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!

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.

Beachfront Condo Resort on Treasure Island

Be among the first to experience this new condo resort. 992 sq ft of beachfront luxury with full resort amenities. These upper-floor corner units have gorgeous views of the ocean, and each room has a window with beach views. With 2 bedrooms and 2 bathrooms and a pullout couch in the living room, these units can comfortably house 6 people. After arriving in your open concept living area, you will access your private balcony through retractable sliding doors that let the ocean air in.

Boardwalk Bungalow - Johns Pass & beach steps away

LOCATION LOCATION LOCATION!! Boardwalk Bungalow is located right at the end of Johns Pass Boardwalk! With easy beach access from just under the Pass bridge, and no need to even cross Gulf Blvd. This 3-story duplex has 2 units, and this unit features 2 bedrooms, 1.5 bathrooms! The kitchen has grey solid wood cabinets, quartz countertops, and stainless appliances (NO DISHWASHER.) Updated bathrooms with chic tile selections & a small balcony with a peek at the Pass water views!

Tiki Bungalow | Gorgeous Htd Pool | Steps to Beach

An original early 1900 Indian Rocks Beach bungalow, beautiful and bright with pool! Across Gulf Boulevard from 8th Ave beach access with all the comforts of home. Rest in the tropical garden pool, hang out in the private tiki hut out back , hop on the trolley to explore the area. Many shops and restaurants are within walking distance. Splash Harbour water park at the Holiday Inn is walking distance for a day of fun! Have an unforgettable stay! City tax#1479

Modern 1BR Suite Steps to Madeira Beach

Welcome to your dreamy beach escape—just a few sandy steps from the shimmering Gulf! - Modern 1BR suite with stylish design - Cozy living room with Smart TV, Cable, and WiFi - Full kitchen stocked with essentials - Courtyard Grill & Al Fresco Dining - Beach Gear Included — chairs, towels, umbrella - Free Private Parking for 1 vehicle - Onsite Laundry (coin-operated) - Fresh linens, towels, shampoo & more provided

2BR | Oceanfront, Backyard Beach, Fully Equipped

Experience luxury coastal living at Indian Shores in this beautifully appointed beachfront retreat at Sunplace. Featuring 2 spacious bedrooms with a king and queen bed, plus a full-size roll-out bed and Pack ’n Play, this fully equipped condo is perfect for families and groups. Enjoy direct beach access, stunning Gulf surroundings, resort-style amenities, and easy access to local dining, shops, and nearby Clearwater Beach.

Beachside Escape | 2 min walk to Shore · Sleeps 7

Escape to our bright, stylish 2-bedroom beachside retreat, just one block from the shore! Perfect for families or couples, this apartment comfortably sleeps up to 6. Enjoy modern amenities, a fully equipped kitchen, and a dedicated workspace. A 5-minute stroll takes you to the beach for the perfect sunny getaway. Your tranquil coastal haven awaits! As reminder the space does have stairs that lead to the bedrooms

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! .

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.