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!
- 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.
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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
About the area
Holmes Beach
Located in Holmes Beach, this holiday 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. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with ecotours and hiking/biking trails.
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 38 min drive
Restaurants
Anna Maria Island Beach Cafe - 6 min walk
The Ugly Grouper - 15 min walk
Ginny's & Jane E's - 7 min drive
Smoqehouse - 4 min drive
Slim's Place - 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 8 May 2026, prices found for a 1-night stay for 2 adults at Updated Home with Pool, Spa, and Outdoor Bar! By the Beach! on 22 Aug 2026 start from AU$498, 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 at Updated Home with Pool, Spa, and Outdoor Bar! By the Beach!?
On-site 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!?
Checkout is at 10:00 AM.
Where is Updated Home with Pool, Spa, and Outdoor Bar! By the Beach! located?
Situated by the sea, this holiday 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 labelled.
Fantastic home with all the amenities for a carefree vacation.
Anne S.
Stayed 7 nights in Mar 2026
Response from VrboOwner on 24 Mar 2026
So happy you enjoyed your stay at Pineapple Key by Anna Maria Vacations, Scott! It’s great that the home had everything you needed to just settle in, relax, and enjoy island time without a worry. That easy, carefree vibe is what it’s all about. We’d love to have you back anytime for another laid-back getaway!
Amazing location! House included everything we needed for the beach, plus an amazing pool and patio area. We couldn't have asked for anything more. Will definitely be back!
Sabra W.
Stayed 7 nights in Mar 2026
Response from VrboOwner on 30 Mar 2026
Couldn’t ask for a better setup, Sabra! We’re so happy you loved your stay at Pineapple Key by Anna Maria Vacations. Having everything ready for beach days plus that pool and patio to come back to really makes it feel like a true island getaway. We’d love to have you back anytime and come soak up some more sunshine with us soon!
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.
Jennessa S.
Stayed 7 nights in Mar 2026
Response from VrboOwner on 24 Mar 2026
We’re so happy your family had such a great stay at Pineapple Key by Anna Maria Vacations, Jennessa! It sounds like the location made everything easy from quick beach walks to grocery runs and we love that the kids enjoyed the pool and hot tub so much. It’s great that the home had everything you needed, from comfy beds to a well-stocked kitchen and beach toys. And we really appreciate you sharing those helpful notes for future guests, too! Thanks for staying with us and we’d love to welcome your family back for another fun, easy island getaway!
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
Jeff A.
Stayed 7 nights in Mar 2025
Response from VrboOwner on 11 Mar 2025
Thank you for choosing us for your recent stay!
Every review and every star you give us makes a huge difference to our success. If you enjoyed your stay, we'd love your 5-star review!
We hope to host you again in the future!
Thank you for choosing us for your recent stay!
Every review and every star you give us makes a huge difference to our success. If you enjoyed your stay, we'd love your 5-star review!
We hope to host you again in the future!
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.
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!
patrice p.
Stayed 8 nights in Nov 2023
Response from VrboOwner on 18 Jan 2024
Patrice, we're delighted to hear that you were pleased with your stay and found the kitchen well-equipped. Thank you for your suggestion regarding the knives and additional hand towels and washcloths. Your feedback is valuable, and we'll make sure to communicate it for consideration. If you have any more thoughts or specific preferences, feel free to share. We appreciate your input and hope to welcome you back for another enjoyable stay in the future!
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!
Angela P.
Stayed 7 nights in Mar 2025
Response from VrboOwner on 31 Mar 2025
Thank you for choosing us for your recent stay!
Every review and every star you give us makes a huge difference to our success. If you enjoyed your stay, we'd love your 5-star review!
We hope to host you again in the future!
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.
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.
Robert W.
Stayed 7 nights in Apr 2024
Response from VrboOwner on 20 May 2024
Robert, thank you for sharing your experience! We're glad to hear that you had a great time and enjoyed the convenient location, pool, and spa. We appreciate your feedback about the driveway exit and traffic, and we'll take it into consideration for future improvements. It's wonderful that the setup of the living spaces and bedrooms worked well for your group. We're happy to hear that the beach carts were helpful for your short walk to the beach. We look forward to welcoming you back for another great stay!
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.
Proximity to the beach is excellent. We had a great time.
Todd M.
Stayed 7 nights in Apr 2026
Response from VrboOwner on 4 May 2026
That easy beach access makes all the difference, Todd! We’re so glad you had a great time at Pineapple Key by Anna Maria Vacations from quick trips back and forth to the sand are what it’s all about. We’d love to have you back anytime for more sunny island days!
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.
Cynthia H.
Stayed 7 nights in Oct 2022
Response from VrboOwner on 15 Nov 2022
Cynthia, thank you for taking the time to share your experience with us. We are happy to hear you enjoyed your stay, and we hope to host you again soon!