Compare vacation rentals in South Pasadena, FL from 100+ sites!

70 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
South Pasadena, FL vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Vacation rentals and Airbnb offers in South Pasadena, FL

Find Vacation Rentals in Downtown of South Pasadena, FL

These vacation rentals in the downtown area of South Pasadena, FL offer unbeatable walking access to vibrant local life, dining, and culture.

409 - Island Inn - South Pasadena, FL
9.1 192 reviews

409 - Island Inn

house, Treasure Island
This beachfront rental is located just steps away from Treasure Island's beautiful beaches and a short walk from Sunset Beach, offering easy access to the area's best attractions. The property has received excellent user ratings for location and cleanliness, ensuring a comfortable and enjoyable stay.
The one-bedroom vacation home comfortably accommodates up to 3 guests and features a fully equipped kitchen, air conditioning, and a private terrace. Enjoy the convenience of free Wi-Fi, a swimming pool, and a garden, perfect for relaxing and enjoying the Florida sunshine.
Amazing Beachside Studio - South Pasadena, FL
9.3 166 reviews

Amazing Beachside Studio

apartment, St. Pete Beach
This St. Pete Beach apartment is located just steps from Upham Beach Park and a short walk from the vibrant Corey Ave, where you'll find shops, restaurants, and bars. The apartment boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The one-bedroom, one-bathroom apartment provides 500 square feet of space and can comfortably accommodate up to four guests. Enjoy amenities like a swimming pool, jacuzzi, and a fully equipped kitchen, along with a terrace, garden, and spa for relaxation.
Steps To St. Pete Beach: Condo W/ Pool! - South Pasadena, FL
9.5 119 reviews

Steps To St. Pete Beach: Condo W/ Pool!

house, St. Pete Beach
This St. Pete Beach apartment is located just a 5-minute walk from the beautiful sands and turquoise waters, and a short drive from John's Pass and John's Pass Village and Boardwalk. Guests have consistently rated this rental highly for its excellent location, cleanliness, and overall experience.
This 1-bedroom, 1-bathroom apartment offers 570 square feet of space, comfortably accommodating up to 4 guests. Relax and enjoy the amenities, including a heated pool, a peaceful garden, and a fully equipped kitchen, perfect for preparing meals and enjoying the beautiful Florida sunshine.
Bella Sirena Inn - South Pasadena, FL
9.5 298 reviews

Bella Sirena Inn

apartment, St. Pete Beach
This St. Pete Beach apartment is a short walk from St. Pete Beach Theater and a short drive from Dolphin Landings Charter Boat Center, putting you in the heart of the action. Guests consistently rate the apartment excellent for location, cleanliness, and overall experience.
The apartment has one bedroom and one bathroom, perfect for a couple or small family. Enjoy amenities like a swimming pool, terrace, garden, and free parking, along with a fully equipped kitchen and free Wi-Fi.

Best South Pasadena, FL vacation rentals with air conditioning

Pelican's Nest - Tiny House - South Pasadena, FL
9.8 267 reviews

Pelican's Nest - Tiny House

house, Gulfport
The Pelican's Nest is a cozy tiny home located just a mile from Gulfport's beach boulevard, putting you within easy reach of shops, restaurants, and the beach. It's also just a short drive from St. Pete Beach and the St. Pete Pier, offering plenty of opportunities for sightseeing and activities. This Gulfport accommodation has consistently received excellent ratings for location, cleanliness, and overall user experience.
The Pelican's Nest comfortably sleeps two guests and features a queen-size bed, a loveseat-sized couch, and a foldable desk. It includes a fully equipped kitchen, a spacious bathroom, a private yard with a fire pit, and shared laundry facilities.
Beach View 1b 1b - Balcony - King - Surf Song #346 - South Pasadena, FL
9.3 254 reviews

Beach View 1b 1b - Balcony - King - Surf Song #346

apartment, Madeira Beach
This house is located in Madeira Beach, just a short walk from John's Pass Village and Boardwalk, a popular area for shopping, dining, and entertainment. The house has excellent user, location, and cleanliness ratings.
The house has one bedroom and one bathroom. It features a fully equipped kitchen, a swimming pool, a terrace, a garden, and free parking. You can also enjoy free Wi-Fi, cable TV, and air conditioning.
Historic Charm Meets Historic District Beach Chic - South Pasadena, FL
9.8 253 reviews

