Holiday rentals with a pool in Anna Maria

4.94 out of 5 average rating, 159 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.

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, 121 reviews

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

Conveniently located just 12 minutes drive from the beaches, close to IMG Academy and all amenities, this second floor corner condo has much to offer. Its picturesque lake view, modern upgrades, and spectacular open-concept design combine to enhance your vacation experience. Facilities at Shorewalk Palms include heated swimming pools, hot tubs, tennis court, basketball court, shuffle board court, pool table, ping pong table, BBQ area and a kid's playground. All are available for your enjoyment

4.96 out of 5 average rating, 101 reviews

Steps to the beach! Updated Condo at The Terrace

Just 200 steps from the white sands of Holmes Beach, this beautifully updated 2BR/2BA condo has everything to offer! Our unit features high-speed internet, coffee maker, blender, balconies off of each bedroom, 1-car garage, washer/dryer, heated shared pool, and access to all the beach necessities (toys, umbrellas, chairs, tent, cart). This unit sleeps 6 (1-King, 1-Queen, & Full size sofa bed). LOCATION, LOCATION! You'll be just steps from restaurants, cafés, shops, and the free island trolley!

A heated pool is surrounded by lush greenery and palm trees. Lounge chairs are positioned along the perimeter, and a gentle blue hue reflects off the water. The two-story buildings in the background create a tranquil resort-like setting.

4.98 out of 5 average rating, 128 reviews

NEW listing on AMI! Walk to fabulous beach front!

Updated, well appointed, clean and comfortable, my unit at Sandy Pointe II is in a secluded setting just a few minutes walk to a less crowded, quieter section of beautiful AMI beach. From here the Island is at your fingertips! Sink your toes into beautiful white sand, watch gorgeous sunrise and sunsets, enjoy the island vibe and music at our many restaurants! A FREE Island trolly stop is steps from our entrance with grocery, drug store, beach shops and so much more just across E Bay Dr.

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, 115 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

4.94 out of 5 average rating, 120 reviews

The Peachy Beach House, steps to the gulf

The perfect place for a combination family vacation and some romance-when the kids are in bed, turn on the spa and music. June, July and August, Saturday to Saturday only. If custom trip length is wanted- ask Two bedroom, 2 full bathroom, new heated private pool/spa Steps to semi-private gulf beach, on quiet street in N. HB Well-stocked kitchen, 2 TVs, large primary suite and amazing gulf views from bedrooms. Crib, high chair, beach chairs, wagon, umbrella, beach toys and towels

An inviting exterior view of Sunrise Villa showcases a well-maintained landscape featuring lush greenery and vibrant plants. A spacious driveway leads up to a garage, with decorative stone detailing accentuating the garden area. The home is framed by palm trees, contributing to the tropical ambiance.

5 out of 5 average rating, 109 reviews

Sunrise Villa - Tropical 3 bedroom home with pool

Relax with the family at this tropical oasis. Sunrise Villa sits in the corner of a quiet cul-de-sac, just a quarter mile from Palma Sola Bay and 5 miles from the quaint island of Anna Maria and its sandy white beaches. Enjoy the tropical backyard paradise and the abundance of restaurants, beaches, and entertainment in close proximity. Lounge by the pool, take a bike ride along the bay, take a short bike/car ride over to the island, or take a short car ride to downtown Bradenton.

4.97 out of 5 average rating, 185 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 spacious patio is highlighted by a heated pool, surrounded by a decorative stone border. Comfortable outdoor seating is arranged nearby, beneath string lights that create a soft glow. A serene water view and lush greenery are visible in the background, enhancing the outdoor ambiance.

4.95 out of 5 average rating, 124 reviews

Casa Bella-5BR/Waterfront/Pool/Spa-9 Min AMI

Beautifully renovated 5 bedroom home. Located 3 minutes from beach access and 9 minutes to Anna Maria Island. A massive waterfront patio with string lights and heated pool and spa encompass this house. Master bedroom with walk-out to spa. Custom double walk-in shower in master suite. Family room with 86" television, decorative fireplace, and 15' ceiling. Roku TV’s in every bedroom. Outdoor propane grill. Beach chairs, umbrella, and cart. We welcome you to Casa Bella.

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, 151 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, snowbirds, reunions, and couples!

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, 186 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.

An aerial view captures a heated saltwater pool accompanied by a spa hot tub, surrounded by a stone patio and tropical landscaping. Loungers and Adirondack chairs are positioned for relaxation under a shaded umbrella. A serene pond and lush greenery create a tranquil backdrop.

