Condo vacation rentals in South Pasadena

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, 151 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, 212 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 wooden walkway leads directly to a sandy beach, framed by tall grasses on either side. The beach stretches out under a clear sky, with gentle waves visible in the distance. A sign is positioned to the left, indicating the beach entrance.

4.91 out of 5 average rating, 109 reviews

Comfortable 2BR condo, walk to all sand beach

Come, enjoy the beautiful West Coast of Florida. Fabulous sunsets over the Gulf. My condo is walking distance to a beautiful all sand beach, less than 10 minutes. Heated swimming pool and designated free parking for one car on the property. Many restaurants and bars within walking distance. Two free lighted tennis courts across the street. High speed Wifi. My building does not allow pets of any kind. I can't rent to groups of people under the age of 25. Just 1.5 hours to Disney/Universal

A well-maintained swimming pool is surrounded by palm trees and greenery, overlooking the intercoastal waterway. The clear blue water of the pool contrasts with the vibrant landscape, and a serene view of the water can be seen in the background.

4.99 out of 5 average rating, 144 reviews

Treasure Island 1 BR condo intercoastal waterfront

Beautiful 1 BR 1 bath condo with awesome water view of the intercoastal located in Westwinds Waterfront Resort 800 square feet with large living area including 65 in tv, queen sofa sleeper, full kitchen, king bed in master. Short walk to beach of Treasure Island. Grocery store, restaurants and bars all within walking distance. The Resort has heated pool, two gas grills, elevators and 3 docks and peaceful area to just sit and look at the water. Boats up to 24’ welcome with reservation.

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.

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! 🤍

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, 598 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.

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.

4.97 out of 5 average rating, 203 reviews

*Shore Thing* Walk to Beach | Intercoastal Views

🏖️ Shore Thing Condo 🏖️ Experience the ultimate blend of Sunset Bliss at this stylish Treasure Island retreat. Just steps from powdery sands, ocean breezes and breathtaking sunsets. Keep an eye out for local wildlife as dolphins and manatees glide by. Inside, enjoy coastal vibes featuring modern beachy interiors. Whether you are preparing a meal in the luxury kitchen or diving into the intercoastal heated pool, my service ensures your comfort always comes first.

The spacious living area features a blue sofa with decorative pillows, a white coffee table, and a dining space with a round table and four chairs. A ceiling fan circulates air, and the kitchen is visible in the background, complemented by light-colored cabinetry.

4.92 out of 5 average rating, 162 reviews

Updated Condo minutes from the beach - heated pool

Welcome to this fabulous and spacious newly updated condo close to the beach and many restaurants. Closest beach is 12 min walk or 2 min drive. John Pass Village is only 6 minutes drive, Downtown St Pete and newly re-opened St Pete Pier is a must visit for either night life or nice dinner. Egan Park and tennis courts are across the street. Pool is in the building- hours of operation is from dusk to down.Pool is heated to 82f during the day. Roku TV's in the unit.

4.98 out of 5 average rating, 256 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 FREE 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/restaurants and the Pinellas trail !

Popular amenities for South Pasadena condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

4.67 out of 5 average rating, 6 reviews

Bright 2BR beach condo, heated pool. FN 604

5 out of 5 average rating, 5 reviews

Luxury Sky Loft w/ Rooftop Lounge & Garage

A view from the balcony showcases vibrant landscaping with palm trees and colorful plants. The open living space features a dining area, a cozy couch accompanied by a media console, and a well-equipped kitchen visible in the background. The bedroom offers a king-size bed adorned with a blue and white pattern.

4.9 out of 5 average rating, 10 reviews

2BD/2BA Condo w/ Beach Access & Pool on Isla del Sol

Two light blue chairs are positioned on a private deck, providing a view of the calm waters of Boca Ciega Bay. Bright orange umbrellas offer shade, while a wooden dock extends towards the water in the background, framed by lush greenery and a clear blue sky.

4.94 out of 5 average rating, 84 reviews

WOW! What a view!

A private balcony overlooks the beach and Gulf of Mexico. Two red chairs are positioned for comfortable seating, while a railing provides safety and unobstructed views. The serene landscape features green grass leading to the sandy shore and the calm blue waters of the ocean.

4.93 out of 5 average rating, 61 reviews

INCREDIBLE SUNSET BEACH OCEANFRONT TOP FLOOR CONDO

4.94 out of 5 average rating, 17 reviews

Condo in Sand Key

CBC 1-15E–High-End Stay, Low Seasonal Pricing!

A living area features a light-colored sofa and armchairs arranged around a chic coffee table. A television is mounted on the wall, and large sliding glass doors provide views of the outdoors. A decorative plant and a lamp add warmth to the space.

4.97 out of 5 average rating, 31 reviews

Everything You Need - St Pete Condo - Isla Del Sol

4.9 out of 5 average rating, 31 reviews

Bay View Getaway | Relaxation | Stunning Views

Pet-friendly condo rentals

Condo in Clearwater Beach

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.

4.81 out of 5 average rating, 149 reviews

Luxury condo at Avalon Club

4.82 out of 5 average rating, 33 reviews

Treasure Island Condo: 2BR/2BA, Bay Views

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, 135 reviews

Breathtaking Waterview Condo!

4.94 out of 5 average rating, 109 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 Madeira Beach

Penthouse,intercoastal, 3/3 views/heated pool

4.98 out of 5 average rating, 103 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, 184 reviews

Waterside Studio in the heart of TI, walk to beach

4.76 out of 5 average rating, 478 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.

Condo in Madeira Beach

Beach Chill Inn #3 - Studio

Condo in Indian Rocks Beach

An inviting private deck area is shown, featuring a dining table with six chairs. The space is surrounded by lush greenery, providing a tranquil atmosphere. Large sliding glass doors lead into the interior living space, enhancing the connection between indoor and outdoor areas.

4.92 out of 5 average rating, 186 reviews

Beach Retreat I

Condo rentals with a pool

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.

4.97 out of 5 average rating, 75 reviews

Beautiful waterfront condo at St. Petersburg Beach

An aerial view captures the sprawling golf course, interspersed with palm trees and manicured greens. Surrounding residential buildings with terracotta roofs and a community pool are visible. The tranquil waters of the inland waterway and the distant skyline create a serene backdrop.

4.87 out of 5 average rating, 71 reviews

Roomy 2 bed/2 bath (+pullout sofa) condo with pool

4.92 out of 5 average rating, 90 reviews

Condo in Tierra Verde

Your Island Escape! • Discounted Summer Rates

4.92 out of 5 average rating, 74 reviews

3 bedroom condo with a pool on Boca Ciega Bay

4.96 out of 5 average rating, 84 reviews

Private balcony, waterfront condo, pool, hot tub

A tranquil beach scene captures a vibrant sunset casting warm hues across the sky. The sun descends towards the horizon, reflecting off the ocean surface. Rocky formations are positioned along the shoreline, providing a natural contrast to the soft sandy beach.

4.9 out of 5 average rating, 52 reviews

Updated Studio - Steps to the beach & heated pool

A refreshing pool area is surrounded by palm trees and well-maintained landscaping, offering ample seating around the water. The pool has a curved shape with clear blue water, ideal for relaxation under the sunny sky.

4.9 out of 5 average rating, 52 reviews

St Pete Beach/Isla Del Sol 2 bedroom 2 bath Condo

A vibrant sunset casts warm orange and yellow hues across the sky, with the sun nearing the horizon over the calm ocean. Silhouettes of palm trees frame the scene, while people stroll along the beach, creating a serene coastal atmosphere.