House vacation rentals in Holmes Beach

A private heated pool is surrounded by tropical landscaping and palm trees, creating a serene outdoor space. Two lounge chairs are positioned beside the pool, and a small table is visible on the lawn. Bright sunlight casts a warm glow over the vibrant plants.

4.95 out of 5 average rating, 104 reviews

Breezy Harbor AMI pool retreat near the Beach

Stunning Fall 2024 renovation done! Charming Breezy Harbor boasts a private heated pool and sits on a quaint corner of AMI. Upon arriving you will immediately feel stress melting away. You'll love grilling in the lush yard and a 6-min walk to the beach or the AMI trolley stop. A supermarket is a couple of streets over. The home is perfect for families, couples, 1-50Lb pet, and working remotely. Ample Parking for 2 vehicles and toys. *Ask us for shorter stays and always discuss your pets with us*

The image depicts a bright, two-story beach house with light blue siding, surrounded by palm trees and lush greenery. A white picket fence lines the front, offering a sense of privacy. The sky is clear with soft clouds, conveying a tranquil coastal atmosphere.

5 out of 5 average rating, 55 reviews

Luxury Home Steps to Quiet Beach on 78th St

No hurricane damage! Stylishly renovated top to bottom, our sunny beach house with 3/4 BR and 2 BA is 1.3 blocks (a 3 min stroll) from the beach. Perfect for one family or two small families, it's an incredible value considering its location and quality. The house has every thing you need for a great vacation, including a kitchen for serious cooks, Weber grill, dining deck, shaded patio lounge and lovely lawn. To see availability 12 months from now, use the website, not the app. VRC18-000181

Superhost

The living area features light-colored furniture with decorative pillows and wall art. Large windows allow natural light to fill the space, and a cooling ceiling fan is present. A decorative bowl rests on the low coffee table, complementing the warm wood flooring.

4.87 out of 5 average rating, 110 reviews

New Golf cart + 4bd/3b w pool/2100 sq ft home

Urban Oasis is a privately owned 2100 sq ft 4 bd, 3 bth on Anna Maria Island. 4 minute walk on a quiet residential street to walk to the beach.This home features grey blue hues, coastal furniture, driftwood accents, themed rooms and designer accents. A brand new 2024 6 str golf cart is included in your rental as well as a premium linen service including all towels and linens. Urban Oasis is truly a turnkey Vacation Rental! We also have a second property, Urban Oasis Too, if you like our style!

A spacious bedroom features a large bed with striped bedding, complemented by two nightstands with lamps. Sliding glass doors open to a private backyard with a plunge pool. Natural light floods the room, highlighting the warm wooden ceiling and inviting decor.

4.96 out of 5 average rating, 182 reviews

Be an AMI

This stylish and light home offers single-level private accommodations. The recently updated interior and private backyard oasis with plunge pool offers the perfect space for a truly relaxing and enjoyable vacation. Inside, the stylish and comfy space has room for everyone to spread out and relax while enjoying the two flat screen TVs. No expense was spared in designing and furnishing this home. The sleeper sofa pulls out to a memory foam queen bed, meaning the cottage can comfortably sleep 4.

A private heated pool is surrounded by a spacious patio, offering views of the bay. Lounge chairs are positioned nearby for relaxation. The shimmering water reflects the clear blue sky, creating a serene atmosphere for outdoor enjoyment.

4.93 out of 5 average rating, 60 reviews

Bayfront Gem Pool, Spa & walk to Anna Maria Beach

Gorgeous home with direct bay views! Lounge in the private heated pool. Enjoy morning coffee while watching sunrises. Walk across the street to the beach to enjoy swimming in the most amazing water. Dock can accommodate large boats "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." VRC21-000105

Superhost

A private heated pool is surrounded by lush tropical landscaping and tall palm trees. Two lounge chairs are positioned near the pool, and a shaded area is provided by a large umbrella. White fencing encloses the yard, enhancing privacy in the outdoor space.

Home in Anna Maria

5 out of 5 average rating, 3 reviews

Birdsong-Steps to Bean Point Beach Heated Pool!

