Vacation rentals with outdoor seating in Anna Maria

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, 196 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, 111 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

Bungalow in Bradenton Beach

A tranquil outdoor space features a wooden dining table surrounded by eight chairs set on a tiled patio. A small, curved swimming pool is framed by lush tropical plants, and umbrellas provide shaded areas. The vibrant greenery creates a serene atmosphere.

4.91 out of 5 average rating, 110 reviews

Bougie Bungalow at the Beach

This newly renovated, completely private, comfortable Anna Maria Island bungalow is super clean & very comfortable. It has an open, split floor plan, 2 king bedrooms, each with private baths, separate dining and Florida room & is only 3 houses from the amazing white sand beach, the bay & Pier. Only 1 block over is Historic Bridge Street with cool restaurants, mini golf, quaint shops & bars with live music. Once here, you never need to drive -everything is within a block walking distance!

4.96 out of 5 average rating, 164 reviews

An open living space is captured, featuring a dining area with a round table set for meals. Natural light fills the room, highlighting a stylish sideboard adorned with decorative items. A decorative mirror and green plants enhance the modern, welcoming atmosphere.

Apartment in Anna Maria

Beach Don't Kill My Vibe by Beach Boutique Rentals

*Features include* * Modern vacation rental directly on Pine Ave! * King bedroom with TV * Queen bedroom with TV * Bathroom with walk in shower * Small kitchenette with full-size refrigerator * Private deck with table and umbrella * Private back yard with putting green and outdoor seating * Off-street parking for one vehicle * Trolley stop across the street * Walkable to all shops and restaurants on Pine Avenue * Beach chairs, umbrella, and cart * Steps to the beach!

4.97 out of 5 average rating, 179 reviews

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.

Home in Bradenton Beach

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.

4.96 out of 5 average rating, 110 reviews

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.

Home in Bradenton Beach

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!

Townhouse in Holmes Beach

An aerial view captures the coastal neighborhood, showcasing a collection of charming homes with grey rooftops. The vibrant blue ocean and sandy beach are visible in the background, while lush palm trees surround the area, contributing to the serene island atmosphere.

4.99 out of 5 average rating, 149 reviews

Heated Pool & Spacious Lanai! Steps from Beach!

Welcome to Your Dream Beach Escape! Just one block from the sugar-white sands of Holmes Beach, this newly renovated home has everything you need for the perfect getaway. Bikes, paddle boards, and all the beach gear are included for endless fun! Unwind in the shared HEATED pool or soak up the charm of Anna Maria Island. Shopping, dining, and tropical attractions are just a stroll, bike, or trolley ride away. Perfect for families, reunions, and couples!

Guesthouse in Bradenton Beach

A vibrant yellow cottage is depicted with a landscaped area featuring palm trees and a gravel yard. Colorful adirondack chairs in pastel shades of pink and blue offer seating options, creating a casual outdoor space. Nearby cottages are visible, enhancing the beachfront setting.

4.99 out of 5 average rating, 192 reviews

Bradenton Beach Sunsets 1, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

Apartment in Holmes Beach

A serene outdoor area features a clear blue swimming pool, flanked by palm trees. Comfortable lounge chairs are positioned alongside the pool, and a shaded dining table is visible in the background. The white exterior of the building reflects a bright, inviting atmosphere.

4.96 out of 5 average rating, 185 reviews

Cabin 2 at Spinnakers Vacation Cottages

My place is close to the beach, family-friendly activities, the free AMI trolley, and nightlife. You’ll love my place because of the location and the ambiance. It is nestled in the lush tropical landscape of Spinnakers Vacation Cottages. You will find Cabin 2 is a perfect spot for an island getaway. My place is good for couples, solo adventurers, families (with kids), and certain size breed and weight dogs. Spa maintains same temperature as pool.

5 out of 5 average rating, 113 reviews

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.

Home in Bradenton

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!

Apartment in Bradenton Beach

The exterior of a charming yellow bungalow is visible, featuring a covered patio area with potted plants. The entrance is accessed via a set of steps leading to the upper level, while brick pavers create a welcoming pathway.

4.87 out of 5 average rating, 399 reviews

Las Palmas Beach Rentals unit 2

Unit 2 Ground floor;800 sq ft; patio; limited beach view . Steps to the white sandy beach across the street Free parking to registered guest. Fully equipped kitchen with markets nearby, Restaurants and shopping, within walking or hop free trolly. Trolly stop nearby. Linens and basic supplies are included. Overnight guest are welcome to arrive early to adventure the island, stay parked until after sunset on departure day.

4.96 out of 5 average rating, 255 reviews

A private outdoor space featuring a heated pool and spa, surrounded by palm trees and lounge chairs. The vibrant blue cottage is visible in the background, complemented by carefully arranged landscaping. A pathway of stepping stones leads toward the entrance of the cottage.

Cottage in Anna Maria

Turtle Cottage - Anna Maria Island

Great 1 bedroom, 1 bathroom cottage on the quiet north end of the island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Gladiolus Street/Alamanda Road. Spectacular sunrises are just a short walk away at the Rod and Reel Pier, and the sunsets at Bean Point Beach are second to none, just a few blocks away. This great getaway sleeps up to 4.

Popular amenities for Anna Maria outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

The exterior of the vacation rental features a spacious two-level design surrounded by lush tropical landscaping. A private pool is visible, accompanied by lounge chairs, and a covered patio offers shaded seating for relaxation.

4.94 out of 5 average rating, 34 reviews

Sunsets on Carissa - Pool & Steps to Gulf Beaches

An outdoor dining area is set with plates and glasses, accompanied by a lantern centerpiece. The space overlooks a private heated pool surrounded by tropical plants. A grill is positioned nearby, enhancing the convenience for outdoor meals.

5 out of 5 average rating, 41 reviews

Veselka - Canal front w private heated pool & dock

A lagoon-style pool is surrounded by a patio featuring lounge chairs and an umbrella, offering a shaded spot for relaxation. Lush palm trees line the space, and the elevated home is visible in the background, completing the serene outdoor setting.

4.89 out of 5 average rating, 61 reviews

Island in the Sun, luxury beach house,private 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, 12 reviews

The Shell House

A private lagoon-style pool is surrounded by lush tropical landscaping. A small rock waterfall flows into the gently curved pool, which is complemented by comfortable seating. Sunlight filters through the foliage, creating a serene outdoor retreat.

4.97 out of 5 average rating, 143 reviews

Twin Palms: Big House Steps to Beach w/Lush Pool

4.97 out of 5 average rating, 31 reviews

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.

Home in Bradenton Beach

Location! Beach Access/Trolley/ Restaurants!

A private pool is surrounded by a tropical landscape, featuring palm trees and vibrant plants. The clear water reflects the blue sky, and a spacious deck with paver stones offers a welcoming area for relaxation. A canal can be seen in the background.

4.95 out of 5 average rating, 186 reviews

Discounted October Stays w/Private 30' Dock & Pool

A spacious covered lanai contains a large wooden dining table surrounded by six dark wicker chairs. A ceiling fan provides airflow in the area. Large windows offer views of the private heated pool and tropical landscaping, while the light-colored tile flooring adds a clean, bright appearance.

5 out of 5 average rating, 12 reviews

Private heated pool,2 minute walk to the beach! W

Apartment rentals with outdoor seating

Apartment in Bradenton Beach

A comfortable living space is presented, featuring a green sofa paired with two armchairs. A round coffee table with neatly arranged towels is centered on a patterned rug. Natural light filters through the shuttered window, enhancing the warm ambiance of the room.

4.9 out of 5 average rating, 110 reviews

2 min walk to beach Paradise

Apartment in St. Petersburg

A cozy studio space is showcased with natural light streaming in through two windows. A spacious bed with light bedding is complemented by a decorative wall piece. A small dining table with two chairs and a comfortable sofa add to the inviting atmosphere.

4.99 out of 5 average rating, 121 reviews

Cozy Gem Near Madeira Beach

Superhost

A cozy sleeping area is presented with a plush bed covered in a light-colored bedspread. Nightstands with lamps frame the bed, providing soft lighting. A decorative painting and a floral art piece adorn the walls, enhancing the serene ambiance of the room.

