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.

Stylish & Eclectic Modern 2/2 Apt - Wearegrateful - South Pasadena, FL
9.9 249 reviews

Stylish & Eclectic Modern 2/2 Apt - Wearegrateful

apartment, South Pasadena
This family-friendly apartment is located in St. Petersburg, just a short walk from the beach, Pasadena Shopping Center, and Sunset Park. It's also within a 2-mile radius of Corey Ave and Palms of Pasadena Hospital, offering easy access to amenities and services. This rental has received excellent user ratings for location, cleanliness, and overall experience.
The apartment has two bedrooms and two bathrooms, comfortably accommodating up to five guests. It features a fully equipped kitchen, a patio, and access to a garden and parking, providing everything you need for a relaxing and enjoyable stay.
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.
Waves 14 Condo Beautiful 1 Bedroom With Pool - South Pasadena, FL
9.0 2 reviews

Waves 14 Condo Beautiful 1 Bedroom With Pool

house, St. Pete Beach
Waves 14 Condo, a St. Pete Beach rental, is a 4-minute walk from the beach, 4.3 miles from John's Pass Village & Boardwalk, and under 10 miles from the Dali Museum and Chihuly Collection.
This one-bedroom, one-bathroom beachfront condo offers 680 square feet of space, sleeps seven guests, and includes a fully equipped kitchen, in-unit laundry, a swimming pool, and free Wi-Fi.
Waves 14 Condo: Beautiful 1-bedroom With Pool - South Pasadena, FL
9.3 104 reviews

Waves 14 Condo: Beautiful 1-bedroom With Pool

apartment, St. Pete Beach
This St. Pete Beach condo is conveniently located within walking distance of Corey Avenue and Upham Beach Park, offering easy access to shops, restaurants, and the beach. Guests have consistently rated this rental excellent for location, cleanliness, and overall experience.
The unit features a fully equipped kitchen, a comfortable living area with a sofa bed, and a private bathroom. Enjoy the convenience of on-site amenities like a swimming pool, barbecue grills, and parking.

Best South Pasadena, FL vacation rentals with air conditioning

Madeira Bay Resort 509 - South Pasadena, FL
9.3 558 reviews

Madeira Bay Resort 509

house, Madeira Beach
Madeira Bay Resort 509 is located just steps from the white sands of Madeira Beach and a short walk from the lively John's Pass Village and Boardwalk. The resort has consistently received excellent ratings for its location, cleanliness, and overall experience.
The resort offers comfortable rooms with air conditioning, TVs, and private bathrooms. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, sauna, spa, fitness center, restaurant, bar, and free Wi-Fi.
1 Br Gulf Gardens Madeira Beach Cottage - South Pasadena, FL
9.7 211 reviews

1 Br Gulf Gardens Madeira Beach Cottage

apartment, Madeira Beach
This apartment is located in the heart of Madeira Beach, within walking distance of the beach, restaurants, and shops. It has excellent user, location, and cleanliness ratings.
The apartment has one bedroom, one bathroom, and a floor area of 550 square feet. It features a private balcony or patio with stunning views of the Gulf of Mexico. Guests have access to a shared water park, spa tub, and barbecue grills. The apartment also includes a fully equipped kitchen, a washer and dryer, a spacious living area with a Smart TV for entertainment, free Wi-Fi, and parking.
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.
Stylish & Eclectic Modern 2/1 Apt  Weareauthentic - South Pasadena, FL
9.9 230 reviews

Stylish & Eclectic Modern 2/1 Apt Weareauthentic

apartment, South Pasadena
This family-friendly apartment is located in St. Petersburg, Florida, just a short walk from the beach, Pasadena Shopping Center, and Palms of Pasadena Hospital. The apartment has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This 2-bedroom, 1-bathroom apartment comfortably sleeps 4 guests and offers 800 square feet of living space. The apartment includes a fully equipped kitchen, a terrace or balcony, a garden, parking, internet, and air conditioning, allowing guests to relax and enjoy their stay.

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.

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
335 Surf Song Resort is ideally located in the heart of Madeira Beach, a short stroll from the lively John's Pass Village and Boardwalk, and just steps from the pristine Madeira Beach. With excellent ratings for its prime location, cleanliness, and amenities, this vacation home offers a comfortable and convenient stay for travelers.
The air-conditioned vacation home features a separate bedroom, a bathroom, and a TV with cable channels, providing comfortable accommodations for up to 2 guests in its 370 square feet of floor area. Guests can enjoy a fully equipped kitchen, free Wi-Fi, a private balcony, and access to a swimming pool, garden, and parking.
Charming Hideaway -Pool, Patio, Walk To Gulf Sands - South Pasadena, FL
9.7 231 reviews

Charming Hideaway -Pool, Patio, Walk To Gulf Sands

apartment, St. Pete Beach
This quiet corner condo is located just across the road from the beach in St. Pete Beach, within walking distance of restaurants and bars. It has received excellent ratings for its location, cleanliness, and overall experience.
This one-bedroom, one-bathroom studio spans 510 square feet and comfortably accommodates up to four guests. The studio offers a full kitchen, a private patio, access to a heated pool, and other community amenities like shuffleboard courts and charcoal grills.
Prime St Pete Beach Spot  Gulf Winds Resort - South Pasadena, FL
9.8 263 reviews

