Waterfront vacation rentals in Bay Pines

An aerial view captures the waterfront community, highlighting the proximity to the beach and nearby amenities. Serene blue waters of the canal intertwine with the residential buildings, while the expansive shoreline stretches in the background, offering a picturesque setting for relaxation and exploration.

4.98 out of 5 average rating, 149 reviews

Beach, dolphin/manatee sightings, fishing, sunsets

Welcome to the newly remodeled condo in the Heart of Treasure Island. This bright and modern retreat is perfect for relaxing and avoiding the crowds. Perfect location for beach lovers and wildlife watchers alike with waterfront views of the canal from the living room, kitchen and bedroom windows and beautiful sunsets. Just 2 blocks or a 5 minute walk to the beautiful white sandy beach and a few feet from the canal and heated pool. Visit nearby restaurants, John's Pass Boardwalk and live music.

An aerial view captures a multi-story condominium overlooking a beach. Lush palm trees surround a heated pool area, with docks lining the waterfront. The expansive coastline is visible in the background, highlighting the scenic proximity of beach and bay.

4.99 out of 5 average rating, 211 reviews

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.

A cozy living area features a comfortable gray sofa and a blue accent chest. Large glass doors open to a balcony, showcasing water views. A ceiling fan provides a gentle breeze, while decorative elements like wall art and a rug add a touch of charm.

4.97 out of 5 average rating, 152 reviews

waterfront condo! Dolphins in the bay

Wake up to waterfront views! Sip morning coffee on 20-ft private balcony overlooking Boca Ciega Bay, watch dolphins, unwind in the heated pool & spa while taking in stunning sunsets. This quiet corner condo offers a serene escape minutes from Madeira Beach, St. Pete, and local attractions, perfect for couples or solo travelers. Highlights: • Direct waterfront views • Heated pool, hot tub • Nearby boat rentals, trails, & Madeira Beach • 5 mins to Gulf beaches + 15 mins to Downtown St. Pete

Superhost

A cozy sleeping area is presented with a spacious bed, dressed in neutral linens. A light wood frame complements the soft color palette. Wall-mounted light fixtures provide gentle illumination, while a shelf adorned with plants adds a touch of greenery. A small stool is positioned beside the bed.

Tiny home in St. Petersburg

4.88 out of 5 average rating, 150 reviews

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. 🌴☀️🏖️

Tiny home in St. Petersburg

A light-filled studio space features a comfortable bed along with a simple wooden table and chairs. A mounted TV is present on the wall, and a plant adds a touch of greenery. The flooring consists of neutral tiles, enhancing the spacious feel of the room.

4.91 out of 5 average rating, 172 reviews

King Bed Studio | Outdoor Kitchen | Free Parking

Tiny home in St. Petersburg

A cozy sleeping area features a wooden bed with a light-colored comforter. Soft lighting is provided by pendant fixtures on either side. A shelf above the bed displays various plants, adding a touch of greenery to the earthy tones of the room.

4.88 out of 5 average rating, 133 reviews

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. 🌴☀️🏖️

Apartment in St. Petersburg

A balcony area features a round wooden table surrounded by two chairs, one woven and one metal. A decorative piece is displayed on the wall, with two fishing poles leaning against the balcony railing overlooking the water and marina.

4.91 out of 5 average rating, 182 reviews

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.

A serene balcony offers a view of the waterfront, with two green chairs and a glass table positioned to enjoy the scenery. Palm trees are visible in the foreground, and the calm water reflects the bright blue sky, creating a tranquil outdoor space.

4.98 out of 5 average rating, 282 reviews

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.

4.98 out of 5 average rating, 206 reviews

Home in St. Petersburg

Sparkling Modern Pool Home with Guest Bungalow!

This recently renovated like new home features 4BR/3BA, and sleeps 12 guests. The interior design is a showstopper—photos don’t do it justice! You’ll love the outdoor entertainment space and will soak up the sun around a saltwater pool overlooking a lake filled w/ exciting wildlife. Located 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.

A serene waterfront view is offered from the balcony, featuring a round table with two chairs. Palm trees frame the view, while calm waters reflect the clear sky, creating a peaceful outdoor space perfect for relaxation.

4.81 out of 5 average rating, 215 reviews

🏝🏝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.

4.99 out of 5 average rating, 218 reviews

The kitchen features navy blue cabinets, providing a stylish contrast to the stainless steel appliances. A spacious countertop holds essential kitchen gadgets, and a modern backsplash adds texture. Adequate storage is available with cabinets and drawers, contributing to a well-organized cooking space.

Condo in Madeira Beach

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.

Apartment in Treasure Island

An inviting studio interior is shown with light-coloured walls and a modern kitchenette visible in the background. A doorway leads to a bathroom featuring tropical-themed wallpaper. A small dining table and chair are positioned in front of a cozy seating area with a dark sofa.

4.98 out of 5 average rating, 132 reviews

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.

Popular amenities for Bay Pines waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

Apartment in Madeira Beach

The entrance to the bungalow is lined with a stone pathway and surrounded by tropical landscaping. Colorful plants and shrubs frame the orange exterior of the building, which features two doors leading to separate units. A sign indicates the name of the property.

4.91 out of 5 average rating, 100 reviews

#3-Sea Turtle Bungalows@John's Pass 1B/1B

Apartment in Madeira Beach

A direct view of the Gulf shoreline is visible from the balcony, showcasing a sandy beach with beach chairs and umbrellas. A private pool is located below, surrounded by a patio area with several lounge chairs, creating an inviting setting for relaxation.

