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Updated Home with Pool, Spa, and Outdoor Bar! By the Beach!

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Pineapple Key
Pool/Ping Pong Table
Covered Outdoor Area
Living Area
Fully Equipped Kitchen

Reviews

9.6 out of 10
Exceptional
4 bedrooms2 bathroomsSleeps 81650 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi

Explore the area

View in a map
Holmes Beach, FL
  • Place, Bradenton Beach
    ‪5 min walk‬
  • Place, Holmes Beach Beaches
    ‪5 min walk‬
  • Place, Manatee Public Beach
    ‪6 min walk‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪27 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 1

1 Queen Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Bedroom 4

2 Twin Bunk Beds

2 bathrooms

Bathroom 1

Bathroom 2

Spaces

Kitchen
Balcony

About this property

Updated Home with Pool, Spa, and Outdoor Bar! By the Beach!

Pineapple Key by Anna Maria Vacations
Home in Holmes Beach, Florida
VRC16-000364

Welcome to Pineapple Key, a charming beach house just minutes from the sugar-white sands of the Manatee Beach! This beautifully landscaped four-bedroom, two-bath home features a private pool, in-ground spa, and tropical outdoor living spaces, making it ideal for friends and family gatherings. Located within walking distance of the beach, shops, and restaurants, Pineapple Key embodies relaxed island living with all the comforts you need for a memorable Anna Maria Island escape!

Highlights
• 3-minute walk to Manatee Public Beach
• 4 Bedroom / 2 Bath
• 2 Kings, 1 Queen, 2 Twin-over-twin bunks plus trundle
• Private pool and in-ground spa
• Outdoor lanai and tiki bar
• BBQ grill
• Pool and Ping Pong Table
• Wii gaming system
• Short walk or trolley ride to shops, waterfront dining, and local attractions
• Washer and dryer
• 8 Parking Spaces

Step inside Coastal Comfort, where vibrant coastal decor and relaxed island vibes create the perfect backdrop for your beach getaway. The main living area features a spacious layout with a large sectional sofa, cozy chairs, and a smart TV, ideal for movie nights or relaxing after a day on the sand. A second living room offers a more intimate retreat, complete with its own sectional, TV, and Wii gaming system, providing a fun hangout spot for kids or an extra lounge area for guests.

The fully equipped kitchen is designed for convenience with high-end appliances, ample counter space, and all the cookware needed to prepare your favorite meals. Gather for casual breakfasts or family dinners in the open dining area or step out to the covered lanai for outdoor dining and a true taste of island living.

This home offers a thoughtful layout with two bedrooms and a shared bathroom on each side, ideal for couples traveling together or families seeking both comfort and privacy. On the East Side, you’ll find a serene king bedroom with crisp linens and a shared bathroom featuring a walk-in shower, along with a cozy queen bedroom nearby. The West Side includes another king bedroom with a premium mattress and coastal decor, plus a fourth bedroom designed with families in mind featuring two sets of bunk beds and a trundle bed. A shared bathroom with a shower/tub combination provides added comfort and flexibility for all guests.

Room Details
• Primary Bedroom: Queen bed, ensuite bathroom
• Second Bedroom: King bed
• Third Bedroom: King bed
• Fourth Bedroom: Twin-over-twin bunk beds

Book Pineapple Key today and enjoy an unforgettable getaway on Anna Maria Island. With its beautiful water views, private pool and spa, outdoor entertainment, and nearby beaches, this home offers everything you need for a relaxing and memorable escape!


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This property participates in our Professional Linen Program. In Anna Maria Vacation's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you with high quality linens; including bedding, bath towels, wash cloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed in a commercial setting using the latest and best technology.

This home is managed by Anna Maria Vacations, an Anna Maria Island property management company.

8 cars maximum are able to park at this home. 2 parking spaces are covered while the additional 6 are uncovered. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.

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 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.

