Condo holiday 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, 150 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.

A beachfront balcony features a round table with four striped chairs, inviting outdoor relaxation. The expansive view showcases sandy shores meeting the calm turquoise waters under a clear blue sky. Sliding glass doors provide easy access to the living space.

4.99 out of 5 average rating, 118 reviews

Five Star Beachfront Condo Newly Renovated

A newly transformed beachfront Condo offers five-star accommodations in sleepy Indian Shores, Florida. This is the second renovated unit by a Superhost/owner. This unit is only feet from the beautiful white sand & crystal clear water. The sunsets are epic from the balcony. Several great restaurants & bars are within walking distance of your front door. Amenities include a fully stocked kitchen, heated pool, SmartTV's, high speed Wi-Fi, reserved parking and only minutes from the Tampa airport.

4.93 out of 5 average rating, 137 reviews

Panoramic Summer Sunsets I Beachfront Condo + Pool

✨ Summer Dates Just Released! 🏖️ Welcome to The Tweet Retreat—a true beachfront sanctuary with a one-of-a-kind layout. What once was the building's original owner's penthouse is now a standalone gem with no shared walls, offering a level of peace rarely found on the beach. Experience authentic Old Florida charm with panoramic views of TI's renowned sunsets, direct beach access and a sparkling pool. Park once and enjoy—everything you need is just steps away in the heart of Treasure Island!

A private balcony offers a serene view of the bay, framed by lush palm trees. A glass table and two chairs are positioned for easy enjoyment of the surroundings, while the sparkling water glimmers under a clear blue sky.

4.96 out of 5 average rating, 277 reviews

Waterfront Condo w/ Pool & Hot Tub! Mins to Beach!

This unit is completely updated and modern! Enjoy a GORGEOUS view from the 20' private balcony overlooking the Bay, pool and hot tub! Watch dolphins every morning while sipping coffee, or while enjoying a glass of wine with the sunset! A 6-minute drive to Madeira Beach, close to all amenities, many restaurants nearby, incl. Doc Ford's next door, rated #1, shopping 7 mins. Lots to do; close to fishing including deep sea, jet skiing. 1 bedroom w/KING bed, comfy QUEEN pull-out; SLEEPS 4.

A tranquil view captures the sandy shoreline meeting the calm waters of the Gulf, with gentle waves lapping at the beach. Lush palm trees are positioned in the foreground, while a small blue trash bin is nestled among the greenery. The sky features soft clouds, hinting at the day's potential.

4.97 out of 5 average rating, 144 reviews

Beach Front Penthouse Riley's Retreat Island Inn

800 sq ft top floor condo with spectacular views of the Gulf of Mexico, Boca Ciega Bay, and the City. Located in the iconic Island Inn Beach Resort; step out of the lobby and onto the sand! Florida sunrises and sunsets are legendary, and you can enjoy both from your private top floor balcony. We offer one of the finest condo's in the building with the unique ability to enjoy North, South, East, and West vistas. This condo is unlike any other unit in the building--a must see!

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, 283 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.

The exterior of the Ocean Club building is showcased, featuring a modern design with a white façade and large balconies. Palm trees line the front, enhancing the tropical setting. A welcoming entrance is visible, set against a backdrop of a bright sky with soft clouds.

4.86 out of 5 average rating, 591 reviews

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.

A serene sunset is captured over the calm ocean, with vibrant orange and yellow hues reflecting on the water's surface. Silhouettes of palm fronds frame the view, while a faint outline of the shoreline can be seen in the foreground.

4.98 out of 5 average rating, 147 reviews

The Seascape Premier Beachfront Cottage-Gulf View

Treat yourself, you deserve it! Our condo is updated and furnished for your comfort and convenience. It's the perfect place for a romantic couples getaway, fun in the sun for families or a paradise of peace for seniors. Enjoy watching the boats sail by from our balcony or laying by our pool and basking in the sunshine. Step out to the beach, feel the warm sand between your toes and indulge in the Gulf. Make lifelong memories and melt your stress away at Indian Shores.

4.97 out of 5 average rating, 265 reviews

An open-concept living area is displayed, featuring a cozy seating arrangement and a stylish electric fireplace. A modern kitchen with white cabinetry and granite countertops is visible in the background, alongside a dining area with a round table and upholstered chairs.

