Holiday houses 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.

Location · Family · TV

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.

Family · Location · Walkability

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.

Family · Location · Beach

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.

Family · Location · Pets

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!

Location · Family · Comfort

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.

Location · View · Nearby

Sunset Beach Suites - Madeira Beach Getaway

Welcome to your perfect beach getaway at Sunset Beach Suites. - Bright, contemporary interior designed for relaxation - Open-concept living area with two TVs - Fully equipped kitchen for home-cooked meals - Peaceful bedroom with plush king-size bed - Complimentary beach chairs for sunbathing - Breathtaking sunset views over the Gulf Book your stay at Sunset Beach Suites today—your slice of paradise awaits.

Location · Family · Condition

Treasure Island Waterfront

Escape to a peaceful waterfront condo in Treasure Island’s Isle of Capri. This bright 1-bedroom retreat features canal views, a private patio, fast Wi-Fi, free parking, self-check-in, complimentary e-bikes, and an e-scooter. Walk to Treasure Island Beach, John’s Pass, restaurants, and nightlife. Enjoy the shared fishing dock, BBQ grill, and relaxing Florida Gulf Coast atmosphere perfect for couples and small families.

Location · Value · Beach

GulfPort Paradise, Bali-like Oasis with Pool

The perfect vacation spot. If you’re looking for a quiet, comfortable, boho-modern house, this is the place for you. Perfect for guests that want to experience living like a Gulfport local with chill vibes. The location couldn't be better for exploring everything that the area has to offer. Nestled in the adorable town of Gulfport, the property is just a 1 block walk from the Marina and waterfront of Boca Ciega bay.

Family · Value · Accuracy

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

Family · Value · Sleep quality

Beachfront Condo - Sunset Views at Madeira Towers

Your mornings start with coffee on a wrap-around balcony overlooking the Gulf. Your evenings end with sunsets that stretch for miles. Step outside, you're on the beach. This beachfront corner condo has three bedrooms, two baths, and everything you need: beach chairs, umbrella, wagon, and towels all provided. Heated pool and hot tub, parking for one car, high-speed Wi-Fi. Complete package.

Kitchen · View · Checkout

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.

Family · Location · Parks