House holiday rentals in Anna Maria

An outdoor lounge area is showcased under a wooden ceiling, featuring a heated pool and elegant patio furnishings. A television is mounted on the wall, and a dining set is positioned nearby, with a barbecue grill just outside the lounging space, surrounded by tropical landscaping.

5 out of 5 average rating, 50 reviews

Book Family Tides 7 Nts get 3 FREE~Pool~Beach view

Let me know if you need a stay for a period not listed. Unbeatable location, HEATED POOL, ultimate makeover & NEW bedrm, bathrm, lounge, & covered patio additions for spacious beauty are a few things that set us apart! Hidden behind our private gate, the beach is just a few steps away & remains uncrowded-even during busiest season. Premium fixtures, appliances, & plush furnishings create elegance. Garage/parking for 6 cars! Near restaurants, Publix, activities! 30 steps to FREE TROLLEY pick up!

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, 197 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 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, 112 reviews

Breezy Harbor AMI pool retreat near the Beach

Charming Breezy Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for 2 vehicles and even a boat: -We typically have shorter stays available, just ask! -If you don't have a single 50Lb pet, please discuss it with us -One of the twin boutique MyAnnaMariaStay homes, look us up! You'll love the luxury mid-century feel, lush yard, and a 6-min walk to the beach, Publix or the trolley stop. AMI was voted a top 50 vacation spot in the world in 2024

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.

5 out of 5 average rating, 27 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.

The backyard features a saltwater pool surrounded by artificial turf, creating a refreshing oasis. Sunlight brightens the outdoor space, accentuated by lush tropical landscaping. The elevated home showcases multiple balconies, while palm trees lend to the coastal atmosphere of the property.

4.93 out of 5 average rating, 15 reviews

Bayfront Beach access with Heated Pool!

Our modern yet beachy retreat is the perfect oasis on the North end of Anna Maria Island w/breathtaking panoramic views of Tampa Bay & the iconic Skyway Bridge. The backyard oasis features a refreshing saltwater pool & fully fenced backyard, complete w/artificial turf & outdoor shower. Just steps away, you'll find full access to a stunning white sandy beach & the crystal-clear waters of Tampa Bay! Conveniences have been carefully considered, creating the most ideal vacation destination!

5 out of 5 average rating, 9 reviews

Casa Cay by Duncan Real Estate

Welcome to Casa Cay! This Bay front pool home on Anna Maria Island is an absolute paradise! With its prime location on the North end with stunning views of the bay and the Sunshine Skyway Bridge, and direct access to a private bay beach, it offers the quintessential Island experience. The layout of the house, featuring three bedrooms and three bathrooms, including two suites with Ensuite bathrooms, is perfect for families or groups of friends looking for comfort and privacy.

A heated saltwater pool is surrounded by lush tropical vegetation, creating a serene atmosphere. Poolside seating is offered by several lounge chairs, alongside a shaded area with an umbrella. Sunlight reflects off the water's surface, enhancing the tranquil setting.

4.97 out of 5 average rating, 179 reviews

STEPs to BEACH! /Heated Salt Pool/Sunsets/5 STAR!

Less than a 2 min WALK to the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. Large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with bathrooms on opposite ends of the house (a pocket door adds privacy). Private heated saltwater pool sits amidst the tropical yard. Hop on the free trolley and explore Florida's gorgeous Anna Maria Island.

Two bright turquoise adirondack chairs are positioned on a pebbled shoreline, facing a calm canal. Lush palm trees and greenery surround the area, while distant houses line the opposite bank under a clear blue sky.

4.96 out of 5 average rating, 110 reviews

Waterfront Gem/ Pool Spa+ Dock/ Near Bridge Street

Anna Maria Waterfront oasis! **5 min walk to beach, private dock, pool heat included!!** Relax in the private heated pool, sip coffee on the dock, or walk to the beach. This bright, updated home has spacious living areas, a stocked kitchen, smart TVs, fast Wi-Fi, and cozy beds. Great for families or couples! Grill by the pool, dine under the stars, or fish from the dock. Includes washer/dryer, beach gear, and parking. Your peaceful, sunny getaway awaits—book now!

An aerial view showcases a serene coastal area, emphasizing the proximity to a sandy beach just a short walk away. The vibrant blue water contrasts with the green palm trees and white homes lining the streets, creating a peaceful atmosphere typical of Anna Maria Island.

5 out of 5 average rating, 79 reviews

New Prof Decorated-Pool/Spa 5 minute walk 2 Ocean

This brand new rebuild on Anna Maria Island located within Anna Maria city has 3 Bedroom, 3 Bathroom home plus loft is professionally decorated throughout, with state-of-the art quartz counter tops, JennAir professional stainless-steel appliances, wide plank wood tile floors, bead board ceilings. All bathrooms have basket weave marble and quartz counters and there is a Whirlpool Washer & Dryer. The house has everything necessary for a perfect beach vacation.