Condo in Seminole

UPDATEDVacation condo! HEATEDpool3 miles to beach

Wow!! Super value !! 2 bed 1 bath condo 1st floor - Welcome to Beachway Condos a GATED SAFE private full amenity community featuring a gym, tennis courts, HEATED POOL, grills, located 3 miles to the beautiful gulf beaches. You are close to everything - the Pinellas trail biking/walking is 1/4 mile away, Indian shores beach is the closest beach at 3 miles away. Clearwater/st Pete beaches are 7 miles away. Across the street are grocery stores malls, restaurants

Condo in Indian Rocks Beach

A bright living area features a comfortable light-colored sofa and armchairs, complemented by a decorative round coffee table. Large glass doors provide an unobstructed view of the beach and palm trees outside, allowing natural light to fill the space.

4.97 out of 5 average rating, 154 reviews

Private Ocean View Beach Retreat with Balcony

Only steps from the beach, this newly updated and perfectly located beach condo is your luxury getaway. The large bedroom, lofty living area and modern open kitchen, as well as the generous balcony with direct view of the Gulf will make you never want to leave again. This condo is better equipped than your average vacation rental and comes with your private daily sunset spectacle. Continue to read for more...

4.94 out of 5 average rating, 106 reviews

A spacious open-concept living area includes a sleek kitchen with modern appliances and ample counter space. A dining table with six chairs and a pool table provide options for entertainment. Bright overhead lights create a welcoming atmosphere, with light-colored cabinets complementing the room.

Condo in Redington Beach

Penthouse,intercoastal, 3/3 views/heated pool

This stylish place to stay is perfect for group trips. Brand New Luxury Madeira Beach Penthouse With Heated Pool 4 floors up with partial beach and intercoastal views, all on a level floor plan 4 stories up with elevator access! Enjoy the comforts of new unit with modern appliances and fixtures in this 3/3 that bolsters a king master bedroom, two guest queen bedrooms all with in suite full bathrooms.

An inviting balcony view overlooks a spacious pool area and the intercoastal waters, framed by palm trees. A light-filled living area features comfortable furnishings and a television, while the dining space and kitchen are visible, providing a warm atmosphere for relaxation and enjoyment.

4.86 out of 5 average rating, 321 reviews

Breathtaking Waterview & Pool View Condo

Waterfront condo with pool view. The view of the intercoastal is fantastic. Especially beautiful sunsets! Pinellas trail across the street to ride your bike or hike, a beautiful 38 mile trail. Plenty of restaurants nearby and grocery stores. Only 8 min drive to beach. 15 min from downtown St. Pete. Enjoy pool and hot tub overlooking intercoastal or stay indoors and enjoy puzzles and games.

Popular amenities for Bay Pines condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

4.96 out of 5 average rating, 57 reviews

A sparkling heated salt-water pool is surrounded by lounge chairs and palm trees, creating a relaxing atmosphere. The area features a safety fence, and the clubhouse is visible in the background, enhancing the community's inviting design.

Condo in Seminole

Minutes from the Beautiful Sandy Beaches!

5 out of 5 average rating, 6 reviews

Modern 2BR Suite Steps to Madeira Beach

4.97 out of 5 average rating, 73 reviews

A tranquil scene shows an outdoor heated pool surrounded by lounge chairs and umbrellas. Palm trees sway gently in the breeze, framing the view of the calm water and distant bridge under a partly cloudy sky.

Condo in Isla del Sol

Location, Comfort & Indulgence is key here!

Condo in Indian Rocks Beach

A spacious balcony features two wooden chairs and a small table, offering unobstructed views of the sandy beach and calm ocean waters. The tranquil atmosphere is highlighted by the bright blue sky and gentle waves, creating an ideal spot to enjoy the surrounding natural beauty.

4.99 out of 5 average rating, 78 reviews

BEACHFRONT/Panoramic Views of the Gulf #301

4.92 out of 5 average rating, 87 reviews

Condo in Tierra Verde

Your Island Escape! • Discounted Summer Rates

A modern kitchen arrangement features sleek stainless steel appliances, including a stove, microwave, and dishwasher. Light-colored cabinetry is paired with a large stone countertop. The open space is well-lit with recessed lighting, and views of the balcony area are visible through the nearby sliding glass doors.

4.91 out of 5 average rating, 44 reviews

Updated Beachfront Condo, Pool, walk to Johns Pass

Condo in Redington Shores

A panoramic view of a serene beach is presented, featuring soft white sand and gentle waves. Colorful umbrellas and beach chairs are scattered along the shore, with a few beachgoers enjoying the tranquil ocean. The clear blue sky reflects the calm atmosphere of the seaside.

