Family-friendly vacation rentals in South Pasadena

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Top-rated family-friendly rentals in South Pasadena

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Superhost

Condo in St. Pete Beach

4.87 out of 5 average rating, 128 reviews

2BD/2BR Modern Condo Steps to Pool & Sunset Beach

We're excited to be able to share our home again after the completion of our renovations after the Hurricane! Modern and charming ground-floor 2BR/2BA condo with a large, private patio —steps from the pool! Walk to waterfront cafes, bars, and Sunset Beach (10 min) or a quick 5 min drive/Uber to top dining and nightlife. Note that photos currently are from pre-renovation to begin accepting reservations (New photos to come, even nicer now!) Military discounts w/ valid ID—message us to inquire.

Guest favorite

Condo in St. Pete Beach

4.9 out of 5 average rating, 105 reviews

Comfortable 2BR condo, walk to all sand beach

No damage from hurricanes. Come, enjoy the beautiful West Coast of Florida. My condo is walking distance to a beautiful all sand beach, less than 10 minutes. Heated swimming pool and designated free parking for one car on the property. Many restaurants and bars within walking distance. 2 free lighted tennis courts across the street. Unlimited high speed Wifi. My building does not allow pets of any kind. I can't rent to groups of people under the age of 25. Just 1.5 hours to Disney/Universal

Guest favorite

Loft in Central Oak Park

4.97 out of 5 average rating, 170 reviews

Adorable Suite: 15min to beach, 10min downtown

Entire apartment with a complete kitchen, full bath, A/C, WiFi (300mbps), you have a private entrance and all the comforts of home. Comfortable queen size bed. You are located 15 minutes from St Pete Beach and 10 minutes to downtown St Pete. You have off street parking. Very safe and quiet location. You have an easy check in via lock box after 3pm, and check out is simple, leave the key then lock the door behind you. We have plenty of secret spots to recommend. Very experienced Super Hosts.

Guest favorite

Home in Gulfport

4.78 out of 5 average rating, 293 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!

Superhost

Home in St. Petersburg

4.85 out of 5 average rating, 342 reviews

Pool home with beach a few minutes away

This recently updated European style home comes with 3 bedrooms 2 bathrooms, screened-in pool and pool deck. Located in an upscale neighborhood, this beautiful home offers patio areas and large living room for relaxing. Equipped with a full size washer, dryer and full kitchen for a home away from home experience. 5min drive to beaches, parks, lakes, trails, shopping & restaurants. 10min to downtown, St. Pete. Boat Trailer parking available. Large driveway can accommodate up to 3 vehicles.

Superhost

Bungalow in Gulfport

4.9 out of 5 average rating, 133 reviews

Shady Paradise Close to All!

Totally remodeled 1960's bungalow with retro old Florida furnishings, two bedrooms with comfy new mattresses on 3 beds, and a foldout bed to sleep extra guests. Comes equipped with everything you need for a great vacation! Full kitchen, dining area, and private yard with mature trees. Free laundry facilities on site. Perfect for families- and pets are welcome too! Parrot Park is a shady and quiet vacation retreat, located a short walk from restaurants, nightlife and Gulfport beach!

Top guest favorite

Condo in St. Petersburg

4.98 out of 5 average rating, 273 reviews

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

My place is across the street from Target and many restaurants within walking distance. There is a PSTA Bus stop right at the entrance to the condo property.Uner and Lyft are availablThe Pinellas Trail is across the street. The VA Hospital and Bay Pines Park are biking or walking distance. The closest beach is Madeira Beach 2 miles from the condo. All Utilities, Cable/Internet are included. Parking is free and close to the elevators. Plenty of parking spaces are available also.

Top guest favorite

Cottage in Gulfport

4.99 out of 5 average rating, 272 reviews

Gulfport Art District - One Block From Beach!

Welcome to Uncle Finley's! Situated in the heart of Gulfport's Art and Waterfront District, This cottage listing is for unit A of the duplex. 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.

Top guest favorite

Guesthouse in Gulfport

4.94 out of 5 average rating, 299 reviews

Lovely Guesthouse

We are ideally situated close to Tampa, Sarasota,Clearwater and St. Petersburg. Our neighborhood is wonderful, eclectic, alive. We have incredible restaurants a walk away. Our beach is walking distance. If you prefer you never have to leave Gulfport from the day you arrive. Everything you want is right here. There is free access for charging your electric vehicle on the beach in town which is walking distance from our guesthouse

Superhost

Home in Gulfport

4.84 out of 5 average rating, 92 reviews

Fresh & Friendly in Marina District Private Oasis

Bright, clean, and thoughtfully appointed, Harbor Mist brings new meaning to home-away-from-home. This Gulfport gem is tucked in one of the town’s friendliest neighborhoods - home to smiling locals who gather and relax at the marina just down the street. Bring your pup along and you’re both guaranteed to make new friends. Or re-connect with your loved ones in the comfort of laid-back living spaces.

Superhost

Condo in St. Petersburg

4.86 out of 5 average rating, 473 reviews

Waterfront condo on top floor @ Boca Ciega Resort

Great view of water. 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 the intercoastal or stay indoors and enjoy puzzles and games.

Guest favorite

Condo in St. Pete Beach

4.89 out of 5 average rating, 132 reviews

Elegant & Relaxing Beachside Paradise - Pool

Hurricane Update!! This condo is currently undergoing a full renovation due to some storm damage, with a projected reopening date of July 15th. It will be refreshed and better than ever—stay tuned! The grounds have been completed, with some first-floor renovations still ongoing in the community, and the pool is open and heated!!