Beach house holiday rentals in Madeira Beach

Beach front cottage on Treasure Island, FL

Beautiful brand new cottage located directly on the Gulf of Mexico. Quiet and quaint, old style cottage that has miles of beach to walk and enjoy. The cottage is newly built, and includes state of the art bathroom and kitchenette. The kitchen includes fridge with ice maker, microwave, airfryer, induction cooktop, and fully equipped. The cottage is within walking distance to grocery store, trolley transit, dining, and is only 15-20 minutes to downtown St. Pete. Mainly weekly or monthly rentals.

Sunshine Beach Bungalow That Is a Unique Treasure

Charming, Light-filled 1938 bungalow, surrounded by tropical gardens, steps to Sunshine Beach. Offering both original detail and current amenity, this one-of-a-kind bungalow experience is located on Treasure Island near John's Pass in St Petersburg Florida. Situated on the gulf side of Gulf Boulevard, it makes for a most relaxing and convenient beach experience, all day and every day. No need to cross a busy intersection to reach the white sand and waves, just step out your back door to two co

Tropical Oasis Near Treasure Island Beach

Settle into The Break, your tropical oasis near Treasure Island Beach. - 2 bedrooms, 1 bath for up to 4 guests - Calming hot tub and BBQ in the tropical backyard - Fully-equipped kitchen for gourmet meals - Welcoming living room with smart TV and board games - Beach gear provided for your convenience - Step into our little corner of paradise at our newly refurbished property, a true family-friendly sanctuary with a Florida twist. - Short walk to local attractions and the beach.

Elevator | Heated Pool & Hot Tub | Pool Table

Welcome to our IRB beach retreat, just a short stroll to the pristine white sands and calm Gulf waters of Indian Rocks Beach! Unwind on the spacious outdoor patio, splash around in the heated pool, relax in the hot tub, or fire up the grill. This beautifully updated beach house offers bright, open living spaces perfect for families or groups seeking a relaxing getaway. Your serene white sand beach escape awaits – no crowded tourist spots here, just pure beach bliss! PETS MUST BE APPROVED

Billy's Beach Bungalow

Welcome to Billy’s Beach Bungalow—your cozy coastal escape just steps from the sand. Located directly across from the beach, this charming 2BR/1BA retreat sleeps up to six with a queen bed, bunk beds, and a pull-out sofa. Enjoy beach chairs, 2 kayak with a launche and fishing docks, walkable rentals, and a beach trolley every 30 minutes. Close to dining, live music, and beach-town fun. Please note: this is a pet-free property to help keep the space fresh and comfortable for all guests.

Quiet Escape | Pool, Theater, Game Room & Hot Tub

This spacious 5-bedroom, 3-bath retreat in peaceful Seminole—just one exit from the Gulf Coast beaches—was created for comfort, relaxation, and fun. Ideal for families, groups, or multi-generational stays, it offers the perfect balance of a tranquil getaway with quick access to sunshine, sandy shores, and coastal adventures. Spend your days relaxing by the private pool, soaking in the hot tub, or making the most of the home’s entertainment features while enjoying time together.

Luxury Waterfront Sunset Beach with Jacuzzi

Pure Luxury at Sunset Beach with a Premium Jacuzzi Live like a Celebrity at this spectacular waterfront 3 story house all to yourself in Sunset Beach!! Fresh and Completely Renovated with impressive views of the water from every level! Your own private dock where you can pull up your own jet ski or boat! This location extremely unique with full Waterfront access & view from the house, and you can walk just steps away to the perfect white sands & warm ocean on Sunset Beach

Coastal Dream Beach House | Private Path to Sand

SUNNY ORANGE STAYS presents… Coastal Dream ➠19622 Gulf Experience Indian Shores magic in this spacious, single-level beachside sanctuary. Just 150 feet from sugar-white sands, Coastal Dream offers standalone privacy with a "private beach" feel. The rare 3-bedroom, 3-bathroom layout gives every guest space to unwind. Perfect for grilling after a day in the surf or strolling to local coffee shops, this home embodies the effortless "Old Florida" lifestyle. Learn more below…👇

High-end Beach heaven, Sleeps 10, 3 private decks

Ideal for those who appreciate single-level living. 3 bedrooms & 2 baths located on the main floor, & loft-style 4th bedroom upstairs. Enjoy 3 decks!: a private beach deck just a 30-second walk away + front & upper decks offering partial ocean views perfect for morning coffee or for cocktails. The primary booking guest must be at least 27 years old, stay on-site during the reservation, and provide valid government-issued ID to host within 24 hrs of booking. Vtr -1609

Ocean Breeze at Redington Beach

Welcome to The Ocean Breeze, a luxury 4-bedroom, 3.5-bath coastal townhome just steps from the white sands of Redington Beach. Designed for comfort and connection, the home features light-filled spaces, refined finishes, and an open layout perfect for families and friends. This is our family’s beach home—not a commercially managed rental—thoughtfully cared for and shared with guests seeking an elevated, relaxed, and memorable coastal escape.

Sun-drenched Townhome on beautiful Madeira Beach!

Enjoy stunning Gulf views over the dunes in the heart of Madeira Beach, known for its relaxed, family-friendly atmosphere. This spacious, modern home offers everything you need, including beach chairs, towels, umbrellas, and toys. Restaurants are nearby, and John’s Pass is just a few blocks away. The home features an open living area with beach access, a fully equipped kitchen, multiple bedrooms, and a private balcony overlooking the beach.

Beautiful New Home with Ocean View, Steps to Beach

Luxurious 3BR/3BA fully furnished new home that sleeps 11. Enjoy the gorgeous ocean views with two large balconies, perfectly located across the street from the beach, Caddy's restaurant and walking distance to several diverse options, and a 15-min walk to John's Pass (jet skis, fishing, restaurants, and more!) Amenities: - Smart TVs in all rooms - Fully equipped Kitchen - Gas grill - Beach accessories - Board Games - Family friendly