4 Bedroom Short Term Rental With Private Pool in Holmes Beach, FL

Hawaiian Hideaway is a four-bedroom, two-bath duplex in Holmes Beach, Florida, set in a waterfront-nearby area and listed as near a beach. With 1,225 square feet and sleeping for up to eight guests, it combines a practical group-friendly layout with standout outdoor features, including a private pool and a backyard set up for time outside. Parking is limited to two vehicles, and the home is dog-friendly with host approval.

Inside, the home centers on an open living area with TV seating and a full kitchen equipped for everyday cooking, including a dishwasher and a Keurig coffee maker. Sleeping is arranged as one king bedroom, two queen bedrooms, and a fourth bedroom with two twin beds. Two bathrooms support the layout, and a washer/dryer adds convenience for longer stays. Outdoor amenities include a grill, outdoor shower, patio/deck areas, and a fenced yard with outdoor dining and loungers. A 7-night minimum stay applies, and occupancy may not exceed eight.

Good fit for

Pet-friendly stays Group and reunion

Private Pool Backyard includes a private pool plus outdoor seating and dining areas.

Sleeps Eight Four bedrooms sleep up to 8 with 1 king, 2 queens, and 2 twins.

Dog Friendly Dogs are allowed with host approval prior to check-in (no cats).

Near a Beach The home is listed as near a beach and in a waterfront-nearby setting.

Two Parking Spaces Parking is limited to two vehicles; no overnight parking for extra cars.

Waterfront - NearbyLocation Setting

Near a BeachBeach Access

4 BedroomsBedrooms

2 Full BathroomsBathrooms

Sleeps 8Guest Capacity

1225 sq. ft.Living Space

Pool (Private)Pool

Internet AccessInternet

TelevisionTelevision

YesAir Conditioning

YesPet Friendly

YesWasher / Dryer

Sleeping Arrangements 1 King Bed, 2 Queen Beds, 2 Twin Beds

Virtual Tour Hawaiian Hideaway - Virtual Tour

Holmes Beach Florida

206 81st Street Unit A, Holmes Beach Florida 34217

Location & nearby Explore the Area

Hawaiian Hideaway is in Holmes Beach, Florida, on Anna Maria Island, on a residential street. The listing notes a waterfront-nearby setting and identifies the home as near a beach. Local services are referenced as well, including a hospital close by. Parking at the home is limited to two vehicles, with no overnight parking available for additional cars.

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

$125 per night

7-day minimum stay

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Live booking details are maintained by Anna Maria Vacations.

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Hawaiian Hideaway is a duplex in Holmes Beach on Anna Maria Island, offering four bedrooms and two full bathrooms within 1,225 square feet. The home sleeps up to eight guests with a mix of bed types (1 king, 2 queens, and 2 twins). It is listed as waterfront-nearby and near a beach, and it includes a private entrance and keyless lock for arrival.

The backyard is designed for outdoor downtime, anchored by a private pool and supported by multiple ways to relax or dine outside. Amenities include outdoor seating, an outdoor dining area, sun loungers, outdoor lighting, and a grill. A fenced yard and an outdoor shower are also provided.

Indoors, the main living space is arranged for shared time, with a living room and television alongside a full kitchen. Kitchen features include a refrigerator/freezer, stove, oven, microwave, dishwasher, ice maker, toaster, blender, cookware, and dishes/utensils, plus a kitchen island and dining table. Comfort and convenience items include air conditioning, heating, ceiling fans, towels/linens, hair dryer, iron/ironing board, and in-home washer/dryer.

Bedroom details include a primary bedroom with a king bed and an ensuite bathroom with a walk-in shower, two additional bedrooms with queen beds, and a fourth bedroom with two twin beds. Dogs are allowed with host approval prior to check-in (no cats), and an additional pet fee applies. The property has a 7-night minimum stay, a two-car maximum with no overnight parking for additional vehicles, and a maximum occupancy of eight.

