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Family-friendly holiday rentals in South Pasadena

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in South Pasadena

  • Total holiday rentals

    Explore 190 holiday rentals in South Pasadena

  • Nightly prices starting at

    South Pasadena holiday rentals start at $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 4,820 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    130 properties feature pools

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wifi availability

    190 of South Pasadena holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across South Pasadena rentals

  • 4.8 Average rating

    South Pasadena stays are highly rated by guests – averaging 4.8 out of 5!

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
A stylish living area is presented, featuring two comfortable teal chairs and a wooden coffee table. Decorative pillows are arranged on the seating. A large piece of wall art adds color to the space, and warm lighting highlights the decor. A doorway leads to another room.
Flat in South Pasadena

Stylish & Eclectic Modern 2/1 Apt - WeAreJoyful

Our apartment 'Joyful' is a combination of pleasing colors and a delicate attention to detail in every corner that will let you experience the magic of an eclectic space in the heart of St Petersburg. With the beautiful sand beaches under 5 minutes away driving, you can feel the breeze as soon as you step outside. You also can try St Petersburg’s diverse restaurant scene and visit the museums displaying art permanent collections and traveling exhibits. This apartment is on the second floor 2/1.

4.93 out of 5 average rating, 221 reviews
Superhost
Home in St. Petersburg

Inground Pool w/ Game Room - Fully Renovated House

Beautifully remodeled 3 bedroom 2 bath farmhouse with INGROUND POOL in the heart of Gulfport. Looking for the BEACH?(St Pete Beach, Treasure Island etc) We are 6 mins away! If you are looking for amazing restaurants and bars in the middle of St Petes we are only 10 minutes to DOWNTOWN! If your are here for some baseball we are 15 minutes away from Tropicana field and St Pete Pier! If you are looking to explore In clearwater or Downtown Tampa we are only 25 minutes away including TAMPA Airport!

4.87 out of 5 average rating, 134 reviews
Guest favourite
Home in St. Petersburg

Waterfront Oasis, Hot Tub, Sauna

Welcome to our beautiful waterfront home nestled between St Pete Beach & Gulfport, FL, where you'll experience the joys of the quintessential Florida lifestyle! Relax in the large outdoor living space, fish off the dock, boat on the pristine waters of the Gulf of Mexico and take in the ocean breeze. ☑ 2 mi to St. Pete Beach, 2.5 mi to Gulfport & 5 mi to John's Pass ☑ On the Intracoastal Waterway w/boat access out to the Gulf of Mexico ☑ Hot tub, Sauna, Outdoor kitchen, bar, dock, boat lift

4.71 out of 5 average rating, 116 reviews
Top guest favourite
A well-lit kitchen is equipped with wooden cabinets and a spacious countertop. Three white bar stools are arranged at the island, which is adorned with a vase of fresh flowers and a platter. Large windows allow natural light to brighten the room.
Home in St. Pete Beach

Gulfside Resort: 3 bed, 2 bath /pool access

Welcome to GulfSide Resort, a family-owned gem just a block and a half from St. Pete Beach! Our comfortable vacation suites face a beautiful pool and are a short stroll away from beach bars, restaurants, and shopping. Enjoy our pool, shuffleboard, and putting green, plus complimentary beach chairs and toys. Perfect for group gatherings, we can host up to 35 guests comfortably. Experience relaxation and fun with your loved ones at GulfSide Resort—your ideal vacation spot! The house sleeps 6.

4.99 out of 5 average rating, 110 reviews
Guest favourite
The kitchen features modern white cabinetry and a large island with a light countertop. A dining table for multiple guests is set nearby, adorned with tableware. Natural light fills the space through the window blinds, highlighting the open layout connecting to the living area.
Home in South Pasadena

** Home Away From Home **

Why book 3 or 4 hotel rooms when you can book this beautiful and completely remodeled 4-bedroom, 2.5 bath 1788 sq. ft. home, centrally located in desirable South Pasadena Florida. Professionally decorated in a contemporary beach décor, stunning, spacious and very private! There is no lack of amazing things to do around the home, but if you want to be close to the St. Pete Beach, you are only 2.5 miles away and 6.5 miles to downtown St. Petersburg where night life entertainment abounds.

