House holiday rentals in South Pasadena

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.

Value · Location · Quiet

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)

Value · Location · Layout

Waterfront Oasis, Hot Tub, Sauna

Welcome to our beautiful waterfront home nestled between St Pete Beach & Gulfport, FL, where you'll experience the joys of the quintessential Florida lifestyle! Relax in the large outdoor living space, fish off the dock, boat on the pristine waters of the Gulf of Mexico and take in the ocean breeze. ☑ 2 mi to St. Pete Beach, 2.5 mi to Gulfport & 5 mi to John's Pass ☑ On the Intracoastal Waterway w/boat access out to the Gulf of Mexico ☑ Hot tub, Sauna, Outdoor kitchen, bar, dock, boat lift

Family · Value · Barbecue

Gulfside Resort: 3 bed, 2 bath /pool access

Welcome to GulfSide Resort, a family-owned gem just a block and a half from St. Pete Beach! Our comfortable vacation suites face a beautiful pool and are a short stroll away from beach bars, restaurants, and shopping. Enjoy our pool, shuffleboard, and putting green, plus complimentary beach chairs and toys. Perfect for group gatherings, we can host up to 35 guests comfortably. Experience relaxation and fun with your loved ones at GulfSide Resort—your ideal vacation spot! The house sleeps 6.

Location · Value · Comfort

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!🌊

Value · Family · Beach

** Home Away From Home **

Why book 3 or 4 hotel rooms when you can book this beautiful and completely remodeled 4-bedroom, 2.5 bath 1788 sq. ft. home, centrally located in desirable South Pasadena Florida. Professionally decorated in a contemporary beach décor, stunning, spacious and very private! There is no lack of amazing things to do around the home, but if you want to be close to the St. Pete Beach, you are only 2.5 miles away and 6.5 miles to downtown St. Petersburg where night life entertainment abounds.

Value · Family · Pool

Beautiful Tampa Bay Pool Home Near Gulf Beaches

A beautiful Gulf Coast residence with many amenities to offer. Bright and open furnished spaces, for relaxing and entertaining up to 10 guests. A quiet, upscale neighborhood , your just 6 minutes from Madeira Beach and many other Gulf of Mexico beaches. Or, fun & sun in the private pool outback. 20 minutes from Downtown St Pete, which offers restaurants, museums, the new Pier, and excellent night life. Very close to countless restaurants, shopping, coffee shops, and grocery stores.

Location · Value · Backyard

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.

Family · Value · Beach

SAUNA! Huge HOT TUB & Heated POOL! 3 KING beds!

Make some special memories at this unique and family-friendly home! Your vacation home just completed a head to toe renovation. Everything ( and we mean everything ) is new! Relax and detox in the RARE 4 person SAUNA! Enjoy the HUGE 6 person HOT TUB. Soak up the rich Florida sun by the pool under the large 27 foot resort style pergola. Only 3 miles away from the closest beach 🏖️ 300 feet from the Pinellas Trail!! FASTEST WIFI AVAILABLE -668mbp Have a question?? Message me!

Family · Location · Hospitality

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!

Family · Location · Access

Sunset Waterfront Retreat| Firepit, Dock&Game Room

🌴 Escape slice of paradise, just minutes from the beach and surrounded by Florida’s natural beauty. This 2BR waterfront home features a private dock for boat, a fully stocked game room, and a Florida room with sunset views and a cozy coffee bar. Relax outdoors with a fire pit, BBQ grill, and 6 lounge chairs. This is a single-story property. Whether you’re here to unwind, explore, or entertain, this home has it all.

Location · Family · Laundry

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.

Value · Location · Laundry