Condo holiday rentals in Bay Pines

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.

4.92 out of 5 average rating, 169 reviews

Waterside Studio in the heart of TI, walk to beach

Location!!! This charming 2nd floor studio is located in the heart of legendary Treasure Island on the Intracoastal waterway of Boca Ciega Bay, only 3-7 min walk from the beautiful Gulf beaches, restaurants, shopping, and many great beach bars. Relax in the heated pool, have a cookout with the grills and screened waterfront cabana, complete with TV and minifridge, and watch the sunset or fish on one of two docks as dolphins frolic in the warm Gulf waters around you! Your perfect vacation awaits!

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, 268 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 your coffee, or while enjoying a glass of wine in the evening! A 6-minute drive to Madeira Beach, and close to all amenities with many restaurants nearby, including Doc Ford's next door, and shopping within 7 minutes. Lots to do; close to fishing including deep sea, and jet skiing. 1 bedroom, sleeps 4; comfy pull-out.

4.86 out of 5 average rating, 141 reviews

Condo in Redington Beach

Island Chic Cutie @theBeach@HeatedPool

Great studio located few steps to the Gulf of America. Most everything you need for the beach or pool has been provided, The space is very convenient to great restaurants, grocery stores and nightlife. The neighborhood around the area is really nice and safe. There is a park next door with basketball and outdoor gym equipment plus kids play areas as well. You'll love it here, everyone does. We provide cozy essentials. Some condos being updated inside. Our lower than usual price reflects that.

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, 206 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, 147 reviews

Dolphins from private balcony! 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

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, 279 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.

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, 209 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.

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.

4.99 out of 5 average rating, 215 reviews

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.

An open-concept living area features a light-colored, patterned sofa paired with a wooden coffee table. A large flat-screen TV is mounted on the wall, and a serene window nook offers natural light, enhancing the coastal charm of the space.

4.96 out of 5 average rating, 190 reviews

~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

4.98 out of 5 average rating, 243 reviews

An open living area features a modern kitchen with white cabinetry and a large island with bar seating. A comfortable couch is positioned in front of an electric fireplace, accompanied by a coffee table displaying books and a decorative plant. A wall-mounted TV displays a vibrant underwater scene.

Condo in Seminole

SHEEK and Glam- heated pool Updated! 3 mi to beach

UPDATED modern Light and bright colorful condo w HEATED POOL! First floor NO stairs. 2 miles from the beach. Crazy FAST WIFI- at 600mbps !!! Great central location close to 2 malls, restaurants, parks and many local gulf coast beaches. SAFE GATED quiet community has a heated pool, gym, tennis courts and gas grills for you to enjoy. Just bring your beach blanket and swim suit and RELAX! Walking distance to so many stores/rest

4.86 out of 5 average rating, 352 reviews

An inviting courtyard area is showcased, featuring a sparkling heated pool surrounded by lounge chairs. Lush greenery and well-maintained gardens add a natural touch, while the two-story yellow building encloses the area, creating a serene and communal atmosphere for relaxation.

Condo in Redington Beach

Royal Orleans at Redington Beach ( Studio )

Royal Orleans 208 is a studio condo with one queen size bed that sleeps up to 2 . The condo is located on the second floor overlooking the (heated) pool . A super relaxing Gulf shore vacation that puts you just across from the beach, restaurants, and shops. In addition to the beautiful pool at Royal Orleans , you are close to golf and boating opportunities. It’s a recipe for a wonderful vacation in Redington Beach, Florida.

4.93 out of 5 average rating, 115 reviews

An aerial view presents a vibrant community with a central pool area surrounded by lounge chairs. Nearby, tennis courts and landscaped green spaces enhance the outdoor environment. The multiple buildings feature warm-colored exteriors with tiled roofs, creating a harmonious residential atmosphere.

Condo in Seminole

Two Bedroom Pool View Condo in Seminole

Fantastic pool view Two Bed/Two Bath condo in gated community centrally located in southern Pinellas county. Enjoy the pool or just lounge around! 40 minutes to Tampa Airport, 20 minutes from downtown St. Petersburg, 10 minutes to the beaches. Fully equipped kitchen and washer/dryer inside the condo for your use. Third floor condo (stairs only) with vaulted ceilings and no one above you.

Popular amenities for Bay Pines condo rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly 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.

4.74 out of 5 average rating, 65 reviews

Beautiful Sunset and Bay Views

A modern kitchen is presented with stylish white cabinetry and a spacious concrete countertop. Two pendant lights hang above the bar seating, which features four black chairs. Stainless steel appliances, including a refrigerator and microwave, are visible, providing a well-equipped cooking space.

5 out of 5 average rating, 53 reviews

Wonderful Condo at Avalon - Fully Renovated

A scenic sunset is captured over calm waters, with warm orange and yellow hues reflecting on the surface. A small boat is visible on the horizon, adding a serene element to the tranquil evening scene.

