids loved the slide in the bunk room! This was just an amazing house for our family vacation and I can't wait to come back!
Mike V from Cape Coral, FL
Posted: 10/26/2023
5
Amazing home
This rental was absolutely beautiful. Tastefully decorated and comfortably designed, it seems like the owner really thought through what his guests would enjoy while staying here. We all appreciated how sparkling clean this house was when we checked in, and we are crazy particular about that kind of thing! The views are incredible from the rooftop. The home is about a block away from the beach and has a private pool area that is better than any I have seen before. We really enjoyed our time here.
Adam D from Chicago
Posted: 2/21/2023
5
Fun place to stay
This rental was absolutely beautiful. Tastefully decorated and comfortably designed, it seems like the owner really thought through what his guests would enjoy while staying here. We all appreciated how sparkling clean this house was when we checked in, and we are crazy particular about that kind of thing! The views are incredible from the rooftop. The home is about a block away from the beach and has a private pool area that is better than any I have seen before. We really enjoyed our time here.
Adam D.
Posted: 2/21/2023
Adam, thank you for taking the time to share your experience with us. We are glad you were comfortable and enjoyed the rooftop views. We hope to have the opportunity to host you again in the future!