Historic Charm Meets Historic District Beach Chic

apartment, Gulfport
The Sand Dollar is a second-story apartment in Gulfport's Waterfront District, walking distance from the Pinellas Bike Trail, Stetson School of Law, and Eckerd College. It has received excellent ratings for location, cleanliness, and user experience. The apartment is a one-bedroom, one-bathroom unit with a guest capacity of four. It offers a unique blend of classic charm and modern beach vibes, with a private tropical patio, a fully equipped kitchen, free Wi-Fi, and Netflix.
Large 1b1b Unit - Pool Side - Surf Song #229 - South Pasadena, FL
9.2 312 reviews

Large 1b1b Unit - Pool Side - Surf Song #229

apartment, Madeira Beach
This beachfront vacation home is located just a 2-minute walk from Madeira Beach, offering easy access to the area's attractions. The house has received excellent ratings for its location, cleanliness, and user experience.
The vacation home features one separate bedroom, a fully equipped kitchen, and a bathroom, providing ample space for a comfortable stay. Guests can enjoy amenities such as free Wi-Fi, a dishwasher, an oven, cable TV, air conditioning, a swimming pool, a terrace or balcony, a garden, and parking. Pets are also allowed, making it a great option for travelers with furry companions.

Frequently Asked Questions about vacation rentals in South Pasadena, FL

  • Which walking or cycling routes are the best in South Pasadena, FL?

    South Pasadena is a great place to explore on foot or by bike. You can take a stroll along the waterfront on the Pinellas Trail, which runs for miles along the Gulf Coast. The trail is paved, flat, and perfect for a leisurely walk or bike ride.
  • What are the best Airbnb and vacation rentals in South Pasadena, FL?

    **Home Away From Home**, 2 Bed 2 Baths Eclectic Modern Apt - Wearegrateful and 2 Bedroom 2 Baths Eclectic Modern Apartment - We Are Peaceful are the most popular Airbnb and vacation rentals in South Pasadena, FL among travelers.

  • What sports or outdoor activites can visitors enjoy in and around South Pasadena, FL?

    South Pasadena is a great place to enjoy the outdoors. You can go fishing, kayaking, or paddleboarding in the Gulf of Mexico. There are also plenty of parks and green spaces where you can go for a walk, jog, or play a game of frisbee.
  • What are the most popular Airbnbs in South Pasadena, FL?

  • What other towns or cities can be easily accessed from South Pasadena, FL?

    South Pasadena is a great base for exploring the Tampa Bay area. You can easily drive to St. Petersburg, Clearwater, Tampa, and even Sarasota. You can hop on the Pinellas Trail and ride your bike to St. Petersburg, which is only about 10 miles away.
  • What are the best vacation rentals with a pool in South Pasadena, FL?

  • What amenities are commonly available in vacation rentals in South Pasadena, FL?

    Vacation rentals in South Pasadena usually come with all the comforts of home, like a kitchen, laundry facilities, and a living room. Many also have a private pool or hot tub, and some even have a view of the Gulf of Mexico.
  • What are the best rentals for families and kids in South Pasadena, FL?

  • What time of year is best to rent a vacation rental South Pasadena, FL?

    The best time to visit South Pasadena is during the spring or fall when the weather is mild and the crowds are smaller. You can also visit during the summer, but it can get hot and humid, and there are more tourists.
  • What are the best rentals or Airbnbs with a jacuzzi in South Pasadena, FL?

    The best vacation rentals or Airbnb with a jacuzzi in South Pasadena, FL are **Home Away From Home**, Pasadena Pineapple Palace and Gorgeous Home 10 Minutes To Madeira Beach With Jacuzzi.

  • What are the local dishes in South Pasadena, FL region?

    You'll find lots of fresh seafood in South Pasadena, so be sure to try some grouper, snapper, or shrimp. There are also plenty of great restaurants serving up classic Southern comfort food, like fried chicken, biscuits and gravy, and collard greens.

Popular destinations

Best Vacation Rentals with Balconies in South Pasadena, FL

Enjoy stunning views from your private terrace when you book one of these vacation rentals in South Pasadena, FL.

