House - Rating 5 (16)

Carefree Cay


Bedroom 3 bedrooms
Bathroom 2 baths
Half Bathroom 1 half baths
Guests 6 guests
Pets Not Allowed Pets Not Allowed

  • Address: 217 Sycamore Ave
  • Location: Anna Maria
  • Type: House

Location Location

Description Description
Carefree Cay by Anna Maria Island Accommodations
217 Sycamore Avenue, Anna Maria, FL, 34216
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.

Availability Calendar Availability Calendar
Available
Unavailable
Check-In
Check-Out
December 2025
Su Mo Tu We Th Fr Sa
  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 2026
Su Mo Tu We Th Fr Sa
        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 2026
Su Mo Tu We Th Fr Sa
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 2026
Su Mo Tu We Th Fr Sa
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        
April 2026
Su Mo Tu We Th Fr Sa
      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
Su Mo Tu We Th Fr Sa
          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
Su Mo Tu We Th Fr Sa
  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
Su Mo Tu We Th Fr Sa
      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
Su Mo Tu We Th Fr Sa
            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
Su Mo Tu We Th Fr Sa
    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
Su Mo Tu We Th Fr Sa
        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
Su Mo Tu We Th Fr Sa
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          
Swipe Swipe for Availability

Bedding Bedding
Bedroom 1
1 King

Attached Bathroom

Bedroom 2
1 King

Bedroom 3
2 Twin


Amenities 77 Amenities
Essentials
  • Air Conditioning
  • Beach Chairs Provided
  • Beach Towels Included
  • Bed Linens
  • Dryer
  • Free Wifi
  • Hair Dryer
  • Heating
  • Hospital Close By
  • Hot Water
  • Iron and Ironing Board
  • Long Term Stays Allowed
  • Pets Allowed
  • Private Entrance
  • Required Stairs
  • Towels
  • Washer
  • Wifi
Exterior
  • Backyard
  • Balcony
  • BBQ Grill
  • Fenced Yard
  • Heated Pool
  • Hot Tub or Spa
  • Outdoor Dining Area
  • Outdoor Seating
  • Outdoor Shower
  • Private Pool
  • Sun Loungers
  • Uncovered Deck
Fun and Entertainment
  • Board Games
  • Books and Reading Material
  • Game Room
  • Games
  • Smart TV
  • TV
  • TV with Cable
Home Safety
  • Carbon Monoxide Detector
  • Contactless Check-In
  • Deadbolt Lock
  • Fire Extinguisher
  • Keyless Lock
  • Smoke Detector
Interior
  • Bathtub
  • Ceiling Fans
  • Clothes Hangers
  • Clothing Storage
  • Dedicated Workspace
  • Desk
  • Full Kitchen
  • Living Room
Kitchen
  • Baking Sheet
  • BBQ Utensils
  • Blender
  • Coffee Maker
  • Dining table
  • Dishes and Utensils
  • Dishwasher
  • Freezer
  • Hot Water Kettle
  • Ice Maker
  • Keurig Coffee Maker
  • Kitchen Island
  • Microwave
  • Oven
  • Pots and Pans
  • Refrigerator
  • Stove
  • Toaster
  • Wine Glasses
Location
  • Anna Maria
  • Anna Maria Island
  • Beach Access Nearby
  • Less than a 5-minute walk to the beach
  • Residential Street
  • Walking Distance to Beach
Parking
  • Three (3) Parking Spaces

