Holiday rentals with outdoor seating in Johns Pass

King Bed Studio| Clean & Private |Central Location

Welcome to a thoughtfully designed private studio—efficient and exceptionally clean. If your priority is a comfortable king bed, a well-maintained space, and easy access to both downtown St. Petersburg and the beaches (about a 20-minute drive), this is a reliable choice. This is one of two private studios within a tiny house setup, ideal for solo travelers or couples. Guests also have access to a shared outdoor gazebo with seating, hammocks, greenery, dining space, and a fully equipped kitchen.

Welcome to Gulf-Front Paradise!

This Gorgeous 1st floor, Direct Gulf-Front condo is located on the South end of beautiful Madeira Beach, directly across the street from World Famous John's Pass Village & Boardwalk. Enjoy this 1/1 + premium queen pull-out sleeper sofa with full-sized kitchen, private heated Pool, Outdoor Grills w/ Tiki Huts on one of the Top 10 Beaches in the US. Best Attractions: Dining, Shopping, Boating, Fishing, Dolphin tours, Jet skiing, Paragliding - ALL w/in Walking Distance! Free covered parking GND FL

Spectacular beach to bay views from this resort.

Our condo has spectacular water views from the Bay to the Beach. We have a large one of a kind kitchen that is unique to our resort, with granite counter tops, hardwood cabinets, and all stainless steel appliances. Everything you need to prepare a meal is provided along with basic spices and condiments, Coffee, creamer, and sugar. The master bedroom has a new king size bed and walk in closet with all beach gear also available for your use. We have 2 - 50" flat screen TV's with cable as well.

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**

Family Friendly Beach Cottage in Madeira Beach, FL

Mad Beach Cottage is a single family home in the Surf Song Resort on Madeira Beach 60 flip-flop steps to SAND! No streets, boardwalks or stairs! You'll enjoy a heated pool, 3 Weber grills, shuffleboard and sundeck with lounge chairs for gazing at spectacular sunsets every night. It's located across from famous John's Pass Fishing Village Boardwalk for shopping, dining, ice cream, coffee, live music, brew pubs, dolphin/fishing/sunset/pirate boat cruises, wave runner/kayak rentals. 5* LOCATION!

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! 🤍

Penthouse Water View, Pool, @ Johns Pass!

Penthouse corner unit with stunning water view from the living room, bedrooms and balcony! This waterfront condo is in prime location. A block away from Johns Pass Boardwalk (#1 tourist destination in the county) and RIGHT across from the pristine white sands & sunsets of the Gulf of Mexico. The property offers a heated pool, hot tub, fitness room & event center. Our condo has everything you need including fully stocked kitchen, laundry in unit, high speed wifi & beach equipment.

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!

Beachfront Condo in Exclusive Resort

The most stunning views from this brand new condo directly on Treasure Island Beach. This lovely unit is on the 4th, 5th, or 6th floor and provides sweeping views of the ocean. This units has 2 bedrooms and 2 full bathrooms. The inviting open concept living area has one of the best views of the ocean, especially when the retractable sliding doors are opened. The dining table on your private balcony provides a perfect dining area, with the ocean providing a beautiful backdrop.

Lux Madeira Beachfront Home

Wake up to sweeping Gulf views in this rare 4BR/sleeps 10 Gulf-front home on Madeira Beach — direct sand access from your door. Spread across multiple levels of living with panoramic water views and private balconies. Designed for relaxed beach living with patio & outdoor BBQ area, perfect for sunset dining. Beach chairs, umbrella & gear included. Minutes from John's Pass. High-speed WiFi & parking included. Private, spacious & truly Gulf-front — Madeira Beach at its finest.

Coastal Retreat Near Madeira Beach With Game Room

This 2-bedroom unit with a bonus Game Room and Sunroom is the perfect getaway for up to 6 people looking to enjoy the beautiful beaches of this area. Located in a quiet neighborhood on a private cul-de-sac, it is the perfect place to rest and recharge between trips to the most beautiful beaches in the world. This location is just a quick 5-minute drive (2 miles) to the Madeira Beach access and a 10-minute drive (3.7 miles) to the famous John's Pass Village and Boardwalk.

*Shore Thing* Walk to Beach | Intercoastal Views

🏖️ Shore Thing Condo 🏖️ Escape to pure coastal paradise at this chic Treasure Island condo. You are mere footsteps from sugar-sand beaches, refreshing salt air, and unmatched sunsets. Keep an eye on the water as dolphins and manatees drift right by! 🐬🌅 Indoors, unwind in elevated, modern coastal design. From cooking in the upscale kitchen to swimming in the heated pool, our signature service guarantees your peace of mind is the top priority. Book today! ✨🐚