Family-friendly vacation rentals in Anna Maria

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

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*

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

One block from beautiful beach & waterfront dining. Newly renovated Villa in quaint quiet condo building close to everything on Anna Maria Island. Pickleball across the street. Pool literally out your back door. Perfect for a small family or a romantic getaway. *Min. renter age 25. Two minute walk to beach, trendy Bridge Street shops, marina, restaurants, bars, boat tours, mini golf and more. Brand new beds, furniture & appliances. Kitchen has everything you need. Beach supplies in hall closet.

Apartment in Holmes Beach

A clear blue pool is surrounded by palm trees and a well-maintained patio area. Lounge chairs are arranged nearby, and a dining set is visible in the background, enhancing the outdoor space. The sun-filled setting creates a vibrant atmosphere.

4.97 out of 5 average rating, 195 reviews

Crows Nest at Spinnakers Vacation Cottages

Close to the beach, family-friendly activities, nightlife, and the free AMI trolley. You’ll love the location, the ambiance, and the high ceilings. Located in the lush tropical paradise of Spinnakers Vacation Cottages. Offers a spacious living area, with the bedroom and bathroom on the living floor with a spiral staircase leading to a loft with two twin beds. Great for couples, families and dogs (with small pet fee) Great private deck for star gazing! Spa maintains same temperature as pool

The exterior of the white house features a welcoming front porch with two dark seating areas. A well-maintained pathway of gravel leads to the entrance, while lush greenery and decorative plants enhance the surroundings, and a festive wreath adorns the front door.

4.97 out of 5 average rating, 162 reviews

Downtown Bradenton & close to Beaches, quiet area

Your family will be close to everything when you stay at this centrally-located private home with fenced in yard near downtown and beaches. Three bedrooms and 2 bathrooms await your next vacation to Florida's beaches. Located 1 mile to downtown - restaurants, shops, markets, Riverwalk, Theater, Bishop Museum and more. Only 4 miles to beaches. Stroll the neighborhood oak lined sidewalks and river. Front porch & private back fire pit & grill. Note - only 3 vehicles permitted.

A serene backyard features a heated pool surrounded by lounge chairs and shaded areas. Tropical plants and flowers add color, while the setting sun casts a warm glow. Umbrellas provide shade over the seating, creating a welcoming space for relaxation and outdoor enjoyment.

4.97 out of 5 average rating, 102 reviews

Orange Oasis: Clean, heated pool, near beaches.

Enjoy your little slice of paradise at the beautifully decorated Orange Oasis! 3 bedrooms & 2 baths, plus a daybed with trundle. Heated Pool. High speed wifi & 4 TV's all with Hulu, Apple TV, Disney+, & ESPN. Vaulted ceiling, rainfall walk-in shower, washer & dryer, large fenced backyard, pool, garage parking, Weber grill, & a quiet safe neighborhood. The home comes fully stocked with Ziploc bags, cooking/kitchen essentials, coffee, beach essentials, & outdoor/indoor games.

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.

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, 390 reviews

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

Enjoy Florida sun in a stunning, newly renovated 4/2 pool home! We have provided almost everything we could think of including five 4k TVs w/ Netflix and cable, wifi, heated (optional) salt water pool w/ 7' privacy fencing, adult bikes, beach gear, Pack & Play, office, board games, relaxing lounge chairs, stocked kitchen, washer & dryer, garage parking, dog crate, all in a quiet and safe neighborhood. Oh, and of course it's just 5 miles to world renowned beaches.

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!

A fire table is positioned near large glass windows that frame a stunning sunset over the water. The reflection of the vibrant sunset is visible in the water, while the outdoor landscape is softly illuminated by the fading light.

4.98 out of 5 average rating, 189 reviews

Luxury 3/3 Margaritaville Resort

Our luxury 3 BR/ 3 Bath Margaritaville inspired condo features one of the best unobstructed water views of Anna Maria Sound and Tampa Bay in the community. The unit features a gourmet kitchen, high-end mattresses, furniture and electronics. The unit comes with bikes and plenty of beach gear. Come enjoy one of the best units in the only luxury development in the area. Skip the hassle of a trip to the off-site management office with keyless entry.

5 out of 5 average rating, 22 reviews

Villa in Holmes Beach

Beachfront Paradise! Ground level with Heated pool

Gulf-front getaway with unbeatable beach access—step out your back door and right onto the sand! Enjoy a king bed, queen sleeper, fully stocked kitchen, in-unit washer/dryer, and professional linen service. Beach towels, two chairs, and an umbrella are included. Relax or grill by the shared heated pool and soak in the stunning Gulf views. Everything you need for the perfect beach escape—just bring your sunscreen and unwind!

The dining area features a wooden table set for four, complemented by a light fixture above. A comfortable sofa is arranged in the living area, with sliding glass doors providing views of the greenery outside. Artwork adorns the walls, enhancing the ambiance.

4.98 out of 5 average rating, 223 reviews

Shorewalk full condo IMG Beaches Anna Maria

1174 Sqft first floor 2 bedroom and 2 bathroom with a nice kitchen full condo in the beautiful Shorewalk community. Within very short walking distance to movies, groceries ,shopping and dining This condo is about 9 miles from Sarasota airport and about 13 miles from downtown Sarasota, about 6.8miles from the Bradenton Beach , about 10 miles from Anna Maria Island Less than 1 mile to the big gate of the IMG academy

4.93 out of 5 average rating, 142 reviews

A cozy sleeping area is highlighted by a framed beach scene above a bed adorned with green and white patterned pillows. A white tray holds two glasses and a small potted plant, positioned on a white quilt. Light wood paneling accents the walls.

Tiny home in Bradenton

Cozy, relaxing studio 17 minutes from the beach.

This is a (small) space in my home (162 square feet), renovated, cozy and beautiful, Fully equipped so you can enjoy a pleasant and comfortable stay. Totally private and independent. Located in a very quiet and safe neighborhood, just 17 minutes from Anna Maria and other beautiful beaches, nature reserves and other attractions. ready for 1 or 2 people.( We have another beautiful stay for 2 people on the same property).

Popular amenities for Anna Maria family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.97 out of 5 average rating, 30 reviews

Ocean72, 2bed 2bath with pool

A comfortable living area is furnished with a gray sofa and decorative pillows. A large beanbag sits on the textured rug, while a medium-sized TV is positioned on a light-colored console. Natural light fills the space through sliding glass doors, adorned with sheer curtains.

4.96 out of 5 average rating, 112 reviews

Waterfront View Mins To AMI Beaches

A modern kitchen showcases sleek, white cabinetry and a dark granite countertop. Stainless steel appliances include a microwave and oven, complemented by a mosaic tile backsplash. The space is well-lit with natural light from an adjacent living area, creating an open and airy environment.

4.77 out of 5 average rating, 137 reviews

Shorewalk upgraded condo 4505.

A newly-built home is set amidst lush greenery, featuring palm trees and tropical plants. The light blue exterior is complemented by a welcoming entry with coral accents. A gravel pathway leads to the front door, enhancing the inviting outdoor space.

5 out of 5 average rating, 11 reviews

Bubbles Up by Beach Boutique Rentals

A private outdoor space features a cushioned hot tub under a gazebo. Two lounge chairs with turquoise cushions are placed nearby on a wooden deck, surrounded by lush greenery. A textured outdoor rug adds warmth to the area, enhancing the overall relaxation vibe.

4.91 out of 5 average rating, 122 reviews

Tropical Cottage w SPA near Anna Maria Island IMG

4.97 out of 5 average rating, 338 reviews

A stunning pool area is surrounded by lush greenery and tropical plants. A prominent rock feature with multiple waterfalls is visible, providing a serene focal point in the outdoor space. The vibrant blue water complements the natural elements, creating a tranquil retreat.

