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

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Carefree Cay-Private Pool
Aerial VIew
Exterior View
Private Pool
Main Level Patio

Reviews

10 out of 10
Exceptional
3 bedrooms2+ bathroomsSleeps 6160.9 sq m

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Hot tub
  • Air conditioning

Explore the area

Map
Anna Maria, FL
  • Bean Point Beach
    ‪8 min walk‬
  • Anna Maria City Pier
    ‪10 min walk‬
  • Anna Maria Beach
    ‪15 min walk‬
  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪45 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

2 Single Beds

2 bathrooms, 1 half bathroom

Bathroom 1

Bathroom 2

Half Bathroom 1

Spaces

Deck or patio
Kitchen

About this property

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

Carefree Cay by Anna Maria Island Accommodations
Home in Anna Maria, FL 34216
VR16-000412

Welcome to Carefree Cay, a vacation getaway located in the north end of Anna Maria Island. This spacious house offers three bedrooms and two and a half bathrooms, making it the perfect fit for families and groups seeking rest and relaxation. The backyard boasts a private pool and an in-ground spa, along with plenty of lounge chairs for soaking up the beautiful Florida sunshine.

Highlights
• Less than a 5-minute walk to the beach
• Private pool with in-ground spa
• Outdoor living space
• Close to restaurants and shops
• Shuffleboard

As you enter the spacious living area, you'll feel the laid-back island atmosphere and will love all the comfortable seating options. In the kitchen, you'll find essential dishware, pots, pans, and a coffee maker. Guests can dine at the island bar, dining room table, or on the deck, your choice. The second living area features an incredible beach mural, cozy sofas, a table perfect for playing board games, and even a shuffleboard!

The primary bedroom boasts a walk-in closet, a large television, and a spa-like ensuite bathroom with a walk-in shower and a lavish soaking tub. Each bedroom is designed with comfort in mind, and the two guest rooms have storage space and televisions as well. The hall bathroom has a fun colors and a shower and tub combination. Plus, there is a washer and dryer that can be found right off the kitchen and there is a half bath.

Room Details
-Primary Bedroom, 2nd floor: King bed and ensuite bathroom with walk-in shower and soaking tub
-Second Bedroom, 2nd floor: King bed
-Third Bedroom, 2nd floor: Two twin beds

The boutiques and restaurants located on Pine Avenues, along with the pristine Gulf of Mexico beaches, are just a short walk away. Book Carefree Cay today and enjoy all the wonderful attractions nearby!

-
The garage is not available for guest use

There are no pets allowed in this home.

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.

Property manager

Anna Maria Island Accommodations
Premier Host

Languages

English

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washer
Dryer
Air conditioning

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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

No 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
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

About the area

Anna Maria

Located in Anna Maria, this holiday home is near the beach. The area's natural beauty can be seen at Bean Point Beach and Anna Maria Beach. AMI Paddleboard Adventures and Fish Hole Adventure Golf are also worth visiting. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with hiking/biking trails and ecotours.
Map
Anna Maria, FL

What's nearby

  • Island Players - 4 min walk - 0.4 km
  • Anna Maria Island Museum and Historical Park - 4 min walk - 0.4 km
  • Bean Point Beach - 8 min walk - 0.7 km
  • Anna Maria City Pier - 10 min walk - 0.9 km
  • Anna Maria Beach - 15 min walk - 1.3 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 45 min drive

Restaurants

  • ‪Anna Maria Island Beach Cafe - ‬6 min drive
  • ‪Rod & Reel Pier - ‬15 min walk
  • ‪Two Scoops - ‬10 min walk
  • ‪Sandbar Seafood & Spirits - ‬6 min walk
  • ‪The Waterfront Restaurant - ‬12 min walk

Frequently asked questions

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

Yes, this property has a pool. Pool types include heated pools.

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

No, pets are not allowed at this property.

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

Check-in begins at 4:00 PM.

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

Checkout is at 10:00 AM.

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

Situated by the sea, this holiday home is within a 10-minute walk of Island Players and Bean Point Beach. Anna Maria Island Museum and Historical Park and Bradenton Beach are also within 5 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 29 out of 31 reviews
Rating 8 - Good. 2 out of 31 reviews
Rating 6 - Okay. 0 out of 31 reviews
Rating 4 - Poor. 0 out of 31 reviews
Rating 2 - Terrible. 0 out of 31 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

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

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

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

10/10 Excellent

Michael S.

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

Paradise...

Even better then expected.
Stayed 5 nights in Sep 2024

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

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

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

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

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

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

10/10 Excellent

Kathy E., Portage

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

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

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

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

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

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

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

10/10 Excellent

Carrie C., Omaha, ne

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

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

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

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

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

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

10/10 Excellent

Janet O.

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

Wonderful Location!

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!
Stayed 7 nights in Sep 2019

10/10 Excellent

Christine W.

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

Home away from home

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 .
Stayed 7 nights in Jul 2019

About the host

Hosted by Anna Maria Island Accommodations

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Languages:

English

Premier Host

They consistently provide great experiences for their guests