Waterfront holiday rentals in South Pasadena

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

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!

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 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, 197 reviews

~Shore Thing~ Coastal Exquisite Waterfront Condo

🏖️ Shore Thing Condo 🏖️ ✨ 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 🌅 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. 🌊 Pool Dreams - Dive into bliss in the intercoastal heated pool

4.96 out of 5 average rating, 161 reviews

Condo in Sunset Beach

Stunning BEACH FRONT Condo, KING Size Bed, Balcony

NEWLY FULLY RENOVATED breathtaking beachfront condo on private beach. Walking distance to bars, restaurants, live music and more! Brand new king size bed, high speed wi-fi, Smart TVs with cable/Netflix, heated swimming pool, BBQ/Grills, outdoor tables, showers, beachfront balcony, workspace and you are RIGHT on the beach! Short drive to TPA/PIE airports, Downtown St Pete, Dali Museum & more! The condo is fully equipped with everything you need and run by a Superhost for a perfect Beach vacation!

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

4.91 out of 5 average rating, 164 reviews

A private entrance is visible, highlighted by a bright blue door adorned with a sun-shaped decor. Lush greenery and vibrant flowers frame the pathway, leading to a serene courtyard featuring lounge chairs, enhancing the inviting and tropical ambiance.

Condo in St. Pete Beach

Tropical Courtyard Paradise on St. Pete Beach

Charming, cozy, well-appointed/fully stocked ground floor 1 Bedroom Unit with its own Private Entrance, Courtyard & spacious heated Pool. A short 1 minute walk to either St. Pete's Gulf side Upham Beach or all the abundant Nightlife & Restaurants on Gulf Blvd. Free WiFi(Spectrum) & 2 separate 32" HD TV's (Living Room sofa bed & Bedroom Queen bed), have all Premium movie, news, & sports channels. This Unit is affordably priced for the Budget Conscious desiring that Premium Beach Location.

Condo in Pass-a-Grille Beach

Two beach chairs are placed under a large white umbrella on the pristine white sand. The tranquil blue water of the ocean is visible in the background, complemented by clear skies and palm fronds gently swaying in the breeze.

5 out of 5 average rating, 165 reviews

Beachfront in Pass-A-Grille w/ 2 bikes

Enjoy an intimate and relaxing stay on the best stretch of the St. Pete Beach of Pass-a-Grille. Walk out your door to the white sand towards the famous Don Cesar or dine on your deck facing the water. Free parking, 2 bikes, SUP board, towels, umbrella, beach chairs, & cooler! We are allowed 3 rentals under 28 yearly. Please inquire to see if you are one of the lucky guests to come. We love long term guests but understand not everyone can do this and simply need a little escape! 🤍

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. 🌴☀️🏖️

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.

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.

Townhouse in Pass-a-Grille Beach

4.9 out of 5 average rating, 243 reviews

Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear

Tucked away in quiet Pass-a-Grille, SeaBreeze is a cozy, clean beach cottage just steps from one of Florida’s most beautiful white-sand beaches. Park once and walk or bike everywhere—restaurants, bars, shops, and famous sunsets are minutes away. Enjoy old-Florida charm, a sunny patio, smart TVs with sports, bikes, beach chairs, towels, and a wagon. Best for couples or small families seeking a peaceful, walkable St. Pete Beach escape.

Popular amenities for South Pasadena waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

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

4.95 out of 5 average rating, 110 reviews

“Beach Walk Retreat • Free Parking

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 Pass-a-Grille Beach

4.78 out of 5 average rating, 112 reviews

Pass a grille Gulf Way Beachfront Parking WiFi 13

Apartment in Treasure Island

4.85 out of 5 average rating, 121 reviews

Complete Renovation-everything new! Amazing views

Apartment in Indian Shores

The living area features a spacious couch and a flat-screen television, with a soft area rug anchoring the space. Floor-to-ceiling sliding glass doors provide sweeping ocean views and direct access to the private balcony, creating an inviting connection to the beach.

4.92 out of 5 average rating, 137 reviews

Ocean Front Condo!

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, 181 reviews

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

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

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

4.98 out of 5 average rating, 206 reviews

Home in St. Petersburg

Sparkling Modern Pool Home with Guest Bungalow!

4.97 out of 5 average rating, 245 reviews

Home in Clearwater Beach

Waterfront Townhome w/Game Room & Boat Slip! Walk

4.9 out of 5 average rating, 144 reviews

A private pool area is surrounded by lush greenery, featuring a spacious pool with a spa at one end. Sunlight reflects off the clear water, highlighting the relaxing atmosphere of the outdoor space.

Home in Sunset Park

Tampa Waterfront Heated Pool/ Hot Tub Oasis w Dock

Superhost

A modern kitchen and dining area is featured, showcasing a spacious marble-topped dining table surrounded by white chairs. The kitchen counters and appliances in sleek black and stainless steel complement the light color palette of the walls, creating a clean and inviting atmosphere.

Home in Tampa

4.81 out of 5 average rating, 100 reviews

Paradise Villa Central Tampa-Walk to Bucs Stadium

Waterfront condo accommodation

A spacious studio features a king-sized bed adorned with a patterned comforter. A cozy seating area includes a light-colored sofa and a small table. Large glass doors offer direct oceanfront views, with a balcony visible in the background, allowing natural light to fill the space.

4.86 out of 5 average rating, 153 reviews

Beachfront Studio w/ KING Sized Bed!

4.97 out of 5 average rating, 75 reviews

A private balcony is shown, featuring a round table and four light blue chairs. A bottle of champagne is positioned on the table, while a serene water view is visible in the background, with clear skies and scattered clouds enhancing the scene.

Condo in Isla del Sol

Beautiful waterfront condo at St. Petersburg Beach

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

4.93 out of 5 average rating, 29 reviews

A panoramic view showcases Boca Ciega Bay, surrounded by lush greenery and coastal homes. The image captures a clear blue sky dotted with wispy clouds. In the foreground, the heated pool area offers lounge chairs, inviting relaxation while enjoying the scenic waterfront backdrop.

Condo in St. Pete Beach

Seaside Serenity: Modern Comforts/Prime Location

A serene sunset over the intercoastal waterway is captured, with warm hues reflecting on the calm water. Lush palm fronds frame the scene, enhancing the tranquil atmosphere as the sun dips below the horizon.

4.94 out of 5 average rating, 226 reviews

Sea La Vie- Studio by the bay!

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

4.91 out of 5 average rating, 101 reviews

An aerial view captures the spacious beachfront property bordered by crystal-clear waters and soft sand. The five-story building features a sunlit exterior and is surrounded by lush green landscapes, with nearby residential areas and waterways visible in the background.

Condo in Sunset Beach

Direct Gulf View On The Beach w/ Music & Food #502

A spacious bedroom features a comfortable bed adorned with colorful bedding. Floor-to-ceiling glass doors provide direct views of the ocean and access to a balcony. Nearby seating is visible, surrounded by light blue accents matching the coastal theme.