Holiday rentals in South Pasadena

Private Guest House sleeps 4 w/POOL & near beach!

This adorable pool house is light and airy with plenty of room for 4. There’s a king size bed, queen pullout sofa, dining area, efficiency kitchen perfect for light cooking, oversized closet and a newly remodeled bathroom. Guests have private entrance with small yard and patio of their own, and are encouraged to use the pool and backyard anytime, which we enjoy along with our sweet dogs, Frog and Bella. 3 miles from beach and downtown, lots of restaurants and shopping centers within 1.5 miles.

Private Guest Suite 2 miles from Beach

Private, small completely renovated Guest Suite with Private parking, private separate entrance with deck. Space is best for 1-2 people: small, but thought out. 2 miles from Treasure Island beach. 2.5 miles from the St Pete beach! Beautiful quaint neighborhood. Near great fishing spot Kitchenette Full Bathroom Comfy queen size bed Cool AC unit ❗️WE HAVE GREAT REVIEWS, but please view before booking “Is this guest suite right for you” below under “things to note” to have the trip you desire

Shipwreck Bungalow

Shipwreck Bungalow, your own private paradise! Nestled in a quaint Gulfport neighborhood. Just 10 minutes from St. Pete beach, 10 minutes from lively downtown St. Pete and a few short minutes from funky downtown Gulfport. The Bungalow is surrounded by palms, tropical plants and flowers, beautiful outdoor shower, Tiki bar, heated stock tank pool, fire pit, outdoor games, grill and spacious outdoor seating area. Enjoy lounging by the pool or exploring all this sunny area has to offer!

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.

Sweet & Simple guest suite Close to Everything.

Keep it sweet & simple at this peaceful and centrally-located private room close to downtown and the beaches. The room has it's own entryway from outside and boasts, TV, Wi-Fi, a full private bathrooms. The walk in closet space functions as a breakfast nook with mini refrigerator, microwave, and the necessary basic breakfast utensils. The room is also pet-friendly and close to major highways and transportation hubs. Come and call this space home for your stay in Saint Petersburg.

*Dog Friendly* Shuffleboard - Close to Beaches!

Add my listing to your wishlist by clicking the heart in upper right corner • 4 dedicated parking spaces • Smart Locks + self check-in • Ring camera for security • Fully equipped kitchen + essentials “The house was immaculately clean!" • HUGE fenced-in yard • Outdoor shuffleboard court, corn hole & BBQ • Onsite washer+dryer • 2 adult bikes + 2 kids bikes --ride to downtown Gulfport! • 8min drive to beaches • Dedicated Work space + 730Mpbs wifi • 65in smart TV + streaming apps

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!

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.

FREE NIGHT:FlamingoVibes|Walk to Beach<1Mile|4plex

🦩 FREE NIGHT! Stay 3 nights, get the 4th FREE for August stays – Limited Time! 🌺 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. 💬 Guests say: “So fun, vibrant, and Insta-worthy!” Book now and let the good vibes roll! 🌴☀️🦩