Family-friendly holiday rentals in St. Petersburg

Flat in Historic Old Northeast

A bright bedroom features a seaside theme with a quilt displaying starfish and seashells. A rattan headboard frames the spacious bed, complemented by two nightstands with lamps. A ceiling fan adds to the comfort, while light beige walls enhance the airy ambiance.

Apartment in St. Petersburg

Upstairs apt. Great location less than 10 min to busy downtown St. Petersburg, Spa Beach and the St. Petersburg Pier. Walk to major restaurants, Starbucks, & Sunken Gardens. Less than 30 min. to the white sand island beaches & Tampa Airport. Large patio with gas grill. Separate kitchen. Encl. sitting porch. Queen bed, washer and dryer on premises. Beach chairs and towels. Lots of linens & kitchen supplies for long or short-term stay. Clean and comfortable. Owner on premises. No Smoking No pets.

4.98 out of 5 average rating, 281 reviews

4.86 out of 5 average rating, 181 reviews

A spacious living area features a mix of comfortable seating, including a dark leather sectional and various armchairs. A decorative area rug adds warmth over the hardwood floor. Natural light streams in through large windows, and a decorative fireplace stands as a central element.

Home in Historic Kenwood

Casa Kenwood

This delightful Spanish-style house is located in Historic Kenwood, a desirable neighborhood close to downtown St. Pete and the trendy Grand Central district. It's a spacious two bedroom , one bath house with an office attached to the master bedroom. Tastefully decorated with vintage magazine posters and comfortable furniture, all the amenities you need are here: laundry, bikes, patio, grill and plentiful street parking. The fully-stocked kitchen has a gas range and dishwasher. Come visit!

Bungalow in Historic Kenwood

3 BR Garden Bungalow in Historic Kenwood

Fully furnished 3-bed house in charming Historic Kenwood, 15 minutes from white sand beaches and less than 10 minutes from downtown St. Petersburg. Highly walkable location to parks, restaurants, coffee shops, breweries, beach trolley, bike share, and more in the Edge and Grand Central districts. Enjoy mornings in the sunny breakfast nook, work remotely from the dedicated workspace in the serene Florida room, and enjoy a relaxing evening under string lights on the private backyard patio.

4.98 out of 5 average rating, 138 reviews

A spacious living and dining area showcases a large wooden dining table with four chairs. Comfortable seating consists of a brown couch and a decorative area rug. A fireplace adds charm, with natural light filtering through multiple windows.

4.94 out of 5 average rating, 277 reviews

C'est La Vie [RENOVATION COMPLETED JUNE 2020]

[Remodel completed June 2020] Stay in the beautiful Woodlawn Neighborhood of St. Petersburg in this gorgeous bungalow home. This fun and completely renovated two bedroom house can accommodate up to six guests comfortable and has plenty of open space to plan your excursions or relax and rejuvenate. You're only 6 minutes to downtown, 2 minutes to interstate, 11 miles to the main gulf beaches, 90 minutes to Disney World , 25 minutes to Busch Gardens, & 20 minutes to Tampa Int'l Airport.

4.93 out of 5 average rating, 122 reviews

Home in Clearwater

Clearwater-Pickleball/SltPool/Golf/Theatre/Arcade

Welcome to Clearwater Tranquility- Our unique space offers endless amenities and fun! With over 5000sq ft there's room for the whole family to enjoy. Most rooms have a view of the yard &pool! Inside includes a movie theatre, 3 dining spaces, 2 living rooms, 2 primary bedrooms, game room, yoga studio,arcade games, home gym/sauna and a wet bar to make your favorite cocktails or juices. Outside presents an Olympic sized swimming pool, pickle ball, mini golf, outside dining, fire pit &more

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.

4.91 out of 5 average rating, 191 reviews

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.

A private heated pool is surrounded by wooden decking, offering lounge chairs for relaxation. An oversized umbrella provides shade, while tropical plants enhance the outdoor space. The rear of the house is visible, along with a patio door leading into the home.

