Family-friendly vacation rentals in South Pasadena

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in South Pasadena

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favourite

Condo in Saint Petersburg

4.99 out of 5 average rating, 246 reviews

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

My place is close to Bay Pines VA Hospital, Madeira Beach, Tyrone Mall, Pinellas Trail, Bay Pines Park for biking and running, and restaurants. Wave runner, boat, kayak & paddle board rental available very nearby. There is a storage area for kayaks, paddle boards and bikes (please lock your items inside) . You’ll love my place because of the beautiful water view, peaceful good for the soul atmosphere and walkable to shopping, eating, and activities to suit all ages. Newly updated interior 2023.

Nov. 5 – 12

$322 CAD per night

Guest favourite

Guesthouse in Saint Petersburg

4.84 out of 5 average rating, 719 reviews

Private & Cozy Tiny Home/Cottage

This is a cozy converted workshop with all the amenities of a traditional home! You'll have a comfy bed that sleeps 2, cable, Netflix, WiFi, air conditioning, W/D, closet space, cooking stuff, & bathroom. If you love tiny homes, you'll love this. Because of it being a converted workshop, it still has that feeling in some regard. It's a little rustic, but still charming. It's not a hotel, nor does it try to be. It's definitely a great place to relax and get a good night's sleep. Pets welcome.

Sep. 13 – 20

$121 CAD per night

Guest favourite

Guest suite in Gulfport

4.92 out of 5 average rating, 453 reviews

Gulfport Studio STEPS to Beach & Restaurants

Calling all beach lovers! Fall in love with this unique Gulfport Beach Cottage! Colorful, light & bright. Located on a corner lot STEPS from popular Beach Blvd & Gulfport beach, fishing pier, eclectic Gulfport shops, cafes and everything FUN! Gulfport has artsy and quirky shops, fabulous waterfront restaurants and a thriving art scene. Gulfport is a funky community all its own. Gulfport has an Art Walk on the First Friday and Third Saturday and a Tuesday market every week. Don’t miss it!

Sep. 20 – 27

$200 CAD per night

Superhost

Home in Gulfport

4.78 out of 5 average rating, 241 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!

Aug. 4 – 11

$136 CAD per night

Guest favourite

Apartment in Treasure Island

4.92 out of 5 average rating, 162 reviews

Treasure Island Beach Apartment #1

Location! Situated on Gulf Blvd, directly across from the 123rd Street beach access in Treasure Island. Walk to John's Pass for restaurants, shopping, bars and music, boat trips and fishing. Two bedroom, one bath private apartment, with all the amenities you need for a great beach vacation - beach chairs, umbrella, cooler, barbecue, bicycles. Master bedroom has queen bed, and Roku tv. Smaller bedroom has twin trundle bed, perfect for the kids. Full kitchen. Off street parking for one car.

Mar. 18 – 25

$212 CAD per night

Guest favourite

Condo in Tierra Verde

4.96 out of 5 average rating, 237 reviews

Natural Beauty on Tierra Verde, Waterfront Condo

Feels like the Florida Keys! Fully renovated & well appointed second floor, 1 bed, 1 bath condo in Holiday Island condo resort. The condo features a beautiful waterfront & pool view, tennis, bicycles, hot tub, dock with grills, gym, and more. Remodeled in 2015 the condo features a fully equipped kitchen, Keurig coffee maker, beautiful views from the living room, dining room, kitchen, balcony. Walking distance to many local restaurants & minutes away from St. Pete Beach & Fort DeSoto.

Oct. 25 – Nov. 1

$211 CAD per night

Superhost

Condo in Saint Petersburg

4.85 out of 5 average rating, 407 reviews

Waterfront condo on top floor @ Boca Ciega Resort

The view of water is fantastic. Especially beautiful sunsets! Top floor end unit for privacy. Pinellas trail across the street to ride your bike or hike, a beautiful 38 mile trail. Plenty of restaurants nearby and grocery stores. Only 8 min drive to beach. 15 min from downtown St. Pete. Enjoy pool and hot tub overlooking bay for the condominium guests or can stay indoors and enjoy puzzles and games. We have a kayak that can fit up to 2 adults for our guests to use.

Jul. 27 – Aug. 3

$227 CAD per night

Guest favourite

Apartment in Gulfport

4.99 out of 5 average rating, 166 reviews

Studio- Gulfport Art District - 1 Block from Beach

Situated in the heart of Gulfport's Art and Waterfront District, this studio space is ideal for experiencing all Tampa Bay has to offer. Step outside and walk to Gulfport Beach only one short block away, experience the highly-rated restaurants and shops, or browse local arts and crafts during the weekly Tuesday Morning Market during your stay. Want to experience more of Tampa Bay? Downtown St. Pete, St. Pete Beach, and I-275 access are only ten minutes away.

Sep. 20 – 27

$214 CAD per night

Superhost

Condo in Treasure Island

4.91 out of 5 average rating, 159 reviews

Gorgeous One Bedroom on Sunset Beach #52

Stay in my luxury one bedroom condo with a stunning view of the beach. Full kitchen with new stainless fridge, full size oven and microwave. The sofa makes into a queen size bed with a memory foam mattress. In the living room is a 55" flat screen smart TV with cable. Wifi access is free. The bedroom has a comfortable king size bed and the bedroom has a view of the intercoastal waterway. Just steps from the beach. Laundry room is available on premise.

Aug. 9 – 16

$265 CAD per night

Guest favourite

Guest suite in Gulfport

4.97 out of 5 average rating, 337 reviews

WATERFRONT SUITE WITH POOL

PLEASE READ THE LISTING and some reviews before booking, and ask questions...we love questions! . 'Like a private retreat on the water'. This is a Private Suite plus use of shared areas, pool, etc, IN A SHARED HOME, close to downtown Gulfport and convenient to all of Tampa Bay. Room 1 has a queen bed. Room 2, a double. The comfy bath features a ceiling fan and massage jets. The suite is all yours...not shared with other guests.

Jan. 5 – 12

$280 CAD per night

Guest favourite

Bungalow in Saint Petersburg

4.99 out of 5 average rating, 107 reviews

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**

May 14 – 21

$310 CAD per night

Guest favourite

Home in Pinellas Park

4.9 out of 5 average rating, 286 reviews

Lovely Home in Quiet Neighborhood!

This is a lovely home in quiet neighborhood. Beautiful wood laminate flooring, modern feel with wifi, 55" smart tv, Sleep Number queen bed and tv in master bedroom. Quick access to Tampa and St. Pete/Clearwater airports, beaches, nightlife and culture in St. Petersburg and Tampa plus shops, restaurants and malls. Getting around Tampa bay is a cinch from here!

Oct. 3 – 10

$171 CAD per night