Waterfront holiday rentals in Bay Pines

New Building: Gulf Views, Pool, Johns Pass!

$0 Cleaning Fee, $0 Airbnb Guest Service Fee – we cover this fee. What you see is what you pay! We’re proud to be early adopters of Airbnb’s no-fee model, offering simple, transparent pricing. Experience coastal comfort at Madeira Bay Resort, where style meets relaxation across from the Gulf’s sparkling shoreline. Enjoy Gulf views from your private balcony, unwind at the heated pool and spa and take advantage of easy beach access. Includes Wi-Fi, gym, parking for one vehicle and beach gear.

Sparkling Modern Pool Home- Sleeps 12 guests!

This recently remodeled home features 4BR/3BA, including a charming poolside guest bungalow. The interior design is a showstopper—photos don’t do it justice! Enjoy a dream kitchen and saltwater pool overlooking a lake teeming w/ wildlife. Smart TVs in every room and outside (with WiFi)! Located just 8 minutes from the beach in a family-friendly neighborhood near dining and shopping. Professionally cleaned for a pristine stay. Heated pool option available for an extra cost. Book now!

Charming Studio | Outdoor Kitchen | Free Parking

Welcome to our thoughtfully designed studio—small but full of comfort, efficiency, and charm. If your priority is a cozy bed , a truly clean space and location, look no further. Loved by hundreds of wonderful guests, this is one of two private studios in a tiny house, ideal for solo travelers or couples. You’ll have everything you need, plus access to a beautiful shared gazebo with seating, dining areas, and lush greenery. We have a team of four Superhosts, available to help. 🌴☀️🏖️

King Bed Studio | Outdoor Kitchen | Free Parking

Welcome to our thoughtfully designed studio—small but full of comfort, efficiency, and charm. If your priority is a cozy bed , a truly clean space and location, look no further. Loved by hundreds of wonderful guests, this is one of two private studios in a tiny house, ideal for solo travelers or couples. You’ll have everything you need, plus access to a beautiful shared gazebo with seating, dining areas, and lush greenery. We have a team of four Superhosts, available to help. 🌴☀️🏖️

Charming Studio | Outdoor Kitchen | Free Parking

Welcome to our tiny but thoughtfully designed studio—small in size yet big on comfort, care, and cleanliness. Each space is lovingly maintained by my mother, ensuring an extra spotless stay. Perfect for solo travelers or couples, you’ll enjoy a cozy bed, efficient design, and unbeatable value. Step outside to our lush shared gazebo with seating, dining areas, BBQ, and outdoor kitchen appliances—a favorite gathering spot for guests. Superhost team of four always here to help. 🌴☀️🏖️

Waterfront Condo - Dolphin sightings-Walk to beach

Welcome to Paradise! Charming, beautifully renovated, clean, waterfront second story 2BR/2BA condo located in Pointe Capri on Treasure Island and just a couple of blocks from the white sands of the Treasure Island beaches! Take a dip in the shared resort-style pool, fish right off the shared dock, or enjoy waterfront dining on the patio. Please note: 1) owner has allergy so we cannot accommodate any cats or dogs. 2) this 2nd floor condo is only accessible via one flight of stairs.

The Oasis

Welcome to Boca Ciega Oasis! The "Oasis" suite 409 has been totally remodeled in January 2022. This includes a new queen sofa couch in LR, new refrigerator, stove, washer/dryer, and balcony tables and chairs. The 4th-floor view is the best but 409 is also centered beautifully to take in the expansive Boca Ciega Bay! Directly below the balcony is the swimming pool, Hot tub, and observation pier! The marina is to your left. See all while sitting in our bar height chairs and tables.

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

My place is across the street from Target and many restaurants within walking distance. There is a PSTA Bus stop right at the entrance to the condo property.Uner and Lyft are availablThe Pinellas Trail is across the street. The VA Hospital and Bay Pines Park are biking or walking distance. The closest beach is Madeira Beach 2 miles from the condo. All Utilities, Cable/Internet are included. Parking is free and close to the elevators. Plenty of parking spaces are available also.

🏝🏝Charming Bayfront Condo at Boca Ciega

This lovely waterfront condo located in wonderful Boca Ciega Resort in St. Petersburg, FL has everything you need for an extended stay. Centrally located with great views and amenities. Enjoy the sunset and gorgeous views whether it’s inside while lounging on the sofa or outside on the balcony. It sleeps up to 3 people (one bedroom and a sofa in the living room). Full kitchen, TV in living/bedroom, WiFi, and close proximity to the best beaches Florida has to offer.

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!