Anna Maria Island Vacation Rentals With a Pool
Looking for a refreshing vacation? Explore these fantastic Anna Maria Island rentals with pools! After a day at the beach, a relaxing swim in your pool is the perfect way to unwind.
A vacation rental with a pool adds significant value to your getaway. A private pool offers a relaxing escape from crowded beaches, providing a convenient way to cool off with a refreshing swim whenever desired. It also creates a safe and enjoyable space for family fun, especially for children. It grants you a personal area to unwind and soak up the Florida sunshine in complete privacy.
169 properties available
Sea Grape Escape by AMI Locals VRC18-000063 Welcome to Sea Grape Escape by AMI Locals, a beautifully appointed two-bedroom, two-bathroom elevated home in the heart of Holmes Beach on Anna Maria Island. Perfect for small families or couples seeking a stylish and peaceful retreat, this coastal chic getaway combines modern comfort with relaxed island
Bleuphoria by AMI Locals Welcome to Bleuphoria, a four-bedroom, four-bath luxury beach home on the peaceful North End of Anna Maria Island. Just three houses away from the sugar white sands of the Gulf and steps from Pine Avenue’s boutique shops and restaurants, this designer retreat delivers modern coastal elegance and resort-style amenities. With
Welcome to Bay View Beauty, part of our Exclusive Collection. This luxurious seven-bedroom, seven and a half bath waterfront home with unobstructed bay views. Ideally located along Anna Maria’s North Shore Drive, this luxury retreat places you steps from the white-sand Bay beaches, minutes from the Gulf beaches and Bean Point, and within walking di
Emerald Shores by Anna Maria Island Accommodations Home in Anna Maria, FloridaWelcome to Emerald Shores, a six-bedroom, four-bath duplex vacation rental just one minute from the Gulf beaches of Anna Maria Island. Perfect for large families and groups, this property offers two separate units with identical floor plans, each featuring three bedrooms,
Beach to Bay by AMI Locals Vacation Rental License #VPL22-000064, DWE5105473 Get ready to indulge in the ultimate luxury vacation at Beach to Bay, a stunning three-level waterfront home in Bradenton Beach! This spacious bayfront estate features a private dock, a brand-new infinity pool with an in-ground spa and waterslide, and a sunny rooftop deck
Seas the Day by AMI Locals VRC22-000025 Welcome to Seas the Day by AMI Locals, an extraordinary six-bedroom, five-bath luxury home designed for families and groups seeking the perfect Anna Maria Island vacation rental. Just a six-minute walk to Holmes Beach, this three-level retreat combines style, comfort, and fun with its private pool and spa, ro
Ariel’s Island by AMI Locals Vacation Rental License #VRC18-000078 / VRC18-000079 Welcome to Ariel’s Island, a one-of-a-kind duplex vacation rental in Holmes Beach, just a 3-minute walk to the turquoise shores of Anna Maria Island! This spacious property combines two vibrant units, Ariel’s by the Sea and My Island Paradise, ideal for large familie
The James by AMI Locals Welcome to The James by AMI Locals, your ultimate North End beach getaway on Anna Maria Island. This brand-new four bedroom, four and a half bath luxury home is just a short six-minute walk from the island’s world-famous Gulf beaches and offers a rooftop deck with stunning Gulf views, a private pool with spa, and resort-styl
Under the Sun by AMI Locals Vacation Rental License #VR22-000075 Welcome to Under the Sun! This five bedroom, four and a half bath Anna Maria Island vacation rental blends modern luxury with laid-back island charm. Just a two-minute walk from the white sandy shores of Anna Maria Beach, this home invites you to relax in style with a rooftop deck, pr
Deckadence by Exclusive Vacations Bayfront Luxury | Rooftop Spa, Resort Pool + Golf Cart VR25-000002 Welcome to Deckadence by Exclusive Vacations, a luxury coastal retreat ideally located across the street from the bay and just a short walk to the Gulf beaches on Anna Maria Island. This four-bedroom, four-and-a-half-bath home features a rooftop dec
Welcome to A Wave From It All, a luxurious five-bedroom, six-and-a-half-bath vacation rental in the heart of Anna Maria Island. Just a short seven-minute walk to the island’s white-sand beaches and steps from the boutiques and eateries along Pine Avenue, this family-friendly retreat is ideal for large families and groups seeking comfort, fun, and r
Blissful Bungalow by AMI Locals VRC21-000131 Welcome to Blissful Bungalow by AMI Locals, a stylish three bedroom, two and a half bath vacation home that perfectly captures the charm of Anna Maria Island. Just an 8-minute walk to the pristine Gulf beaches, this beautifully updated ranch-style retreat offers a private pool, lush tropical landscaping,
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