Hawaiian Hideaway by Anna Maria Vacations
Duplex in Holmes Beach, Florida
VRC16-000298

Welcome to Hawaiian Hideaway, a tropical duplex paradise just a short 5-minute walk from Holmes Beach! This spacious four-bedroom, two-bath home offers a serene backyard retreat featuring a private pool with a built in table, ample outdoor seating, and a BBQ grill. Perfect for families or groups seeking sunshine, relaxation, and island adventures, Hawaiian Hideaway provides everything you need for an unforgettable vacation in Anna Maria Island paradise!

Highlights
• 5-minute Walk to Holmes Beach and the Gulf beaches 
• Duplex - 4 Bedroom / 2 Bath
• 1 King, 2 Queens, 2 Twin beds
• Private pool
• BBQ Grill
• Minutes from Anna Maria Island Trolley stop
• Pet friendly with host approval
• Near Pine Avenue’s restaurants, shops, and boutiques
• Great for large groups or multiple families, with neighboring Hawaiian Tide available to rent for even more space!
• 2 Parking spaces

Enjoy your tropical escape in the backyard oasis featuring a private pool, ample outdoor seating, and a built in table for outdoor dining or cocktails. The BBQ grill makes it easy to savor fresh island-inspired meals, while the lush landscaping creates a serene setting for relaxation. With Holmes Beach beaches and shops just minutes away, every day on Anna Maria Island can be filled with sunshine and adventure.

Step inside and be greeted by a bright, coastal open living area featuring plush sofas and a TV, perfect for family movie nights. The fully equipped kitchen boasts a full suite of stainless steel appliances, ample counter space, and a chic dining table for memorable meals. Whether cooking together or enjoying island takeout, this space fosters relaxation and togetherness.

Unwind in the primary bedroom, a tranquil sanctuary featuring a king-sized bed, plenty of closet space, large windows with lush landscaping views, and an ensuite bathroom with a walk-in shower. The second and third bedrooms each offer queen beds, comfortable retreats after busy days of island exploration. The fourth bedroom, equipped with two twin beds, is ideal for kids or young guests. A hall bathroom with a walk-in shower and a washer and dryer add convenience for your stay, ensuring everyone’s needs are met in style.

Room Details
• Primary Bedroom: King bed, ensuite with walk-in shower 
• Second Bedroom: Queen bed 
• Third Bedroom: Queen bed 
• Fourth Bedroom: Two twin beds

Book Hawaiian Hideaway today and start planning your dream vacation. With its unbeatable location, luxurious pool, and lush outdoor space, this retreat is the perfect home base for exploring Anna Maria Island’s treasure-filled beaches, charming Pine Avenue, and scenic parks. Reserve now and create unforgettable memories in paradise!

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This property requires a 7-night minimum stay as set forth by Holmes Beach’s Land Development Code. Occupancy may not exceed 8.

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

With host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Anna Maria Vacations Rental Policies for full details.

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

Group and Reunion

State National Parks

Ocean

Pet Friendly

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

Internet Access

Pets Allowed

Pool (Private)

Television

Washer/Dryer

Property Features

Balcony

Blender

Ceiling Fan(s)

Coffee Maker

Freezer

Full Kitchen

Hair Dryer

Ice Maker

Microwave

Oven

Refrigerator

Stove

Toaster

Towels/Linens

Other Property Amenities

Residential Street

Holmes Beach

Anna Maria Island

Dishes and Utensils

Clothes Hangers

Hot Water

Iron and Ironing Board

Long Term Stays Allowed

Private Entrance

Ground Floor Property

Hospital Close By

Carbon Monoxide Detector

Outdoor Seating

Fire Extinguisher

Heating

Smoke Detector

Deadbolt Lock

Pots and Pans

Contactless Check-In

Pack 'n Play

Video Game Console

Living Room

Backyard

Patio

Fenced Yard

Kitchen Island

Dining Table

Two (2) Parking Spaces

Bathtub

Keurig Coffee Maker

Keyless Lock

Outdoor Shower

Clothing Storage

Wine Glasses

Baking Sheet

Hot Water Kettle

Outdoor Dining Area

Sun Loungers

Outdoor Lighting

Required Stairs

Uncovered Deck

5

The place was exactly what we were hoping for. The space was perfect for our family of six. It was close to the beach and even closer to multiple trolley stops that made exploring the rest of the island a breeze. The backyard pool and grill were exactly what our family needed after a long day at the beach or exploring what AMI has to offer. We would definitely stay there again.