An aerial view captures a serene private pool encompassed by a stone patio, with several lounge chairs arranged nearby. Lush greenery and tropical plants border the scene, while a dark pond reflects the surrounding nature, enhancing a tranquil outdoor space.

5 out of 5 average rating, 113 reviews

Relaxing 3BR Retreat+ Hot Tub + Pool +Beaches +IMG

🌴Welcome to Beachway Haven! This 5-Star ⭐️ hideaway is just mins from Anna Maria Island's Pristine Beaches & the Gulf of Mexico. Dive into relaxation with your own Heated Saltwater Pool & Spa Hot Tub, nestled in a tropical oasis. Only a skip away from Golf Courses, Nature Parks, IMG Academy, & Palma Sola Causeway's Beach Access – your gateway to Horseback Riding, Kayaking, & endless sandy adventures. Shopping & dining are only a few mins away too!

A vibrant outdoor space features a large pool surrounded by lush greenery and manicured grass. The two-story house overlooks the pool area with a spacious patio beneath, offering seating for relaxation. Chaise loungers are placed beside the pool, inviting leisure under the sunny sky.

5 out of 5 average rating, 41 reviews

Paradise Blu by Beach Boutique Rentals

*Features include* * Featured in 'Travel and Leisure' Magazine * Huge heated pool and spa * Rooftop deck with sweeping water views * 4 bedrooms, 4 ½ baths * 3 king master suites with attached baths * Indoor/outdoor living on all 3 levels * Patio dining for 6, plus lounge area * Chaise loungers by the pool * Outdoor TV * Air hockey, darts, cornhole and more * 2 blocks to beautiful Bean Point beach! * Beach chairs, umbrella, and cart

The open-concept living area features a modern dining table set with intricate lace placemats. A pink sofa and white chairs provide ample seating, complemented by a stylish chandelier overhead. Bright natural light fills the space, highlighting decorative plants and framed artwork.

5 out of 5 average rating, 84 reviews

Wanderlust Villa

Welcome to Wanderlust Villa! This Anna Maria beachside beauty is a chic slice of paradise on AMI. Hues of pink and gold give the villa a warm and cozy yet ultra-chic vibe. It’s a total INSTA-WORTHY space! Wanderlust Villa is a quick half-mile walk to the beach and a 10 minute walk to a variety of restaurant options. Your gulf-view sunsets are waiting for you! 🩷 Any questions or booking requests outside of what is outlined please message!

Popular amenities for Anna Maria house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A private heated pool is surrounded by tropical palms, featuring a gently curved shape with clear blue water. Two white adirondack chairs are positioned nearby on a paved patio, inviting relaxation in a tranquil outdoor setting.

5 out of 5 average rating, 13 reviews

The Shell House

A private heated pool, approximately 33 feet long, is surrounded by lush greenery. Covered in-pool seating and a small table are visible, along with a patio area featuring an outdoor shower and an umbrella-shaded dining table for six.

4.83 out of 5 average rating, 6 reviews

Turtle Nest! Private Heated Pool and Access to the

An aerial view showcases a private pool surrounded by lush tropical landscaping. The pool features a unique shape with gentle curves, and a sun lounger is placed nearby. The composition highlights the vibrant greens of palm trees framing the pool area.

4.97 out of 5 average rating, 31 reviews

Location! Beach Access/Trolley/ Restaurants!

An aerial view showcases a vibrant outdoor space featuring a heated saltwater pool and hot tub, surrounded by sun loungers with yellow umbrellas. Nearby, a lush green yard includes a playground, mini-golf course, and a pickleball court, creating a lively recreational area.

5 out of 5 average rating, 10 reviews

Private Splash Pad, Pickleball, Htd Pool, Hot Tub

A serene outdoor space features a sparkling pool surrounded by lush greenery and tropical plants. Comfortable lounge chairs are placed along the poolside, and string lights cast a warm glow overhead. A shaded seating area with a gazebo can be seen in the background.

4.91 out of 5 average rating, 391 reviews

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI

The image showcases a vibrant backyard area featuring a heated swimming pool under a screened enclosure. Comfortable seating is arranged, and a private mini golf course is visible. A separate game room with entertaining equipment like shuffleboard and a colorful mural is also displayed.

5 out of 5 average rating, 42 reviews

Heated Pool•Mini Golf•Arcade•Spa•AMI 6mi•IMG

A serene outdoor space showcases a sparkling pool framed by lush tropical landscaping. Palms and vibrant plants surround the area, with a flamingo statue in the foreground. Soft lighting from string lights enhances the tranquil atmosphere as the sky transitions to dusk.

5 out of 5 average rating, 51 reviews

Flamingo Royale — Beach Luxury Resort

A private heated splash pool is framed by lush tropical foliage and palm trees. Dining furniture is arranged nearby, providing a space for outdoor meals. Natural stone accents enhance the pool's shape, while a paved area ensures easy access and a relaxing environment.