4.98 out of 5 average rating, 121 reviews

ST Urban Oasis heated pool

Located in unincorporated St. Pete, you can keep it simple at this peaceful and centrally-located oasis. Want to be near the city and beaches while having your own private backyard sanctuary? This is your place to enjoy it all. This home features two bedrooms, one bathroom, and a private heated pool. The backyard has been filled with beautiful large palms, bamboo, and other zen features to allow you and your family to enjoy a relaxing and easily accessible stay in beautiful St. Pete.

4.96 out of 5 average rating, 142 reviews

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!

A welcoming pathway made of slate leads to the intricately designed entrance of the home. Lush green grass and tropical plants frame the walkway, while ornamental lampposts stand beside the path. Trees provide shade, contributing to the serene atmosphere of the property.

4.96 out of 5 average rating, 125 reviews

Kenwood Oasis

January 2027 just became available!!!. Spanish Mediterranean style with rustic charm and modern amenities compliment this homes beautiful exposed brick and stained glass doors. The outdoor living space is amazing with a screened in 30’x30’ breezeway for perfect FL living. Lush tropical landscaping, a great yard and tons of parking on a completely fenced in 1/2 acre lot and all the privacy guests could ask for. Located just 5 minute drive to Central Ave. Downtown St. Pete.

4.97 out of 5 average rating, 172 reviews

Flat in St. Petersburg

Coastal Retreat Near Madeira Beach With Game Room

This 2-bedroom unit with a bonus Game Room and Sunroom is the perfect getaway for up to 6 people looking to enjoy the beautiful beaches of this area. Located in a quiet neighborhood on a private cul-de-sac, it is the perfect place to rest and recharge between trips to the most beautiful beaches in the world. This location is just a quick 5-minute drive (2 miles) to the Madeira Beach access and a 10-minute drive (3.7 miles) to the famous John's Pass Village and Boardwalk.

Flat in Historic Old Northeast

Sun Soaked Designer Condo w/ Patio

🌴 Walk to downtown St. Pete (1 mile) + waterfront in minutes Stay in a bright, stylish 2BR condo just 5 minutes from downtown St. Pete. Walk to Beach Drive, top restaurants, bars, art galleries, and waterfront parks Unwind on your private patio after a day out, or relax inside a fully updated space with modern finishes, cozy design, fast WiFi, and smart TVs. Free parking (rare for this area) + pet-friendly make this an easy, comfortable stay.

4.89 out of 5 average rating, 102 reviews

Guest house in Historic Kenwood

Charming apartment in Historic Kenwood

Cute, spacious apartment located in Historic Kenwood, which was named 2020 “Neighborhood of the year” by NUSA. Our apartment is above our large garage. Lots of charm and just enough space to spread out a little for some privacy. Located close to downtown, walking distance to lots of restaurants, breweries and bars but still a short drive to our beautiful beaches. You access the apartment through our side gate and up an exterior stairway.

4.97 out of 5 average rating, 383 reviews

Popular amenities for St. Petersburg family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Bungalow in St. Petersburg

The exterior of the cottage features bright blue siding and a welcoming yellow front door, framed by lush green grass and palm trees. A charming white picket fence encloses the yard, providing a serene outdoor space. Light filters down from a clear blue sky.

Crescent lake Mins to Downtown Hot Tub

4.96 out of 5 average rating, 102 reviews

Apartment in St. Pete Beach

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.

Gulf Strand Beach Resort

4.86 out of 5 average rating, 281 reviews

4.86 out of 5 average rating, 147 reviews

Private Guesthouse in St. Pete w/ Pool & Jacuzzi

Apartment in Isla del Sol

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.

Sunsets on the Island

4.96 out of 5 average rating, 115 reviews

4.99 out of 5 average rating, 126 reviews

Aerial view of a tropical backyard featuring a shaped pool with floating loungers. Surrounding the pool, lounge chairs with umbrellas are positioned next to a wooden deck. The yard is covered in turf, and there are colorful pool toys and deck furniture visible.

