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.

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!

Magical Guesthouse 1 mi from SRQ airport

@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

Silver Sands: Open Tomm, $99/nt + Fees!

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!

Charming and Updated 1 Bedroom in Runaway Bay

Our charming 1 BR/ 1 Bath condo is a new to the rental market. It was formerly owner occupied. The property is in the Bradenton Beach area of Anna Maria Island. Beach is right across the street with deeded access. The pool is the largest heated pool on the island. Fitness center has newer equipment. There is a fishing pier which also works as a great way to enjoy beautiful views of the Anna Maria sound. Free trolley stop is right in front of the property. Washer/dryer in unit.

Waterfront Gem/ Pool Spa+ Dock/ Near Bridge Street

Anna Maria Waterfront oasis! **5 min walk to beach, private dock, pool heat included!!** Relax in the private heated pool, sip coffee on the dock, or walk to the beach. This bright, updated home has spacious living areas, a stocked kitchen, smart TVs, fast Wi-Fi, and cozy beds. Great for families or couples! Grill by the pool, dine under the stars, or fish from the dock. Includes washer/dryer, beach gear, and parking. Your peaceful, sunny getaway awaits—book now!

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

Aloha and welcome to Ohana, our island home where guests are treated like family! This updated 2-bedroom, 1.5-bath retreat offers charm, comfort, and convenience. Enjoy a bright, open living space and a well-equipped kitchen perfect for relaxing or entertaining. Just steps from the beach, with access to a shared 3rd-floor deck—ideal for watching stunning Gulf sunsets. Your perfect Anna Maria Island getaway starts here!

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).

My Peaceful place on the bay.

Tucked away from the hustle and bustle, my mobile home is located in a very unique neighborhood right on the bay with a little beach 2 min. down the road from my house, where you can sit and enjoy the views or fish. The homes are a combination of mobile homes like mine and houses with the most wonderful people of all walks of life. Very quiet, friendly and 5 min. to Bradenton beach and 10 min. to AMI.