4.84 out of 5 average rating, 242 reviews
Top guest favourite
A welcoming living area features light-colored seating with orange and gray accents. A wooden coffee table is centered on a decorative rug. Natural light filters through the vertical blinds, illuminating the room's neutral tones, complemented by a potted plant and wall-mounted lighting.
Home in St. Petersburg

Hibernate in our Bear Creek Home

This 3 bedroom 2 bath home is located in beautiful Bear Creek. Don't worry, no bears! Great place to relax and enjoy the pool, in a quiet, safe neighborhood. Next to Pinellas Trail, a 40 mile paved trail. Great for walking, running and biking. You can bike downtown 6 mi or 4.6 miles to beaches. We have bikes and for those more adventuresome we have kayaks you may use. House features stable, high speed internet. Close to great restaurants, drugstores, supermarkets and coffee shops.

4.91 out of 5 average rating, 191 reviews
Top guest favourite
A quaint blue bungalow is framed by lush greenery, with tropical plants flanking a brick pathway leading to the entrance. Sunlight filters through the trees, casting gentle shadows on the charming exterior.
Guest house in St. Petersburg

Blue Bungalow of St. Pete Beach - Great Location !

Whether you're seeking a quiet respite or fun filled days and exciting nights, you'll feel right at home in your new, home away from home, The Blue Bungalow of St. Pete Beach! Located only 2mi from St.Pete Beach in a historic district of South Pasadena. Are you a bicyclist? We're conveniently located next to the Pinellas Trail which takes you directly into downtown via 20 minute ride! We're perfectly situated between the beach and downtown. Washing machine/ clothes line avail.

4.99 out of 5 average rating, 100 reviews
Guest favourite
An inviting view into the living area is framed by a decorative arch. A vibrant green plant adds a touch of nature, while a cozy brown couch and accent chairs are arranged around a circular coffee table. Colorful artwork decorates the walls.
Guest house in Gulfport

Gulf Guesthouse - king bed, 3 blocks to downtown.

Be our guest! Welcome to our family compound where you will enjoy the treetop views from our second story carriage house guest apartment. You'll be surrounded by the tropical serenity of lush palms and plants, both inside and out, while being just around the corner from the excitement of downtown Gulfport. Our updated one bedroom apartment is fully furnished and stocked with all of the things you'll need for an extra comfortable, enjoyable stay. We look forward to hosting you!

4.96 out of 5 average rating, 142 reviews
Guest favourite
An outdoor patio area features a tiled surface surrounded by greenery and a wooden fence. A round table with chairs is positioned next to a gas grill, while a large tree provides shade. Potted plants add a touch of nature to the space.
Tiny home in Gulfport

Avocado Casita 10 mins to Beaches

Newly built studio -- small space, smart design. An intimate studio space meant for a minimalist lifestyle complete with full amenities. Compact yet comfortable, it’s the perfect place for a restful sleep in between your daytime adventures. Pack light, live easy. 3 blocks from Stetson Law School 3-4 blocks from the Pinellas Trail ~1.5 miles to Gulfport’s Beach Blvd 3 miles to Award Winning St. Pete Beach 4 miles to Award Winning Treasure Island ~4.5 miles to Downtown St Pete

4.93 out of 5 average rating, 138 reviews
Superhost
A lively dining area features a glass-top table surrounded by rattan chairs, adorned with floral upholstery. A vibrant flamingo mural covers the wall, complemented by tropical greenery. A television is mounted nearby, and the open kitchen is visible in the background, characterized by bright white cabinetry.
Flat in St. Pete Beach

FLASH SALE! Sleeps4|Lets Flamingle! <1mi to beach!

🚨Special Offer: We’re running a limited-time Flash Sale for select dates! Message us to unlock exclusive savings for your short term or mid term stay‼️ 🦩Let’s Flamingle in this bold, pink 1BR retreat near Upham Beach! Located in a gated complex, this tropical paradise features cozy flamingo decor, FAST Wi-Fi, smart TV, full kitchen, and lush vacation vibes. One of 4 fun themed units perfect for beachside escapes. Book now and let the good vibes roll! 🌴☀️🦩

4.77 out of 5 average rating, 318 reviews
Top guest favourite
A private garden space is presented, featuring a small wooden table with two folding chairs positioned on a red pathway. Lush greenery, including a palm tree and flowering plants, surrounds the area, creating a serene outdoor setting.
Guest suite in St. Petersburg

Charming Side Garden Suite (no cleaning fee)

This private guest suite is centrally located between the beaches of Treasure Island and the nightlife, shopping, and dining of the Grand Central and Pier districts, along the Sun Runner public transportation route. The suite includes one bedroom, bathroom, and kitchenette, separated from the main house, with a private entrance through the side garden. Come enjoy your morning coffee in the garden, and all that St. Petersburg has to offer.

4.95 out of 5 average rating, 193 reviews
Superhost
Two light blue beach cruiser bicycles with tan seats are positioned on a concrete surface. A window and a chair in a welcoming yellow tone are visible in the background, framed by greenery. The entrance to the rental is accessible and inviting.
Cottage in Gulfport

Gulfport Getaway-Close to Everything!