5 out of 5 average rating, 117 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!

Popular amenities for Anna Maria rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

An inviting outdoor space is showcased with a turquoise pool surrounded by well-maintained greenery. Comfortable lounge chairs are positioned near the pool, and tropical plants provide privacy and a lush atmosphere. The area features a mix of sun and shade, enhancing the tranquil environment.

4.97 out of 5 average rating, 98 reviews

Luxury BEACH HOME! 2 King Suites! Heated Pool/Spa!

4.97 out of 5 average rating, 30 reviews

Ocean72, 2bed 2bath with pool

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, 198 reviews

Sea AMI

4.97 out of 5 average rating, 34 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

4.88 out of 5 average rating, 42 reviews

A private, fenced backyard features a heated swimming pool surrounded by lush landscaping. Loungers are positioned nearby for relaxation. A striped umbrella provides shade, adding to the inviting outdoor space that complements the cottage style of the home.

Home in Anna Maria

The Cottage on Pine - Pine Ave Cottage w/ Pool

A serene outdoor area features a well-maintained lawn with stone pathways and tropical landscaping. Palm trees provide shade around a bar area, overlooking the water. A private dock is visible in the background, with the gentle bayou waters reflecting the blue sky.

5 out of 5 average rating, 58 reviews

Waterfront Bungalow• Dock•Heated Swim Spa•Near AMI

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, 36 reviews

Blessed Haven Peaceful Getaway 3 Miles to Beach

Condo rentals with a pool

4.87 out of 5 average rating, 141 reviews

Condo in St. Pete Beach

Livin' Poolside Steps to Upham Beach Condo Sleep 6

A heated pool is surrounded by a paved patio and lush tropical landscaping. Comfortable seating under an umbrella is positioned nearby, creating a relaxing outdoor space. The building above features a balcony, adding a vertical dimension to the inviting environment.

4.88 out of 5 average rating, 128 reviews

Steps from the beach

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, 194 reviews

Luxury 3/3 Margaritaville Resort

4.99 out of 5 average rating, 207 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.

4.98 out of 5 average rating, 219 reviews

Condo in Longboat Key

Oceanfront: Lots of January Availability!

A spacious living and dining area features a table set for four with light-colored chairs. A comfortable sofa is arranged against the wall, and large sliding glass doors allow natural light to flood the space, providing views of the nearby lake and greenery.

4.98 out of 5 average rating, 203 reviews

Shorewalk full condo AnnaMaria Beaches IMG

4.95 out of 5 average rating, 152 reviews

Condo in Sunset Beach

Stunning BEACH FRONT Condo, KING Size Bed, Balcony

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.

4.99 out of 5 average rating, 145 reviews

Short Stroll to the Surf! ~ Make Memories on AMI

Other holiday rentals with a pool

5 out of 5 average rating, 41 reviews

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.

Home in Anna Maria

Veselka - Canal front w private heated pool & dock

Apartment in Holmes Beach

A spacious living area features a light-colored sofa adorned with colorful cushions. A round coffee table sits centrally on a patterned rug, while large windows invite natural light. A charming dining set can be seen in the background, creating an open and inviting atmosphere.

5 out of 5 average rating, 18 reviews

Sand & Sea Oasis: Condo with Private Beach Access

5 out of 5 average rating, 96 reviews

Heated Pool-Game Room-EV-Near AMI Beaches/IMG!

A serene backyard scene showcases a saltwater pool with a calming waterfall cascading over smooth rocks. Lush tropical plants and palm trees create a vibrant, green backdrop, enhancing the natural beauty of the private oasis.

4.97 out of 5 average rating, 29 reviews

Waterfall | Spa | Saltwater Pool | Private Oasis B

Holiday home in Holmes Beach

5 out of 5 average rating, 12 reviews

pink peacock

4.97 out of 5 average rating, 72 reviews

A serene pool area is surrounded by lush palm trees and tropical foliage, providing privacy. The rectangular pool features clear water and is accompanied by lounge chairs placed on a spacious patio. Bright blue skies complete the tranquil outdoor setting.

Home in Anna Maria

Anna Maria Chateau. Private Home With Heated Pool.

A spacious balcony is furnished with a large, green sectional sofa and a glass-topped coffee table. It offers stunning water views through expansive glass panels, with a dining set in the background. Soft hues of pink and purple adorn the sky at sunset.

5 out of 5 average rating, 6 reviews

Bradenton Retreat-Pool, Stunning Views & More!

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.