4.9 out of 5 average rating, 102 reviews

Welcome to Gulf-Front Paradise!

Apartment in Treasure Island

4.85 out of 5 average rating, 121 reviews

Complete Renovation-everything new! Amazing views

Apartment in Indian Rocks Beach

A sandy pathway leads from a wooden deck to the beach, framed by wooden railings. The expansive shoreline is visible, with gentle waves lapping at the shore under a bright blue sky. Beachgoers can be seen enjoying the sun and water in the distance.

4.78 out of 5 average rating, 101 reviews

20 Steps To The Beach | Private 1BR Unit On Beach

Apartment in Treasure Island

4.87 out of 5 average rating, 15 reviews

Relax & Reconnect | Heated Salt Pool + Beaches

Apartment in Indian Shores

A serene beach scene features soft white sand and gentle waves lapping at the shore. Dune grass and natural vegetation frame a red bench overlooking the coastline, creating a peaceful spot to enjoy the expansive ocean view under a clear blue sky.

4.98 out of 5 average rating, 89 reviews

Waterfront Oasis / Gameroom / Pool & Beach Access

Apartment in Indian Shores

A sunset view is captured through a large tropical plant, framing the beach scene. Silhouetted figures are seen strolling along the sandy shore as the sun descends on the horizon, creating a warm glow over the water.

4.96 out of 5 average rating, 201 reviews

Barefoot Beach Resort Indian Shores

Apartment in Madeira Beach

An aerial view captures the beachfront landscape, highlighting an inviting shoreline bordered by a mix of residential and commercial properties. The water showcases varying shades of blue, while the sandy beach stretches invitingly. Identifiable structures are situated near the coast, establishing a vibrant neighborhood.

4.87 out of 5 average rating, 126 reviews

MadeiraC2 Waterfront & 2-3 minutes Walktothe Beach

Waterfront house rentals

4.96 out of 5 average rating, 139 reviews

Home in Largo

Stars by the Sea - Cozy home close to beaches

4.93 out of 5 average rating, 141 reviews

A spacious living area features a large sectional sofa adorned with various decorative pillows. A light-colored coffee table is positioned in the center, complemented by a decorative basket. Natural light filters through two window blinds, creating a bright and inviting environment.

Home in Dunedin

Ocean Sunsets & Downtown Biking Trails

Home in Indian Rocks Beach

Two lounge chairs are positioned beside a small table, offering a view of the serene canal. Tall palm trees and lush greenery frame the scene as the sky transitions with hues of purple and orange during sunset.

4.89 out of 5 average rating, 151 reviews

Azule|Waterfront | Walk to Beach-Dock-Bikes-Kayaks

4.93 out of 5 average rating, 315 reviews

An aerial view of a modern two-story home surrounded by lush greenery and palm trees, with a backdrop of tranquil water. The property's landscaping features a paved driveway leading to the entrance, while nearby boats are docked along the shoreline.

Home in Seminole

Waterfront Luxury Heated Pool/Hot Tub 5 bedrooms

4.89 out of 5 average rating, 9 reviews

Home in St. Petersburg

Heated Pool & Coffee Bar• 5-min to Madeira Beach

4.97 out of 5 average rating, 245 reviews

Home in Clearwater Beach

Waterfront Townhome w/Game Room & Boat Slip! Walk

4.97 out of 5 average rating, 39 reviews

Home in Madeira Beach

Waterfront Stay Where the Manatees Play!

5 out of 5 average rating, 24 reviews

Home in St. Petersburg

Delma's Waterfront Oasis Open Water View

Waterfront condo rentals

A heated pool is surrounded by palm trees and lounge chairs, with a view of the sunset reflecting on the water. The area features a brick paved deck, creating a welcoming space for relaxation by the water.

4.75 out of 5 average rating, 67 reviews

Beautiful Sunset and Bay Views

A private balcony showcases a stunning sunset view, framed by palm trees. The spacious area features a green chair and overlooks the resort's pool and surrounding buildings, creating a serene outdoor space for relaxation.

4.98 out of 5 average rating, 139 reviews

Sunset Nest: Two Bedroom Condo with Sunset Views

4.93 out of 5 average rating, 154 reviews

Waterfront-Dolphin Sightings-Walk to Beach-Pool

4.94 out of 5 average rating, 103 reviews

Aerial view of a beachfront building located near Madeira Beach, showcasing proximity to the ocean and nearby establishments. The scene includes colorful structures along the coast, palm trees lining the street, and a clear blue sky reflecting sunlight over the water.

Condo in Madeira Beach

Beachfront building across from Johns Pass Village

4.81 out of 5 average rating, 111 reviews

The aerial view displays a modern four-story condo building with a mix of orange and white façades. Balconies extend from each level, and a marina with boats is visible at the base, along with beach access in the background.

Condo in Madeira Beach

Steps to beach with Marina Sunsets – 3 -Bed condo

4.98 out of 5 average rating, 81 reviews

Private balcony, waterfront condo, pool hottub

Condo in Indian Rocks Beach

Two inviting armchairs are positioned facing a large sliding glass door, which opens to reveal a serene view of the ocean and beach. The soft evening light highlights the space, creating a calm atmosphere with gentle coastal tones.

4.85 out of 5 average rating, 126 reviews

Winter Storm Escape Sale Ocean View Steps to Beach

A swimming pool features a unique, organic shape, surrounded by palm trees and lounge chairs. The pool's clear blue water reflects the sky and offers views of the Boca Ciega Bay in the background, separated by a safety fence.