Vacation rentals in South Pasadena

Guest Favorite in St. Pete Beach| Pool & Hot Tub

Dreaming of a Florida getaway with sunny beach days, golf course views, and dolphin sightings? This guest-favorite 2BR/2BA condo is just 5 minutes from St. Pete Beach, dining and shopping. Enjoy resort-style perks: a heated pool and hot tub steps from your front door, plus a private bay front beach with tiki umbrellas and sun loungers. Inside, a king suite, full kitchen, balcony views, and beach gear await. As one of the few owner managed Airbnb's, rest assured, your comfort is our top priority.

Vista Verde East 8-164

Vista Verde East 8-164 is a ground-floor Verde East condo at Isla Del Sol. This unit is a two-bedroom, two-bath unit with 3 flat-screen TVs, free WiFi,  and all of the comforts of home. The beautifully renovated unit features a updated kitchen, an updated master bathroom , and updated guest bathroom. The unit comfortably sleeps 6 guests with a queen-size bed in the master bedroom and a queen-size bed in the guest bedroom. Both bedrooms have walk-in closets! This unit is extremely peaceful and tr

Pet Friendly Pool Oasis St Pete/Gulfport

Exceptionally private artist's home with a salt pool ( not heated) in a tropical landscaped fenced backyard and a large screened porch, surrounded by palm trees. 10 mns to St Pete beach , Treasure Island, Sunset beach or downtown St Petersburg. 5 mns to the old Florida downtown Gulfport and one block to pinellas trail. Our Eco and pet friendly ,(only green cleaning products and no pesticides) 1400 sqft home ( plus the 300 sqft porch) home is in a safe residential area, close to everything.

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.

Stylish & Eclectic Modern 2/2 Apt - WeAreGrateful

2 Bedroom 2 Baths Eclectic Modern Apartment Our apartment 'GRATEFUL' is a combination of pleasing colors and a delicate attention to detail in every corner that will let you experience the magic of an eclectic space in the heart of St Petersburg. With the beautiful sand beaches under 5 minutes away, you can feel the breeze as soon as you step outside. You also can try St Petersburg’s diverse restaurant scene and visit the museums displaying art permanent collections and traveling exhibits.

Casa Azul

Newly renovated 2-bed, 1.5-bath home is the perfect blend of comfort, style, and location—just a few minutes' drive to Treasure Island & St Pete beach. Step inside to a coastal-inspired space including a chefs kitchen, bedrooms designed with relaxation in mind, luxury bathrooms offer spa-like finishes. The open living room features a 75" TV. Outside, your private tropical backyard awaits. Lounge poolside under swaying palms, enjoy outdoor dining, or take a dip in the new salt water pool.

Gulfport Hideaway, Close to Entertainment District

This large & light-filled 3-bedroom, 2-bath home offers a spacious, open layout perfect for relaxing, gathering, or remote working. Surrounded by mature canopy trees, the home feels like a private sanctuary close to the vibrant arts & entertainment district. A short walk to Gulfport’s restaurants, galleries, coffee shops, yet tucked away from the buzz for peaceful & private nights. Treasure Island and St. Pete Beach are only 5 minutes away, and Downtown St. Pete is just a 10-minute drive.

** Home Away From Home **

Why book 3 or 4 hotel rooms when you can book this beautiful and completely remodeled 4-bedroom, 2.5 bath 1788 sq. ft. home, centrally located in desirable South Pasadena Florida. Professionally decorated in a contemporary beach décor, stunning, spacious and very private! There is no lack of amazing things to do around the home, but if you want to be close to the St. Pete Beach, you are only 2.5 miles away and 6.5 miles to downtown St. Petersburg where night life entertainment abounds.

Cozy Cottage for Lovers

Relax, reconnect and revitalize in this private, intimate cottage that has everything you need to leave the hustle and bustle behind. Surrounded by lush tropical vegetation in the shade of giant live oaks and located in the Gulfport Arts District, you're a short walk or bike ride from excellent urban parks, restaurants, live music, fashion and art boutiques, dancing at the Gulfport Casino, community theater, and a beautiful beach that looks out over sailboats moored in Boca Ciega Bay.

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!

Pelican's Nest - Pet Friendly

The Pelican's Nest is a cozy tiny home that has been remodeled with you in mind. Enjoy the beachy vibes inside the home or relax outside where you can connect to nature with your private yard. Enjoy a fire or dinner on your outdoor dining table. Have your pet staying with you? No worries! They are welcome here. Located a mile from Gulfport's beach blvd. Where you can shop, dine, or stroll the beach. 6 miles away will take you to the famous St Pete Beach or the St Pete pier.

FLASH SALE! Lets Flamingle! Sleeps 4 <1mi to beach

🚨Special Offer: We’re running a limited-time Flash Sale for select dates! Message us to unlock exclusive savings for your short term or mid term stay‼️ 🦩Let’s Flamingle in this bold, pink 1BR retreat near Upham Beach! Located in a gated complex, this tropical paradise features cozy flamingo decor, FAST Wi-Fi, smart TV, full kitchen, and lush vacation vibes. One of 4 fun themed units perfect for beachside escapes. Book now and let the good vibes roll! 🌴☀️🦩