Holiday houses 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 · Family · Wi-Fi

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)

Location · Value · Beach

Quiet & Cozy Studio Near Beach & Downtown

Welcome to our charming studio in the heart of St. Petersburg, Florida! Our cozy dog-friendly space is the perfect retreat for solo travelers or couples looking to experience all this vibrant city offers. Located just 10 mins from Treasure Island and less than a half mile from a Sun Runner bus stop, the location offers easy access to all of the city’s great destinations. Enjoy your own private entrance and plenty of street parking in our quiet, shaded neighborhood. We can't wait to host you!

Location · Value · View

Stylish & Eclectic Modern 2/2 Apt - WeAreGrateful

2 Bedroom 2 Baths Eclectic Modern Apartment Our apartment 'GRATEFUL' is a combination of pleasing colors and a delicate attention to detail in every corner that 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.

Location · Family · Long stay

ABC Pet Friendly Pool & Hot Tub| 5' St. Pete Beach

Welcome to the ABC Lux perfect for FAMILIES & GROUPS seeking luxury, comfort, and unforgettable memories on Florida’s Gulf Coast. Experience upscale living just minutes from the award-winning beaches of St. Pete Beach and Treasure Island. Relax in your private resort-style featuring a Heated Pool, Hot Tub, BBQ, Fire Pit, Game Room, Outdoor Entertainment , High-Speed Wi-Fi, and beautifully designed interiors. 5' St. Pete Beach | 8' Treasure Island | 14' Downtown St. Petersburg | 35' TPA

Location · Family · Beach

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 · Location · Backyard

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.

Value · Location · Hiking

Gulfport Art District - One Block From Beach!

Welcome to Uncle Finley's! Situated in the heart of Gulfport's Art and Waterfront District, This cottage listing is for unit A of the duplex. Step outside and walk to Gulfport Beach only one short block away, experience the highly-rated restaurants and shops, or browse local arts and crafts during the weekly Tuesday Morning Market during your stay. Want to experience more of Tampa Bay? Downtown St. Pete, St. Pete Beach, and I-275 access are only ten minutes away.

Value · Location · TV

FLASH SALE! Lets Flamingle! <1mi to beach! Sleeps4

🚨Special Offer: We’re running a limited-time Flash Sale for select dates! Message us to unlock exclusive savings for your short term or mid term stay‼️ 🦩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. Book now and let the good vibes roll! 🌴☀️🦩

Location · Value · Accuracy

Dolphin Cove Waterfront St. Pete Beach w/ Pool

THIS is the Florida life! A private oasis with a stunning tropical backyard and an oversized SALTWATER pool. Enjoy 140+ ft of waterfront on Bear Creek canal, where manatees and dolphins visit daily! Kayak just 15 minutes to nearby islands. Beaches are a quick 7-minute drive, downtown is 15 minutes away, and shops/restaurants are right across the street. The home is simple and unupdated, but the backyard is a true paradise you won’t forget!

Location · Value · Biking

Waterfront Paradise• Pool, Hot Tub, Dock & Games

Escape to this stunning 5BR/3BA waterfront oasis in Gulfport! Enjoy a private pool, hot tub, boat dock, and game room with pool table and arcade fun. Fully remodeled with stylish finishes, this spacious retreat is perfect for family vacations or group getaways. Soak in water views, relax outdoors, or set off on a boating adventure. Just minutes to Gulfport Beach, shops, and dining—this home is your gateway to the ultimate Florida getaway!

Value · Location · Hospitality

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.

Family · Location · Getting around