Holiday houses 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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Guest favourite
A charming two-story building stands in a landscaped yard, featuring a light blue exterior and large windows that invite natural light. A gravel pathway leads to the entrance, bordered by vibrant greenery and decorative red bricks.
Home in Gulfport
4.77 out of 5 average rating, 162 reviews

The Gecko House Unit 3

Romantic little apartment next to Downtown Gulfport. It is up one flight of stairs as shown in the pics. 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 10 blocks away. 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.

Top Guest favourite
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
4.99 out of 5 average rating, 210 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.

Top Guest favourite
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.
Guest suite in St. Petersburg
4.98 out of 5 average rating, 1,009 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

Top Guest favourite
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.
Guest suite in St. Petersburg
4.96 out of 5 average rating, 166 reviews

Modern Studio | Close To St. Pete Beach | Private

Welcome to our Modern Guest Suite! Perfect for couples and traveling professionals, our suite is central 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
A charming cottage is surrounded by lush greenery, featuring a covered porch adorned with blue rocking chairs and a decorative whale motif. Tropical plants frame the view, while a wooden fence adds to the property’s privacy and character.
Cottage in Gulfport
4.98 out of 5 average rating, 100 reviews

Cozy Cottage for Lovers

Relax, reconnect and revitalize in this private, intimate cottage that has everything you need to leave the hustle and bustle behind. Surrounded by lush tropical vegetation in the shade of giant live oaks and located in the Gulfport Arts District, you're a short walk or bike ride from excellent urban parks, restaurants, live music, fashion and art boutiques, dancing at the Gulfport Casino, community theater, and a beautiful beach that looks out over sailboats moored in Boca Ciega Bay.

Guest favourite
A welcoming exterior showcases a bright yellow door framed by grey walls and distinctive column accents. Lush green grass surrounds the entrance, complemented by flowering shrubs near the pathway. Two large windows allow natural light to illuminate the space, creating an inviting first impression.
Guest suite in St. Petersburg
4.92 out of 5 average rating, 301 reviews

Sweet & Simple guest suite Close to Everything.

Keep it sweet & simple at this peaceful and centrally-located private room close to downtown and the beaches. The room has it's own entryway from outside and boasts, TV, Wi-Fi, a full private bathrooms. The walk in closet space functions as a breakfast nook with mini refrigerator, microwave, and the necessary basic breakfast utensils. The room is also pet-friendly and close to major highways and transportation hubs. Come and call this space home for your stay in Saint Petersburg.

Guest favourite
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
4.96 out of 5 average rating, 130 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
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.
Tiny home in Gulfport
4.94 out of 5 average rating, 108 reviews

Avocado Casita 10 mins to Beaches

Newly built studio -- small space, smart design. An intimate studio space meant for a minimalist lifestyle complete with full amenities. Compact yet comfortable, it’s the perfect place for a restful sleep in between your daytime adventures. Pack light, live easy. 3 blocks from Stetson Law School 3-4 blocks from the Pinellas Trail ~1.5 miles to Gulfport’s Beach Blvd 3 miles to Award Winning St. Pete Beach 4 miles to Award Winning Treasure Island ~4.5 miles to Downtown St Pete

Top Guest favourite
An inviting studio interior is shown with light-coloured walls and a modern kitchenette visible in the background. A doorway leads to a bathroom featuring tropical-themed wallpaper. A small dining table and chair are positioned in front of a cozy seating area with a dark sofa.
Apartment in Treasure Island
4.98 out of 5 average rating, 132 reviews

Popular Beachside Studio w Relaxing Patio & Palms!

The true gem of Treasure Island! Tucked right off of Gulf Blvd this is one of three stylish studio units nestled in a coconut palm-fringed private courtyard with a residential cottage onsite. This cozy spot overlooking a lush tropical garden is just steps from a white sand beach & walking distance to dozens of laid back beach bars, live music & dining. Please note: There’s no guest parking on-site, but paid parking is nearby as well as a frequent public trolley.

Guest favourite
Apartment in St. Pete Beach
4.77 out of 5 average rating, 302 reviews

FLASH SALE! Lets Flamingle! Sleeps 4 <1mi to beach

🚨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! 🌴☀️🦩

Top Guest favourite
Apartment in St. Petersburg
4.94 out of 5 average rating, 126 reviews

Waterfront studio! Heated pool and hottub

Wake up to stunning waterfront views! Unwind in this bright studio overlooking Boca Ciega Bay, sip coffee on your private balcony while watching dolphins. Highlights: • Direct waterfront views from balcony • Heated pool, spa & fitness center overlooking bay • Minutes to Madeira Beach, St. Pete, & War Veterans’ Memorial Park • Cozy king bed • Close to boat rentals, trails, and waterfront dining Perfect for romantic getaway or peaceful solo escape!

Guest favourite
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.
Apartment in South Pasadena
4.94 out of 5 average rating, 210 reviews

Stylish & 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.

Popular amenities for South Pasadena holiday rentals

When is the best time to visit South Pasadena?

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Avg. price$251 NZD$345 NZD$382 NZD$310 NZD$268 NZD$255 NZD$265 NZD$245 NZD$224 NZD$233 NZD$243 NZD$261 NZD
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Frequently Asked Questions

  • Where should I stay in South Pasadena?

    Make yourself at home in South Pasadena by choosing from our most frequently booked neighborhoods. We have over 5,520 vacation rentals in South Pasadena, and over 3,400 vacation rentals in Corey Ave.

  • Are there pet-friendly vacation rentals in South Pasadena?

    Four-legged friends are welcome in South Pasadena. Choose from more than 70 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in South Pasadena?

    Yes! Work meets play with ease at over 170 vacation rentals in South Pasadena featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there South Pasadena vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 240 vacation homes with pools in South Pasadena, available on Airbnb. Make a splash and soak up the sun in style!

  • Do apartment rentals in South Pasadena have a gym?

    Absolutely! We offer over 10 apartment rentals with a gym in South Pasadena. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in condo rentals in South Pasadena?

    Experience the best of South Pasadena with our condo rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly condo rentals in South Pasadena?

    South Pasadena has more than 60 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do condo rentals in South Pasadena have a bbq area?

    Absolutely! We offer over 50 condo rentals with a bbq area in South Pasadena. Enjoy a tailored experience with all the comforts you desire.

  • Do hotel rentals in South Pasadena have wifi?

    Absolutely! We offer over 10 hotel rentals with wifi in South Pasadena. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in South Pasadena have air conditioning?

    Absolutely! We offer over 90 apartment rentals with air conditioning in South Pasadena. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in South Pasadena

  • Total holiday rentals

    Explore 360 holiday rentals in South Pasadena

  • Nightly prices starting at

    South Pasadena holiday rentals start at $67 NZD per night before taxes and fees

  • Verified guest reviews

    Over 14,320 verified reviews to help you choose

  • Family-friendly holiday rentals

    140 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 80 rentals that welcome pets

  • Holiday rentals with a pool

    230 properties feature pools

  • Rentals with dedicated workspaces

    180 properties have a dedicated workspace

  • Wi-Fi availability

    360 of South Pasadena holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across South Pasadena rentals

  • 4.8 Average rating

    South Pasadena stays are highly rated by guests—averaging 4.8 out of 5!

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