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

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Carefree Cay-Private Pool
Exterior View
Private Pool
Main Level Patio
Living Area

Reviews

10 out of 10, Loved by Guests
Top 10% based on
3 bedrooms2+ bathroomsSleeps 61732 sq ft

Popular amenities

  • Pool
  • 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.)
    ‪34 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

2 Twin 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!


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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.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Hot Tub
Kitchen
Washer
Dryer
Pet friendly

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

Pets allowed
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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

About the neighborhood

Anna Maria

Located in Anna Maria, this vacation home is near the beach. The area's natural beauty can be seen at Bradenton Beach and Bean Point Beach. Fish Hole Adventure Golf and H2O Watersportz are also worth visiting. Be sure to check out the area's animals with activities such as game walks and birdwatching.
View more Vacation Homes in Anna MariaOpens in a new window
Map
Anna Maria, FL

What's nearby

  • Bradenton Beach - 3 min walk - 0.3 km
  • Island Players - 3 min walk - 0.3 km
  • Anna Maria Island Museum and Historical Park - 5 min walk - 0.4 km
  • Anna Maria City Pier - 11 min walk - 1.0 km
  • Bean Point Beach - 12 min walk - 1.1 km

Getting around

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

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

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

Yes, pets are allowed at this property.

How much does it cost to stay at Beautiful North-End Home! Pool with In-ground Spa, Shuffleboard, Near Beach and?

As of Mar 26, 2026, prices found for a 1-night stay for 2 adults at Beautiful North-End Home! Pool with In-ground Spa, Shuffleboard, Near Beach and on Apr 11, 2026 start from $703, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Beautiful North-End Home! Pool with In-ground Spa, Shuffleboard, Near Beach and?

Check-in begins at 4:00 PM.

What time is check-out at Beautiful North-End Home! Pool with In-ground Spa, Shuffleboard, Near Beach and?

Check-out is at 10:00 AM.

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

Situated by the sea, this vacation home is within a 10-minute walk of Bradenton Beach and Bean Point Beach. Palmetto Avenue Beach and Island Players are also within 5 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 31 out of 33 reviews
Rating 8 - Good. 2 out of 33 reviews
Rating 6 - Okay. 0 out of 33 reviews
Rating 4 - Poor. 0 out of 33 reviews
Rating 2 - Terrible. 0 out of 33 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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
Verified

10/10 Excellent

Carrie C.

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

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!
Stayed 7 nights in May 2021
Verified

8/10 Good

Jeff R.

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

Great location, pool

The house is in a great location, just a few blocks from the beach. Nice pool w/ hot tub that gets very hot. House itself could use some updates but it was ok overall.
Stayed 14 nights in Jan 2021
Verified

10/10 Excellent

Jean Carlo L.

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

Surpass our expectations!

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.
Stayed 7 nights in Aug 2020
Verified

10/10 Excellent

Sharon D.

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

Fantastic House

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!
Stayed 7 nights in Jul 2020
Verified

10/10 Excellent

Eric D.

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

This house and property are exactly as pictured on VRBO.

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!
Stayed 7 nights in Jun 2020
Verified

10/10 Excellent

becky v.

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

Perfect

Great, Absolutely zero negative things to say about this property.
Stayed 14 nights in Oct 2019

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