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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 two-story house with a wooden staircase, a garage, and palm trees.
A backyard with a swimming pool, palm trees, and outdoor seating.
A room with a beach mural, a ceiling fan, a blue sofa, a glass coffee table, and a red umbrella.

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms3 bathroomsSleeps 6161 sq m

Popular amenities

  • Pool
  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly

Explore the area

View 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

About the area

Anna Maria

At this holiday home you'll be within just a 10-minute stroll of popular attractions like Bradenton Beach and Bean Point Beach. Highlights at this holiday home include a kitchen, a private pool and a washing machine. .Home features free WiFi, 2.5 bathrooms and a balcony. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A living room, a fenced private garden and a Smart TV are also available. .This pet-friendly holiday home offers a games room and barbecues. Added amenities include a hot tub and laundry facilities. .Attractions within a 15-minute drive of this Anna Maria holiday home include Anna Maria Beach and Cortez Beach.
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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
  • Bean Point Beach - 12 min walk - 1.1 km
  • Anna Maria City Pier - 12 min walk - 1.1 km

Getting around

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

Restaurants

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

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Property amenities

Beach

  • Beach nearby
  • Beach towels

Pool/Spa

  • Heated pool
  • Hot tub
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Onsite parking options include a garage

Kitchen

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

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping centre
  • 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
  • Snorkelling 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 and check-out are 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 are welcome
    • Service animals 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
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
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. 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. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector and a deadbolt lock in all accommodation.

Property is also known as

421

Frequently asked questions

Are there any beaches close to Beautiful North-End Home! Pool with In-ground Spa, Shuffleboard, Near Beach and?

Yep, Beautiful North-End Home! Pool with In-ground Spa, Shuffleboard, Near Beach and is a short 10-minute walk from Bean Point Beach. Fun beach activities include jet skiing, snorkelling and body boarding. You can also find motor boats.

Does Beautiful North-End Home! Pool with In-ground Spa, Shuffleboard, Near Beach and have a pool?

Beautiful North-End Home! Pool with In-ground Spa, Shuffleboard, Near Beach and has a heated pool.

What luxury perks are available at Beautiful North-End Home! Pool with In-ground Spa, Shuffleboard, Near Beach and?

This property features a heated pool, as well as a private pool and a living room.

What makes Beautiful North-End Home! Pool with In-ground Spa, Shuffleboard, Near Beach and a romantic place to stay?

1 hot tub, private pools, and private balconies all help set the scene for a sizzling getaway at Beautiful North-End Home! Pool with In-ground Spa, Shuffleboard, Near Beach and.

Is there a private hot tub at Beautiful North-End Home! Pool with In-ground Spa, Shuffleboard, Near Beach and?

Yep, there is a hot tub.

Is there a free airport shuttle available at Beautiful North-End Home! Pool with In-ground Spa, Shuffleboard, Near Beach and?

No, Beautiful North-End Home! Pool with In-ground Spa, Shuffleboard, Near Beach and does not offer an airport shuttle service.

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

Check-in begins at 4:00 PM. Check-out time is 10:00 AM.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 38 out of 40 reviews
Rating 8 - Good. 2 out of 40 reviews
Rating 6 - Okay. 0 out of 40 reviews
Rating 4 - Poor. 0 out of 40 reviews
Rating 2 - Terrible. 0 out of 40 reviews

9.8/10

Cleanliness

Reviews

Verified

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

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

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

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

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

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

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

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

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