Family-friendly vacation rentals in Oldsmar

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Oldsmar

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
A cozy master bedroom is depicted with soft blue walls and ambient lighting from two bedside lamps. A spacious bed, adorned with a neutral-tone blanket, is centered against the wall. An air conditioning unit is mounted above, ensuring comfort during warmer days.
Guest suite in Tampa
4.91 out of 5 average rating, 381 reviews

The Oak

Private & Cozy Guest Suite with Kitchen, Dinning space, Spacious Master Bedroom with a King Size Bed and Full bathroom , Smart TV and fast Wifi available. Families with little ones we provide per request Pack n Play which allow your little one (up to 24 months old) play safe and sleep. We also can provide a high chair, outlet covers and formula warmer if needed. Free parking (left side of driveway) Our place has private entrance that leads you to a small but peaceful patio to enjoy the breeze.

Superhost
A modern bathroom is shown featuring a sleek vanity with a rectangular sink and black fixtures. A round mirror is illuminated by three overhead lights. Storage is provided by wooden drawers beneath the sink, and towels are neatly arranged on shelves.
Guesthouse in Palm Harbor
4.86 out of 5 average rating, 160 reviews

Home away from home

Private unit has designated parking, pool access, its own water heater, water softener, filtration system, 2 ceiling fans, heater, air purifier & a/c. Featuring a queen bed, dresser, 42” tv & fire stick w/ streaming accounts, wifi, full length mirror, recliner, eating table & chairs. The bathroom has a walk-in shower, large vanity mirror, & all the needed bathroom accessories. Full kitchenette w/ microwave, dual burner, air fryer, tea kettle, coffee maker, & more. Owner lives on property.

Top guest favorite
A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.
Bungalow in Oldsmar
4.99 out of 5 average rating, 141 reviews

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

Guest favorite
A well-maintained entryway is showcased, featuring a covered area with patterned stone flooring. A potted plant and a small table with decorative flowers are positioned beside a chair. The entrance leads to a white front door, framed by light-colored walls and fencing.
Apartment in Tampa
4.87 out of 5 average rating, 165 reviews

Lovely cozy guest studio

Kick back and relax in this calm, stylish space. Our apartment has all you need to spend an amazing time in our beautiful city, 8 minute drive from the tampa international airport, many malls no more than 15 minutes away from each other, as well as supermarkets and pharmacies 3 minutes away from our stay. Fire rescue is 1 minute from our stay. You will be greeted with all the amenities you’d want such as a cozy bed, clean and organized space. Last but not least Enjoy your stay. Thank you

Guest favorite
An outdoor seating area is sheltered by a wooden pergola adorned with string lights. A cozy couch is positioned on a decorative area rug, complemented by a small table. Lush greenery surrounds the space, providing a tranquil environment for relaxation.
Guesthouse in Dunedin
4.84 out of 5 average rating, 126 reviews

Guest House in prime location!

This special place is close to everything, making it easy to plan your visit. Less than 30 minutes to TPA Airport, 13 miles to Clearwater Beach, 2.2 Miles to Honeymoon Island, 1.0 miles to US-19 to easily get to surrounding areas, and 3.5 miles to downtown Dunedin. Guest house located on property with friendly host. There is one parking space provided for guests onsite. Happy to provide recommendations for a local experience during your stay! Beach necessities available upon request.

Top guest favorite
A combined living and sleeping area is shown, featuring a spacious bed with a black and white plaid coverlet. A kitchenette with modern appliances is visible, alongside a small dining space accommodating two stools. A futon, designed for ample seating, is situated to the side.
Guest suite in Tampa
4.96 out of 5 average rating, 251 reviews

Soothing Breeze

This is a private studio suit located at Carrollwood community. Easy access to Supermarket, Veterans Express Way. There is a fridge, microwave, coffee maker. TV with Roku , Netflix and spectrum channels with wireless internet.There is a queen size bed, individual futon, full bathroom, small dinning room. Nearby Places: TPA Airport 12 miles, 15 ‘ Raymond James Stadium 11 miles 18’ Citrus Park Mall 1.9 miles, 6 ‘ Busch Garden 11 miles, 33 ‘ Adventure Island 11 miles, 28’

