Anna Maria Island 4 Bedroom House With Pool Holmes Beach, FL

Pineapple Key is a four-bedroom, two-bath home in Holmes Beach, Florida that sleeps up to eight guests in 1,650 square feet. Set in a residential area with a waterfront-nearby setting and near a beach, it pairs an outdoor-focused layout with a private pool and hot tub. The sleeping mix includes two king beds, one queen bed, and bunk beds, giving flexibility for different room preferences within one home.

Inside, the home includes two living areas for spreading out, plus a full kitchen with major appliances and small essentials such as a coffee maker, toaster, blender, and cookware. Outdoor features include a covered deck/lanai with seating and dining space, a grill, sun loungers, and a tiki bar. For downtime at home, amenities include a pool table, foosball, and a video game console. Practical conveniences include washer/dryer, towels and linens, air conditioning, internet access, and keyless entry. Parking is available on-site, including covered spaces.

Good fit for

Family Vacations Long-term stays

Private pool and hot tub Includes a private pool plus an in-ground hot tub for at-home downtime.

Sleeps up to 8 Accommodates 8 guests with 2 kings, 1 queen, and bunk beds.

Two living areas Two separate living rooms provide extra space to spread out.

Outdoor lanai and tiki bar Covered outdoor areas include seating, dining space, and a tiki bar.

On-site parking Parking for up to 8 vehicles, including 2 covered spaces.

Waterfront - NearbyLocation Setting

Near a BeachBeach Access

4 BedroomsBedrooms

2 Full BathroomsBathrooms

Sleeps 8Guest Capacity

1650 sq. ft.Living Space

Pool (Private)Pool

Internet AccessInternet

TelevisionTelevision

YesAir Conditioning

YesWasher / Dryer

Holmes Beach Florida

4505 Gulf Dr, Holmes Beach Florida 34217

Location & nearby Explore the Area

Pineapple Key is located in Holmes Beach, Florida, on Anna Maria Island in the South Gulf Coast region. The home is on a residential street and is described as waterfront-nearby and near a beach. The listing notes that a hospital is close by, and it references nearby options for boating and other water activities in the surrounding area.

Holmes Beach Vacation Rentals Holmes Beach Travel Guide Artists' Guild of Anna Maria Island Anna Maria Island Beach Cafe in Holmes Beach FL

Rates from

$200 per night

7-day minimum stay

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Live booking details are maintained by Anna Maria Vacations.

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Pineapple Key is a 4-bedroom home in Holmes Beach on Anna Maria Island, offering 1,650 square feet of indoor space and accommodations for up to 8 guests. The property is listed as waterfront-nearby and near a beach, and it is located on a residential street. A private entrance and keyless lock support straightforward arrivals, including contactless check-in.

The interior is arranged for both shared time and separate downtime, with two living areas and multiple entertainment options. In addition to televisions, the home includes a pool table, foosball, and a video game console. Climate and comfort features include air conditioning, ceiling fans, and heating. Safety items noted include smoke and carbon monoxide detectors, a fire extinguisher, and a deadbolt lock.

For meals at home, the full kitchen includes a refrigerator and freezer, stove, oven, microwave, dishwasher, and small appliances such as a blender, toaster, and coffee makers (including a Keurig). Cookware and dining basics are provided, along with a dining table and wine glasses. Laundry is supported with an in-home washer and dryer.

Outdoor amenities center on the private pool and hot tub, with additional spaces for relaxing and dining outside. The yard is fenced and includes outdoor seating, an outdoor dining area, sun loungers, outdoor lighting, and a covered deck/lanai. Parking is available for up to eight vehicles, with two covered spaces and additional uncovered parking.

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.

Check In

4:00 PM

Check Out

10:00 AM

This property provides access to the following activities and special interests:

Beach

Biking

Boating

Canoeing

Fishing

Deep Sea Fishing

Golfing

State National Parks

Ocean

Sailing

Scuba Diving

Surfing

Fly Fishing

Wind Surfing

Hiking

Family Vacations

Kayaking

Other Activities and Special Interests

Boating Nearby

Local Eco Tourism Nearby

Horseback Riding Nearby

Outlet Shopping Nearby

Wildlife Viewing Nearby

Fitness Center Nearby

Laundromat Close By

Tennis Court Nearby

Hiking Nearby

Jet Skiing Nearby

Parasailing Nearby

Sailing Nearby

Snorkeling Nearby

Surfing Nearby

Swimming Nearby

Health Beauty Spa Nearby

Marina Nearby

Shopping Nearby

Bird Watching Nearby

Kayaking Nearby

Museums Nearby

Water Sports Nearby

Featured Amenities

Air Conditioning

Dishwasher

Grill

Hot Tub

Internet Access

Pool (Private)

Television

Washer/Dryer

Property Features

Balcony

Blender

Ceiling Fan(s)

