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Beautiful North-End Home! Pool with In-ground Spa, Shuffleboard, Near Beach and
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Reviews
10 out of 10
Exceptional
3 bedrooms 2+ bathrooms Sleeps 6 160.9 sq m
Popular amenities
Explore the area

Anna Maria, FL
- Anna Maria City Pier11 min walk
- Anna Maria Beach17 min walk
- Bean Point Beach1 min drive
- Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)40 min drive
Rooms & beds
3 bedrooms (sleeps 6)
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed
Bedroom 3
2 Single Beds
2 bathrooms, 1 half bathroom
Bathroom 1
Bathroom 2
Half Bathroom 1
Spaces
Deck or patio
Kitchen
Office
Balcony
About this property
Beautiful North-End Home! Pool with In-ground Spa, Shuffleboard, Near Beach and
Carefree Cay by Anna Maria Island Accommodations
217 Sycamore Avenue, Anna Maria, FL, 34216
VR16-000412
Welcome to Carefree Cay, a spacious vacation home nestled in the desirable north end of Anna Maria Island. This three bedroom, two and a half bath retreat offers a private pool, in-ground spa, and lush outdoor living, perfect for families or groups seeking relaxation and fun. Located just a short walk from pristine Gulf beaches, boutique shops, waterfront dining, and a trolley stop, Carefree Cay provides the ideal setting for an unforgettable island escape filled with sunshine, water adventures, and island charm.
Highlights
-3-minutes / 2 Blocks to Anna Maria Beach
-3 Bedroom / 2.5 Bathrooms
-2 Kings, 2 twin beds
-Private heated pool, in-ground spa
-Outdoor living space
-BBQ grill
-2 living areas
-Shuffleboard
-2 Blocks to Pine Avenue shops and waterfront restaurants
-Parking for 3 vehicles
Inside, the home offers a laid-back island atmosphere accented by tropical decor, vibrant colors, and natural light. The main living room features plush seating and a large TV, ideal for enjoying family movies or relaxing after a day on the water. The additional second living area downstairs boasts a beautiful beach mural, cozy sofas, a game table perfect for board games, and a shuffleboard, creating a perfect space for fun or quiet relaxation. The fully stocked kitchen includes essential appliances and a breakfast bar for casual dining.
Retreat to the primary bedroom, located on the second floor, with a king bed, a large TV, and a spa-like ensuite bathroom with a walk-in shower and luxurious soaking tub. The second bedroom also features a king bed and ample closet space, while the third bedroom has two twin beds, ideal for kids or additional guests. The hall bathroom, with a fun color scheme, offers a shower/tub combo and stylish fixtures. A washer and dryer are conveniently located nearby for freshening up your clothes.
Room Details
-Primary Bedroom (2nd floor): King bed, ensuite with walk-in shower and soaking tub
-Second Bedroom (2nd floor): King bed
-Third Bedroom (2nd floor): Two twin beds
Enjoy relaxing outside in your tropical backyard oasis. Dip in the private pool or unwind in the in-ground spa, surrounded by lush landscaping and plenty of loungers. The outdoor dining area and BBQ grill make meals in paradise easy and fun. Just two blocks from the beach and local shopping or dining on Pine Avenue, this home offers endless ways to enjoy the island’s natural beauty and vibrant community.
Book Carefree Cay today for a relaxing, water-accessible, family-friendly vacation. With its spacious outdoor spaces, water views, and close proximity to beaches, shops, and world-class dining, this home offers everything you need for a memorable Anna Maria Island experience. Reserve your dates now and start living your best island life!
-
Please note: The garage is not available for guest use.
There are no pets allowed in this home.
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.
217 Sycamore Avenue, Anna Maria, FL, 34216
VR16-000412
Welcome to Carefree Cay, a spacious vacation home nestled in the desirable north end of Anna Maria Island. This three bedroom, two and a half bath retreat offers a private pool, in-ground spa, and lush outdoor living, perfect for families or groups seeking relaxation and fun. Located just a short walk from pristine Gulf beaches, boutique shops, waterfront dining, and a trolley stop, Carefree Cay provides the ideal setting for an unforgettable island escape filled with sunshine, water adventures, and island charm.
Highlights
-3-minutes / 2 Blocks to Anna Maria Beach
-3 Bedroom / 2.5 Bathrooms
-2 Kings, 2 twin beds
-Private heated pool, in-ground spa
-Outdoor living space
-BBQ grill
-2 living areas
-Shuffleboard
-2 Blocks to Pine Avenue shops and waterfront restaurants
-Parking for 3 vehicles
Inside, the home offers a laid-back island atmosphere accented by tropical decor, vibrant colors, and natural light. The main living room features plush seating and a large TV, ideal for enjoying family movies or relaxing after a day on the water. The additional second living area downstairs boasts a beautiful beach mural, cozy sofas, a game table perfect for board games, and a shuffleboard, creating a perfect space for fun or quiet relaxation. The fully stocked kitchen includes essential appliances and a breakfast bar for casual dining.
Retreat to the primary bedroom, located on the second floor, with a king bed, a large TV, and a spa-like ensuite bathroom with a walk-in shower and luxurious soaking tub. The second bedroom also features a king bed and ample closet space, while the third bedroom has two twin beds, ideal for kids or additional guests. The hall bathroom, with a fun color scheme, offers a shower/tub combo and stylish fixtures. A washer and dryer are conveniently located nearby for freshening up your clothes.
Room Details
-Primary Bedroom (2nd floor): King bed, ensuite with walk-in shower and soaking tub
-Second Bedroom (2nd floor): King bed
-Third Bedroom (2nd floor): Two twin beds
Enjoy relaxing outside in your tropical backyard oasis. Dip in the private pool or unwind in the in-ground spa, surrounded by lush landscaping and plenty of loungers. The outdoor dining area and BBQ grill make meals in paradise easy and fun. Just two blocks from the beach and local shopping or dining on Pine Avenue, this home offers endless ways to enjoy the island’s natural beauty and vibrant community.
Book Carefree Cay today for a relaxing, water-accessible, family-friendly vacation. With its spacious outdoor spaces, water views, and close proximity to beaches, shops, and world-class dining, this home offers everything you need for a memorable Anna Maria Island experience. Reserve your dates now and start living your best island life!
-
Please note: The garage is not available for guest use.
There are no pets allowed in this home.
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.
Add dates for prices
Amenities
Pool
Hot tub
Kitchen
Washing machine
Dryer
Free WiFi
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House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Anna Maria
Located in Anna Maria, this holiday home is near the beach. The area's natural beauty can be seen at Bean Point Beach and Anna Maria Beach. Fish Hole Adventure Golf and H2O Watersportz are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Anna Maria, FL
What's nearby
- Anna Maria Island Museum and Historical Park - 5 min walk - 0.4 km
- Anna Maria City Pier - 11 min walk - 1.0 km
- Anna Maria Beach - 17 min walk - 1.5 km
- Bean Point Beach - 1 min drive - 0.7 km
- Bradenton Beach - 4 min drive - 2.4 km
Getting around
Restaurants
- Anna Maria Island Beach Cafe - 8 min drive
- The Sandbar Restaurant - 6 min walk
- Skinny's Place - 8 min drive
- Hurricane Hanks - 6 min drive
- The Waterfront Restaurant - 11 min walk
Frequently asked questions
About the host
Hosted by Anna Maria Island Accommodations

Languages:
English
Premier Host
They consistently provide great experiences for their guests
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