Home rentals with a pool near Cortez Beach

Walk to it all! Restaurants + Heated Pool +Beach!

🌊🏖️Welcome to Making Waves on Anna Maria Island-where you are steps from the beach and centrally located to it all, footsteps to the trolley stop! Escape to paradise and experience the ultimate beach getaway at this stylish beach house with heated pool, nestled in the heart of Anna Maria. Walk outside the door to the pristine beaches, renowned local restaurants, and the vibrant Bridge Street with live music, restaurants, bars, and shopping. Our beach retreat promises an unforgettable vacation!

AMI Dock of the Bay - "Over the Water" 2nd Floor

AMI Beach + Bay Home with Fishing Pier + Heated Pool on Sarasota Bay - "Dock of the Bay" - "Over the Water" / 2nd floor of duplex • Unbelievable views of water + birds + wildlife + night lights! • Relax with fish jumping and birds flying along 1 of only 34 coveted docks/piers south of Cortez Bridge! • Fish off our dock and rod holders! • Heated pool w/ spa jets/benches only 10 feet from Bay! • Walk 2 blocks to Bridge Street/Key West-style restaurants,bars • Live Music heard on dock + WiFi!

Coastal Luxe Villa! Near AMI

Welcome to Coastal Luxe Villa, your perfect Florida escape—nestled in historic Cortez and just minutes from the sandy shores of Anna Maria Island. This spacious three-level coastal retreat combines modern comfort with beach-town charm, offering stunning bay views and endless amenities for unforgettable memories. Private garage with a bonus table tennis setup Sparkling heated saltwater pool with outdoor seating, dining, firepit table, and gas grill Convenient elevator access to all three floors

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.

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!

Spectacular Beach/Bay views private pool elevator

TWO MASTER SUITES! Modern home within walking distance to Beach, Bay, Historic Bridge Street, pier, restaurants, shops, ice cream, mini golf, fishing, water sports, this location has it all! You will absolutely love the convenience here! Enjoy our beautiful beaches, watch sunsets and sunrises from your balconies or enjoying the heated pool. We are the second house from the beach 50 yards and your toes will be in the sand. Clean quiet street but close enough to walk anywhere.

Bayview Pointe! Luxury Villa near Anna Maria isle!

Welcome to Bayview Pointe - A Private Gated Luxury Resort Residence on Florida’s Gulf Coast, just minutes from world-famous sandy shores of Anna Maria Island. From the moment you arrive, Bayview Pointe feels like a private boutique resort. The home’s airy coastal design, sweeping bay views from multiple levels, sparkling heated saltwater pool, convenient elevator access to all three floors, private garage and elevated amenities create an atmosphere of effortless luxury.

Mermaid Tale by Duncan Real Estate

Welcome to Mermaid Tale! Relax stress-free in this two-bedroom accommodation which is on the top floor of this cute vacation triplex, only 5 houses from the Bradenton Beach gulf beaches and walking distance to restaurants, bars and shopping. Mermaid Tale is very comfortably located close to Bridge Street. Mermaid Tale is a great getaway for 4 people. Walk up the stairs to the first floor entrance and be greeted by coastal flair. The kitchen is fully equipped.

Rustic Coastal Escape| Pool | Fire Pit

Welcome to Rustic Coastal Escape, a charming 3-bedroom, 2-bath retreat inspired by relaxed beach living and vintage coastal style nestled in historic Cortez village. Thoughtfully decorated with rustic touches and coastal décor throughout, this home offers a warm, inviting atmosphere perfect for families, couples, and friends looking to unwind near Florida’s Gulf Coast. The beach is just a 2 minute drive or just a 15 to 20 minute walk away.

NEW! Sideways~Heated Pool and Spa! Steps to Beach!

🌊 Sideways is a beachside retreat perfectly set between the Gulf and the Intracoastal Waterway 🌴. Just a 1-minute walk to the beach, this home features a private heated pool & spa, rooftop deck with panoramic water views, screened porch with TV, and BBQ grill. Dog-friendly with approval, close to dining and shopping, and parking for up to four cars—Sideways offers the perfect blend of comfort, views, and island relaxation ☀️🏖️🍹

Pelican Cove 1 - Anna Maria Island - Condo 2 Bedro

Pelican Cove 1- Anna Maria Island - Condo 2 Bedroom /2 Bath, maximum occupancy of 6 people. Gulf View Florida's Finest Beach to Bay Resort with a Community pool! Located south of the shops and restaurants on Bridge Street, Pelican Cove lures those who appreciate a lively vacation. Start your day with a game of tennis, swim your laps, jog on the white sand beaches, or grab fins and mask for snorkeling.

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