5 out of 5 average rating, 5 reviews

Walk to beach•Private Heated Pool•75" TV•Luxury

Weekly house rentals

The exterior of a modern two-story house is illuminated by soft evening light. A spacious deck is adorned with wooden chairs, and palm trees frame the entrance, enhancing the tropical ambiance. The house showcases a sleek design with large windows and a welcoming entrance.

4.99 out of 5 average rating, 86 reviews

Gulf Beach Front! Walk to Restaurants + Pier!

A private heated pool reflects the blue sky, surrounded by tropical landscaping. Two lounge chairs are positioned along the pool's edge, beneath large umbrellas. The modern home showcases a combination of light and dark exterior finishes, with large windows allowing natural light to fill the interior.

5 out of 5 average rating, 21 reviews

Feelin' Salty-Pool Modern Beach House w/Pool/Spa

A light-filled living area features a comfortable, neutral-toned sofa adorned with textured pillows. A wooden coffee table rests on warm-toned flooring. The space includes a cozy lamp and a small dining area with two stools, complemented by natural decor elements on the walls.

5 out of 5 average rating, 11 reviews

NEW Charming Coastal, so close to beach!

An open living area is visible, featuring a kitchen island with a light granite countertop. Nearby, a comfortable gray sofa faces a smart TV mounted on the wall. Large glass doors provide a view of the waterfront, while varied seating options are positioned throughout the space.

5 out of 5 average rating, 7 reviews

Lakeview Lookout - Canal front Cottage

Superhost

5 out of 5 average rating, 4 reviews

Dolphin Resort | Pool, Spa, Game Room & Beach

Superhost

The image features a landscaped outdoor area with a shared heated pool and multiple lounge chairs arranged around it. The vibrant greenery of tropical plants complements the charming villa, which showcases detailed architecture and outdoor balcony spaces above the pool, creating an inviting atmosphere.

5 out of 5 average rating, 4 reviews

Duplex Heated Pool Walk to Beach

The duplex features a light blue exterior with a welcoming porch adorned with yellow and blue chairs. Lush palm trees and vibrant landscaping enhance the outdoor space, while a clear blue sky adds brightness to the scene. Graveled parking is visible in front of the unit.

4.95 out of 5 average rating, 95 reviews

Do you love the beach?

An outdoor area features a heated pool surrounded by lounge chairs and umbrellas. A fire pit is positioned in front of a seating arrangement, creating a cozy gathering spot. Soft lighting from string lights adds ambiance to the serene space, enhanced by lush greenery.

5 out of 5 average rating, 34 reviews

Blessed Haven Peaceful Getaway 3 Miles to Beach

Private house rentals

A private saltwater pool is framed by swaying palm trees and a sun shelf. Two lounge chairs are positioned nearby for relaxation. The surrounding space is brightened by natural sunlight, with a white fence and lush greenery enhancing the serene atmosphere.

5 out of 5 average rating, 47 reviews

Modern 3BR Retreat + Anna Maria Beaches + IMG!

A private backyard features a curved pool surrounded by tropical landscaping. A thatched tiki hut provides shade over a dining table, while a large umbrella shades additional seating. A flamingo float is visible in the water, enhancing the relaxed outdoor atmosphere.

4.78 out of 5 average rating, 18 reviews

Steps Away from the Sandy Shores of Holmes Beach!

A winding stone path is bordered by lush greenery, leading through the expansive yard surrounded by tall trees. Various native plants are visible, creating a natural and serene environment.

4.79 out of 5 average rating, 227 reviews

Charming Beach house amongst huge Banyon Trees

4.88 out of 5 average rating, 8 reviews

Beach Front Duplex! Direct Beach Access and Views

A spacious living area features large windows offering water views and ample natural light. A comfortable sectional sofa is arranged around a round coffee table, and a cozy armchair is positioned nearby. Light-colored flooring complements the open layout, creating a bright and airy atmosphere.

5 out of 5 average rating, 16 reviews

Villa Mar- 2BD Waterfront Home in Holmes Beach, FL

A serene outdoor area features a heated pool surrounded by tropical landscaping. Light-colored pavers outline the pool, and large sliding glass doors lead to an inviting sunroom. Towering palm trees provide shade, contributing to the tranquil ambiance.

5 out of 5 average rating, 72 reviews

Private Luxurious Ground Level Home

A spacious outdoor area is featured, showcasing a deck with patio dining furniture and lounge chairs, accompanied by vibrant beach umbrellas. A charcoal grill is positioned nearby, with the sandy beach and the Gulf of Mexico visible in the background.

5 out of 5 average rating, 13 reviews

Fins to the Right: On the Gulf of Mexico! Beach!

An inviting two-story blue house is surrounded by lush greenery and palm trees, providing a tropical feel. A paved driveway leads to two garage doors, while a welcoming front porch with white railings offers a glimpse of the home's charm.