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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
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

Holmes Beach

Located in Holmes Beach, this vacation home is near the beach. The area's natural beauty can be seen at Bean Point Beach and Anna Maria 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 Holmes BeachOpens in a new window
Map
Holmes Beach, FL

What's nearby

  • Bradenton Beach - 5 min walk - 0.4 km
  • Holmes Beach Beaches - 5 min walk - 0.4 km
  • Manatee Public Beach - 6 min walk - 0.6 km
  • AMI Paddleboard Adventures - 6 min walk - 0.6 km
  • West Coast Surf Shop - 6 min walk - 0.6 km

Getting around

  • Sarasota-Bradenton Intl. Airport (SRQ) - 38 min drive

Restaurants

  • ‪The Ugly Grouper - ‬15 min walk
  • ‪Anna Maria Island Beach Cafe - ‬6 min walk
  • ‪Smoqehouse - ‬4 min drive
  • ‪Anchor Inn - ‬2 min drive
  • ‪Ginny's & Jane E's - ‬7 min drive

Frequently asked questions

Does Updated Home with Pool, Spa, and Outdoor Bar! By the Beach! have a pool?

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

How much does it cost to stay at Updated Home with Pool, Spa, and Outdoor Bar! By the Beach!?

As of Mar 26, 2026, prices found for a 1-night stay for 2 adults at Updated Home with Pool, Spa, and Outdoor Bar! By the Beach! on Jul 11, 2026 start from $623, 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.

Is Updated Home with Pool, Spa, and Outdoor Bar! By the Beach! pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Updated Home with Pool, Spa, and Outdoor Bar! By the Beach!?

Check-in begins at 4:00 PM.

What time is check-out at Updated Home with Pool, Spa, and Outdoor Bar! By the Beach!?

Check-out is at 10:00 AM.

Where is Updated Home with Pool, Spa, and Outdoor Bar! By the Beach! located?

Situated by the sea, this vacation home is within a 10-minute walk of Bradenton Beach, Holmes Beach Beaches, and Manatee Public Beach. West Coast Surf Shop and AMI Paddleboard Adventures are also within 10 minutes.

Reviews

9.6

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. 11 out of 12 reviews
Rating 8 - Good. 0 out of 12 reviews
Rating 6 - Okay. 0 out of 12 reviews
Rating 4 - Poor. 1 out of 12 reviews
Rating 2 - Terrible. 0 out of 12 reviews

9.6/10

Cleanliness

9.0/10

Check-in

9.6/10

Communication

9.6/10

Location

9.4/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Anne S.

Liked: Cleanliness, check-in, communication, listing accuracy
Fantastic home with all the amenities for a carefree vacation.
Stayed 7 nights in Mar 2026
Verified

10/10 Excellent

Jennessa S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This home was ideal for our week vacation with 3 young children. The location: Perfect! A very short walk to the beach and about a 10 min walk to the grocery store. Beach: It was beautiful, lots of sea shells to collect. Clean and lots of space to find a spot Pool and Hot tub: Huge highlight for our kids. Perfect for a relaxing afternoon since it was shaded later in the day. Home: Very comfortable beds, the kitchen was well stocked for cooking and there was also beach/pool toysThings to consider: Large set of stairs to get into the home, not an issue for us but something to note. Traffic on the island is very busy, there is a free trolly you can take throughout the island or just plan ahead for traffic delays. Overall, great property, excellent location. This home has all you need for a wonderful beach vacation.
Stayed 7 nights in Mar 2026
Verified

10/10 Excellent

Jeff A.

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

Very casual and relaxing

We had a great stay here. Property was exactly how it was listed and it was in a great location. Pool and Hot tub was very nice and was a hit with our teenage daughters
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Robert P.

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

Nice house

House was clean and well stocked. Love the pool!
Stayed 7 nights in Feb 2025
Verified

10/10 Excellent

Jayln S.