5 out of 5 average rating, 28 reviews

Oceanfront Condo Corner Unit2BR/2BA Great Location

The image captures a stunning sunset over the beach, with vibrant hues of orange, pink, and purple reflecting on the water. Silhouettes of people can be seen walking along the shore, while gentle waves lap at the sandy beach, creating a serene coastal atmosphere.

4.99 out of 5 average rating, 89 reviews

White Sand Beachfront Condo with Stunning Sunsets

Pet-friendly condo rentals

Superhost

A wide expanse of white sandy beach stretches under a bright blue sky. The gentle waves of the ocean can be seen in the distance, complemented by scattered beach umbrellas. Coastal buildings line the horizon, indicating proximity to amenities.

Condo in Clearwater Beach

4.81 out of 5 average rating, 147 reviews

Luxury condo at Avalon Club

Superhost

A view from the balcony showcases lush tropical palm trees framing the serene waters of the bay. A small boat can be seen gliding through the calm water, enhancing the tranquil atmosphere. Vibrant greenery is present in the foreground, completing the coastal scene.

4.81 out of 5 average rating, 134 reviews

Breathtaking Waterview Condo!

4.87 out of 5 average rating, 151 reviews

The marina features a variety of boats docked in calm waters, with a warehouse structure visible in the background. The scene includes several sailboats and a large yacht, complemented by industrial surroundings, reflecting a serene nautical atmosphere.

Condo in Maximo

"The Merry Yacht" excellent location

4.98 out of 5 average rating, 102 reviews

Condo in Clearwater

Lovely Condo minutes from beach & King bed

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.

4.9 out of 5 average rating, 182 reviews

Waterside Studio in the heart of TI, walk to beach

A sunset is captured over the intercoastal waterway, with warm hues reflecting on the water's surface. Silhouettes of palm trees line the foreground, while distant markers indicate the waterway's navigation. The scene conveys a tranquil ambiance, enhanced by the fading light.

4.91 out of 5 average rating, 188 reviews

Heron's Hideaway- Studio by the bay!

A wooden walkway leads through a natural landscape, flanked by tropical vegetation and palm trees. The pathway extends toward the horizon, inviting visitors to the nearby ocean. Soft clouds fill the sky, enhancing the serene setting of Madeira Beach.

4.76 out of 5 average rating, 476 reviews

Beach Chill Inn #3 - Studio

Two wicker chairs with cushions are positioned around a small table on a balcony overlooking the beach. The expansive view reveals the Gulf of Mexico and a clear sky with scattered clouds. Beachgoers can be seen in the distance enjoying the shoreline.

4.8 out of 5 average rating, 104 reviews

Casa de B.O.B ... Best on Beach

Condo rentals with a pool

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

4.97 out of 5 average rating, 138 reviews

Condo in Clearwater

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

4.99 out of 5 average rating, 69 reviews

A modern kitchen area is highlighted with sleek white cabinetry and stylish pendant lighting. A large island with seating is arranged alongside stainless steel appliances. Natural light enters from sliding glass doors that open to a scenic outdoor space.

Condo in Clearwater

Amazing Condo at Avalon - Fully Renovated!

Superhost

Condo in St. Pete Beach

4.74 out of 5 average rating, 35 reviews

Stunning Bay Views | Walkable Retreat

An image captures a group of four individuals standing on the beach at sunset. The water reflects vibrant hues of orange and pink, creating a serene atmosphere. The silhouettes of the people contrast gently against the colorful sky and shimmering water.

4.98 out of 5 average rating, 58 reviews

"Haven at the Shores" 2/2 Beachfront

The living area is furnished with a light-toned sectional sofa, accompanied by a side chair. A round dining table for four is visible, along with a modern kitchen behind it. Decorative plants and a media console add a touch of greenery and organization to the space.

4.91 out of 5 average rating, 69 reviews

Chateaux Beachfront Condo/Top Unit - Indian Shores

Condo in North Redington Beach

A serene beachfront view is captured under a clear blue sky. The vivid turquoise water reflects sunlight, creating a shimmering pathway across the calm sea. Gentle waves roll onto the soft sandy shore, where a person is seen walking along the beach.

4.91 out of 5 average rating, 124 reviews

Toes in the Sand Beachfront penthouse condo

An aerial view captures the coastline with sandy beaches meeting the gentle waves. The vibrant waterfront community features a mix of buildings and greenery, with beachgoers enjoying the open space. The location is highlighted by a marker indicating proximity to the water.