Beach, Dolphin/manatee Sightings, Fishing, Sunsets - South Pasadena, FL
10 179 reviews

Beach, Dolphin/manatee Sightings, Fishing, Sunsets

apartment, Treasure Island
This Treasure Island apartment is located within a mile of several attractions, including the beach, John's Pass Village & Boardwalk, and Hubbards Marina. The apartment has received excellent ratings for location, cleanliness, and overall experience.
This 1-bedroom, 1-bathroom apartment can comfortably accommodate up to 3 guests in its 670 square feet of space. Amenities include a fully equipped kitchen, a swimming pool, a garden, a terrace, a spa, free Wi-Fi, a Smart TV, and parking.
Waterfront Escape· Steps To Beach · Marina View - South Pasadena, FL
9.7 229 reviews

Waterfront Escape· Steps To Beach · Marina View

apartment, Madeira Beach
This waterfront condo in Madeira Beach is just steps from the beach and a block from Johns Pass Boardwalk, which offers dining, shopping, and entertainment. The apartment has excellent user, location, and cleanliness ratings.
The 730-square-foot apartment has 2 bedrooms, 2 bathrooms, and can accommodate up to 6 guests. It features a private balcony with intercoastal and marina views, a fully stocked kitchen, high-speed internet, a fitness room, a pool, and a hot tub.
Beach House Retreat Near Gulfport's Beach Blvd - South Pasadena, FL
9.5 279 reviews

Beach House Retreat Near Gulfport's Beach Blvd

apartment, Gulfport
This charming 2-bedroom apartment in Gulfport is located steps away from a large public park, pier, restaurants, shops, and live music venues. It has excellent user, location, and cleanliness ratings.
The apartment has a floor area of 1000 square feet and can accommodate up to 5 guests. It features hardwood floors, a king-size bed, a fully equipped kitchen, air conditioning, a Jacuzzi, a terrace, a garden, and parking. Guests can enjoy a shared backyard with ample shade and outdoor seating, as well as a private beach shared with other guests, ideal for bird watching and sea life exploration.
403 - Madeira Norte - South Pasadena, FL
9.0 108 reviews

403 - Madeira Norte

house, Madeira Beach
This comfortable house in St. Pete Beach is located just 3.7 miles from the St Pete Beach Theatre and 5 miles from the Boca Ciega Bay Aquatic Preserve, offering easy access to both attractions and the beautiful white sand beaches. Guests consistently rate this property excellent for its cleanliness, location, and overall experience.
The house features two bedrooms and can accommodate up to six guests, perfect for families or groups of friends. Enjoy a fully equipped kitchen, air conditioning, a swimming pool, a terrace or balcony, a garden, and parking, along with easy access to the beach and other attractions.

Top Vacation Rentals for Families in South Pasadena, FL

These kid-friendly vacation rentals in South Pasadena, FL keep you close to top city attractions for a stress-free family vacation.

Steps To Beach Relaxing Getaway On A Bay W/pool. - South Pasadena, FL
10 34 reviews

Steps To Beach Relaxing Getaway On A Bay W/pool.

apartment, Madeira Beach
This ground floor condo in the gated Madeira Beach Yacht Club community is located directly across from Madeira Beach's white sands, just 50 feet from the beach, and within walking distance of shops, restaurants, and ROC Park.
This 1-bedroom, 1-bathroom apartment accommodates up to 4 guests and features a fully equipped kitchen, air conditioning, a private screened-in patio with a gas grill, and access to community amenities including two heated outdoor pools, a fitness center, sauna, and indoor hot tub.
Sunset Beach Suites Unit 3 - South Pasadena, FL
10 3 reviews

Sunset Beach Suites Unit 3

house, Madeira Beach
Sunset Beach Suites Unit 3, a condo in St. Pete Beach, is located 1.3 miles from John's Pass Village and Boardwalk and near Madeira Beach.
This 500 sq ft condo accommodates up to 7 guests with 1 bedroom and 1 bathroom, featuring air conditioning, a full kitchen with an oven and microwave, spa access, and direct access to water sports and an on-site water park.
Majestic Beach Condo In Beachfront Resort In St Pete Beach - South Pasadena, FL
9.8 97 reviews

Majestic Beach Condo In Beachfront Resort In St Pete Beach

apartment, St. Pete Beach
This recently renovated one-bedroom apartment is just a 1-minute walk from the beach and 4.4 miles from John's Pass, offering easy access to the area's attractions and activities. The apartment has received excellent ratings for user experience, location, and cleanliness.
The 510-square-foot apartment includes a fully equipped kitchen, a terrace/balcony, and a garden. Guests can enjoy a heated pool, a water slide, a restaurant, a bar, a fitness center, a tennis court, yoga classes, and free parking and Wi-Fi.
Breathtaking Waterview Condo! - South Pasadena, FL
9.6 158 reviews

Breathtaking Waterview Condo!

apartment, Seminole
This waterfront condo is located in St. Petersburg, just a short walk from War Veteran Memorial Park and Bay Pines VA Medical Center, offering a convenient and peaceful setting for your stay. Guests consistently rate the property as excellent for cleanliness, location, and overall experience.
The unit features one bedroom and one bathroom, comfortably accommodating up to four guests. Enjoy access to a range of amenities, including a swimming pool, fitness center, spa, and a garden, as well as a fully equipped kitchen and a balcony for relaxing.

