Book Carefree Cay

3 bedrooms · 4 beds · 2.5 bathrooms · Sleeps 6

HousePet friendlyHot Tub

Where you’ll sleep

King

Bedroom 1

King

Bedroom 2

2x Full over Full over Full Bunk Bed

Bedroom 3

Your carefree Anna Maria Island escape with a private pool, spa, and game room, just steps from the beach.

–Private backyard oasis with heated pool and spa
–Indoor game room with pool table and shuffleboard
–Prime location: short walk to beach, shops, and restaurants

Carefree Cay is located on a quiet residential street on the north end of Anna Maria Island with an immaculate backyard with a pool and in-ground spa!

About this property

Carefree Cay by Anna Maria Island Accommodations
Home in Anna Maria, Florida
VR16-000412

Welcome to Carefree Cay, a three-bedroom, two-and-a-half-bath vacation home in the north end of Anna Maria Island. Just a short two-block stroll from the soft white sands of Anna Maria Beach and the charming shops and restaurants along Pine Avenue, this spacious retreat offers a private pool, spa, shuffleboard, and inviting indoor and outdoor living spaces. Designed with families and groups in mind, Carefree Cay has everything you need for a carefree and memorable Anna Maria Island getaway.

Highlights
• 2-Minute Walk to Anna Maria Beach
• 3 Bedrooms / 2.5 Bathrooms
• 2 Kings, 1 Full over Full Bunk
• Private Heated Pool and Spa
• Outdoor Dining with BBQ Grill
• Deck for sun lounging or star gazing in the peaceful evenings
• Indoor Shuffleboard
• Pool table
• Poolside TV
• Designated outside golf cart charging outlet
• Washer and Dryer
• Steps to Pine Avenue Shops and Restaurants
• Dog friendly (with approval, fee, and restrictions)
• Parking for 3 Vehicles

Step into your private backyard oasis where a heated pool and spa are surrounded by lush greenery and plenty of lounge seating. Fire up the BBQ grill and enjoy meals at the outdoor dining table, catch your favorite shows on the poolside TV, or relax with family and friends under the Florida sunshine. A designated outdoor golf cart charging outlet adds extra convenience for island exploring. For more fun, head indoors to the game area featuring a pool table, shuffleboard, and cozy seating.

Inside, the home is filled with tropical décor, natural light, and vibrant touches that make it feel both fun and relaxing. The main living room has plush seating and a large TV for family movies, while the second living area downstairs offers board games, shuffleboard, and an inviting spot to gather. The fully stocked kitchen includes all the essentials plus a breakfast bar for casual dining, and the dining table is ready for memorable meals after a day exploring the island.

The primary suite on the second floor is designed for relaxation with a king bed, flatscreen TV, and spa-inspired ensuite bathroom featuring a walk-in shower and soaking tub. Another upstairs bedroom has a king bed and ample closet space, while the third bedroom includes a set of full over full bunks, perfect for kids or additional guests. A cheerful hall bathroom with a shower/tub combo serves the guest rooms, and a washer and dryer are available for added convenience.

Room Details
• Primary Bedroom (2nd Floor): King bed, ensuite bathroom with walk-in shower and soaking tub
• Second Bedroom (2nd Floor): King bed
• Third Bedroom (2nd Floor): Full over full bunks
• Hall Bathroom: Shower/tub combo

Carefree Cay offers parking for three vehicles and a location that makes exploring easy. Walk two blocks to Anna Maria Beach for sunny days on the sand, or head over to Pine Avenue for boutique shopping, local dining, and island attractions. Hop on the island trolley for a carefree ride to Holmes Beach, Bradenton Beach, and beyond.

With its spacious layout, private pool and spa, fun game spaces, and prime location near beaches and shops, Carefree Cay by Anna Maria Island Accommodations is the perfect choice for your next island escape. Book today and start making unforgettable memories on beautiful Anna Maria Island!

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Please note: The garage is not available for guest use.

With host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). A maximum of two dogs are permitted with a maximum combined weight of 50 pounds. Breed restrictions apply. An additional pet fee will apply.

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.

This home is managed by AMI Accommodations, an Anna Maria Island property management company.

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 Accommodations 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.

full description

Managed by Anna Maria Island Accommodations

Holmes Beach, FL

4.7★

4,660 reviews

Make yourself at home on Anna Maria Island — beachfront, pool, and pet-friendly vacation rentals across the island's three communities, with personalized local service. Creating memories, one stay at a time.

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www.annamariaparadise.com

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Guest Reviews

4.8★ · 5 reviews

★★★★★

“It was a pleasure to host Daniel! We hope to host them again in the future! Had an incredible stay, beautiful decorated home with an amazing outdoor pool area. Could not have asked for more”

Daniel · Oct 2025

★★★★★

“Caleb was a pleasure !”

Caleb · Jul 2025

★★★★★

“Great location- close to beach and close to Pine St. For shopping and restaurants! We walked most everywhere. Heated pool and hot tub were nice for the cooler days. Very responsive property managers too. Stairs are only way in/out which was no issue for us, just good to be aware of if that’s an issue for anyone in your group. Overall a very nice rental!”

Kathy · Feb 2024

Good for

PetsBeach daysRemote workHot tub nights

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Carefree Cay

Carefree Cay

Carefree Cay

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About this property

Managed by Anna Maria Island Accommodations

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