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

Pineapple key at AMI

Property was beautiful and had everything we needed plus more. The pool was perfect for entertaining the kids and lots of gaming options for the adults as well. The property was very clean and well prepared for guests.
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

patrice p.

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

Anna Maria island

We were very pleased with everything. The kitchen was well equipped( but you may want to get better knives for chopping etc, I would also have liked a few more hand towels and wash clothes( only 2 for 8 people). Location was perfect as was the beach!
Stayed 8 nights in Nov 2023
Verified

10/10 Excellent

Angela P.

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

Great location and stay!

Our check in process was smooth, and all communication with the property management company was fast and easy. For example, we asked for early check in and needed the propane refilled and they responded right away. The place itself is great, exactly as shown in the photos. It’s a 3 minute walk to the beach. The only downside is that the house is on a busy road and you can hear cars passing late at night and early in the morning.The place came well stocked with kitchen supplies and TONs of beach gear and toys. The one thing that was missing from the listing is that it does have a washer and dryer, which was a huge plus (at the time we booked, the listing only mentioned laundry nearby). I hope they update the listing with this info as we almost decided to pass because of this. Overall we were happy with our stay and would stay again!
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Thomas P.

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

Great House

We had 4 couples at Spring Break and the house was awesome. Plenty of room, well equipped, clean and really close to the beach. By well equipped I mean not only the kitchen, but there is a closet downstairs with chairs, umbrellas, games, floats, even a metal detector (needs 2 (v batteries). When we weren't at the beach (mornings and evenings) we were downstairs having pool (i.e. billiard) tournaments, hanging out in the pool or hot tub and grilling. We would rent this house again if it available. Beach is 2 minutes away the way I walk, if you walk really slow maybe 5 minutes.
Stayed 7 nights in Mar 2023
Verified

10/10 Excellent

Robert W.

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

Great beach house

We had a great time! The location was great. The only draw back was trying to exit the driveway with cars on the main road. The cars yield to walkers but getting out with the car took some time depending on traffic. The pool and spa were a hit with everyone. The 2 living spaces were nice. We kept the kids up front in the bunk room and the adults too the back two rooms. There really isn’t a master suite. The bathrooms are in hallways which made it easier to use either one. The beach carts were great to have even though the walk was maybe 5 minutes at the most. We had a great time and would love to stay there again.
Stayed 7 nights in Apr 2024
Verified

4/10 Poor

Natalie W.

Liked: Cleanliness, location
Disliked: Check-in, communication, listing accuracy

Green pool and access issues

Our group was given 3 incorrect access codes and instructions for a lock box (which did not exist) and about an hour of back and forth texts before we could enter the home. Not ideal after a long travel day, but not a deal breaker.The real issue is the pool and hot tub were as green as pond water, looking nothing like the photos. When I reported this issue, the pool company showed up the following morning to fix it. They nuked the pool, pouring who knows what into it (gallons and gallons of bleach?). We were told that in the afternoon (hours after treatment) it was fine to enter the pool. Adults and children swam in the pool and hot tub. Afterward, the smell of chlorine was so strong it was intoxicating. The kids were crying and asking why their skin was burning and itching. They had red patches. Everyone's skin was extremely dry and irritated. After 2 full days, the pool and hot tub were fine to use without adverse affects. The second half of our stay in this home was great.Long story short, the pool and hot tub should have been prepared properly before our arrival - that was the biggest draw for us renting this place.
Stayed 7 nights in Jan 2025
Verified

10/10 Excellent

Cynthia H.

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

Great beach house

The house had everything you need for a beach location. Pool was fun and outdoor area was well laid out with bar-b-q, table, etc. Appreciated the beach chairs and cooler. The two living areas of the house were perfect for the two families staying with us.
Stayed 7 nights in Oct 2022
Verified

10/10 Excellent

Lawrence H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Feb 2025

About the host

Hosted by Anna Maria Vacations

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Languages:

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