Overview
Guests 8 guests
Bedroom 4 bedrooms
Bathroom 4.5 bathrooms
Pets Allowed Yes Pets
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.

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.
Guest Sleeping Arrangements
Master Suite
Master Suite 1
Master Bathroom
Chevron
Chevron

2nd floor: Step into a luxurious master bedroom in Florida, a sanctuary where sophisticated elegance meets relaxed coastal living.

  • Checkmark King Bed
  • Checkmark Balcony Access
  • Checkmark Smart TV
  • Checkmark Ensuite bathroom with shower
King Suite 1
King Suite 1.1
King Suite 1 Bathroom
Chevron
Chevron

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.

  • Checkmark King Bed
  • Checkmark Balcony Access
  • Checkmark Smart TV
  • Checkmark Ensuite bathroom with shower
King Suite 2
King Suite 2.1
Master Suite 2 Balcony
King Suite 2 Bathroom
Chevron
Chevron

2nd floor luxurious king bedroom designed for relaxation, complete with a calming ensuite bathroom that features a spacious walk-in shower.

  • Checkmark King Bed
  • Checkmark Balcony Access
  • Checkmark Smart TV
  • Checkmark Ensuite bathroom with shower
Bunk Room
Bunk Room 1
Bunk Room 2
Bunk Room Bathroom
Chevron
Chevron

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.

  • Checkmark Full Bunk over a Twin Bunk
  • Checkmark Balcony Access
  • Checkmark Smart TV
  • Checkmark Slide
  • Checkmark Ensuite bathroom with bathtub and shower
Chevron
Chevron
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
Availability
April 2026
S M T W T F S
      1 2 3 4
5 6 7 8 9 10 11
12 13 14 15 16 17 18
19 20 21 22 23 24 25
26 27 28 29 30    
May 2026
S M T W T F S
          1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31            
June 2026
S M T W T F S
  1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30        
July 2026
S M T W T F S
      1 2 3 4
5 6 7 8 9 10 11
12 13 14 15 16 17 18
19 20 21 22 23 24 25
26 27 28 29 30 31  
August 2026
S M T W T F S
            1
2 3 4 5 6 7 8
9 10 11 12 13 14 15
16 17 18 19 20 21 22
23 24 25 26 27 28 29
30 31          
September 2026
S M T W T F S
    1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30      
October 2026
S M T W T F S
        1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
November 2026
S M T W T F S
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30          
December 2026
S M T W T F S
    1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31    
January 2027
S M T W T F S
          1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31            
February 2027
S M T W T F S
  1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28            
March 2027
S M T W T F S
  1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30 31      
Selected Dates
Unavailable Dates
Today
Location
Map Marker
9306 Gulf Drive
Anna Maria, FL
Beach Access
1 minute walk
Pine Avenue
3 minute walk
Free Trolley
1 minute walk
SRQ Airport
30 minute drive
Guest Reviews Rating Rating Rating Rating Rating 5 (8 Reviews)
Anastasia T.
10/27/2025
Rating Rating Rating Rating Rating
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
Rating Rating Rating Rating Rating
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
Rating Rating Rating Rating Rating
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
Rating Rating Rating Rating Rating
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
Rating Rating Rating Rating Rating
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
Rating Rating Rating Rating Rating
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.
Mike V
10/26/2023
Rating Rating Rating Rating Rating
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
Rating Rating Rating Rating Rating
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.