Prime St Pete Beach Spot Gulf Winds Resort

apartment, St. Pete Beach
This remodeled condo on Upham Beach is just steps from the sand and within walking distance of bars, restaurants, and shops. It has consistently received excellent ratings for location, cleanliness, and user experience.
The 540 square foot apartment has one bedroom, one bathroom, and can comfortably accommodate up to four guests. Enjoy the private patio, access to the heated pool, and on-site amenities like charcoal BBQ grills, shuffleboard courts, and a laundry room.
319 - Island Inn - South Pasadena, FL
9.4 229 reviews

319 - Island Inn

house, Treasure Island
This beach house is just steps from Treasure Island and a short walk from Sunset Beach, offering easy access to the area's best beaches and attractions. It has received excellent ratings for location, cleanliness, and overall experience.
This 1-bedroom, 1-bathroom vacation rental comfortably sleeps 4 guests. It features a fully equipped kitchen, air conditioning, a private bathroom, a swimming pool, a terrace, and free Wi-Fi.

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.

Madeira Beach Tropic Breeze Unit 11 Second Floor - South Pasadena, FL
9.0 2 reviews

Madeira Beach Tropic Breeze Unit 11 Second Floor

house, Madeira Beach
Madeira Beach Tropic Breeze Unit 11, located in St. Pete Beach, Florida, offers direct beach access and is minutes from Treasure Island and North Redington Beach.
This 460-square-foot condo features one bedroom, one bathroom, sleeps seven guests, includes a fully equipped kitchen, swimming pool, tennis court, and free Wi-Fi, plus nearby water park, fishing, and golfing.
Sunny Delightheated Pool 3 Miles To The Beach - South Pasadena, FL
10 312 reviews

Sunny Delightheated Pool 3 Miles To The Beach

apartment, Seminole
This 2-bedroom apartment in Seminole is conveniently located within a mile of Treasure Island Fun Center, Lake Seminole Park, and Seminole City Center, offering easy access to attractions and dining options. The apartment consistently receives excellent ratings for cleanliness, location, and overall user experience.
The apartment is perfect for families or groups of up to 5 guests. It features a fully equipped kitchen, modern amenities, and a comfortable living space. Enjoy the on-site amenities like the swimming pool, fitness center, and garden, or take advantage of the nearby parks and attractions.
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.
Poolside Updated Studio Across From The Beach!! - South Pasadena, FL
9.9 107 reviews

Poolside Updated Studio Across From The Beach!!

apartment, St. Pete Beach
This waterfront apartment is located just a short walk from Upham Beach Park, a beautiful stretch of white sand, and is within easy reach of the vibrant Corey Ave and the attractions of St. Petersburg - Clearwater Beaches. It has consistently received excellent ratings for location, cleanliness, and overall guest experience.
The apartment comfortably accommodates up to four guests and features a kitchen, a private patio, and a swimming pool. Enjoy free Wi-Fi, a smart TV, and other amenities designed to enhance your stay.

Best South Pasadena, FL vacation rentals with parking

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

Surf Song By Travel Resort Services

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

Beach, Dolphin/manatee Sightings, Fishing, Sunsets

apartment, Treasure Island
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
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

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.

506 - Crystal Palms - South Pasadena, FL
9.3 237 reviews

506 - Crystal Palms

house, Treasure Island

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
Walk To Art District + Beach: Pet-friendly Getaway - South Pasadena, FL
9.0 5 reviews

Walk To Art District + Beach: Pet-friendly Getaway

house, Gulfport
Teal Tide Beach Escape! Walkable, Steps To Beach - South Pasadena, FL
10 2 reviews

Teal Tide Beach Escape! Walkable, Steps To Beach

apartment, Madeira Beach
Covare #5 - Walk To St Pete Beach & Restaurants! - South Pasadena, FL
9.5 2 reviews

Covare #5 - Walk To St Pete Beach & Restaurants!

apartment, St. Pete Beach

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.

Waterfront Condo W/ Arcade In Treasure Island! - South Pasadena, FL
10 29 reviews

Waterfront Condo W/ Arcade In Treasure Island!

house, Treasure Island
Waves 18 - South Pasadena, FL
8.5 138 reviews

Waves 18

apartment, St. Pete Beach
Madeira Bay Resort I 1504 - South Pasadena, FL
9.3 183 reviews

Madeira Bay Resort I 1504

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

1501 - Gulf Winds

house, St. Pete 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.

Bay Views | Updated Stay In Prime Beach Location - South Pasadena, FL
9.5 66 reviews

Bay Views | Updated Stay In Prime Beach Location

apartment, St. Pete Beach
Waterfront Condo With Stunning View/pool & Hot Tub - South Pasadena, FL
9.8 150 reviews

Waterfront Condo With Stunning View/pool & Hot Tub

apartment, Seminole
Escape 2 Lands End Your Beachside Paradise On T.i. - South Pasadena, FL
9.0 37 reviews

Escape 2 Lands End Your Beachside Paradise On T.i.

apartment, 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
©2026 cozycozy.com