Guest favorite
Guesthouse in Tampa
4.88 out of 5 average rating, 100 reviews

Y&O Castle

Tu hogar lejos de casa 🏡 Disfruta de un espacio acogedor, moderno y perfectamente ubicado para tus vacaciones en Tampa. A solo minutos de restaurantes (McDonald’s, Olivos, Michael’s Kitchen y Church’s Chicken) supermercados, bancos y todo lo que necesitas. A 15 minutos del Aeropuerto Internacional de Tampa, 20 minutos de Busch Gardens y a 35 minutos de las playas más hermosas como Clearwater y Honeymoon Island. Ideal para relajarte, explorar y sentirte como en casa. 🌴☀️

Guest favorite
A private entrance is visible, featuring a clean white gate that leads into the apartment area. A paved walkway of gray stones is bordered by white gravel and greenery, creating an inviting access point. Nearby structures can be seen, emphasizing the neighborhood's quiet environment.
Apartment in Tampa
4.84 out of 5 average rating, 175 reviews

Private apartment perfectly located in Citrus park

A comfortable, quiet, and private apartment located in the Citrus Park area. A private entrance to a fully furnished apartment; includes a small kitchen, washer and wifi. The veterans expressway is 1.5 miles away, that can get you anywhere in Tampa within 15 minutes! Citrus Park mall 1.7 miles away. Several eateries, shops, and Tampa trail within a 1 mile radius. Tampa internal airport 12 miles away.

Guest favorite
A work area is positioned near a window, featuring a sleek desk and an adjustable white chair. Light gray curtains frame the window, allowing for natural light. A small lamp and decorative item are placed on the desk, contributing to the space's functional design.
Home in Tampa
4.85 out of 5 average rating, 132 reviews

My Little White Space .

My apartment is located an excellent position of access to different places of Tampa bay .Apartment with independent entrance.Near to: Tampa international airport-4miles Mall international plaza-4 miles Downtown Tampa 8.7 miles Raymond James stadium Beaches within 5 miles. NO CHILDREN OR PETS WILL BE ADMITTED.

Top guest favorite
The charming cottage features a bright yellow front door, flanked by potted plants. A welcoming porch is screened with white framing. The well-maintained yard is adorned with manicured grass and a path leading to the entrance, with a white picket fence visible in the background.
Cottage in Oldsmar
4.96 out of 5 average rating, 303 reviews

Louisa's Cottage

This Cottage is located in the heart of Oldsmar. Walking distance to many of Oldsmar’s main attractions, beaches and parks 3 blocks away &Amazing variety of restaurants .This charming cottage was built in 1925 with great craftsmanship, from the wainscoting to crown mouldings .Relax and enjoy a key west Atmosphere.

Guest favorite
A modern bedroom features a spacious bed with patterned bedding. A flat-screen television is mounted on the wall opposite the bed. A small desk and chair occupy a corner, while a door leads to a bathroom area. Light-colored walls enhance the bright, airy feel.
Apartment in Tampa
4.86 out of 5 average rating, 194 reviews

Lovely 1-bedroom rental 10 min from TPA

Enjoy easy access to everything from this perfectly located home base. We are just 10 mins away from the airport. Our home is located in a quite neighborhood where you can relax and rest. This place was recently renovated so you will be enjoying modern luxury.

Top guest favorite
A spacious bed is centered in the room, embellished with a patterned bedspread. Nightstands with lamps are positioned on either side. A ceiling fan is visible overhead, and a large piece of wall art adds a touch of character. A bathroom can be glimpsed through an open door.
Home in Tampa
4.98 out of 5 average rating, 264 reviews

Private Studio-2, Exquisite space/King Bed /TAMPA

Enjoy your stay in Tampa in this cozy, newly remodeled studio! This studio is located at the center of Town and Country and is a short drive from Tampa International Airport (7 miles, which is 14 minutes away from the studio).

Popular amenities for Oldsmar family-friendly rentals

When is the best time to visit Oldsmar?

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Avg. priceﺩ.ﺇ731ﺩ.ﺇ845ﺩ.ﺇ896ﺩ.ﺇ735ﺩ.ﺇ716ﺩ.ﺇ676ﺩ.ﺇ698ﺩ.ﺇ643ﺩ.ﺇ643ﺩ.ﺇ661ﺩ.ﺇ716ﺩ.ﺇ716
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Quick stats about vacation rentals that are family-friendly in Oldsmar

  • Total vacation rentals

    Explore 90 vacation rentals in Oldsmar

  • Nightly prices starting at

    Oldsmar vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

  • Verified guest reviews

    Over 2,460 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Oldsmar vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Oldsmar rentals

  • 4.8 Average rating

    Oldsmar stays are highly rated by guests—averaging 4.8 out of 5!