Take a step off the beaten path with a stay at this tropical 2-bedroom, 1-bath Gulfport Beach vacation rental! The 'Sirens Cove' is ideally situated between St Pete Beach, downtown St. Petersburg, and the quirky, vibrant Gulfport Arts District. Take a ride on our beach cruisers and enjoy the Gulfport vibe! You'll have plenty of opportunities to recharge your soul, relax, and soak up the beautiful Florida sun! 30+ Day Rentals Available!

4.85 out of 5 average rating, 189 reviews

Popular amenities for South Pasadena family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favourite
The outdoor pool area, surrounded by palm trees, features a clean, inviting pool with lounge chairs positioned around it. In the background, the beach can be seen, with soft white sand meeting the clear ocean waters.
Apartment in St. Pete Beach

Gulf Strand Beach Resort

4.86 out of 5 average rating, 281 reviews
Superhost
The exterior of the Ocean Club building is showcased, featuring a modern design with a white façade and large balconies. Palm trees line the front, enhancing the tropical setting. A welcoming entrance is visible, set against a backdrop of a bright sky with soft clouds.
Apartment in Treasure Island

Beachfront Condo in Exclusive Resort

4.86 out of 5 average rating, 674 reviews
Guest favourite
A view from the balcony showcases a sandy beach lined with palm trees and manicured green lawns. The calm blue water reflects clear skies, while a distant shoreline is visible. A bench can be seen on the grass, inviting relaxation.
Apartment in Isla del Sol

Sunsets on the Island

4.96 out of 5 average rating, 115 reviews
Guest favourite
A comfortable living area features light-colored furnishings with striped patterns, complemented by a large artwork on the wall. A round coffee table sits in the center, while a ceiling fan provides airflow. Floor-to-ceiling glass doors offer a view of the Gulf and access to a balcony.
Apartment in St. Pete Beach

1145 Sqft! - 2 Bedroom 2 Bath (GULF FACING!) Condo

4.92 out of 5 average rating, 150 reviews
Top guest favourite
The kitchen features navy blue cabinets, providing a stylish contrast to the stainless steel appliances. A spacious countertop holds essential kitchen gadgets, and a modern backsplash adds texture. Adequate storage is available with cabinets and drawers, contributing to a well-organized cooking space.
Apartment in Madeira Beach

Rincón Divino MB 2 Balconies, Ocean & Marina Views

4.99 out of 5 average rating, 243 reviews
Top guest favourite
A private balcony showcases a stunning sunset view, framed by palm trees. The spacious area features a green chair and overlooks the resort's pool and surrounding buildings, creating a serene outdoor space for relaxation.
Apartment in Treasure Island

Sunset Nest: Two Bedroom Condo with Sunset Views

4.98 out of 5 average rating, 165 reviews
Top guest favourite
A modern living area features a circular dining table set for four, complemented by plush armchairs and a sofa. Large windows allow natural light to fill the room, adorned with light-colored curtains. A television is mounted on one wall, alongside decorative elements including a palm plant.
Apartment in Madeira Beach

Steps to Johns Pass+Beach | Water View | Htd. Pool

4.99 out of 5 average rating, 101 reviews
Top guest favourite
The aerial view displays a modern four-story condo building with a mix of orange and white façades. Balconies extend from each level, and a marina with boats is visible at the base, along with beach access in the background.
Apartment in Madeira Beach

Steps to beach with Marina Sunsets – 3 -Bed condo

4.84 out of 5 average rating, 131 reviews

Family- and pet-friendly home rentals

Top guest favourite
The studio features a spacious layout with a comfortable futon couch adorned with decorative cushions. A fully equipped kitchen is visible in the background, complemented by a dining table with white chairs. Large windows provide natural light, enhancing the airy feel of the blue walls.
Guest house in St. Petersburg

Private Guesthouse Near Beach & Downtown

4.94 out of 5 average rating, 116 reviews
Guest favourite
A private yard is showcased with a spacious patio featuring a picnic table and four chairs arranged around a firepit. Lush green grass surrounds a stone pathway, and a large umbrella offers shade. The home’s blue exterior is visible in the background.
Tiny home in Gulfport

Pelican's Nest - Tiny House

4.91 out of 5 average rating, 274 reviews
Top guest favourite
A spacious backyard is featured, bordered by a wooden fence for privacy and lined with tropical plants and trees. A concrete patio area is included, which features a grill covered for protection. The lawn is open and well-maintained, providing a serene outdoor space.
Cottage in Gulfport

