House holiday rentals in Madeira Beach

Waterfront Stay Where the Manatees Play!

Welcome to The Manatee — a laid-back waterfront retreat where coastal charm meets life on the water. Spend your days kayaking the canal, watching for manatees nearby, enjoying waterfront views, or exploring John’s Pass just steps away with its restaurants, shops, bars, and local attractions. Designed for relaxed Gulf Coast living, The Manatee offers the perfect blend of fun, comfort, and waterfront escape. Private dock access may be available during your stay; message for details and pricing.

Value · Location · Sleep quality

Paradise on the Pass - 360 Rooftop water views!

Looking for a family friendly space central to everything you could need for a fun beach vacation? Look no more! Paradise on the Pass is located at the end of World Famous John's Pass Boardwalk, just walk out your front door and you are steps away. 360 rooftop water views and beach access from under the Pass bridge, without having to even cross Gulf Blvd. This duplex unit features 2 bedrooms, 2 bathrooms and sleeps 8. Everything is BRAND NEW... full kitchen, baths, paint, appliances & more!

Value · Family · Cleanliness

Easy Walk to Beach! 3 BR/2 BATH! Pets OK!

This charming retreat offers the perfect blend of relaxation and adventure. Located just steps from the pristine white sands and sparkling waters of the Gulf of Mexico, this home is ideal for families, couples, or friends looking for a sunny getaway! Inside, you'll find a beautifully decorated and spacious home with amenities like a fully-stocked kitchen, WiFi, and a smart TV! Nearby, you'll find John's Pass Village, a vibrant hub of local shops, restaurants, and water sports activities!

Value · Location · Air conditioning

Tranquil "Ocean Breeze Retreat"

Escape to our serene and coastal "Ocean Breeze Retreat", ideally located across the street from the BEAUTIFUL, Redington Beach! This charming home has been designed to create the most relaxing spa-like atmosphere along with plenty of entertainment and essentials to keep your family entertained and comfortable with everything you need. Nestled in a quiet neighborhood, with your own tropical oasis in the backyard featuring lush landscape, a lit up heated pool, spa, fire pit, games and more!

Location · Family · Indoor spaces

Beautiful Tampa Bay Pool Home Near Gulf Beaches

A beautiful Gulf Coast residence with many amenities to offer. Bright and open furnished spaces, for relaxing and entertaining up to 10 guests. A quiet, upscale neighborhood , your just 6 minutes from Madeira Beach and many other Gulf of Mexico beaches. Or, fun & sun in the private pool outback. 20 minutes from Downtown St Pete, which offers restaurants, museums, the new Pier, and excellent night life. Very close to countless restaurants, shopping, coffee shops, and grocery stores.

Value · Family · Sleep quality

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.

Location · Family · Checkout

Sea Vue -King Beds | Stunning Views | 2MI to Beach

Welcome to Sea Vue, a luxury Western facing home offering unparalleled water views, superior outdoor living, 5 bedrooms with dreamy hotel style bedding and activities for the entire group. Located just 2 miles to award winning St. Pete Beach & a short drive to the booming Downtown area this home is sure to exceed guest's highest expectations. Prepare to experience the highest level of customer service and indulge in your own private oasis inside and out.

Family · Location · Outdoor spaces

Gulf Gardens Madeira Beach Studio Cottage

Experience the charm of Gulf Gardens, a serene oasis that captures the essence of classic Florida living. Just steps away from the powder-white sands of Madeira Beach, our property offers public beach access directly across the street, making it the perfect spot for your next romantic getaway or relaxing vacation. After a sun-filled day on the beach, unwind by our sparkling pool, surrounded by lush tropical landscaping and vibrant greenery.

Location · Family · Walkability

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

Family · Value · Laundry

Tulum-Inspired Luxury Townhouse in Madeira Beach

Welcome to Your Tulum-Inspired Beach Oasis in Madeira Beach. - Luxury townhouse with Tulum-inspired design - Five bedrooms with premium Sealy Black Label mattresses - Open living area with a 70" Smart TV - Private rooftop with a hot tub and 65" outdoor TV - Tranquil Intercoastal waterway views - Resort-style community pool nearby - Private 2-car garage and elevator access - Beach gear provided for your convenience

Location · Family · Check-in

Waterfront Condo with Boat Slip & Fishing Dock

Escape to this peaceful, 2-bedroom waterfront condo on Boca Ciega Bay. Perfect for families, this ground-floor retreat offers stunning bay views, a heated pool, and a private dock. Rent your own private boat slip or just fish right off the dock. Enjoy a bright, modern space that comfortably sleeps your group. You're just a short walk from the beach, local dining, and vibrant nightlife. Your serene coastal getaway awaits!

Location · Family · Comfort

Mad Beach HideAway • Private Pool • 4 Bed • 3 Bath

Cozy coastal retreat just 5 min from the beach! Clean and freshly updated with all the amenities you'll need for a perfect vacation. Ideal for families, we have 4 bedrooms and 3 full bathrooms in 2000 sqft with a solar heated pool! There is plenty of space for you and your family to spread out and enjoy the two separate living rooms or the private back yard.

Value · Family · Kitchen