Family-friendly 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.

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.

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

The Flamingo Flat

This is a charming freshly painted mid-century modern "Old Florida Coastal" home! Great location with off-street parking. Fully furnished covered porch with ceiling fans in very private partially fenced yard. Just a 1 mile walk or ride to Gulfport Beach and Arts District, and 3 miles to Sunset Beach on the pristine Gulf of Mexico. Two bedrooms (1 queen and 1 twin). People of ALL sizes, colors, beliefs, cultures, religions, sexes and backgrounds are welcome here as long they DO NOT SMOKE!

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

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!

Relaxing & Charming Hideaway

Welcome to this centrally located St Petersburg guest suite. Our renovated guest house is located less than 10 minutes from Downtown and less than 10 minutes from Treasure Island Beach. You will be an 8-minute walk to the St Pete SunRunner - connecting St Pete Beach with downtown. The apartment has been carefully designed to include everything you will need to make your stay as comfortable as possible including private parking, a private side entrance, and an enclosed private yard.

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.

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.