Waterfront vacation rentals in Bay Pines

Guesthouse in St. Petersburg

A hot tub is surrounded by lush greenery and vibrant red flowers, creating a serene atmosphere. A tall palm plant is visible beside the tub, complementing the tropical landscape. A large umbrella is positioned nearby, providing shade on bright sunny days.

4.96 out of 5 average rating, 120 reviews

Cozy Tropical 2BR Casita + Hot Tub • Near Downtown

NO CLEANING FEES! Welcome to our cozy 2-bedroom, 1-bath guesthouse — perfectly located near everything you’ll want to explore! 🛏️ Two comfy queen beds 🌴 Private, fully fenced yard with beautiful landscaping 📍 Just 8 minutes to Downtown St. Pete & the Pier 🍽️ Surrounded by restaurants, bars, cafés & shopping 🌺 5 minutes to Sunken Gardens 🏖️ 20 minutes to the beach ✈️ 15 mins to Tampa Intl, 12 mins to St. Pete Intl Perfect for a relaxing getaway or a fun-filled stay in the heart of it all.

4.97 out of 5 average rating, 110 reviews

A spiral staircase with a black railing leads to an upper level. A seating area is furnished with a gray couch and a wooden coffee table. Blue bar stools are positioned at a modern kitchen island, and light-colored cabinetry is visible in the background.

Home in Madeira Beach

Boardwalk Bungalow - Johns Pass & beach steps away

LOCATION LOCATION LOCATION!! Boardwalk Bungalow is located right at the end of World Famous Johns Pass Boardwalk, just steps outside your front door. With 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! Kitchen has grey solid wood soft close cabinets, quartz countertops, stainless appliances. Updated bathrooms with chic tile selections & a small balcony with a peek at the Pass water views!

4.99 out of 5 average rating, 202 reviews

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.

Condo in Treasure Island

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.

4.96 out of 5 average rating, 142 reviews

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.

Condo in St. Petersburg

dolphins in the bay | heated pool | hottub

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

4.99 out of 5 average rating, 139 reviews

A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.

Bungalow in Oldsmar

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

4.98 out of 5 average rating, 194 reviews

Home in St. Petersburg

SPARKLING HOT Modern Pool Home- Minutes to beach!

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!

Tiny home in St. Petersburg

A bright studio space features a comfortable bed with soft linens, flanked by two wooden benches. A small vanity with a mirror and sink is positioned nearby, while warm overhead lights complement natural light streaming in from the window.

4.96 out of 5 average rating, 187 reviews

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. 🌴☀️🏖️

Tiny home in St. Petersburg

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.

4.87 out of 5 average rating, 138 reviews

Charming 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.

4.86 out of 5 average rating, 115 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, 179 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.

4.98 out of 5 average rating, 277 reviews

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.

Condo in St. Petersburg

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.

4.81 out of 5 average rating, 204 reviews

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.

Condo in St. Petersburg

🏝🏝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.

Popular amenities for Bay Pines waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

Apartment in Clearwater Beach

A bright and airy bedroom features a spacious bed with white linens and decorative pillows. A ceiling fan is present above, and a window with sheer curtains allows natural light to enter. A cozy seating area and a small refrigerator are visible in the room.

4.85 out of 5 average rating, 158 reviews

Stylish Waterside Studio 2 blocks to Beach

Apartment in St. Petersburg

A serene view of the water is captured at sunset, with palms gently swaying in the breeze. The pool area features lounge chairs arranged on a paved patio, while a hot tub is positioned nearby. Lush greenery surrounds the tranquil scene.

4.92 out of 5 average rating, 25 reviews

BOCA CIEGA Condominium - 203

Apartment in Independence Square

A view from the balcony captures a stunning sunset over the Gulf, where vibrant hues blend in the sky. The sandy beach is visible below, with a winding path leading to the shoreline. Figures can be seen strolling along the beach, adding life to the serene scene.

4.96 out of 5 average rating, 174 reviews

Direct Ocean View Top Floor Renovated. 2BR, 2 Bath

Apartment in Indian Rocks Beach

A welcoming living area features a comfortable leather sofa and an accent chair, accompanied by a light-colored coffee table. A flat screen TV is mounted on the wall, and natural light filters through the adjacent window with blinds. The space is adorned with coastal-themed decor.

4.87 out of 5 average rating, 134 reviews

Your Own Private Hideaway Steps From the Beach-4

Apartment in Madeira Beach

A vibrant blue bungalow is surrounded by lush green palm trees and colorful plants. A well-maintained lawn features a stone pathway leading to the entrance, with a covered porch visible. The bright blue exterior creates a welcoming appearance against the clear blue sky.

4.92 out of 5 average rating, 101 reviews

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

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, 120 reviews

Popular Beachside Studio w/ Shady Patio & Palms!

Apartment in St. Petersburg

A private balcony overlooks tranquil waterfront views, featuring a round table surrounded by white wicker chairs. Lush greenery and palm trees frame the scene, while sunlight casts gentle shadows across the space, enhancing the connection to the serene outdoor environment.

5 out of 5 average rating, 18 reviews

Dolphin Views and Resort Pool!

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, 200 reviews

Barefoot Beach Resort Indian Shores

Waterfront house rentals

Home in Pass-a-Grille Beach

A beach path leads to soft, white sand and the turquoise waters of the Gulf. A blue bicycle rests against a wooden railing, surrounded by grassy dunes under a bright blue sky with scattered clouds.

4.82 out of 5 average rating, 180 reviews

Steps 2 Beach-Island Cottage w/king bd+2bike+parki

4.93 out of 5 average rating, 129 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

A spacious wooden dock extends over calm waters, flanked by moored boats under a clear blue sky. The dock features sturdy railings and provides an inviting access point to the waterfront scenery.

4.85 out of 5 average rating, 256 reviews

Amazing water front view home newly renovated

4.95 out of 5 average rating, 222 reviews

Two beach bungalows are visible on either side of the sandy pathway leading towards the shore. The vibrant blue bungalow is located on the left, while a pastel-colored bungalow stands to the right, both elevated on pilings. Lush greenery borders the sandy area.

Home in Belleair Beach

Steps to a Private Beach Clearwater Belleair

Home in Indian Rocks Beach

A tranquil outdoor space features a circular hot tub adjacent to a rectangular swimming pool, both surrounded by brick pavers. The sunset casts soft colors across the water, with a view of boats docked nearby and the silhouette of trees in the distance.

5 out of 5 average rating, 178 reviews

Piece of paradise in Indian Rocks Beach.

5 out of 5 average rating, 25 reviews

A serene waterfront view is captured at sunset, reflecting vibrant colors on the calm water. Boat docks line the banks, surrounded by lush greenery and palm trees. The peaceful atmosphere is enhanced by distant sailboats gently bobbing in the marina.

Home in Madeira Beach

Flamingo Flair & Waterfront Air — Pure Paradise!

4.96 out of 5 average rating, 102 reviews

A view from inside the house shows a spacious deck overlooking the lake, with sunlight reflecting off the water. Outdoor seating is positioned beneath a shaded area, and a serene atmosphere is created by the surrounding natural landscape.

Home in Oldsmar

Fountain House On Timberbay Lake

4.79 out of 5 average rating, 150 reviews

A lush green yard surrounds a large swimming pool, with comfortable seating areas nearby. The bright blue water of the pool contrasts with the white house and the clear sky. Palm trees provide shade and add a tropical touch to the outdoor space.

Home in St. Petersburg

Comfortable Home w/Private Pool

Waterfront condo rentals

A balcony space is shown with two white lounge chairs positioned facing the ocean. The beach and turquoise waters are visible in the background, complemented by a clear blue sky. The glass door provides seamless access to the indoor area.

4.97 out of 5 average rating, 105 reviews

Relax in a Newly Renovated Beach Front Paradise

A spacious balcony features two chairs and a round table, providing a stunning view of the Gulf. The horizon shows a clear sky above the tranquil water, with sunbathers visible along the beach. Lush greenery and a palm tree are seen framing the scene.

4.92 out of 5 average rating, 145 reviews

"Jewel At The Shores" Gulf Front, sleeps 5

4.84 out of 5 average rating, 100 reviews

A peaceful heated pool area is framed by a tranquil beachfront. Loungers are arranged around the pool, with the ocean and a warm sunset visible in the background. The building's facade features balconies, offering a glimpse of the inviting coastal scenery.

Condo in Belleair Beach

Courtyard View - Steps From The Sand - Pool

A doorway opens to a view of the coastal pathway, leading to a sandy beach area. Bright skies and a seating area are visible in the distance, framed by the entrance's surroundings and greenery at the base of the walls.

4.98 out of 5 average rating, 119 reviews

Beachfront 1BR • Steps to Sand & Sunset Views

4.93 out of 5 average rating, 145 reviews

A sunroom features large windows that frame picturesque water views, allowing natural light to flood the space. Two woven chairs with soft cushions are positioned around a small wooden table, inviting relaxation and enjoyment of the calming scenery.

Condo in Treasure Island

Waterfront Condo - Dolphin sightings-Walk to beach

4.9 out of 5 average rating, 101 reviews

A clear view of a turquoise pool is presented, surrounded by lounge chairs. Beyond the pool, the white sandy beach stretches out, dotted with blue umbrellas. The calm waters of the Gulf of Mexico can be seen in the background under a bright sky.

Condo in Madeira Beach

Beach Front Gulf View at John’s Pass Medeira Beach

4.91 out of 5 average rating, 158 reviews

An outdoor seating area is shown with a glass-top table surrounded by four blue chairs. Two charcoal grills are positioned nearby under palm trees, with a view of the water in the background. The screened cabana features a thatched roof, providing a relaxing atmosphere.

Condo in Treasure Island

Waterside Studio in the heart of TI, walk to beach

The image captures a tranquil beachfront scene, featuring lush greenery and sandy paths leading to the Gulf of Mexico. Sunshine glistens on the water, while gentle waves lap against the shore. Tall trees frame the view, enhancing the natural coastal setting.