Welcome to Birdsong, a picture-perfect 2-bed, 2-bath home situated in Anna Maria, Florida. Recently refreshed with coastal décor, this inviting property is ideal for families or small groups seeking a relaxing getaway. With just a short 3-minute walk to the beach, Birdsong provides an excellent blend of comfort & convenience, allowing you to fully immerse yourself in the beauty of Anna Maria Island. The fenced backyard features a heated pool, outdoor dining, BBQ grill, beach chairs, & cart.

A light and airy dining area is highlighted by a round table surrounded by four rattan chairs. Natural textures are complemented by a woven pendant light overhead. A small potted plant sits at the center, while sunlight filters through the nearby window, enhancing the inviting space.

5 out of 5 average rating, 8 reviews

NEW Coastal luxury, so close to beach!

Modern & comfortable 2-bedroom, 2-bathroom stay is a short couple minute walk to the white sand beach of Anna Maria Island. The fully equipped kitchen has modern appliances, and the open layout provides plenty of space to relax. Step outside onto private outdoor space to enjoy a morning coffee, sit and relax, or watch the sunset! Newly outfitted for the 2025 season, with brand-new furnishings, linens, and everything you need for a comfortable stay. Side-by-Side Units – Book One or Both!

A spacious pool area features a large, oval-shaped swimming pool surrounded by multiple lounge chairs. The light-colored patio is lined with tropical plants. A shaded umbrella stands near the seating area, complemented by the inviting blue exterior of the single-level beach house.

5 out of 5 average rating, 15 reviews

One Level Large Home 2 Minute Walk to the Beach!

Welcome to our Blue Grotto on the beautiful Anna Maria Island. We hope you will enjoy your stay in our 1850 sq ft beach house with 3 bedrooms and 2 baths. Our property features a living area and a full kitchen with dining area which makes it great for spreading out. Our little slice of heaven is perfect for family vacays, fishing or golfing trips or that annual girls trip! You are only 6 houses to the beach or right out the back door to the large pool (extra charge for heating).

An inviting outdoor space features a hot tub illuminated with soft lighting and a waterfall feature. Surrounding the hot tub are four adirondack chairs arranged around a fire pit with flickering flames, creating a cozy atmosphere amidst tropical palm trees.

5 out of 5 average rating, 12 reviews

Oceanside Retreat-Rest & Recover-Hot Tub-Hammock

Whether escaping the cold winter days, or wanting to unwind from all the stress, Solace West is the perfect place for you. Walking distance to Anna Maria's beautiful beaches, restaurants, shops and more. The hot tub is set to 104*. With its waterfall feature and lights it's waiting for you to step in and unwind those overworked muscles. Whether inside enjoying the beautiful tranquil decor or outside enjoying any of the many amenities, we believe you may never want to leave.

A warm outdoor space features a heated pool surrounded by tropical landscaping. Comfortable black lounge chairs are positioned nearby, providing a relaxing area for guests. Soft lighting illuminates the space, creating a serene atmosphere in the evening.

5 out of 5 average rating, 45 reviews

Perfect Hideaway- Post Storms Better Than Ever!

COMPLETELY RENOVATED AFTER THE 2024 STORMS with new drywall, electrical, plumbing, cabinets, vanities, paint, appliances & furniture. Photos are new and show the house after repairs and renovation. This home is on a quiet, dead-end street & close to everything. It’s a perfect base for you to enjoy the laid back, Old Florida lifestyle of Anna Maria Island. Sandy Palms is managed by the owners who live in FL & are always available if you need anything during your stay.

4.94 out of 5 average rating, 18 reviews

The outdoor area features a spacious pool and a separate spa, surrounded by manicured gardens and palm trees. A covered lanai with steps leads to the upper level of the home, which includes expansive sliding glass doors inviting natural light into the interior.

Home in Anna Maria

Ocean Air Oasis-New Centrally Located AMI Luxury

Immerse yourself in coastal luxury at this exceptional 3-bedroom, 2.5-bathroom custom home, where opulent high-end finishes and stunning pecky cypress floors adorn every nook. Revel in the impeccable features, including Sub-Zero and Wolf appliances, marble countertops, Shaw’s sinks, and exquisite custom woodworking, all bathed in abundant natural light. This delightful space offers panoramic views of the lavish backyard, complete with a heated pool and spa.

A spacious living area is filled with natural light from large windows. A comfortable sectional sofa is arranged with decorative pillows, complemented by a wood coffee table at the center. Two soft reclining chairs are positioned nearby, contributing to the inviting atmosphere.