Coffee Maker

Freezer

Full Kitchen

Hair Dryer

Microwave

Oven

Refrigerator

Stove

Toaster

Towels/Linens

Entertainment

Pool Table

Other Property Amenities

Residential Street

Holmes Beach

Anna Maria Island

Dishes and Utensils

Hot Water

Long Term Stays Allowed

Private Entrance

Hospital Close By

Carbon Monoxide Detector

Outdoor Seating

Fire Extinguisher

Heating

Smoke Detector

Deadbolt Lock

Pots and Pans

Contactless Check-In

Pack 'n Play

Foosball

Video Game Console

Living Room

Backyard

Fenced Yard

Dining Table

Three (3) Parking Spaces

Bathtub

Covered Parking

Keurig Coffee Maker

Keyless Lock

Tiki Bar

Wine Glasses

Baking Sheet

Hot Water Kettle

Outdoor Dining Area

Sun Loungers

Outdoor Lighting

Covered Deck

5

I can't even begin to write about how much we enjoyed our stay at Pineapple Key on Anna Maria Island. If anything, the hosts have undersold how great of a location this is and what the house has to offer. We were an extended family of 7 with two 4-year-olds, a 13-year-old, 3 parents in their 40s and a grandma in her 70s. Everyone had ample space, things to do, and enjoyed everything this house had to offer. From a pool and hot tub that was sunny in morning and shaded in the afternoon, to a very easy 5-minute walk to a beautiful white sand beach that never felt crowded, 15-minute walk to restaurants, shops, and a harbor for boat trips, and 1 block away from trolley stations to get around the island.Where this listing shorts itself is just how stocked they keep this house with everything you could want from a vacation house. TONS of beach/pool toys, chairs, umbrellas, a wagon, and more, a pool table, foosball, lawn games, etc. Enough TVs for everyone. Kitchen tools, pots and pans, a crock pot, blender, etc. for cooking anything you can think of. Closet full of board and card games for all ages. Pineapple Key has it all.Top it all off with a check-in team that was easy to communicate with and helpful, you can't go wrong here.Thank you for an amazing trip for our family!

Jason

Posted: 8/3/2026

What a joy to read your thoughtful review, Jason! It means so much to know Pineapple Key by Anna Maria Vacations brought your whole family together so comfortably, from the youngest beachgoers to grandma. We love hearing that the home's thoughtful amenities, easy walk to the beach, and fun-filled game spaces helped create such special memories. Your kind words about our team's communication truly mean a lot as well. Thank you for letting us be part of such a memorable family vacation—we'd be honored to welcome everyone back for another stay on Anna Maria Island!

Anna Maria Vacations staff

4

We had a great vacation. The house was as promised.

Angela

Posted: 6/23/2026

5

Really enjoyed our stay

Gage

Posted: 5/31/2026

We're glad you enjoyed your time at Pineapple Key by Anna Maria Vacations, Gage. Sometimes a relaxing island getaway is exactly what's needed. Thank you for staying with us, and we’d love to welcome you back for more sunshine, beach days, and island memories!

Anna Maria Vacations staff

5

This place was amazing! Easy walk to beautiful beach. Pool area was peaceful place to hang out/eat dinner, nice quiet back deck to drink coffee in the morning. Lots of beach supplies.

Stacie

Posted: 5/18/2026

Sounds like you found your own little slice of island paradise, Stacie. From morning coffee on the back deck to relaxing evenings by the pool, we’re so happy Pineapple Key by Anna Maria Vacations helped make your getaway so enjoyable. It’s great to hear the beach was an easy stroll away and that the beach supplies came in handy for your adventures. Thanks for staying with us and we’d love to welcome you back for more sunshine, pool time, and peaceful island mornings!

Anna Maria Vacations staff

5

Proximity to the beach is excellent. We had a great time.

Todd

Posted: 4/30/2026

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!

Anna Maria Vacations staff

5

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

Posted: 3/29/2026

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!

Anna Maria Vacations staff

5

We absolutely loved our stay here! The house had everything we needed for an amazing vacation. Beach - we used the wagon, cooler, chairs, and beach toys every day. Beach access is one block away, which made it so easy to go back and forth. Pool - drinking our morning coffee by the pool while the kids played was a highlight. We didn't hear the word "bored" once because there was so much to do at the house. Hot tub was great in the evening. Trolley - we chose to use the free trolley instead of driving and it was clean and fast. Stops are less than a block away. Shopping - we walked north a bit and found some fun shops. Also took the trolley to Bridge Street and to the North end of the island. We loved being right in the middle. I have nothing bad to say about this house - it fit all of our needs and then some. Will definitely be coming back!

Anonymous

Posted: 3/28/2026

5

Fantastic home with all the amenities for a carefree vacation.

Anne S.

Posted: 3/22/2026

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!

Anna Maria Vacations staff