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

Top rated by guests
Pineapple Key
Fully Equipped Kitchen
Dining Area
Covered Outdoor Area
Private Pool
review stars
9.4Outstanding
(18 Ratings)
"Proximity to the beach is excellent. We had a great time."
Todd M.
Don't miss out! Price and availability may change
9.4 / 10
Outstanding(18 Ratings)

House in Holmes Beach, FL

8 guests · 4 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

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.

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

Non-smoking
No pets allowed
Family friendly

Map of Holmes Beach, FL


Ratings and reviews

9.4 / 10
Outstanding(18 Ratings)
10 / 10Outstanding·Apr 2026
Proximity to the beach is excellent. We had a great time.
10 / 10Outstanding·Mar 2026
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!
10 / 10Outstanding·Mar 2026
Fantastic home with all the amenities for a carefree vacation.
10 / 10Outstanding·Mar 2026
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.

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Updated Home with Pool, Spa, and Outdoor Bar! By the Beach!. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

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

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Updated Home with Pool, Spa, and Outdoor Bar! By the Beach!?

We found 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.