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

Pineapple Key is a four-bedroom, two-bath home in Holmes Beach, Florida, set near the waterfront and near a beach. With 1,650 square feet and sleeping up to eight guests, it stands out for its private pool and in-ground hot tub, plus multiple indoor and outdoor hangout areas. A seven-night minimum stay applies.

Inside, the home includes two living rooms with TVs, a video game console, and game options such as foosball and a pool table. The kitchen is fully equipped and includes a Keurig coffee maker, dishwasher, and standard appliances, with dining space indoors and a covered lanai for outdoor meals. Sleeping options include two king beds, one queen bed, and bunk beds. Practical features include air conditioning, washer/dryer, towels and linens, keyless entry, and three parking spaces. Outdoor spaces include a fenced yard, outdoor seating, sun loungers, a grill, and a tiki bar.

Good fit for

Family Vacations

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

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

Game-ready setup On-site entertainment includes a pool table, foosball, and a video game console.

Outdoor lanai and tiki bar Covered outdoor dining area with seating, plus a tiki bar and grill.

Sleeps up to eight Sleeping includes 2 kings, 1 queen, and bunk beds for up to 8 guests.

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 in Holmes Beach, Florida, on Anna Maria Island in the South Gulf Coast region. The setting is listed as waterfront nearby and near a beach, and the home is on a residential street. The listing notes that a hospital is close by and asks guests to keep noise to a respectful level due to the residential 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 1,650-square-foot home in Holmes Beach on Florida’s South Gulf Coast. The property sleeps up to eight guests across four bedrooms and two full bathrooms, and it is listed as waterfront nearby and near a beach. Stays require a minimum of seven nights.

The interior is arranged for both shared time and separate downtime, with two living rooms, each with a TV. For at-home entertainment, the home includes a pool table, foosball, and a video game console. Internet access, air conditioning, heating, ceiling fans, and a private entrance are provided.

The kitchen is set up for self-catering with a full suite of appliances and essentials, including a refrigerator/freezer, stove, oven, microwave, dishwasher, toaster, blender, cookware, dishes and utensils, and both a standard coffee maker and a Keurig. Dining options include an indoor dining table plus outdoor dining space.

Bedrooms include two king beds, one queen bed, and bunk beds. Bathrooms include a bathtub, and towels/linens are supplied. Outside, guests have a private pool and hot tub, a covered deck/lanai with outdoor seating, a tiki bar, outdoor lighting, and a grill. The yard is fenced, and parking is listed for three spaces, including covered parking. Safety features include smoke and carbon monoxide detectors, a fire extinguisher, and a deadbolt lock.

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