4.94 out of 5 average rating, 80 reviews

Madeira Beach getaway; walk to the beach

4.96 out of 5 average rating, 27 reviews

The living area features a leather couch facing a coffee table, complemented by a ceiling fan and high ceilings. A bar area with stools is visible, along with an airy kitchen space. Decor elements include wall art and acoustic guitars, contributing to a creative ambiance.

Condo in Seminole

Tampa Bay/St Petersburg Condo

A spacious living area is furnished with a comfortable sofa and two armchairs, all in calming blue hues. Natural light floods the room through sliding glass doors that lead to a private balcony offering views of the beach. A flat-screen TV is positioned across from the seating area.

4.95 out of 5 average rating, 21 reviews

Chambre 303 - Pool, Hot Tub, Walk to John's Pass!

A wide view of Boca Ciega Bay is presented, showcasing calm waters under a partly cloudy sky. Lush palm trees frame the foreground, while boats can be seen in the distance, contributing to the serene waterfront atmosphere.

4.9 out of 5 average rating, 62 reviews

Gulf Waterfront Studio! Near Madeira 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.

4.97 out of 5 average rating, 36 reviews

Paradise Found ! Pet friendly

A serene swimming pool is bordered by palm trees, with lounge chairs positioned around the edge. The pool area is complemented by views of the water and lush greenery, creating a tranquil outdoor escape.

4.86 out of 5 average rating, 87 reviews

Sunny St. Pete Getaway with Dolphins

Pet-friendly condo rentals

5 out of 5 average rating, 14 reviews

Best Sunset View 3/3 Beachfront Penthouse Condo

4.87 out of 5 average rating, 60 reviews

A cozy dining area is positioned next to expansive glass windows offering a view of the ocean. A round table with two white chairs is complemented by rustic decor, while light-colored curtains frame the scene, enhancing the openness and connection to the seaside.

Condo in Belleair Beach

Belleair Beach 215 Beachfront Gem Steps from Sand

4.88 out of 5 average rating, 146 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

5 out of 5 average rating, 18 reviews

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, 471 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.

4.79 out of 5 average rating, 100 reviews

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

A cozy living area features a teal sofa adorned with yellow and white cushions. A round coffee table sits atop a decorative rug. Natural light streams in through the large window, which is dressed in sheer white curtains, illuminating the space alongside a vibrant wall art piece.

4.92 out of 5 average rating, 66 reviews

Happy Clearwater Condo in The Avalon/King bed/gym

Superhost

A set of two white wicker chairs and a small table are positioned on a balcony, providing views of the Gulf of Mexico. The ocean and sandy beach stretch into the distance, with clear blue skies overhead.

Condo in Clearwater Beach

4.9 out of 5 average rating, 400 reviews

Amazing views on beachfront

Condo rentals with a pool

A waterfront view showcases the community pier lined with palm trees, providing access to the Intracoastal waterway. The nearby building features balconies and patio furniture under blue umbrellas, enhancing the leisure atmosphere. Multiple docks extend into the clear water, inviting relaxation.

4.99 out of 5 average rating, 110 reviews

Blue Sea Renity -Steps to Beach| Heated Pool

The living area features light-colored furnishings, including a comfortable sofa and recliner. A wall art piece of fish adds interest above the sofa. A light area rug is placed underfoot, and a tall plant enhances the natural ambiance. The kitchen is visible in the background.

4.94 out of 5 average rating, 86 reviews

Beach & Intercoastal Access -Indian Shores, FL

A serene view of the sun setting over calm waters is captured from a wooden deck. The sky transitions from soft orange to deep blue, while silhouettes of distant islands are visible on the horizon. A glass rests on the railing, complementing the tranquil scene.

4.92 out of 5 average rating, 83 reviews

Your Cozy Island Oasis with Special Winter Rates!

Superhost

A furnished balcony provides a serene view of Boca Ciega Bay, featuring a seating area with two wicker chairs and a small table. Palm trees frame the horizon, and the sunset casts warm colors across the tranquil water, with the pool area visible below.

4.94 out of 5 average rating, 85 reviews

Breath taking views of sunsets and dolphins.

A spacious heated pool is surrounded by palm trees, loungers, and a decorative island. The pool area features sunlit tiles, offering a refreshing escape. Nearby, a covered seating area with tables adds to the inviting atmosphere of the community.

4.89 out of 5 average rating, 83 reviews

Clearwater Vacation Rental Condo/Heated Pool

A modern kitchen is presented, featuring white cabinetry and light countertops. Equipped with a stove, oven, refrigerator, and dishwasher, it offers essential appliances. Bright pendant lights hang above the island, enhancing the open layout that connects to the living area visible in the background.

5 out of 5 average rating, 25 reviews

Newly Renovated Condo with Pool

A comfortable living area features a large sectional sofa adorned with decorative pillows. A mounted flat-screen TV displays a beach scene, while light-colored wooden paneling adds warmth. Natural light enters through sliding glass doors, which lead to a screened-in balcony, creating an inviting space.

5 out of 5 average rating, 18 reviews

Seaside Serenity,SeaClub #39~Updated, Pool,Fishing