Family-friendly vacation rentals in South Pasadena

Guesthouse in Saint Petersburg

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

Guest suite in Gulfport

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 9 – 16

Home in Gulfport

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!

Oct 2 – 9

Condo in Tierra Verde

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.

Dec 14 – 21

Home in Gulfport

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

Sep 7 – 14

Apartment in Gulfport

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 16 – 23

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**

May 14 – 21

Home in Pinellas Park

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 13 – 20

Home in Saint Petersburg

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.