Andrew

Posted: 8/1/2026

It sounds like Hawaiian Hideaway by Anna Maria Vacations was the perfect home base for your family getaway, Andrew. We're so glad the spacious layout, convenient beach access, and nearby trolley stops made exploring Anna Maria Island easy and enjoyable. Ending the day by relaxing in the pool and grilling together is exactly what island vacations are all about. Thank you for your kind words and we'd love to welcome your family back for another memorable stay!

Anna Maria Vacations staff

5

Our stay was absolutely amazing! The place was clean, comfortable, beautifully decorated, and had everything we needed for a relaxing getaway. The location was perfect and made it so easy to enjoy the beach and explore the area. We truly felt at home from the moment we arrived. The hosts were wonderful, responsive, and made the whole experience stress-free. We would definitely stay here again and highly recommend it to anyone looking for the perfect vacation spot!

Alicia

Posted: 5/30/2026

There's something special about arriving and feeling right at home from the moment you walk through the door, Alicia. We're glad Hawaiian Hideaway by Anna Maria Vacations was everything you hoped for and more. Having the beach nearby and a comfortable, beautifully appointed space to come back to each day makes for a relaxing island getaway. It's also great knowing our team helped make your stay smooth and stress-free along the way. Thank you for the wonderful recommendation. We’d love to welcome you back for another stay at Hawaiian Hideaway soon!

Anna Maria Vacations staff

5

A beautiful and clean home with a great pool.

Sally

Posted: 4/25/2026

A clean home and a great pool make for a pretty perfect island combo, Sally! We’re happy to hear you enjoyed your stay at Hawaiian Hideaway by Anna Maria Vacations. Hope to have you back again soon for more relaxing pool days and sunshine!

Anna Maria Vacations staff

5

Geri

Posted: 3/14/2026

4

Overall it was a very nice stay! Anna Maria island is stunning and we would love to come back.

The location was incredible. Just a few minutes walk to the beach and uptown away from the busier portion of the island (Bradenton). The pool and back patio were great. The beds were super comfy. The communication with property management was very good and they were readily accessible if we needed anything. There could have been more kitchen amenities to make cooking at home better. Small things like a broken arm rest on one of the couches, an arm on one of the patio chairs, the shower curtain fell down on us.

Eric

Posted: 12/19/2025

5

Quiet street, close to the beach

Angela

Posted: 7/5/2025

Thank you for your review, Angela. We're glad to hear that you enjoyed the convenient location of our property, close to the beach. We strive to provide a comfortable and peaceful stay for all our guests. We appreciate your feedback and hope you had an overall pleasant experience with us!

Anna Maria Vacations staff

5

This place was great! It was in a perfect location to walk to the beach, it really is less than 5 minutes, and the area was not to heavily populated for the spring break like other areas. The house was clean, and we had everything we needed for our family of 5. The heated pool was also a huge plus for the kids to swim in as well.

Oliver

Posted: 4/9/2025

5

This place was great! It was in a perfect location to walk to the beach, it really is less than 5 minutes and the area was not heavily populated for spring break like other areas. The house was clean and we had everything we needed for our family of 5. The heated pool was also a huge plus for the kids to swim in as well.

Oliver

Posted: 3/29/2025

Thank you so much for the wonderful review! We are delighted to hear that you and your family enjoyed your stay with us. The location and amenities of our property seem to have been a perfect fit for your needs. We strive to provide a clean, comfortable, and well-equipped environment for all our guests. Your feedback is greatly appreciated and we look forward to welcoming you back in the future.

Anna Maria Vacations staff

5

This place was great! It was in a perfect location to walk to the beach, it really is less than 5 minutes and the area was not heavily populated for spring break like other areas. The house was clean and we had everything we needed for our family of 5. The heated pool was also a huge plus for the kids to swim in as well.

Anonymous

Posted: 3/29/2025