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Beautiful North-End Home! Pool with In-ground Spa, Shuffleboard, Near Beach and

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An aerial view of a coastal residential area with a beach, houses, and clear blue waters.
A room with two blue sofas, a glass table, and a beach-themed painting.
A room with a beach mural, a ceiling fan, a blue sofa, a glass coffee table, and a red umbrella.
A backyard with a swimming pool, palm trees, and outdoor seating.
A two-story house with a wooden staircase, a garage, and palm trees.

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms3 bathroomsSleeps 61732 sq ft

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly

Explore the area

View in a map
Anna Maria, FL
  • Place, Bradenton Beach
    ‪3 min walk‬
  • Place, Anna Maria Island Museum and Historical Park
    ‪5 min walk‬
  • Place, Bean Point Beach
    ‪12 min walk‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪41 min drive‬

Room options

Similar properties

Dining
Compass Hotel by Margaritaville Anna Maria Sound
Bradenton
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
4.7 out of 5, Exceptional, 2,555 reviews
$169 nightly
The price is $191
Sep 20 - Sep 21
Total with taxes and fees
Compass Hotel by Margaritaville Anna Maria Sound

About the neighborhood

Anna Maria

With a stay at this vacation home in Anna Maria, you'll be by the sea, a 3-minute walk from Bradenton Beach and 10 minutes by foot from Bean Point Beach. .This vacation home is 20.9 mi (33.6 km) from Tampa Bay and 0.8 mi (1.3 km) from Anna Maria Beach.
View more Vacation Homes in Anna MariaOpens in a new window

What's nearby

  • Bradenton Beach - 3 min walk - 0.2 miles
  • Anna Maria Island Museum and Historical Park - 5 min walk - 0.3 miles
  • Bean Point Beach - 12 min walk - 0.7 miles
  • Anna Maria City Pier - 12 min walk - 0.7 miles
  • Anna Maria Beach - 17 min walk - 0.9 miles

Getting around

  • Sarasota-Bradenton Intl. Airport (SRQ) - 46 min drive

Restaurants

  • ‪The Sandbar Restaurant - ‬6 min walk
  • ‪Anna Maria Island Beach Cafe - ‬8 min drive
  • ‪The Ugly Grouper - ‬6 min drive
  • ‪Ginny's & Jane E's - ‬6 min walk
  • ‪The Waterfront Restaurant - ‬11 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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
• 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.
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a Smart TV. There's a private balcony. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment.
Take advantage of recreation opportunities such as a hot tub, or other amenities including an arcade/game room and barbecue grills.
Guests will find features like internet access and onsite parking.

Property amenities

Beach

  • Beach nearby
  • Beach towels

Pool/Spa

  • Heated pool
  • Hot tub
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2.5 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Books
  • Games
  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Fenced yard

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Office

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping mall
  • Near the marina
  • Near the sea

Things to do

  • Arcade/game room
  • Billiards/pool table
  • Heated pool
  • Basketball nearby
  • Birdwatching nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Snorkeling nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Wildlife walks nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Unit size: 1,732 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets allowed
Service animals are welcome, and are exempt from fees

Children and extra beds

Children are welcome

Events

No events 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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

421

Beautiful North-End Home! Pool with In-ground Spa, Shuffleboard, Near Beach and Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 41 out of 43 reviews
Rating 8 - Good. 2 out of 43 reviews
Rating 6 - Okay. 0 out of 43 reviews
Rating 4 - Poor. 0 out of 43 reviews
Rating 2 - Terrible. 0 out of 43 reviews

9.8/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Paul C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was a very nice place. Everything was great.
Stayed 6 nights in Mar 2026
Verified review

10/10 Excellent

Kayla M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 6 nights in May 2026
Verified review

10/10 Excellent

Sara H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely LOVED our stay and would love to stay again!! Clean, so much more spacious than the pictures made it seem, best location for food and the beach. Very responsive when we had questions.
Stayed 4 nights in Jan 2026
Verified review

10/10 Excellent

Nicole D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 4 nights in Apr 2026
Verified review

10/10 Excellent

Amanda L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Winter getaway

Great house and close to the beach. Beautiful private backyard with pool and hot tub.
Stayed 7 nights in Feb 2023
Verified review

10/10 Excellent

Erin S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
AMI checked in often and quickly remedied any issues. The house had lots of fun things for the kids to do in the game room that walks out to the pool!
Stayed 6 nights in Jan 2026
Verified review

8/10 Good

Richard S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Anna Maria

Convenient location, wonderful pool/backyard. Would definitely rent again.
Stayed 7 nights in Jul 2022
Verified review

10/10 Excellent

Ralph W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Anna Maria Island

Very nice and peaceful place. Amazing beach. We will probably return.
Stayed 6 nights in May 2023
Verified review

10/10 Excellent

Jeff J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 7 nights in Apr 2025
Verified review

10/10 Excellent

Thomas R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a cozy well-kept older house located very close to the beach, shopping, and restaurants. All within minutes of walking. The hot tub and pool area was very secluded, which was nice for privacy. And the kids loved the game room! We did have a couple minor issues, but Keyon was able to get them taken care of immediately. Keyon was a great host. I would defiantly use their service again for that property or another location in the future.
Stayed 7 nights in Mar 2026
Verified review

10/10 Excellent

Lauren L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Stayed 6 nights in Apr 2025
Verified review

10/10 Excellent

Rachel D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fall Breah

Quick access to the beach and great pool. Could use new beach chairs.
Stayed 6 nights in Oct 2023
Verified review

10/10 Excellent

Patty S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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!
Stayed 6 nights in Jan 2024
Verified review

10/10 Excellent

Sean R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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!!
Stayed 6 nights in May 2024
Verified review

10/10 Excellent

Michael S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Paradise...

Even better then expected.
Stayed 5 nights in Sep 2024
Verified review

10/10 Excellent

Kathy E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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!
Stayed 7 nights in Feb 2024
Verified review

10/10 Excellent

Carol D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 6 nights in Jan 2024
Verified review

10/10 Excellent

marthachase1756

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 4 nights in Apr 2026
Verified review

10/10 Excellent

Timothy W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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).
Stayed 21 nights in Jan 2021
Verified review

10/10 Excellent

Timothy E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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!
Stayed 5 nights in Feb 2025
Verified review

10/10 Excellent

William E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 4 nights in Oct 2023
Verified review

10/10 Excellent

Gin R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

PERFECT paradise!

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!
Stayed 7 nights in Nov 2019
Verified review

10/10 Excellent

Letisha C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in May 2026
Verified review

10/10 Excellent

David B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house and location

Loved the home, pool, hot tub, and location. Worked well for our group. The outside bathroom was great.
Stayed 7 nights in Jun 2021
Verified review

10/10 Excellent

lynsey p.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect for our family!

The location, gorgeous private pool, and fun beachy furnishings were all fantastic. Our family of 6 loved it.
Stayed 7 nights in May 2021