Apartment in St. Petersburg

4.76 out of 5 average rating, 251 reviews

NEW Luxury Apartment w/Bikes! Location Location!

4.97 out of 5 average rating, 383 reviews

A modern bathroom featuring a round mirror above an elegant wooden sink with a metallic bowl. Exposed brick walls and dark accents create an industrial feel. A sleek, black toilet complements the stylish glass shower, which is designed with contemporary tile.

Apartment in Tampa

Hyde Park "Industrial-chic" with Private Backyard

4.9 out of 5 average rating, 177 reviews

A comfortable sleeping area features a queen size bed dressed in white linens and patterned pillows. A decorative bench at the foot complements the dark blue headboard. Nightstands with lamps are positioned on each side, and artwork depicting coastal scenery adorns the wall.

Apartment in Bradenton

Ocean Blue adorable new studio !

Apartment in Historic Kenwood

A wooden deck is surrounded by lush greenery and colorful plants. A shaded gazebo is present, featuring comfortable seating and potted plants. The area exudes a tranquil atmosphere, inviting guests to enjoy the outdoor space among the vibrant foliage.

5 out of 5 average rating, 506 reviews

St Petersburg Garden Studio

Apartment in Holmes Beach

The open living area features a wall-mounted TV and a black bookshelf, providing ample space. The adjoining cozy bedroom is visible, furnished with a queen bed and accented by bright decor. The modern kitchen area includes dining furniture, showcasing a relaxed and functional layout.

4.78 out of 5 average rating, 300 reviews

Ohana Hale North 1 Bedroom

4.93 out of 5 average rating, 203 reviews

A spacious outdoor deck is adorned with comfortable lounge chairs and surrounded by vibrant greenery, including tall palm leaves and flowering plants. Large planters accentuate the area, which is bathed in natural light, creating a serene outdoor retreat.

Apartment in Bradenton

Seahorse Suite Bradenton Hideaway

Condo rentals with outdoor seating

4.93 out of 5 average rating, 150 reviews

Adirondack chairs in soft blue are positioned on the sandy beach, offering scenic views of the ocean and coastline. The sun reflects off the water, enhancing the tranquil atmosphere, while a distant figure strolls along the shore. Lush greenery borders the sandy area.

Condo in Bradenton Beach

Beach Escape & Pool, steps to Beach & restaurants

4.93 out of 5 average rating, 122 reviews

A stylish living room is presented, featuring a comfortable gray sofa paired with a decorative round coffee table. Brightly colored wallpaper adorned with shell patterns enhances the space, while large windows allow natural light to filter in, complemented by light-colored flooring.

Condo in Bradenton

New Renovated Condo + Walk to Bay + 5 Min to AMI

4.97 out of 5 average rating, 115 reviews

A screened lanai offers a peaceful retreat with a view of the pond and trees reflecting on the water. Comfortable seating is provided, accompanied by a small table. Natural light flows in, enhancing the serene atmosphere of the space.

Condo in Bradenton

A&A's Paradise near IMG & Anna Maria beaches

4.91 out of 5 average rating, 135 reviews

A fire table is positioned in view of a vibrant sunset, reflecting shades of orange, pink, and purple across the sky. The scene is framed by large glass panels, offering unobstructed views of the horizon, enhancing the outdoor experience.

Condo in Bradenton

New Luxury 3/3 Condo in Margaritaville Resort

4.99 out of 5 average rating, 203 reviews

An aerial view captures a multi-story condominium overlooking a beach. Lush palm trees surround a heated pool area, with docks lining the waterfront. The expansive coastline is visible in the background, highlighting the scenic proximity of beach and bay.

Condo in Treasure Island

Spectacular beach to bay views from this resort.

4.99 out of 5 average rating, 162 reviews

Condo in Longboat Key

Silver Sands on the Sea!

4.91 out of 5 average rating, 192 reviews

A large window reveals a stunning view of the sunset over the Gulf. Two red adirondack chairs are positioned to face the ocean, inviting relaxation. The soft glow of the setting sun reflects on the water, creating a serene atmosphere in the living space.

Condo in Bradenton Beach

Beachfront condo in paradise with hot tub