The Pelicans Roost / Gulfport

4.97 out of 5 average rating, 179 reviews
Guest favourite
A bright bedroom features a spacious bed adorned with light blue and white striped linens. Natural light floods the room through sliding glass doors that lead to a private balcony with an ocean view. Two decorative lamps and a textured area rug enhance the serene atmosphere.
Apartment in Sunset Beach

2 Story Penthouse | Pool | Balcony | Gulf View 602

4.89 out of 5 average rating, 160 reviews
Guest favourite
Home in Pinellas Park

Insta Worthy Retreat -HTD Pool- Arcade Room- Golf

4.98 out of 5 average rating, 192 reviews
Top guest favourite
An outdoor seating area is shown with a glass-top table surrounded by four blue chairs. Two charcoal grills are positioned nearby under palm trees, with a view of the water in the background. The screened cabana features a thatched roof, providing a relaxing atmosphere.
Apartment in Treasure Island

Waterside Studio in the heart of TI, walk to beach

4.91 out of 5 average rating, 222 reviews
Top guest favourite
The inviting guest suite showcases an open living area with a wooden floor and natural light. A round dining table and chairs sit next to a cozy armchair. A kitchenette is visible in the background, with a small bar and various amenities. Walls are adorned with artwork.
Guest suite in St. Petersburg

Central Oak Pet Friendly Retreat

4.94 out of 5 average rating, 216 reviews
Guest favourite
A spacious bedroom features a king-size bed with a blue quilt and accent pillows, complemented by bedside tables with lamps. A small dining table sits in one corner, with artwork displayed on the wall and natural light coming from a nearby door.
Flat in Gulfport

The Peaceful Turtle Retreat

4.88 out of 5 average rating, 144 reviews

Family-friendly home rentals with a pool

Top guest favourite
Apartment in St. Pete Beach

St Pete Retreat WalktoBEACH*HeatedPOOL*PrivateYARD

4.97 out of 5 average rating, 146 reviews
Top guest favourite
An aerial view captures a multi-story condominium overlooking a beach. Lush palm trees surround a heated pool area, with docks lining the waterfront. The expansive coastline is visible in the background, highlighting the scenic proximity of beach and bay.
Apartment in Treasure Island

Spectacular beach to bay views from this resort.

4.99 out of 5 average rating, 231 reviews
Top guest favourite
Apartment in Sunset Beach

Glorious Sunsets - Beachfront 2BR Condo

5.0 out of 5 average rating, 102 reviews
Guest favourite
A bright kitchen showcases modern appliances, including a stove, microwave, and refrigerator, complemented by a granite countertop. A small island adds functionality, while a dining table with two chairs offers seating. Cheerful yellow walls create a lively atmosphere, contrasting with the subtle blue accents.
Apartment in Sunset Beach

Sunset Beach Cozy Private Condo

4.84 out of 5 average rating, 118 reviews
Guest favourite
A living area features a comfortable blue pullout couch, two wicker chairs, and a round dining table. A modern flat-screen TV is mounted on the wall, while light streams through a window adorned with sheer curtains, enhancing the spacious feel of the room.
Flat in Treasure Island

Molloy Poolside Suite - 2 Full

4.79 out of 5 average rating, 180 reviews
Top guest favourite
A private balcony view showcases a stunning horizon over the ocean, with clear blue skies reflecting on shimmering water. White railings frame the space, while two adirondack chairs invite relaxation. Gentle waves are visible, enhancing the tranquil coastal ambiance.
Apartment in Sunset Beach

Beachfront Treasure Island | Pool | Penthouse

4.91 out of 5 average rating, 275 reviews
Top guest favourite
A heated stock tank pool is surrounded by a lush tropical landscape featuring a variety of green plants. An oversized umbrella provides shade, and a colorful bungalow is visible in the background, creating a serene outdoor retreat.
Tiny home in Gulfport

Shipwreck Bungalow

4.95 out of 5 average rating, 168 reviews
Guest favourite
A sandy pathway, framed by lush green grass, leads to the beach where the ocean meets the sky. Soft clouds drift above, and the vibrant blue water sparkles in the sunlight, creating an inviting atmosphere for beachgoers.
Apartment in St. Pete Beach

Easy access to St. Petersburg beach, a minute walk

4.88 out of 5 average rating, 392 reviews

When is the best time to visit South Pasadena?

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Avg. price$251 SGD$356 SGD$384 SGD$321 SGD$259 SGD$275 SGD$264 SGD$230 SGD$210 SGD$213 SGD$223 SGD$250 SGD
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