Holiday rentals in South Pasadena

Sandcastle I Swim Spa, Art, Starlink, 10 min Beach

Have you ever wanted to live in a Sandcastle? So did we! After years of building them on Florida beaches, we decided to create a modern, artful, unique Sandcastle Home. It's our coastal beach vacation version of glamping! * 10 min to beaches & 20 min to Downtown St. Petersburg * Cool Garage/Flex space that can work as a 4th sleeping area! * Swim Spa for 8 guests * 2 Remote Work Areas & Starlink WIFI * Tesla Universal EV chargers also for NON-Tesla cars *Great Location - close to everything!

The Driftwood - Pet Friendly

Welcome to The Driftwood's nautical retreat. This cozy 2-bedroom home is a haven of maritime-inspired style, offering a unique and refreshing escape for your stay. Unwind in your private yard with a fire or dinner at the outdoor dining area. Have your pet staying with you? They are welcome here! This beautiful diverse neighborhood is one mile away 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 St Pete Pier.

Waterfront/ Sunsets/ Heated Pool/ Tiki Bar/ Dock

Welcome to The Tiki Retreat, Your Waterfront Oasis on Boca Ciega Bay!
Step into a bright, coastal 3 bedroom home where relaxing waterfront living meets vibrant tropical vibes. Enjoy stunning views, a private dock, a heated salt water pool, and your private tiki bar all set against the backdrop of beautiful Boca Ciega Bay, home to dolphins, manatees, and an array of wildlife. This spot has everything you need for an unforgettable stay. Feel free to bring your family pet (with pre-approval)

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.

Charming Gulfport Bungalow, Close to Beach

Step into a one-of a kind Jungalow retreat. The eclectic vacation rental blends vintage treasures, global finds and bold design choices into a vibrant and welcoming getaway. From colorful textiles and artful decor with a Pac-Man arcade, record player and classic records perfect for travelers who crave more than the ordinary. Unwind on the private patio and grill out or make some smores on the fire pit. Gulfport has a quaint downtown and local shops and plenty of wonderful beaches nearby!

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.

Blue Bungalow of St. Pete Beach - Great Location !

Whether you're seeking a quiet respite or fun filled days and exciting nights, you'll feel right at home in your new, home away from home, The Blue Bungalow of St. Pete Beach! Located only 2mi from St.Pete Beach in a historic district of South Pasadena. Are you a bicyclist? We're conveniently located next to the Pinellas Trail which takes you directly into downtown via 20 minute ride! We're perfectly situated between the beach and downtown. Washing machine/ clothes line avail.

*POOL* Fenced Yard *Shuffleboard Court*

Add my listing to your wishlist by clicking the heart in upper right corner • 4 off-street parking spaces • Smart Locks + self check-in • Ring camera for security • Fully equipped kitchen + essentials • 10ft Stock Tank *POOL* • HUGE fenced-in yard • Outdoor shuffleboard court, corn hole & BBQ • Onsite washer+dryer • 2 adult bikes + 2 kids bikes --ride into Gulfport! • 8min drive to beaches • Dedicated Work space + 730Mpbs wifi • 65in smart TV + streaming apps

Casita Bonita, close to Stetson Law School

Take it easy at this unique and tranquil getaway in Florida's eclectic city of Gulfport. This city is close to many beaches, has a vibrant downtown with live music going on all of the time, markets, it's own beach, and great restaurants. The 75 mile Pinnelas Trail is just a few blocks away. This home fits right in to esthetic of the vibe of the city. Casita Bonita is quiet, comfortable and spacious with a nice outdoor space to enjoy the great FL weather.

FLASH SALE| Micro Resort |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 🍋Squeeze the Day in this bold, citrus-inspired 1BR retreat just a quick walk or drive to Upham Beach! Bright, fun, and full of tropical charm, this cozy getaway features FAST Wi-Fi, smart TV, full kitchen, self check-in, and sunny outdoor space. Book now — let’s squeeze the day! 🌴☀️🍊

The Boho | Walk to Gulfport Beach & Restaurants

Boho inspired cottage in the heart of the Gulfport Waterfront District. Steps away from Gulfport beach, restaurants, and nightlife. Enjoy strolling along Beach Boulevard where you'll find local coffee shops, ice cream parlors, Gulfport brewery, and eclectic shops. Relax in the comfort of your backyard oasis or enjoy some fun in the sun with the best Gulfport has to offer right outside your back door.

Oak Tree House

Make yourself at home away from home. Bring your family to this great place and enjoy the evenings in our beautiful patio deck and relax in the Jacuzzi. Now with a brand new outdoor shower. Located Just 2 miles away from Treasure Island beach and close to bars, restaurant’s, world class sporting events, craft beer, art galleries, local shopping and so much more…