House holiday rentals in South Pasadena

4.98 out of 5 average rating, 104 reviews

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.

4.93 out of 5 average rating, 137 reviews

Groove Under Palms Where Disco Vibes meet Paradise

There's even a disco ball! Perfect for Bachelorette, Bachelor, Reunions, Retreats, and Family Vacations! Gather in the spacious living room to watch movies on the 65-inch smart TV or prepare a feast in the well-equipped kitchen, complete with brand-new appliances. After a day of fun in the sun at St. Pete Beach, relax in your private bedroom with comfortable beds, soft linens, and modern decor. Wake up to beautiful natural light and enjoy a cup of coffee on the patio overlooking the pool.

4.79 out of 5 average rating, 303 reviews

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!

4.99 out of 5 average rating, 132 reviews

Home in Seminole

Tootsie’s Beachside Retreat

LUXURY SALTWATER HEATED POOL HOME! JUST 1.5 MILES TO BEAUTIFUL REDINGTON BEACH. AMAZING REMODELED HOME WITH HIGH END FINISHES LOCATED ON 1/2 ACRE LOT. BRAND NEW CUSTOM POOL WITH PEBBLETECH FINISH AND BAJA SHELF. BEAUTIFUL WHITE SAND BEACHES ONLY 1.5 MILE RIDE! 5 MIN. FROM: 3 COFFEE SHOPS,OUTSIDE MALL WITH SHOPPING, RESTAURANTS AND MOVIES. HOUSE IS ON RARE 1/2 ACRE PROPERTY IN UPSCALE NEIGHBORHOOD. RENOVATED WITH HIGH END FURNITURE AND FIXTURES, SAMSUNG 4K LED T.V.’S IN EVERY ROOM.

4.97 out of 5 average rating, 183 reviews

Home in Central Oak Park

Central location - mins to Downtown and Beaches

Rest assured, you’ll wake up close to all the excitement St. Petersburg has to offer! Perfect for solo travelers, couples, or small groups of friends and family, this cozy home is centrally located between downtown and the beaches—offering the ideal balance of fun and relaxation. 🚗 Quick Drive Times: • 8 min – Downtown St. Pete & The Pier • 12 min – St. Pete Beach • 25 min – Clearwater Beach • 25 min – Tampa & Airport Experience the best of St. Petersburg—scroll down to learn more!

4.88 out of 5 average rating, 139 reviews

Hibernate in our Bear Creek Home

This 3 bedroom 2 bath home is located in beautiful Bear Creek. Don't worry, no bears! Great place to relax and enjoy the pool, in a quiet, safe neighborhood. Next to Pinellas Trail, a 40 mile paved trail. Great for walking, running and biking. You can bike downtown 6 mi or 4.6 miles to beaches. We have bikes and for those more adventuresome we have kayaks you may use. House features stable, high speed internet. Close to great restaurants, drugstores, supermarkets and coffee shops.

4.95 out of 5 average rating, 247 reviews

The Flamingo House

Find your balance at the Flamingo House. Fully renovated (2022) house located in a safe and quiet neighborhood just minutes to beaches, Pinellas Trail (75 mile paved walk and bike path), shopping, restaurants. The house has 2 bedrooms and 2 bathrooms (master has a shower spa and other has a clawfoot tub), a fully equipped kitchen, large living room with HD TV, Wi-Fi , front porch, and back yard to relax and enjoy. Open dates book quickly. Don’t miss out!

4.94 out of 5 average rating, 109 reviews

Home in Seminole

Alextoria Retreat

Welcome to Seminole FL! A cozy 1 bedroom home that sleeps 4 conveniently. With a private yard to relax and bbq. Located near beaches, shopping and nightlife. Within minutes to dining and parks with playgrounds, fishing, walking/ jogging/ bike paths and serene views. A 9 minute (3.7 mile) drive to Madeira beach an 20 to 30 minutes to many other popular beaches. A 30 minute drive to Tampa (airport) A 22 minute drive to St Pete (airport) 30 min to downtown.

4.93 out of 5 average rating, 138 reviews

Creamsicle Dreamsicle- Saltwater Pool- Near Beach!

Find us on the 'gram! @creamsicledreamsicle ***This is NOT a party home*** Thanks for viewing our beloved Creamsicle Dreamsicle! Our home features 3 bedrooms, 1 bath, central AC, off street parking, and an in-ground, heated (for a fee) saltwater pool. We are 3 miles to St. Pete Beach and 4.5 miles to downtown St. Pete! Our home is located in a quiet, safe, small community with very little traffic. Welcome to Saint Petersburg!

5 out of 5 average rating, 125 reviews

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!

4.99 out of 5 average rating, 164 reviews

The Boho - 2BR Gulfport Waterfront District House

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.