Family-friendly vacation rentals in Madeira Beach

Gulf View Penthouse | Steps to Beach + Johns Pass

Your Penthouse Paradise awaits at our Gorgeous, 7th-floor Gulf-View Condo in the new Madeira Bay Resort! Enjoy sweeping views of the beach, Gulf of Mexico, & miles of pristine coastline. Just steps from the sand & 1 block from John’s Pass Village & Boardwalk. Walk to dining, shopping, bars, & water sports. Come experience the best of Madeira Beach & make unforgettable memories in our newly furnished, well-stocked, luxury retreat w/all the comforts of home. Perfect for groups or families alike.

Spectacular beach to bay views from this resort.

Our condo has spectacular water views from the Bay to the Beach. We have a large one of a kind kitchen that is unique to our resort, with granite counter tops, hardwood cabinets, and all stainless steel appliances. Everything you need to prepare a meal is provided along with basic spices and condiments, Coffee, creamer, and sugar. The master bedroom has a new king size bed and walk in closet with all beach gear also available for your use. We have 2 - 50" flat screen TV's with cable as well.

Family Friendly Beach Cottage in Madeira Beach, FL

Mad Beach Cottage is a single family home in the Surf Song Resort on Madeira Beach 60 flip-flop steps to SAND! No streets, boardwalks or stairs! You'll enjoy a heated pool, 3 Weber grills, shuffleboard and sundeck with lounge chairs for gazing at spectacular sunsets every night. It's located across from famous John's Pass Fishing Village Boardwalk for shopping, dining, ice cream, coffee, live music, brew pubs, dolphin/fishing/sunset/pirate boat cruises, wave runner/kayak rentals. 5* LOCATION!

Luxury Penthouse Beach Condo

Madeira Beach is Back & Better Than Ever! Whether you’re here for the legendary Gulf sunsets or the vibrant local energy, everything you love is right at your doorstep. Vibe: Catch live music and cold drinks at Saltwater Hippie Play: Challenge the family to a pirate-themed round of mini-golf at Smugglers Cove—located right across the street. And of course, the main event: endless, world-class white sands are waiting for you just 400 feet away. Your perfect beach day starts here!

Beachfront Getaway with Resort-Style Pool

🌴 Escape to your own slice of beachfront paradise at Madeira Beach. This cozy 1BR studio features two queen beds, a private patio overlooking the ocean, and direct beach access just steps away. This unit is located on the 1st floor of the building. Elevator access is available. Enjoy a fully equipped kitchen, fast WiFi, and access to a pool and BBQ grill. With free parking and everything you need to relax and unwind, it’s the perfect getaway for couples, friends, or small families.

Walk to Beach | Private Pool • Mini Golf • Firepit

Welcome to your dream beach getaway! This beautifully renovated 2-bedroom, 2-bathroom coastal home offers the perfect blend of relaxation and fun, just a short walk to the white sands of Redington Beach and all the charming local shops and restaurants. Outside, the backyard is your private paradise! Enjoy our pool with plenty of lounge seating, gather around the fire pit for sunset moments, or challenge your crew to a round of mini golf—there’s endless entertainment right at home.

Luxury Home N/Heated Pool/Rooftop/Steps to Beach

New, 2000 sq ft/3 Bedroom/3 Full Bathrooms 2 living rooms/modern townhome with heated salt water POOL located near a canal and the gulf just two blocks from the beach. Please note the pool is shared with the other side of the duplex. You can enjoy full view of the canal and partial views of the gulf from the balconies and the rooftop! Walking distance to the beach, restaurants, and volleyball. Close to Johns Pass, 2 miles. Please ask for the golf cart availability and a fee.

Coastal Retreat Near Madeira Beach With Game Room

This 2-bedroom unit with a bonus Game Room and Sunroom is the perfect getaway for up to 6 people looking to enjoy the beautiful beaches of this area. Located in a quiet neighborhood on a private cul-de-sac, it is the perfect place to rest and recharge between trips to the most beautiful beaches in the world. This location is just a quick 5-minute drive (2 miles) to the Madeira Beach access and a 10-minute drive (3.7 miles) to the famous John's Pass Village and Boardwalk.

Oceanfront Condo | Rooftop Terrace | Arcades |

Picture this: you step onto the rooftop as the Gulf stretches out in front of you — golden hour, warm breeze, a putting green underfoot and nowhere else you'd rather be. Back inside, the kids are deep into NBA Jam while the waves crash just beyond the balcony. Hello Sunshine is a direct oceanfront condo in the heart of Indian Shores, designed like a magazine spread and stocked for the kind of trip people talk about long after they've unpacked.

Waterfront Escape - Steps to Beach, Dining & Shops

Rest, relax and unwind with family or friends- you're on beach time. Wake up to the serene sunrise over the marina from your private balcony. Soak up the sun on the white powder sand of Madeira beach located directly across the street. Make a splash in the on site outdoor swimming pool or relax in the jacuzzi. Visit famous John's Pass village just a 2 minute walk to vibrant music, delicious food and drinks, and fun water adventures.

Penthouse,intercoastal, 3/3 views/heated pool

This stylish place to stay is perfect for group trips. Brand New Luxury Madeira Beach Penthouse With Heated Pool 4 floors up with partial beach and intercoastal views, all on a level floor plan 4 stories up with elevator access! Enjoy the comforts of new unit with modern appliances and fixtures in this 3/3 that bolsters a king master bedroom, two guest queen bedrooms all with in suite full bathrooms.

Beachfront Luxury Corner Unit, Balcony, Pool

Welcome to your dream getaway! This stunning top-floor corner unit is located directly on the beach in one of Madeira Beach’s premier buildings. Wake up to the sound of waves, soak in panoramic Gulf views, and enjoy the perfect blend of comfort and luxury. Whether you're here for a relaxing retreat or a fun-filled beach adventure, this condo has everything you need for an unforgettable stay.