Holiday rentals in South Pasadena

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Top-rated holiday rentals in South Pasadena

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

Apartment in Treasure Island

4.99 out of 5 average rating, 188 reviews

Spectacular beach to bay views from this resort.

Our condo has spectacular water views from the Bay to the Beach. We have a large one of a kind kitchen that is unique to our resort, with granite counter tops, hardwood cabinets, and all stainless steel appliances. Everything you need to prepare a meal is provided along with basic spices and condiments, Coffee, creamer, and sugar. The master bedroom has a new king size bed and walk in closet with all beach gear also available for your use. We have 2 - 50" flat screen TV's with cable as well.

Guest favourite

Guest suite in St. Petersburg

4.96 out of 5 average rating, 150 reviews

Modern Suite | 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

Top guest favourite

Tiny home in Gulfport

4.96 out of 5 average rating, 112 reviews

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!

Superhost

Home in South Pasadena

4.82 out of 5 average rating, 215 reviews

** 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.

Guest favourite

Flat in Gulfport

4.84 out of 5 average rating, 233 reviews

Studio Garden Apartment

Studio apartment in Gulfport FL. New space with new bathroom and kitchenette, overlooking my garden. Hot plate and toaster oven with air fry capacity with a mini fridge. Sink, counter space and cupboards in kitchenette . George Forman grill outdoors on the deck for outdoor cooking as well. Queen bed Private entrance with no shared space. Updated WiFi with strong signal to support many devices perfect for work space and TV with netflix and ruko. There is only space for one vehicle.

Guest favourite

Home in Gulfport

4.93 out of 5 average rating, 28 reviews

*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

Guest favourite

Tiny home in Gulfport

4.93 out of 5 average rating, 219 reviews

Pelican's Nest - Pet Friendly

The Pelican's Nest is a cozy tiny home that has been remodeled with you in mind. Enjoy the beachy vibes inside the home or relax outside where you can connect to nature with your private yard. Enjoy a fire or dinner on your outdoor dining table. Have your pet staying with you? No worries! They are welcome here. Located a mile 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 the St Pete pier.

Top guest favourite

Guest house in Gulfport

4.98 out of 5 average rating, 110 reviews

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!

Guest favourite

Guest suite in St. Petersburg

4.92 out of 5 average rating, 341 reviews

THE NEST: Separate Unit Near Beaches and Downtown

At the center of everything! Experience this well designed, separate unit in St Pete, close to attractions, downtown restaurants & bars, best beaches, Dali Museum and St Pete Pier. The Airbnb is a separately built addition with its own private entrance, queen bed, dresser, wifi, mini fridge, coffeemaker, microwave, snacks and bathroom. Free driveway parking. The space is completely sanitized for each new guest(s). All touchable surfaces are disinfected.

Guest favourite

Flat in South Pasadena

4.94 out of 5 average rating, 189 reviews

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.

Superhost

Cottage in Gulfport

4.88 out of 5 average rating, 165 reviews

Gulfport Getaway-Close to Everything!

Take a step off the beaten path with a stay at this tropical 2-bedroom, 1-bath Gulfport Beach vacation rental! The 'Sirens Cove' is ideally situated between St Pete Beach, downtown St. Petersburg, and the quirky, vibrant Gulfport Arts District. Take a ride on our beach cruisers and enjoy the Gulfport vibe! You'll have plenty of opportunities to recharge your soul, relax, and soak up the beautiful Florida sun! 30+ Day Rentals Available!

Guest favourite

Flat in St. Pete Beach

4.76 out of 5 average rating, 282 reviews

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

🦩 FREE NIGHT! Stay 3 nights, get the 4th FREE – 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! 🌴☀️🦩