Family-friendly vacation rentals in South Pasadena

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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 favorite

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.

Apr 25 – May 2

R3,729 ZAR per night

Guest favorite

Guesthouse in Saint Petersburg

4.84 out of 5 average rating, 718 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.

Jan 17 – 24

R1,434 ZAR per night

Guest favorite

Guest suite in Gulfport

4.92 out of 5 average rating, 452 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 19 – 26

R2,287 ZAR 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!

Sep 6 – 13

R1,507 ZAR per night

Guest favorite

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

R2,358 ZAR per night

Guest favorite

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 11 – 18

R2,432 ZAR 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.

Nov 28 – Dec 5

R2,415 ZAR per night

Guest favorite

Home in Gulfport

4.9 out of 5 average rating, 101 reviews

Romantic Tropical Retreat in Waterfront District

Welcome to Flamingo Cottage, located in the heart of Gulfport's Art and Beach district. This charming cottage is perfect for a romantic getaway or a leisurely vacation. This a 1 bedroom, 1 bath retreat is just one block from Gulfport Beach. Walk to everything in Gulfport – shops, restaurants, bars, Gulfport Beach and the Tuesday market and other festivities. Access the shared laundry through a door from the kitchen, small fenced courtyard out the front. King bed

Nov 15 – 22

R2,534 ZAR per night

Guest favorite

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.

Apr 22 – 29

R2,488 ZAR per night

Guest favorite

Condo in Treasure Island

4.9 out of 5 average rating, 181 reviews

Sunset Beach Beauty 1 Bedroom Condo #3

#This is the place to relax and unwind. Gorgeous Sunset Beach on Treasure Island has miles of white sugar sand beaches and sparkling gulf water. One of the best kept secrets on the Gulf Coast. The condo is one bedroom, one bath on the ground floor. Newly remodeled. Just steps away from the beach. Laundry facilities are on site as well as barbecues and an outdoor patio area. You are walking distance to the world famous Caddys beach restaurant.

Jul 19 – 26

R2,960 ZAR per night

Guest favorite

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 16 – 23

R3,282 ZAR per night

Guest favorite

Home in Saint Petersburg

4.97 out of 5 average rating, 175 reviews

Fabulously Family Friendly

Fabulous Family friendly home with a backyard paradise located 7 minutes from culinary delights, craft beer, local shopping, world class sporting events, Dali Museum, Art galleries, Saturday Morning Market, and Brocante Market in downtown St. Pete. 12 minutes to the magical sand and waves at St. Pete Beach and Pass-a-grille Beach, 20 minutes to Ft. DeSoto.

Jul 26 – 31

R3,873 ZAR per night