Carefree Cay

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

We are delighted to hear that you and your family had a wonderful time during your stay. It's fantastic that the house met your expectations, with the clean accommodations, great amenities like the pool and hot tub, and the convenient location close to the beach and Pine Street. We're also pleased to know that the host was responsive to your needs. Thank you for the recommendation, and we hope you'll consider staying with us again in the future.

Anna Maria Paradise staff

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

Thank you for choosing us for your recent stay! Every review and every star you give us makes a huge difference to our success. If you enjoyed your stay, we'd love your 5-star review! We hope to host you again in the future!

Anna Maria Paradise staff

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: 2/15/2025

Even better then expected.

Michael S. - Posted: 9/28/2024

Thank you for your kind words! We’re thrilled to hear that your stay exceeded your expectations. It means so much to us that you had such a positive experience, and we hope to welcome you back for another amazing visit soon!

Anna Maria Paradise staff

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

Sean, we're thrilled to hear that you and your family absolutely loved our property! It's wonderful that it had all the amenities you needed, was conveniently close to the beach, and that you enjoyed the beautiful pool. Thank you for sharing your positive experience, and we hope to welcome you all back for another fantastic stay in the future!

Anna Maria Paradise staff

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

Kathy, thank you for your positive review! We're thrilled to hear that you enjoyed the great location of our property, with its proximity to the beach, shopping, and restaurants. It's wonderful that you were able to walk to most places during your stay. We're glad you found the heated pool and hot tub enjoyable, especially on cooler days. We hope to welcome you back again in the future!

Anna Maria Paradise staff

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

Patty, we're thrilled to hear that you had a wonderful first trip to AMI! It's fantastic that our unit's location was perfect for your needs, allowing easy access to the beach, restaurants, and shopping. We're glad that our team was responsive and excellent to work with, ensuring a smooth and enjoyable experience for you. Thank you for your recommendation, and we would love to welcome you back again in the future!

Anna Maria Paradise staff

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

Carol, thank you for your kind words! We're thrilled to hear that you enjoyed your stay at our beautiful home and that you found all the amenities to your satisfaction. It's wonderful that you were able to relax and unwind in the spa and pool, and that the proximity to the beach and city pier added to your enjoyment. We're glad that you appreciated the local restaurants and that our team kept in touch throughout your stay. We look forward to welcoming you back again in the future for a longer stay! Thank you for choosing to spend your quiet week with us. If there's anything else we can do to make your next visit even more enjoyable, please don't hesitate to let us know. We appreciate your feedback!

Anna Maria Paradise staff

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

William, thank you for sharing your experience with us! We're thrilled to hear that you and your family had an amazing time at the house and that it met your expectations. It's wonderful to know that the location near the beach was convenient for you, especially with toddlers, and that you enjoyed the relaxing pool area. We appreciate your feedback regarding the amenities, including the pack 'n play and a way to block off the steps going down into the basement. We'll definitely take your suggestions into consideration to improve the experience for future guests, especially those with young children. Thank you for choosing our property for your family vacation, and we hope to welcome you back again soon! If there's anything else we can do to make your next stay even more enjoyable, please don't hesitate to let us know. We look forward to hosting you again in the future!

Anna Maria Paradise staff

Quick access to the beach and great pool. Could use new beach chairs.

Rachel D. - Posted: 10/13/2023

Rachel, thank you for your feedback! We're glad to hear that you enjoyed the quick beach access and the pool. We appreciate your suggestion about the beach chairs and will pass this on to our team. If you have any other specific preferences or requests for your next stay, feel free to let us know. We strive to provide a comfortable and enjoyable experience for our guests. Thank you for choosing our property, and we hope to host you again in the future!

Anna Maria Paradise staff

Very nice and peaceful place. Amazing beach. We will probably return.

Ralph W. - Posted: 5/29/2023

Thank you for taking the time to share your experience with us, Ralph. We are glad you enjoyed your stay and hope to welcome you back soon!

Anna Maria Paradise staff

Great house and close to the beach. Beautiful private backyard with pool and hot tub.

Amanda L. - Posted: 2/18/2023

Amanda, thank you for taking the time to share your experience with us. We are glad you enjoyed the home, pool, hot tub, and location. We hope to host you again in the future!

Anna Maria Paradise staff

Loved the home, pool, hot tub, and location. Worked well for our group. The outside bathroom was great.

David B. - Posted: 6/11/2021

The location, gorgeous private pool, and fun beachy furnishings were all fantastic. Our family of 6 loved it.

lynsey p. - Posted: 5/28/2021

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: 5/9/2021

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: 3/10/2021

House was better than pictures. Very roomy and cozy. Had everything we needed. Will definitely return. Bottom entertainment room was a major plus. Pool and Jacuzzi were great.