Island in Sarasota

Oct SALE! Private Sarasota #1 Luxery beach Villa

A spacious living area features modern furnishings, highlighted by a large flat-screen TV mounted on a stylish accent wall. The tile floor reflects the soft lighting from recessed ceiling fixtures. A comfortable cream-colored sofa and a sleek coffee table provide a welcoming setting for relaxation.

4.98 out of 5 average rating, 129 reviews

Palmas de Lucia w/Hot Tub+5mi to Beach, Near IMG!

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.

4.97 out of 5 average rating, 115 reviews

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

Family- and pet-friendly home rentals

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

Apartment in Holmes Beach

A sandy pathway is framed by tall grasses leading to a beach with gentle waves. Sun loungers are visible along the shore, while the bright blue sky features a few scattered clouds. The peaceful scene highlights the natural beauty of the coastline.

4.95 out of 5 average rating, 43 reviews

AMI Ohana Beach Resort A with fabulous salt pool!

4.78 out of 5 average rating, 265 reviews

Large Private Pool Paradise - Close Beaches

Bungalow in Indian Shores

A serene beachfront scene showcases soft sand and gentle waves under a clear sky. Lounge chairs are arranged in the foreground, while umbrellas and beach tents are visible further along the shoreline. The bungalow's outdoor seating area is seen, surrounded by lush greenery.

4.96 out of 5 average rating, 165 reviews

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

4.97 out of 5 average rating, 173 reviews

A sandy path leads through lush greenery towards the beach, framed by overhanging branches. The ocean is visible in the distance, with light reflecting off the water. Shadows create a peaceful atmosphere as the sun casts a warm glow.

Cottage in Indian Shores

Beautiful Beachfront Cottage on the Water

4.95 out of 5 average rating, 185 reviews

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.

Home in Anna Maria

Discounted October Stays w/Private 30' Dock & Pool

4.99 out of 5 average rating, 144 reviews

A modern kitchen area features pale blue walls and a round dining table set for four. Stainless steel appliances, including a microwave and oven, are visible. A decorative light fixture made of translucent discs hangs above the table, adding a coastal touch to the space.

Condo in Holmes Beach

Short Stroll to the Surf! ~ Make Memories on AMI

Superhost

The outdoor area showcases a saltwater pool within a screened lanai, surrounded by a patio area with seating. The pool area is illuminated by natural light, enhancing the space's openness. A game room features plush seating arranged for viewing films, with walls designed for a cinematic experience.

Home in Clearwater

4.93 out of 5 average rating, 135 reviews

Clearwater Gameroom- Pool/Mini golf/Home Theatre

Family-friendly home rentals with a pool

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

A vibrant outdoor space is showcased with a table and chairs under a large umbrella, surrounded by lush greenery. The game room features a pool table and retro arcade games, while cozy seating areas inside invite relaxation. A glimpse of the heated pool is visible in the courtyard.

4.95 out of 5 average rating, 39 reviews

Spotlessly Clean, Pool & Hot Tub, 6mi to beach

Townhouse in Holmes Beach

A sandy beach extends towards a calm ocean, where turquoise waters meet a clear blue sky. Colorful umbrellas provide shade for beachgoers, who are relaxing on vibrant towels. The shoreline features soft white sand, inviting visitors to enjoy the peaceful environment.

4.91 out of 5 average rating, 47 reviews

Getaway Family Beach Townhome w/Pool!

An outdoor area features a heated pool surrounded by lounge chairs, a pickleball court, and a putting green, all enhanced by tropical landscaping. The interior reveals a comfortable game room with arcade games and modern amenities, providing a relaxing atmosphere for all guests.

5 out of 5 average rating, 20 reviews

Fall Special! - Family Fun - 9 min to Beach

5 out of 5 average rating, 46 reviews

The private saltwater pool is surrounded by lush palm trees, providing a serene atmosphere. A swim-up table is visible in the water, along with a shallow sunning shelf. A spacious wrap-around deck features a dining area and comfortable lounge chairs, ideal for relaxation.

Home in Anna Maria

༄ Sunset Shore on Anna Maria Island ༄

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 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