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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, Loved by Guests
Top 10% of guest reviews in this area
3 bedrooms2+ bathroomsSleeps 6160.9 sq m
Popular amenities
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
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
• 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 or relax with family and friends under the Florida sunshine. For more fun, head indoors to the game area with a 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.
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
• 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 or relax with family and friends under the Florida sunshine. For more fun, head indoors to the game area with a 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.
Add dates for prices
Amenities
Pool
Hot tub
Kitchen
Washing machine
Dryer
Pet-friendly
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- Pool
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10.0 out of 10, Exceptional, (90 reviews)
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
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 indicated that there is a carbon monoxide detector on the property
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
- Island Players - 3 min walk - 0.3 km
- Anna Maria Island Museum and Historical Park - 5 min walk - 0.4 km
- Bayfront Park - 9 min walk - 0.8 km
- Anna Maria City Pier - 11 min walk - 1.0 km
- Bean Point Beach - 12 min walk - 1.1 km
Getting around
Restaurants
- The Ugly Grouper - 6 min drive
- Anna Maria Island Beach Cafe - 8 min drive
- The Sandbar Restaurant - 6 min walk
- The Waterfront Restaurant - 11 min walk
- Ginny's & Jane E's - 6 min walk
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window9.8/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
Verified
10 Jan 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Jan 2026
Verified
10/10 Excellent
Erin S.
23 Jan 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Erin S.
Stayed 6 nights in Jan 2026
Verified
10/10 Excellent
Amanda L.
18 Feb 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Winter getaway
Amanda L.
Stayed 7 nights in Feb 2023
Verified
10/10 Excellent
Jeff J.
21 Apr 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent Location
Jeff J.
Stayed 7 nights in Apr 2025
Verified
8/10 Good
Richard S.
16 July 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Anna Maria
Richard S.
Stayed 7 nights in Jul 2022
Verified
10/10 Excellent
Lauren L.
12 Apr 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Beach House
Lauren L.
Stayed 6 nights in Apr 2025
Verified
10/10 Excellent
Ralph W.
29 May 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Anna Maria Island
Ralph W.
Stayed 6 nights in May 2023
Verified
10/10 Excellent
Rachel D.
13 Oct 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fall Breah
Rachel D.
Stayed 6 nights in Oct 2023
Verified
10/10 Excellent
Patty S.
5 Feb 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay
Patty S.
Stayed 6 nights in Jan 2024
Verified
10/10 Excellent
Michael S.
28 Sept 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Paradise...
Michael S.
Stayed 5 nights in Sep 2024
Verified
10/10 Excellent
Sean R.
26 May 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
The Beginning of a Tradition
Sean R.
Stayed 6 nights in May 2024
Verified
10/10 Excellent
Kathy E.
15 Feb 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Location!
Kathy E.
Stayed 7 nights in Feb 2024
Verified
10/10 Excellent
Carol D.
29 Jan 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home with spa
Carol D.
Stayed 6 nights in Jan 2024
Verified
10/10 Excellent
Timothy W.
11 Mar 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Carefree Cay - Feb 2022
Timothy W.
Stayed 21 nights in Jan 2021
Verified
10/10 Excellent
Timothy E.
16 Feb 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Break from the MI Winter
Timothy E.
Stayed 5 nights in Feb 2025
Verified
10/10 Excellent
William E.
18 Oct 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful house in the perfect location
William E.
Stayed 4 nights in Oct 2023
Verified
10/10 Excellent
Gin R.
16 Dec 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
PERFECT paradise!
Gin R.
Stayed 7 nights in Nov 2019
Verified
10/10 Excellent
David B.
12 June 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house and location
David B.
Stayed 7 nights in Jun 2021
Verified
10/10 Excellent
lynsey p.
29 May 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect for our family!
lynsey p.
Stayed 7 nights in May 2021
Verified
10/10 Excellent
Carrie C.
10 May 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house!
Carrie C.
Stayed 7 nights in May 2021
Verified
8/10 Good
Jeff R.
11 Feb 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, pool
Jeff R.
Stayed 14 nights in Jan 2021
Verified
10/10 Excellent
Jean Carlo L.
31 Aug 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Surpass our expectations!
Jean Carlo L.
Stayed 7 nights in Aug 2020
Verified
10/10 Excellent
Sharon D.
9 Aug 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic House
Sharon D.
Stayed 7 nights in Jul 2020
Verified
10/10 Excellent
Eric D.
6 July 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
This house and property are exactly as pictured on VRBO.
Eric D.
Stayed 7 nights in Jun 2020
Verified
10/10 Excellent
becky v.
5 Nov 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect
becky v.
Stayed 14 nights in Oct 2019
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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