Vacation rentals in South Pasadena

4.96 out of 5 average rating, 157 reviews

A spacious backyard is featured, bordered by a wooden fence for privacy and lined with tropical plants and trees. A concrete patio area is included, which features a grill covered for protection. The lawn is open and well-maintained, providing a serene outdoor space.

Cottage in Gulfport

The Pelicans Roost / Gulfport

The Pelicans Roost is a remodeled home, with a new fully stocked kitchen with all your cooking and entertaining needs. All new furnishings, a screened in back porch and a patio with an outside table and grill. The yard is completely fenced and lined with tropical plants and trees for your privacy. This spacious and comfortable home is clean and in a quiet neighborhood just 5 blocks from all that downtown Gulfport has to offer- the Marina,Beach,Restaurants, Shops, Fishing, Galleries and more...!

Apartment in South Pasadena

A stylish living area features a unique cow-print loveseat adorned with pink and yellow decorative pillows. Framed art pieces await adornment on the walls. A gold table lamp and textured side tables add to the elegant ambiance of the space.

4.95 out of 5 average rating, 159 reviews

Eclectic Modern 2/1 Apt - WeAreAuthentic

Our apartment 'Authentic' 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 just 5 minutes away driving, 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. This apartment is a second floor unit.

Superhost

A cozy living area features a beige sofa adorned with bright orange pillows, inviting relaxation. A white coffee table sits in front, while a wall shelf displays decorative items. Natural light filters through two windows, brightening the space. A door leads to the outside.

Guesthouse in St. Petersburg

4.88 out of 5 average rating, 523 reviews

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.

Guest suite in St. Petersburg

A comfortable sleeping area features a queen bed dressed in a white and aqua patterned duvet. Two individual pillows rest at the head of the bed. A nightstand with a lamp and a decorative chair are positioned nearby, while light from windows partially covered by blinds illuminates the space.

4.98 out of 5 average rating, 930 reviews

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

A living area features wood-paneled walls complemented by retro artwork. A cozy seating arrangement includes a sofa and armchair, while a coffee table sits atop a vibrant area rug. Natural light is filtered through a window dressed with blinds, and a ceiling fan enhances airflow.

4.78 out of 5 average rating, 293 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!

A charming two-story house is presented in soft turquoise, featuring large front windows that invite natural light. A gravel pathway leads to the entrance, bordered by lush greenery and decorative landscaping. The surrounding area includes trees providing shade and a sense of tranquility.

4.88 out of 5 average rating, 178 reviews

Gecko House Unit #1

Romantic little apartment which is the lower left half of the house next to Downtown Gulfport. Here you will find many shops, restaurants, and even a dancing hall a short walk away. Enjoy live bands during the day and Karaoke at night at some of the greatest bars in Florida. Not to mention, one of the best beaches is right next door. It even contains beach volleyball nets for daily use. Take a stroll down to the pier and enjoy the sites of the marina, or enjoy a beautiful sunset at night.

4.96 out of 5 average rating, 114 reviews

A heated stock tank pool is surrounded by a lush tropical landscape featuring a variety of green plants. An oversized umbrella provides shade, and a colorful bungalow is visible in the background, creating a serene outdoor retreat.

Tiny home in Gulfport

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!

Guesthouse in St. Petersburg

The bright living area features a green sofa with a decorative pillow, a white coffee table, and a dining table with four chairs. Vibrant wall art enhances the space, complemented by large windows allowing natural light. A doorway leads to the private side yard.

4.98 out of 5 average rating, 130 reviews

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.

4.91 out of 5 average rating, 221 reviews

A modern kitchen area is highlighted with wooden countertops and white cabinetry. A stove, microwave, and tea kettle are visible, alongside open shelving displaying glassware and decorative items. Natural light enters through a window, illuminating the space, which leads to a cozy sleeping area.

Tiny home in Gulfport

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.

4.97 out of 5 average rating, 111 reviews

An inviting view into the living area is framed by a decorative arch. A vibrant green plant adds a touch of nature, while a cozy brown couch and accent chairs are arranged around a circular coffee table. Colorful artwork decorates the walls.

Guesthouse in Gulfport

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!

4.94 out of 5 average rating, 128 reviews

A screened-in saltwater pool area is highlighted, featuring colorful pool floats and two blue lounge chairs. Natural light enters through large windows, and a door provides access to the adjacent living space. The bright walls reflect the sun, enhancing the cheerful atmosphere.

Home in St. Petersburg

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!

The exterior of the duplex is showcased with a brick facade and a light blue roof. A small white door is centered under a decorative wall feature. Potted plants and a small bistro table with chairs sit on a grassy area, surrounded by trees.

5 out of 5 average rating, 122 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!

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Popular amenities for South Pasadena vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in South Pasadena

Guesthouse in St. Petersburg

A quaint blue bungalow is framed by lush greenery, with tropical plants flanking a brick pathway leading to the entrance. Sunlight filters through the trees, casting gentle shadows on the charming exterior.

5 out of 5 average rating, 64 reviews

Blue Bungalow of St. Pete Beach - Great Location !

4.95 out of 5 average rating, 58 reviews

The spacious room features a large bed covered in a floral blue quilt. A kitchenette is visible in the background, complemented by a refrigerator and countertop. Soft lighting is provided by a bedside lamp, and a doorway leads to the bathroom area.

Guesthouse in Gulfport

La Casita of Princesa Peach! Stetson & Beaches!

A well-maintained pool area features a crystal-clear swimming pool surrounded by a spacious deck. Two lounge chairs with blue and white towels are placed near the water. Lush greenery and a privacy fence create a serene atmosphere, inviting relaxation and leisure.

5 out of 5 average rating, 16 reviews

Private Pet-Friendly Home with Pool

4.93 out of 5 average rating, 94 reviews

An outdoor lounging area is showcased, featuring a sectional sofa with neutral cushions arranged around a wooden coffee table. A flat-screen TV is mounted on a green wall, with a grill visible nearby. The pool and surrounding patio create an inviting space for relaxation.

Home in St. Petersburg

St Pete Retreat - Heated Salt water pool

4.88 out of 5 average rating, 84 reviews

A bright kitchen features a cheerful, colorful wallpaper with a playful design. A traditional farmhouse sink is situated on a light blue countertop, accompanied by various kitchen utensils and knives mounted on the wall. A vibrant yellow door complements the lively aesthetic, inviting natural light.

Villa in Gulfport

Cozy funky duplex with KING bed

Guest suite in St. Petersburg

An open studio space is highlighted by a spacious bed with neutral bedding. Two dark armchairs are positioned near a window, allowing natural light to fill the area. A ceiling fan and wooden beams create a relaxed atmosphere, complemented by light-colored flooring.

4.89 out of 5 average rating, 66 reviews

King Size Sassy Studio. No Cleaning Fee.