House in Anna Maria Island, FL
6 guests · 3 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
High-end valueWell priced for this area
About this house rental
Carefree Cay by Anna Maria Island Accommodations
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.
Pets allowed with prior permission. (2 dogs max up to 100lbs) Not sure how you want to word or place this.
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.
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!
-
Please note: The garage is not available for guest use.
Pets allowed with prior permission. (2 dogs max up to 100lbs) Not sure how you want to word or place this.
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.
Amenities
Non-smoking
Pets allowed
Family friendly
Map of Anna Maria Island, FL
Ratings and reviews
10 / 10Outstanding·Jun 2026
This house was perfect for my husband and I, and our two daughters who are 22 and 14. We also had our small dog with us.The outdoor space was so much fun, and so relaxing. It was perfect for swimming all the time, and having lunch breaks outside at the table. When we had a few episodes of rain, we enjoyed being able to have the doors open from inside to outside and be able to play pool and hang out and watch TV. We’ve been coming to Anna Maria Island for nine years, and this by far was the cleanest house we’ve ever stayed in. Communication with the owners when we had one issue with a smoke detector going off, was fixed very quickly.I will say there are a few things in the house that are outdated. The washer and dryer worked well, but are definitely showing their age. The cabinets and drawers in the master bathroom are also showing some age. Outside, it was nice to be able to find chairs and floats to use at the beach at the pool. However, the chairs are starting to show a little age as well as the wagon. I also wish, that there were lounge chairs down by the pool instead of just regular chairs. We did move one down from the deck off the kitchen for our stay, but did return it back to its original place before we left.With all that being said, none of that would keep me from ever coming back. This house was wonderful, and we’re actually trying to decide when we’re going to come back next year, and hope to be able to get this house again.
10 / 10Outstanding·Jun 2026
The property was beautiful and amazing. My family very much enjoyed staying and spending our vacation here. Since booking there was renovations done that added bigger beds which was definitely a plus. The beach access with just a short walk and the accommodations of this rental saved us from having to purchase beach chairs, wagon, and etc. I would highly recommend this location and would love to stay again in the future.
10 / 10Outstanding·May 2026
Great spot! Close to the beach. The house is nice. We were surprised to only find 2 beach chairs and no umbrella. I called and they were willing to bring one over right away. I went back to the house from the beach and it took about 2 hours for it to arrive. They had told me 15 min. I called and was told they were short staffed which is fine- I just wish they were honest that it would take a bit when I called the first time. Overall it was an awesome getaway for the 4 of us!
10 / 10Outstanding·Apr 2026
Perfect location, quick walk to beach and restaurants. Backyard is very private with a beautiful spa that feeds into the pool to keep it the perfect temperature. Would definitely stay here again. Host was very responsive! The only thing missing was a beach umbrella, otherwise 10/10!
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Top rated by guests
10Outstanding
(43 Ratings)
"This house was perfect for my husband and I, and our two daughters who are 22 and 14. We also had our small dog with us.The outdoor space was so much fun, and so relaxing. It was perfect for swimming ..."
Letisha C.Don't miss out! Price and availability may change