Best South Pasadena, FL vacation rentals with parking

607 - Madeira Bay Resort - South Pasadena, FL
9.3 457 reviews

607 - Madeira Bay Resort

house, Madeira Beach
Surf Song By Travel Resort Services - South Pasadena, FL
9.1 747 reviews

Surf Song By Travel Resort Services

resort, Madeira Beach
505 - Gulf Strand - South Pasadena, FL
9.4 208 reviews

505 - Gulf Strand

house, St. Pete Beach
306-s - Sunset Vistas - South Pasadena, FL
9.2 224 reviews

306-s - Sunset Vistas

house, Treasure Island

Compare Luxury Vacation Rentals in South Pasadena, FL

Discover high-end comfort in South Pasadena, FL with upscale rentals that prioritize luxury and guest satisfaction.

Delightful 1-bedroom Efficiency - South Pasadena, FL
9.6 108 reviews

Delightful 1-bedroom Efficiency

house, St. Petersburg

Our Favorite Pet-Friendly Vacation Rentals in South Pasadena, FL

Discover pet-friendly vacation rentals in South Pasadena, FL that prioritize comfort for both you and your dog.

Tropical Paradise Tranquility Getaway - South Pasadena, FL
10 33 reviews

Tropical Paradise Tranquility Getaway

apartment, St. Petersburg
Gulfport Beautiful Two Bedroom Cottage - South Pasadena, FL
9.8 148 reviews

Gulfport Beautiful Two Bedroom Cottage

apartment, Gulfport
Walk To Beach: Pet-friendly Treasure Island Home - South Pasadena, FL
9.2 167 reviews

Walk To Beach: Pet-friendly Treasure Island Home

house, Treasure Island
Premier St. Petersburg Unit: Best Views & Layout! - South Pasadena, FL
9.6 77 reviews

Premier St. Petersburg Unit: Best Views & Layout!

house, Seminole

Explore Vacation Rentals with a Pool in South Pasadena, FL

A vacation rental with a pool in South Pasadena, FL makes it easy to fit in a proper swim right in the heart of the city.

Tropic Breeze 6 | Ground-floor Madeira Beach Pool - South Pasadena, FL
9.4 642 reviews

Tropic Breeze 6 | Ground-floor Madeira Beach Pool

apartment, Madeira Beach
1501 - Gulf Winds - South Pasadena, FL
9.2 212 reviews

1501 - Gulf Winds

house, St. Pete Beach
1br 1b - 3rd Floor - King - Surf Song #335 - South Pasadena, FL
9.1 68 reviews

1br 1b - 3rd Floor - King - Surf Song #335

apartment, Madeira Beach
Beachfront Complex - 2b 2b - Beach Place #503 - South Pasadena, FL
8.7 959 reviews

Beachfront Complex - 2b 2b - Beach Place #503

apartment, Madeira Beach

Search Vacation Rentals with Jacuzzi in South Pasadena, FL

Unwind in style with a South Pasadena, FL vacation rental featuring a hot tub, ideal for relaxing after a day in the city.

Treasure Island Condo: Gulf-view Balcony - South Pasadena, FL
8.5 9 reviews

Treasure Island Condo: Gulf-view Balcony

house, Treasure Island
Wander Residence Condo Near Fort Desoto - South Pasadena, FL
9.2 66 reviews

Wander Residence Condo Near Fort Desoto

apartment, Tierra Verde
Madeira Bay Resort #412  Marina-view Comfort With Pet-friendly Charm & Family-friendly - South Pasadena, FL
9.3 101 reviews

Madeira Bay Resort #412 Marina-view Comfort With Pet-friendly Charm & Family-friendly

apartment, Madeira Beach
Beautiful 2 Bedrm/2 Bath Condo In St Pete Beach - South Pasadena, FL
9.8 186 reviews

Beautiful 2 Bedrm/2 Bath Condo In St Pete Beach

apartment, St. Pete Beach
©2026 cozycozy.com