Holiday rentals with outdoor seating in Johns Pass

You Belong on a Beach ! Walk to Beach - Food - Bar

Discover this secluded stretch of beach. Your stunning home is situated across the road from soft white powdery sand and the emerald Gulf waters. The boardwalk dining/entertainment is a leisurely stroll away. Unwind on wraparound decks as you take in the evening sunset view. A memorable vacation awaits families with children, several couples, or a group of friends. All 3 bedrooms come with full bathrooms. Experience true comfort in your thoughtfully designed fully stocked home away from home.

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**

Coastal Retreat Madeira Beach/John’s Pass Pool

$0 Cleaning Fee, $0 Airbnb Guest Service Fee – we cover this fee. What you see is what you pay! Step into coastal style at this Madeira Beach condo with Gulf views. Designed with a beach-inspired theme, this retreat offers a breezy open layout, fully equipped kitchen, and balcony perfect for soaking in sunsets. With resort-style amenities on site and dining, shopping, and entertainment nearby, it’s an ideal escape that blends a laid-back coastal vibe with the convenience of a prime location.

Shangri-La

Located on a Barrier Island beach community in a friendly, residential neighborhood. Guest suite is attached to the main house with it's own separate entrance and living space. Spacious bedroom with En suite bathroom. Kitchenette has sink, small fridge, microwave and air fryer. 5 minute walk to the white sandy beach. Beach chairs, towels and floats provided. Enjoy gorgeous sunsets. Everything is in walking distance. Many restaurants, Tiki bars with live entertainment, shops and grocery store.

Historic Holly House on Treasure Island

This charming Beach Cottage is located in the Coney Island area of Treasure Island. This unique set of Key West Style beach cottages are on the beach block only STEPS to the beach! This awesome beach cottage, known as The Historic Holly House, has some unique history. In 1961 the New York Yankees rented out all the cottages in this Coney Island area for spring training. This cottage was the one the Home Run King Roger Maris stayed in before he went on to hit 61 home runs that season.

Where the Sun Meets the Water

This first-story 670 sq-ft, 1BR/1BA condo, is located just a couple of blocks from the white sands of the Treasure Island beaches. Stroll to John’s Pass to find ample local dining and shopping options. Guests have full access to the grounds including a resort-style pool, a shared fishing dock, and a waterfront patio equipped with gas grills, perfect for enjoying a meal and watching as dolphins and birds pass by. 2025. Come visit & stay a while! Operated by Summer Bloom Estates LLC

Boardwalk Bungalow - Johns Pass & beach steps away

LOCATION LOCATION LOCATION!! Boardwalk Bungalow is located right at the end of the World Famous Johns Pass Boardwalk! With easy beach access from under the Pass bridge, without having to cross Gulf Blvd. This duplex unit features 2 bedrooms, 1.5 bathrooms with everything brand new! 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!

Cozy Gem Near Madeira Beach With Private Patio

This cozy studio unit with its own screened-in large private patio is the perfect getaway for up to 2 people looking to enjoy the beautiful beaches of this area. Located in a quiet neighborhood on a private cal-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 to the famous John's Pass Village and Boardwalk.

Lux Condo w/ 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.

Popular Beachside Studio w Relaxing Patio & Palms!

The true gem of Treasure Island! Tucked right off of Gulf Blvd this is one of three stylish studio units nestled in a coconut palm-fringed private courtyard with a residential cottage onsite. This cozy spot overlooking a lush tropical garden is just steps from a white sand beach & walking distance to dozens of laid back beach bars, live music & dining. Please note: There’s no guest parking on-site, but paid parking is nearby as well as a frequent public trolley.

Snowbird paradise! Waterfront, pool, hottub

Wake up to stunning waterfront views! Unwind in this bright studio overlooking Boca Ciega Bay, sip coffee on your private balcony while watching dolphins. Highlights: • Direct waterfront views from balcony • Heated pool, spa & fitness center overlooking bay • Minutes to Madeira Beach, St. Pete, & War Veterans’ Memorial Park • Cozy king bed • Close to boat rentals, trails, and waterfront dining Perfect for romantic getaway or peaceful solo escape!

~Shore Thing~ Coastal Exquisite Waterfront Condo

🏖️ Shore Thing Condo 🏖️ 🌅 Sunset Serenity — Relax as the sun melts into the horizon. 🚶Beachside Bliss — Just steps from powdery sands and shimmering Treasure Island waters. 🐬 Marine Magic — Spot dolphins dancing and manatees gliding by. ✨ Stylish Coastal Vibes — Modern interiors with breezy beach flair. 🍽️ Chef’s Dream — Cook with ease in a luxury kitchen. 👩‍💼 Service with Heart — Your comfort always comes first