Family-friendly vacation rentals in Madeira Beach

Beach Front at “The Shore”

Welcome to The Shore —a beautifully renovated beachfront retreat in the heart of Madeira Beach. This second-floor 2-bedroom, 2-bath condo offers completely unobstructed Gulf views and the rare feeling of being almost directly on the water. Relax with your morning coffee in the signature blue chairs, watch breathtaking sunsets from the living room, and enjoy easy access to John’s Pass, waterfront dining, shopping, and the best of Gulf Coast beach living, where the shoreline feels just feet away.

40ft Floating Bungalow with Resort Perks

Unmatched Scenic Serenity: Imagine waking up to stunning sunrises and gentle ocean breezes. Your houseboat becomes a floating oasis, providing the comforts of a hotel but floating. Exclusive access to the resort across the street on the beach. Where you can use the heated pool and hot tub. Outdoor grilling area with corn hole boards are available to entertain you while you cook at the Beach Resort. No Grill on the Boat. *Boat is stationary at dock. **MOTION SICKNESS?? PLEASE DO NOT BOOK**

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!

Private Beachfront 4BR 2BA Bungalow*Pool*PETS OK

PRIVATE BEACH OPEN! Barrett Beach Bungalows preserves the traditional Florida beach endearments in style with 4 charming beach bungalows. Why spend your Florida beach vacation in a busy hotel ? Stay in your own private bungalow! No crowded halls, elevators, lobby areas. Enjoy a vacation the way Florida was before the development boom. No waiting for crowded elevators! Direct on sandy beach with sparkling pool! All bungalows have modern amenities, are extra clean & beautifully decorated

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.

*Shore Thing* Walk to Beach | Intercoastal Views

🏖️ Shore Thing Condo 🏖️ Escape to pure coastal paradise at this chic Treasure Island condo. You are mere footsteps from sugar-sand beaches, refreshing salt air, and unmatched sunsets. Keep an eye on the water as dolphins and manatees drift right by! 🐬🌅 Indoors, unwind in elevated, modern coastal design. From cooking in the upscale kitchen to swimming in the heated pool, our signature service guarantees your peace of mind is the top priority. Book today! ✨🐚

Beach Front Condo!

Escape to paradise in this stunning condo, situated right on the sand, you'll wake up each morning to the soothing sounds of the ocean waves and enjoy breathtaking views of the sparkling turquoise waters from your own private balcony. The condo is tastefully decorated in a modern coastal style, that will make you feel right at home. The spacious living area boasts plenty of natural light and comfortable seating for relaxing after a day at the beach.

Luxury Beach Bungalow | Walk to Dining & Sunset

Welcome to Mango! Nestled in the heart of Indian Rocks Beach. IRB is a hidden gem radiating a whimsical, small-town charm that evokes nostalgic memories of carefree childhood summers by the shore. Just ✌🏽 blocks away, the Gulf beckons, offering pristine fluffy sand and unforgettable sunsets. As the sister cottage of Coco, Mango invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits! 🥭

Beachfront balcony view heated pool hot tub

Gorgeous 2 bedroom condo directly on the Gulf of Mexico with a double patio overlooking the view. The pool is heated and there is a hot tub and they are both located directly on the gulf overlooking the water. It is close to John's Pass and in between Clearwater Beach and St. Pete beach. There are shops and restaurants within walking distance. A great place to getaway and relax! .

Modern 2BR Apt Steps to Beach

Bright, modern 2-bedroom beach retreat just one block from the shore with beautiful ocean views. Perfect for families or friends, this stylish apartment comfortably sleeps up to 6. Features a fully equipped kitchen, dedicated workspace, free private parking, and a shared patio with a grill. Enjoy premier beach access just a 5-minute stroll away. Your ideal coastal getaway awaits!

Couples retreat•5 Min Walk Beach. Endless Sunsets

Fall in love with Flipper’s at Mad Beach, a private, newly renovated coastal oasis designed for romantic getaways. Located just a few steps from the sugary sands of Madeira Beach, this intimate retreat offers the perfect blend of modern luxury and relaxed beach vibes. It is the ultimate hidden gem for couples seeking a peaceful, private, and memorable vacation by the ocean.

COASTAL CHIC! Luxury Apartment with Oceanviews

Welcome to our Gulf View Condo SEASIDE #1604 at the "Madeira Bay Resort" - just steps from the beautiful white-sanded Beach and famous John's Pass! Built in 2020, you will enjoy brand new amenities, luxurious furnishings, memory foam beds, an electric fireplace, a gourmet kitchen and all beach essentials, so you only have to pack your flip flops and come on over!