Holiday rentals with outdoor seating in South Pasadena

Cozy Guesthouse Near Downtown (Non-Toxic)

Come relax in this calm, newly renovated guest suite. Clean, natural, & chemical free - diffusers and oils available on site. Amenities like central a/c, laundry, private patio, full kitchen, Netflix & Hulu. A short 5 minute drive from downtown - near tons of local restaurants, entertainment, and beaches. St. Pete loves the local vibe, be sure to check out our visitors guide for suggestions on spots to see while you’re here. It doesn’t get any better than St Pete! Book your stay with us today!

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.

Modern Studio | Close To St. Pete Beach | Private

Welcome to our Modern Guest Suite! Perfect for couples and traveling professionals, our suite is close to beaches and downtown. Enjoy trendy decor, a queen-size memory foam mattress, a comfy couch, and an efficiency kitchen. Relax in your private fenced yard with a patio set, soaking up the Florida sunshine. Conveniently located: ▪️ 5 min drive to St. Pete Beach and Gulfport ▪️ 15-20 min to vibrant Downtown St. Pete ▪️ Blocks to Pinellas County Trail ▪️ 1/2 mile to the new SunRunner bus

Charming Studio | Outdoor Kitchen | Free Parking

Welcome to our thoughtfully designed studio—small but full of comfort, efficiency, and charm. If your priority is a cozy bed , a truly clean space and location, look no further. Loved by hundreds of wonderful guests, this is one of two private studios in a tiny house, ideal for solo travelers or couples. You’ll have everything you need, plus access to a beautiful shared gazebo with seating, dining areas, and lush greenery. We have a team of four Superhosts, available to help. 🌴☀️🏖️

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. 🌴☀️🏖️

Gulf Guesthouse - king bed, 3 blocks to downtown.

Be our guest! Welcome to our family compound where you will enjoy the treetop views from our second story carriage house guest apartment. You'll be surrounded by the tropical serenity of lush palms and plants, both inside and out, while being just around the corner from the excitement of downtown Gulfport. Our updated one bedroom apartment is fully furnished and stocked with all of the things you'll need for an extra comfortable, enjoyable stay. We look forward to hosting you!

Avocado Casita 10 mins to Beaches

Newly built studio -- small space, smart design. An intimate studio space meant for a minimalist lifestyle complete with full amenities. Compact yet comfortable, it’s the perfect place for a restful sleep in between your daytime adventures. Pack light, live easy. 3 blocks from Stetson Law School 3-4 blocks from the Pinellas Trail ~1.5 miles to Gulfport’s Beach Blvd 3 miles to Award Winning St. Pete Beach 4 miles to Award Winning Treasure Island ~4.5 miles to Downtown St Pete

Cozy Gem Near Madeira Beach

This cozy studio unit with its own screened-in large private patio is the perfect getaway for up to 2 people looking to enjoy the beautiful beaches of this area. Located in a quiet neighborhood on a private cal-de-sac, it is the perfect place to rest and recharge between trips to the most beautiful beaches in the world. This location is just a quick 5-minute drive (2 miles) to the Madeira Beach access and a 10-minute drive to the famous John's Pass Village and Boardwalk.

Historic Kenwood Getaway

Fun facts: In 2020, Historic Kenwood was named 'NEIGHBORHOOD of the YEAR as well as a DESIGNATED ARTIST's ENCLAVE. Our quadrant campaigned to limit new homes that were out of step with the Bungalow style and maintain the personality of Historic Kenwood. It was passed. Suitable for 2 adults (No infants or children) Walking distance to Central Ave. & Grand Central District. The area is filled with restaurants, bars, craft breweries, and shopping.

Stylish & Eclectic Modern 2/2 Apt - WeArePeaceful

Our apartments 'Peaceful' is a combination of pleasing colors and a delicate attention to detail in every corner 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 Side Garden Suite (no cleaning fee)

This private guest suite is centrally located between the beaches on Treasure Island and the nightlife, shopping, and dining of the Grand Central and Pier districts, along the Sun Runner public transportation route. The suite includes one bedroom, bathroom, and kitchenette, separated from the main house, with a private entrance through the side garden. Come enjoy your morning coffee in the garden, and all that St. Petersburg has to offer.

Peaceful Getaway Close to Amazing Beaches!

This property is nestled in a quiet neighborhood just a mile from the beautiful Gulfport Waterfront District. It’s the perfect place to get away and relax or work remotely! You’ll be minutes away from our awesome town of Gulfport, renowned beaches on the Gulf, gorgeous local parks and preserves, lots of artsy shopping spots, and dining options for every palette! This sanctuary is furnished with everything you might need!