Jean Carlo L. - Posted: 8/31/2020

Thank you so much for your feedback. Carefree Cay is indeed an amazing home. We’re glad it worked out so well for you and your family Please come see us again!

Anna Maria Paradise staff

My family enjoyed every minute in this house! The pool and backyard was fabulous. The rec room for the kids (I should say adult Kids) provides a space to allow them to stay up late and not keep others awake. The location to the beach is super close to walk. The property had a wagon which was PERFECT! And we were so close to all the places we loved to eat! I would rent this house again!

Sharon D. - Posted: 8/9/2020

Thank you for the great review Sharon! We are so glad to hear that you had a great stay at Carefree Cay!

Anna Maria Paradise staff

The house was clean and the landscaping and pool were beautiful. We loved the beach decor! Our beach was gorgeous and we enjoyed the spectacular sunsets every night. We saw manatee in the clear blue/green waters and the kids found handfuls of sand dollars! The Anna Maria pier opened during our stay. Thank you for sharing your beautiful home with us!

Eric D. - Posted: 7/5/2020

PERFECT place for a vacation on AMI! Ideal location, close to the gorgeous beach and downtown Pine Avenue. Our family of four had plenty of room to eat, sleep and relax in this immaculate home. Layout was fantastic! After soaking up the sun at the beautiful beach, we went for a dip in the refreshing pool right in the backyard. Kitchen stocked with every appliance you can imagine! Openness of kitchen was wonderful.. Beds very comfortable. Super fun basement with shuffleboard opened right to the backyard with pool, hot tub, outdoor bathroom and closet packed with every beach / pool item you need. Plenty of towels, sheets, and pillows. We are already planning to book again so we can make AMI a family tradition!

Gin R. - Posted: 12/16/2019

Thank you so so much for your wonderful review of Carefree Cay. It is indeed a comfortable and stylish home with so many fine amenities. We thrilled that you describe it as perfect. Give us a call as you plan your next visit to Anna Maria Island, we would love to have you stay with us again!

Anna Maria Paradise staff

Great, Absolutely zero negative things to say about this property.

becky v. - Posted: 11/4/2019

Great location, can easily walk to shops & restaurants. Short 2 min walk to beach. Lovely property as pictured. Liked the shade around pool & also sun deck if you wanted that. Would rent again!

Janet O. - Posted: 9/23/2019

We were pleasantly surprised upon arrival. This home was very comfortable and pretty clean. There were a few items of clothing left in two of the bedroom dressers and both of the main floor bathrooms could use a more detailed cleaning behind toilets , baseboards , and in the master bath shower along the grout seams and at base of shower door. Don't let that deter you, the house was very clean other than those few things . It was perfectly decorated inside and also the pool area and complete outdoor landscaping were beautiful . The pool area however does not get much sun for laying out or sunbathing at that level. You can layout on the top deck and also the beach is a very short walk. We enjoyed being close to the little shops and also many choices for restaurants. We walked to Pine Ave and also rented a gulf cart for the week that we used when going out to eat or taking short rides around the island. This was our first time at Anna Maria Island and we will definitely return!! We have already looked at homes for about 25 people to have others join in next year! This was a home away from home. It was a very good choice of home and also location on the island .

Christine W. - Posted: 8/11/2019

We enjoyed the rental and our stay in Florida.

Colette B. - Posted: 6/23/2019

The home was amazing and brought our family much joy. The back yard is a paradise. The short 1-2 minute walk to the beach was perfect. The road to get to the beach wasn’t very busy so there wasn’t much stress about walking on the road. Being only a block from pine ave was great as well, with lots to see and do there. Great island feel and would definitely recommend staying here to anyone.

Broc H. - Posted: 4/15/2019

Great house. We will use it again.

Scott S. - Posted: 4/14/2019

This house is so clean, modern and beach! 2 min walk to a gorgeous clean and open beach. A few blocks to shops and restaurants. Just perfect. We thoroughly enjoyed our stay.

Julie S. S. - Posted: 12/9/2018

Thank you so much for letting us know about your stay with us at Carefree Cay. We're thrilled that you enjoyed the home and the closeness to the beach. We hope to have you stay with us again!

Anna Maria Paradise staff

would highly recommend this house to anyone , exceeded our expectations , location was within a minute or two walk down to the beach we will be back to stay again in the future !!!

Amos G. - Posted: 8/3/2018