House holiday rentals in Madeira Beach

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!

Family · Location · Condition

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!

Family · Value · Layout

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 · Backyard

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.

Location · Family · Long stay

Delma's Waterfront Oasis Open Water View

Open water views from everywhere in the house! The home is completely remodeled and ready to be used for rest and relaxation. Perfectly situated in the Bay Pines area just 9min from the beach, less than 1 mile from the boat ramp, and just a short walk or drive to restaurants and shops.. Relax in the backyard under shaded seating and enjoy a variety of wildlife including dolphins, birds, crab, rays and fish. Bring your boat, kayaks and paddleboards to fish or explore the estuary.

Location · Family · Parking

Providence Cove | Heated Salt Pool • Sleeps 12

Welcome to Providence Cove, your luxury retreat just minutes from Clearwater Beach! Relax in the heated saltwater pool, enjoy private mini golf, gather around the fire pit, and create unforgettable memories with family and friends. Sleeps up to 12 guests and features stylish bedrooms, a fully equipped kitchen, fast Wi-Fi, private parking, and a curated vacation guide with our favorite local beaches, restaurants, and attractions. 🌴✨🌊🫶🏻🌞

Family · TV · Backyard

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 · Location · Heating

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 · Value · Air conditioning

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 · Amenities

Redington Beach near beach on ICW w/pool & dock

Welcome to our Redington Beach Getaway, where the sun, sky and sea meet to give a perfect blend of fun and relaxation. Our home is ideally located for direct access to the Boca Ciega Bay via kayak, and only minutes to world class, soft, white, sandy coastal beaches. There is no shortage of eclectic dining and cuisines, fun activities, and wonderful sunsets.

Family · Location · Sleep quality

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.

Family · Value · Laundry

Guest Favorite! <2 minute walk to beach! Gameroom!

Welcome to Sandy Bell Bottoms in Redington Beach! Newly Renovated in 2024! Beautifully decorated. Bright, classy, elegant & stylish. Desirable location directly across the street from the beach! Sleeps 8! ADA compliant. Your family will be close to everything when you stay at this centrally-located, delightful home. Don’t wait!

Family · Location · Air conditioning