Family-Friendly rentals near Cortez 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.

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

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!

Silver Sands By the Sea: Open Christmas!

This charming seaside condo is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean, this dreamy one-bedroom condo is optimal for sunset viewing from a private, screened lanai. Take a 30-second walk to the pool and onward to the secluded beach with loungers and sun umbrellas. Enjoy a relaxing vacation at our peaceful condo at Silver Sands Gulf Beach Resort!

KING Bed + AMI Beaches + Beach Gear!

🎙️🦩Welcome to the Retro Flamingo! Your tropical getaway that combines style, fun, and the serene beauty of the Gulf Coast. This cozy, vibrant themed condo is the perfect destination for your next Beach vacation. Walking distance to Palma Sola Beach Causeway, where you can enjoy sun-bathing, horseback riding, jet skiing, and fishing! 5 mins or less from the Gulf of Mexico and powdery white sand beaches of Anna Maria Island! Kick back and relax in this retro “Old Florida” themed condo!

Sunset View Pet Friendly w/Pool Beach Home

Perfect Location! Our 3 bed/2 bath home just across the street from the beach & walking to shops & restaurants. Includes 1 king, 1 queen, & 2 twins beds. 2 living rooms each have a sleeper sofa & TV. Upstairs has additional eating area & access to balcony. Both bathrooms are equipped w/showers, hair dryer, & essentials. Full kitchen w/ breakfast bar. Enjoy a sunset from the 2nd floor balcony. Private pool, covered patio w/large eating area, WiFi, AC, washer/dryer, dishwashe

NEW! Beach Views!-Gulf Front!~Heated Pool!

Relax with the whole family at this peaceful place to stay. Welcome to Seagrape Cottage, a gorgeous and newly renovated vacation getaway with a brand-new private pool. This four-bedroom and four-bathroom home is conveniently located right across the street from the stunning white sands of Cortez Beach and is near Bridge Street, which offers a great place to fish, shop, and try new restaurants. Enjoy island life on your tropical getaway by booking Seagrape Cottage!

Kayak w/ Dolphins - Private Entrance Studio

Paddle with dolphins in Palma Sola Bay from this private-entrance, 2-room studio with living room, bedroom w/ queen, bathroom, food prep area (no kitchen sink). Two TVs, WIFI. Dock access in back yard includes use of kayaks/canoe or docking your boat. Quiet on dead-end street. Owner lives in back of house facing canal (see photo). Your space is private with a tropical street entrance & access to the back yard. Non-shedding dog considered with prior approval.

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.

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!

One Block to Beach - Ohana Hale Beachside 2 BR

COMPLETELY REMODELED February 2025! Aloha and welcome to our Island Home Ohana Hale AMI! Our home is designed for the ultimate beach vacation experience, featuring 2 cozy bedrooms and 1.5 baths. The open kitchen and living area create a spacious, inviting atmosphere, perfect for relaxation and fun. Be sure to check out our amazing 3rd-floor shared deck—it's the perfect place to watch stunning sunsets over the Gulf of Mexico.

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).