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.

Stunning Views Beach Front Condo

Beautifully updated 4th floor 3 bedroom beach front condo! Enjoy gorgeous views of the Gulf of Mexico from a large screened in balcony! Gulf view from both the living room and master bedroom. A large updated kitchen is perfect for the whole family. This condo sleeps 6 comfortably. Cable and WIFI are available as well as beach necessities. A view of the Bay from the front door. Walking distance to John’s Pass. Due to the hurricane, there is still minor repairs being done around the building/town.

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.

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**

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

DIRECT BEACHFRONT BUNGALOW "MARLIN'S HIDEAWAY." Rare free standing direct beach front house! with private sandy beach backyard! NOT a condo - No crowded elevators, hallways, lobby area, NO faraway parking spaces FEATURES: Great room plan, Sleeps 6, 2 BR + sleeper sofa, all SMART TVs, high speed Wi-Fi. Kitchen is fully equipped. Bathroom is tub/shower with seat. Approx 850 sq ft. Private, fenced deck - PETS ok. BARRETT BEACH BUNGALOWS is a boutique resort ONLY 4 bungalows share heated pool

Life is better at "The Beach" Cozy Gulfview Condo

Discover the serene beauty of Indian Shores from our charming 2-bedroom condo. This cozy retreat is the ideal place for remote workers, families, seniors seeking paradise or couples looking for a romantic extended stay. Immerse yourself in the sun-soaked shores and crystal-clear waters of the Gulf of Mexico. Imagine sunbathing on the beach, frolicking in Gulf waters, lounging by the pool or relaxing in the hot tub. Our newly renovated, first floor beachfront condo is a few steps from it all.

Waterfront Condo | Gulf Views | Beach Access&Pool

Welcome to beautiful Madeira Beach! Whether you are taking time away from cold weather or planning a staycation getaway, this waterfront condo is the place to relax, unwind, and take in the beautiful water views. Featuring 1 king bedroom 1 bathroom with a queen size sleeper in the living room. Private balcony over looking the water. All new appliances and furniture. Located steps from the community pool, across the street from ROC park, and a 5 minute walk to the beach /local restaurants.

Oceanfront Luxury paradise

Oceanfront Paradise, Resort with brand new heated pool and spa opened in 4/1/2025 , unobstructed ocean views from your balcony and bedroom, magical sunset with jumping dolphins, direct beach access, Condo renovated with Malibu / Nobu style natural wood tones, Master bedroom spacious private retreat with oceanfront views, walk-in closet , en-suite Luxury master bath with Marble floors, Kitchen remodeled fully equipped with all utensils/new appliances, renovated Guest bath , washer /dryer.

Beachfront in Pass-A-Grille w/ 2 bikes

Enjoy an intimate and relaxing stay on the best stretch of the St. Pete Beach of Pass-a-Grille. Walk out your door to the white sand towards the famous Don Cesar or dine on your deck facing the water. Free parking, 2 bikes, SUP board, towels, umbrella, beach chairs, & cooler! We are allowed 3 rentals under 28 yearly. Please inquire to see if you are one of the lucky guests to come. We love long term guests but understand not everyone can do this and simply need a little escape! 🤍

Rincón Divino MB 2 Balconies, Ocean & Marina Views

This luxury condo features 2 private balconies, w/ spectacular ocean & marina views. It's stylish decor, meticulously picked quality & comfortable furnishing/accessories are sure to please. It’s conveniently located just across the street from the pristine white sands and sunsets of the Gulf of Mexico. It is adjacent to the #1 tourist destination in the county, John's Pass Village. The property offers a heated swimming pool, hot tub, fitness room & event center.

Gulf Front, Dual Balconies, Heated Pool, Views!

Welcome to your perfect beachfront retreat in beautiful Madeira Beach! This two-bedroom condo offers breathtaking ocean views, modern amenities, and all the comforts of home. Whether you're looking to relax on the sandy shores, savor spectacular sunsets from your private beachfront balcony, or enjoy tranquil sunrise moments from a second private balcony, our condo is the ideal getaway for families, couples, or friends.

Villa Madeira #605 3 Bedroom 2 Bath Unit WIFI

Absolutely magnificent 3 bedroom 2 bath 6th floor Madeira Beach Gulf Front condo at Villa Madeira with large screened balconies. There's nothing that says Rest and Relaxation better! Enjoy the spectacular beach views and sunsets over the Gulf of Mexico from your private balcony. Expansive view of the Gulf of Mexico. So close to the water, you'll hear the waves crash. Unit #605 features 3 bedrooms and 2 bathrooms.