Home in Largo

Best Celebration - Heated Pool - Hot Tub - Arcade

4.71 out of 5 average rating, 116 reviews

Waterfront Oasis, Hot Tub, Sauna

4.97 out of 5 average rating, 261 reviews

Centrally Located Cozy 1-bed Private Cottage!

A modern living room features a stone accent wall with a large flat-screen TV mounted above a contemporary electric fireplace. Comfortably arranged seating includes a gray sofa and an accent chair. Natural light filters through the window, illuminating the space.

4.86 out of 5 average rating, 225 reviews

Tropical escape house with hot tub

Family- and pet-friendly home rentals

4.87 out of 5 average rating, 118 reviews

An aerial view of a vibrant outdoor space features a heated pool with a unique shape, surrounded by sun loungers and a covered dining area. A basketball court and mini golf area are visible, alongside colorful lounge chairs arranged around a fire pit.

Home in Seminole

Heated Pool, Pickleball, Bowling, Mini Golf, Bball

A private backyard features a custom-made pool surrounded by a wooden deck. Lounge chairs and a sun umbrella are positioned nearby, while palm trees and lush greenery offer a tropical ambiance. A white privacy fence encloses the space, enhancing the serenity.

5.0 out of 5 average rating, 229 reviews

Beautiful Tampa Bay Pool Home Near Gulf Beaches

A charming yellow cottage is framed by lush palm trees and tropical plants, featuring a welcoming front door at the end of a paved walkway. Sunlight filters through the greenery, creating a bright and inviting atmosphere near the entrance.

4.91 out of 5 average rating, 184 reviews

St Pete Casita Studio with Salt Water Pool & Yard

Bungalow in Indian Shores

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

4.97 out of 5 average rating, 206 reviews

Apartment in Sunset Beach

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.

2 Story Penthouse | Pool | Balcony | Gulf View 602

4.89 out of 5 average rating, 160 reviews

Home in Downtown St. Petersburg

A spacious living room features a black reclining sectional sofa and a round glass coffee table atop a patterned area rug. A wall-mounted TV is visible, alongside a painting and an acoustic guitar displayed in the corner. Natural light flows through multiple windows.

Contemporary Family Cottage

4.95 out of 5 average rating, 129 reviews

Home in Downtown St. Petersburg

A historic two-story house is framed by lush greenery and mature trees, with a welcoming brick staircase leading to the front porch. The exterior features a combination of light wood and brick, with large windows allowing for natural light.

Downtown Historic District Estate (Home + Cottage)

4.99 out of 5 average rating, 107 reviews

Apartment in Treasure Island

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.

Waterside Studio in the heart of TI, walk to beach

4.91 out of 5 average rating, 222 reviews

Family-friendly home rentals with a pool

Apartment in Treasure Island

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.

Spectacular beach to bay views from this resort.

4.99 out of 5 average rating, 231 reviews

A spacious outdoor area features a heated pool and a separate hot tub, both illuminated in soft blue light. A covered terrace provides shade, with comfortable seating options visible in the background. The landscape is accentuated by subtle stone textures and professional lighting.

4.93 out of 5 average rating, 107 reviews

Villa Kailāsa-Pool, 6 min drive to the Beach!

Superhost

4.87 out of 5 average rating, 134 reviews

Inground Pool w/ Game Room - Fully Renovated House

4.98 out of 5 average rating, 237 reviews

Home in Clearwater

Specious home W/ Heated Pool ! ! ! Great Location.

Apartment in Sunset Beach

Glorious Sunsets - Beachfront 2BR Condo

5.0 out of 5 average rating, 102 reviews

Apartment in Sunset Beach

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.

Beachfront Treasure Island | Pool | Penthouse

4.91 out of 5 average rating, 275 reviews

4.97 out of 5 average rating, 180 reviews

The inviting pool area features a heated pool with clear turquoise water, surrounded by lounge chairs and a spacious pool deck. A dining area and outdoor kitchen can be seen, with a large TV mounted on the wall, creating a welcoming space for relaxation and entertainment.

Home in Largo

Palm Oasis | Heated Pool | Near Beaches