Reviews Rating 5 (16) Reviews
Rating 5
Excellent Location
We had a great time here for a week with the family. The house was very clean and the pool and hot tub was really great. It's one block to the beach and one block to Pine street where a lot of stores and restaurants. It's really an amazing location. The pool and hot tub were really great and the host was really responsive to any requests. Highly recommend this place.
Jeff - Posted: 4/21/2025
Rating 5
Perfect Beach House
This was our first time on AMI, and this beach house was perfect. Not only is it very nicely set up, but it is well appointed, clean, and a very short walk to the beach. A
Lauren - Posted: 4/12/2025
Rating 5
Great Break from the MI Winter
Beautiful home in a great location. Smooth check in with great communication from management company throughout. Pictures are an accurate representation of the place. Very spacious and clean. Comfortable beds. Heated in ground pool and spa were perfect with convenient outdoor bathroom and shower. Short walk to beach and place provided a wagon, cooler, 3 beach chairs, umbrella.Safety features of door alarms to pool were nice but we did have to rent a gate for an open stairway to the basement. Would strongly recommend and stay again!
Timothy E. - Posted: 2/16/2025
Rating 5
Paradise...
Even better then expected.
Michael S. - Posted: 9/28/2024
Rating 5
The Beginning of a Tradition
My wife, kids, and I all absolutely loved this property! It had all of the amenities that we needed, it was incredibly close to the beach (less than a 3 min walk), and the pool was beautiful. All in all we could not have asked for more!!
Sean R. - Posted: 5/26/2024
Rating 5
Great Location!
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 E., Portage - Posted: 2/15/2024
Rating 5
Great stay
This was our first trip to AMI and we thoroughly enjoyed it! Our rental unit was in a perfect location, walkable to the beach, restaurants, and shopping. Property MGMT was responsive to a minor issue and excellent to work with. Highly recommend!
Patty S. - Posted: 2/5/2024
Rating 5
Beautiful home with spa
Beautiful home with all amenities. The spa and pool were nice and relaxing. 5 minute walk to the beautiful beach and 10 minutes to the city pier. Gorgeous area. Lots of local restaurants to try. AMI kept in touch at all times. We just wish we’d stayed longer and we will definitely be back again. Thank you for a nice quiet week.
Carol D. - Posted: 1/29/2024
Rating 5
Beautiful house in the perfect location
My wife and I, along with our two toddlers, had an amazing time in this house. It was very clean and as described in the listing. Perfect location a block from the beach which made it so convenient with toddlers. The pool area was just a relaxing quiet setting. A few blocks walk to cute little shops and restaurants too. We really enjoyed our time and hope to go back. The only two things I wish they had was possibly a pack ‘n play for younger ones to sleep in, and maybe a way to block or close off the step going down into the basement- I had to barricade the top of the steps with chairs.
William E. - Posted: 10/18/2023
Rating 5
Fall Breah
Quick access to the beach and great pool. Could use new beach chairs.
Rachel D. - Posted: 10/13/2023
Rating 5
Anna Maria Island
Very nice and peaceful place. Amazing beach. We will probably return.
Ralph W. - Posted: 5/29/2023
Rating 5
Winter getaway
Great house and close to the beach. Beautiful private backyard with pool and hot tub.
Amanda L. - Posted: 2/18/2023
Rating 5
Great house and location
Loved the home, pool, hot tub, and location. Worked well for our group. The outside bathroom was great.
David B. - Posted: 6/12/2021
Rating 5
Perfect for our family!
The location, gorgeous private pool, and fun beachy furnishings were all fantastic. Our family of 6 loved it.
lynsey p. - Posted: 5/29/2021
Rating 5
Great house!
We had a great time staying at this property while on AMI. It had everything we needed for our stay and we enjoyed the short distance to the beach, the quiet area, being close to shops and restaurants and especially the pool and hot tub!
Carrie C., Omaha, ne - Posted: 5/10/2021
Rating 5
Carefree Cay - Feb 2022
Great property, the location is absolutely fabulous, close to beach and shops. Would stay here again and again. One suggestion, WiFi is not currently sufficient. It cut out quite a few times on us, and does not reach many parts of the property (downstairs, pool, deck, etc).
Timothy W. - Posted: 3/11/2021
Swipe Swipe for More Reviews

Have a question? Customer Questions & Answers Have a question? Customer Questions & Answers

Want to know specifics? Ask anything about this specific property that you would like to know...

Example: "Is the balcony screened in?" or "Is there a toaster oven?"


Request More Info Request More Info

Want to know specifics? Ask anything in reference to vacationing at this property that you would like to know...

Example: "Are fresh linens provided?"

I agree