Vacation rentals in South Pasadena

4.99 out of 5 average rating, 190 reviews

An aerial view captures a multi-story condominium overlooking a beach. Lush palm trees surround a heated pool area, with docks lining the waterfront. The expansive coastline is visible in the background, highlighting the scenic proximity of beach and bay.

Condo in Treasure Island

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.

Guesthouse in Central Oak Park

A private backyard features a heated pool surrounded by lush tropical plants and trees. The pool has a gentle curve and is accompanied by stone steps leading into the water. A small seating area is partially visible in the background, set amongst vibrant greenery.

4.98 out of 5 average rating, 202 reviews

Central Cozy Cottage w/ Heated Pool & Hot Tub!

Welcome to cute & cozy Turtle Cottage located right in the center of St. Pete, close to both Downtown AND several gorgeous Florida beaches. NO CLEANING FEE with competitive, seasonal pricing = a FANTASTIC DEAL for this space! A BEAUTIFUL NEW HEATED POOL & HOT TUB await in the private, fenced-in tropical backyard. Sorry, no pets/animals or babies/children/teens. Adults 21+ only and limited to 2 verified guests. 100% smoke-free property, inside & out. EVERYONE is welcome here. Come & enjoy!

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.

4.89 out of 5 average rating, 176 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.

Guest suite in St. Petersburg

A sleek kitchen area features a vibrant red refrigerator and modern cabinetry. A textured backsplash adds dimension, while open shelves display glassware. Countertop space is provided for preparation, and a sink is set into the countertop, enhancing functionality in this stylish environment.

4.96 out of 5 average rating, 151 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

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!

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.

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.

4.97 out of 5 average rating, 111 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!

Apartment in South Pasadena

A light-filled living area includes a plush white sofa adorned with colorful cushions. A wooden coffee table with plant arrangements sits at the center, while framed artwork and decorative accents enhance the eclectic vibe. Two doorways lead to additional rooms, adding depth to the space.

4.94 out of 5 average rating, 190 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

Two light blue beach cruiser bicycles with tan seats are positioned on a concrete surface. A window and a chair in a welcoming yellow tone are visible in the background, framed by greenery. The entrance to the rental is accessible and inviting.

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!

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!

Vacation rentals for every style

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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 !

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.

4.95 out of 5 average rating, 58 reviews

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

A private pool area featuring a curved pool surrounded by stone pavers. Colorful lounge chairs and umbrellas provide shaded seating. The backdrop includes a charming cottage, greenery, and clear blue skies, creating a relaxed outdoor space ideal for leisure.

5 out of 5 average rating, 10 reviews

Tropical Oasis Guest House

5 out of 5 average rating, 8 reviews

A multifunctional game room showcases a variety of gaming options, including a foosball table and air hockey. The vibrant outdoor area features lounge chairs arranged around a fire pit, surrounded by manicured landscaping and a saltwater pool in the background.

Home in St. Petersburg

StPeteBeachBungalow-SltPool/golf/gameroom-Slps 10

An outdoor patio area features a tiled surface surrounded by greenery and a wooden fence. A round table with chairs is positioned next to a gas grill, while a large tree provides shade. Potted plants add a touch of nature to the space.

4.92 out of 5 average rating, 85 reviews

Avocado Oasis 10 mins to Beaches

Superhost

A serene outdoor space is highlighted with a saltwater pool surrounded by tropical landscaping. Lounge chairs offer a relaxing spot under a white umbrella, while a variety of lush plants and trees create a private oasis.

Bungalow in Gulfport

4.89 out of 5 average rating, 44 reviews

GulfPort Paradise, Bali-like Oasis with Pool

An outdoor shuffleboard court is featured in the spacious fenced-in yard, lined with gravel and surrounded by lush greenery. A picnic table and black chairs are positioned nearby under a shaded area, creating a welcoming space for relaxation and games.