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Vacation rentals in South Pasadena

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Top-rated vacation rentals in South Pasadena

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

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Guesthouse in Gulfport

graceful haven...

This boutique-sized, moon-drenched studio is more than just a place to lay your head. From the delicate metal birds swirling above your bed, to the tender light reflecting off the burnished aluminum countertop, your senses will be soothed and tickled by its quietly exuberant design & decor. Nestled in a lush tropical garden, the space is just a block away from Gulfport's Art Village with its sunset waterfront, delightful shops, and many fine restaurants. (or, see my “bohemian treat” listing)

Guesthouse in St. Petersburg

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.

Rental unit in South Pasadena

Beautiful 2/2 Eclectic Modern 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.

Condo in St. Pete Beach

A Perfect Condo Near The Beach

Enjoy this first-floor condo with a private patio, just an 11-minute walk to the beach! Close to fabulous restaurants, water sports, Sunset Beach, and the historic Corey Avenue shopping district. This ground-floor condo has everything you need, including a large updated kitchen. We have access to a pool for guests of the complex, and the park across the street has courts for pickleball or tennis, a boat ramp, and a gazebo overlooking the water. Treasure Island is just around the corner!

Bungalow in Gulfport

Gulfport - St. Pete bungalow centrally located

Cozy and private apartment perfectly situated between St Pete Beaches, downtown St. Petersburg, and the quirky vibrant downtown Gulfport Arts District. This is a private apartment with 2 rooms, 1 bath, kitchenette, and patio. We live on the property in the other side of the Duplex, but your suite is completely private with your own entrance. Nature Park & bike trails: down the street! Downtown gulfport: 1mi / 3min St. Pete beach 4.6mi / 10min Downtown St Pete : 5mi / 10min

Guest suite in St. Petersburg

Charming Side Garden Suite (no cleaning fee)

This private guest suite is centrally located between the beaches on Treasure Island and the nightlife, shopping, and dining of the Grand Central and Pier districts, along the Sun Runner public transportation route. The suite includes one bedroom, bathroom, and kitchenette, separated from the main house, with a private entrance through the side garden. Come enjoy your morning coffee in the garden, and all that St. Petersburg has to offer.

Guest suite in Saint Petersburg

Bayside Paradise Inn~ Water Views, Kayaks, Fishing

Private, separate in-law suite apartment on Boca-Ciega Bay has a complete kitchen, living room/dining area, bedroom and bathroom with private entryway. Wake up to Dolphins swimming by your window frolicking in the bay. Kayaks are furnished to be launched from backyard dock. Bring your fishing pole. Our concern for the safety of our guests during this pandemic, has caused us to adopt new enhanced cleaning methods recommended by AirB&B.

Condo in Sunset Beach

Sunset Beach Condo in Treasure Island

Enjoy a beach getaway in this newly renovated 1 bedroom/1 bath (one queen, twin pull out sofa and single bed foldout) condo with partial water views. This top floor condo (2nd floor) is equipped with new stainless steel appliances, new dishwasher and beach front pool. The perfect relaxation! Great view from the balcony. Across the street from the beach. Harbor House in Sunset Beach, is located on the southern tip of Treasure Island.

Home in Gulfport

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!

Bungalow in Saint Petersburg

Sandy Beaches Bungalow

Experience the epitome of Mid-Century Modern elegance in this stunning bungalow nestled within the prestigious waterfront enclave of Causeway Isles. Situated a mere 1.5 miles from the captivating shores of Treasure Island Beach and conveniently positioned along the picturesque Pinellas Bike Trail, this fully furnished haven beckons for 30 day+ rentals. **Snowbirds bring your pup and make this your winter home**

Home in St. Petersburg

☼ Happy Space ☼ Prime Location + Spacious Backyard

Newly renovated, the St. Pete Happy Space, is located close to EVERYTHING. It is just minutes away from Treasure Island Beach, Downtown St. Pete, shopping mall, and restaurants. The house features a spacious backyard, 65” smart TV and very comfortable beds. Bring your dog or even bring your boat! Enhanced cleaning practices are taken after each guest to ensure proper sanitation.

Rental unit in Sunset Beach

West Coast Beach Pad - One Block to Beach Access

What's a short 3 minute walk to picturesque Sunset Beach; Your West Coast Beach Pad, 1st floor. Enjoy the beach with our beach chairs, umbrella, cart, towels and cooler. Relax outside with bistro table and chairs, use the gas grill and enjoy a quiet meal together. Quiet neighborhood. Cozy, light & airy, and modern. Our West Coast is your Key West getaway in Treasure Island.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for South Pasadena vacation rentals

Free parking on premises

Air conditioning

Stay near South Pasadena's top sights

Upham Beach82 locals recommend

Cadys beach bar5 locals recommend

StarLite Sapphire5 locals recommend

Sunset Beach82 locals recommend

Beach Escape Game5 locals recommend

RumFish Grill69 locals recommend

Other great vacation rentals in South Pasadena

Guest suite in St. Petersburg

Modern Romatic Suite: 5 Min to St Pete Beach

Rental unit in Saint Pete Beach

Getaway to St Pete Beach, the Sunset Capital

Guest suite in Gulfport

Gulfport Studio STEPS to Beach & Restaurants

Home in Gulfport

The Brenda Ann/Pet Friendly/Walk to downtown!

Guest suite in Saint Petersburg

Private Guest Suite 2 miles from Beach

Guesthouse in St. Petersburg

Gorgeous 1 bedroom guest space with pool

Guesthouse in Gulfport

La Casita of Princesa Peach! Stetson & Beaches!

Rental unit in South Pasadena

Luxurious Studio Pool, Hot Tub, Volleyball + Games

Quick stats about vacation rentals in South Pasadena

Total rentals
70 properties
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
1.5K reviews
Nightly prices starting at
$10 before taxes and fees

Frequently Asked Questions

Are there pet-friendly vacation rentals in South Pasadena?
Four-legged friends are welcome in South Pasadena. Choose from more than 30 vacation rentals for guests traveling with pets.
What are the most popular amenities for Condo Rentals in South Pasadena?
Enhance your stay in our Condo Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in apartment rentals in South Pasadena?
Experience the best of South Pasadena with our apartment rentals, starting at about $40 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 vacation rentals in South Pasadena?
South Pasadena has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do hotel rentals in South Pasadena have a bbq area?
Absolutely! We offer over 10 hotel rentals with a bbq area in South Pasadena. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in South Pasadena have wifi?
Absolutely! We offer over 10 condo rentals with wifi in South Pasadena. Enjoy a tailored experience with all the comforts you desire.
Are there South Pasadena vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in South Pasadena, available on Airbnb. Make a splash and soak up the sun in style!
Are there vacation rentals with a dedicated workspace in South Pasadena?
Yes! Work meets play with ease at over 40 vacation rentals in South Pasadena featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore