Family-friendly vacation rentals in Oldsmar

A screened-in lanai features a heated saltwater pool surrounded by colorful outdoor furniture. Children’s toys and pool floats are placed nearby, alongside a small bike. The serene space is perfect for relaxation and play, with trees visible beyond the enclosure.

5 out of 5 average rating, 162 reviews

Coastal Escape: Kid-Friendly Pool & Playground

★ Family-friendly Palm Harbor retreat near beautiful beaches - Honeymoon Island: 6 miles away - Clearwater Beach: 15 miles away ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large fenced backyard with playground ★ Outdoor dining area ★ 3 bedrooms with new mattresses - California king size bed - Queen size bed - Kid-friendly room w/ 2 bunk beds ★ Renovated kitchen and bathrooms ★ Open living space for family gatherings and movie nights ★ Toys, games and kid-friendly extras

4.95 out of 5 average rating, 188 reviews

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

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

Superhost

Home in Safety Harbor

4.88 out of 5 average rating, 120 reviews

Modern Paradise home near Clearwater Dunedin Beach

Welcome to Safety Harbor house Florida . Close to downtown main street,fun shops,restaurants ,fishing pier water front park and family friendly activities. the home sleeps 6 guests. Has a nice pool and it is great for couples ,solo adventures,business travelers,families with kids .Fully equipped brand new kitchen brand new bedrooms. Wifi TV Alexa. Tampa international airport 15 minutes Clearwater Beach 15 minutes Palm Harbor tarpon springs sunset beach 10 minutes Saint Petersburg 15 minutes.

4.99 out of 5 average rating, 100 reviews

A screened-in pool area is highlighted by clear blue water and a unicorn float. Surrounding greenery adds a natural touch, while shaded seating is positioned on the deck. Sunlight filters through the enclosure, creating a bright, inviting space for relaxation and leisure.

Guesthouse in Westchase

Cottage in Paradise.

Relax and unwind at our 2 bedroom, 1.5 bath, GUEST HOUSE (ONLY). Enjoy the pool, Beautifully landscaped grounds with Koi pond & mini golf. See birds, butterflies and more in our 1 acre botanical gardens. Free use of Golf Cart. Kayaks are available (with transport fee. I live in the main house and I'm happy to ensure that you have everything you need for an amazing vacation, while still giving you plenty of privacy. Check in & out times are not set & very flexible for your convenience.

4.84 out of 5 average rating, 159 reviews

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

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.

5 out of 5 average rating, 206 reviews

The guesthouse is set on a green lawn, surrounded by trees. A friendly horse grazes nearby, accompanied by a variety of free-ranging chickens and ducks. The exterior features a welcoming porch with wooden railings, adding to the farm's relaxed atmosphere.

Farm stay in Zephyrhills

HORSE FARM Retreat, Newer Built Private Guesthouse

Escape to our private guesthouse located in our peaceful but lively 7-acre farm with our family of horses, ponies, Guinea hens, ducks, roosters, chickens, bunnies, cats, & very lovable dogs. Enjoy grabbing fresh eggs, giving animals treats, puppies belly rubs, grilling, making s’mores at the fire pit, and enjoying the farm life! PLEASE read entire listing if little ones will be joining :-) NOTE: Our horses are not available for riding (see our guidebook for great alternate options)

A serene backyard is featured, highlighting a sparkling pool surrounded by a spacious deck. Several lounge chairs are positioned nearby for relaxation. Lush artificial grass complements the outdoor space, while wooden fencing provides privacy.

4.71 out of 5 average rating, 112 reviews

Private Pool Home Near Clearwater & Tampa

Only 25 minutes from Clearwater Beach and Tampa, 33 minutes from Buch Gardens, 1.5 hrs from Disney, 18 minutes from Tampa International Airport. This house is completely renovated with a lot of space for you, family and/or friends. The entire house for you and your family. We have a beautiful pool with a Grill for your convinience and a garage for your car. 3 bedrooms for up to 7 persons. A 65" TV in the living room. Wi-Fi. The house has everything you need to have a relaxing time.

Guest suite in Clearwater

A peaceful outdoor area is surrounded by lush greenery, featuring palm trees and vibrant plants. A simple table and chairs are positioned beneath a canopy, providing a shaded space for relaxation. A whimsical flamingo decoration adds a playful touch to the serene environment.

5 out of 5 average rating, 113 reviews

Clearwater Studio Getaway

Welcome to Clearwater Studio Getaway! Enjoy a peaceful and centrally-located space just 15 minutes from Clearwater Beach, Downtown Clearwater, and the Tampa Bay área .Just 7 minutes from Safety Harbor and 14 minutes from Dunedin . Perfect for travelers or couples, this cozy studio features a private bathroom, comfy bed, and essential amenities. Relax after a day of sun and fun, with shops, dining, and attractions all within easy reach. Your perfect Florida stay!

4.96 out of 5 average rating, 125 reviews

A stone fire pit is surrounded by two blue chairs, positioned on a grassy area by the waterfront. Trees provide shade, and a dock is visible across the lake, complementing the serene outdoor setting.

Home in Odessa

A perfect Lake House get away

Make some memories at this unique and family-friendly slice of paradise. Located on 100-acre Lake Anne. 20 minutes from beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. Kayak, paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

The grotto-style pool area features natural rock formations with cascading waterfalls and lush tropical plants. A hot tub is integrated into the design, providing a relaxing space. The serene water reflects the clear blue sky, while views of the bay are visible in the background.

5 out of 5 average rating, 163 reviews

Bayside Retreat your tropical oasis

"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport

4.96 out of 5 average rating, 319 reviews

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

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.

Superhost

The outdoor space features a heated pool surrounded by a smooth concrete deck. Several lounge chairs are positioned nearby for relaxation. Lush landscaping includes palm trees, and soft lighting adds ambiance to the area, creating an inviting environment for leisure.

4.82 out of 5 average rating, 119 reviews

Modern & Spacious Retreat with Private Pool!

Welcome to our exquisite Airbnb in Oldsmar, Florida, where luxury and convenience converge in a SINGLE-story haven. This delightful getaway promises an unforgettable stay for travelers seeking relaxation, outdoor adventures, and a touch of historical charm.

Popular amenities for Oldsmar family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Superhost

4.83 out of 5 average rating, 6 reviews

House in Oldsmar near Clearwater / Tampa Hot tub*

Tiny home in Ybor City Historic District

A rustic tiny house stands within a lush garden, featuring a wooden deck adorned with comfortable seating. The entrance showcases large glass doors, framed by greenery, while a charming pathway of stones leads toward the entrance. Subtle decorative elements enhance the inviting outdoor space.

4.98 out of 5 average rating, 601 reviews

Cozy AF Tiny-House Oasis

4.94 out of 5 average rating, 128 reviews

A serene outdoor space features a sparkling pool framed by lush tropical landscaping. A relaxing spa is integrated into the pool area, accompanied by comfortable lounge chairs. A shaded cabana and grilling station are visible in the background, enhancing the inviting ambiance.

Home in Tampa

The Jungalow SOHO - Pool/Hot Tub

A charming farmhouse exterior is showcased under large trees, with a welcoming front porch featuring red seating and decorative plants. A spacious gravel parking area is visible, complemented by a green landscape in the background, enhancing the tranquil setting.

4.91 out of 5 average rating, 161 reviews

Peaceful Pet friendly 2 BR cottage with hot tub.

4.91 out of 5 average rating, 126 reviews

Home in Clearwater

Modern Pet-Friendly Beach House w/ Heated Pool & S

4.95 out of 5 average rating, 338 reviews

A hot tub is set on a wooden deck surrounded by bar stools, with views of a lush backyard and a serene lake beyond. Tall palm trees frame the scene, while the sky displays soft clouds and warm lighting.

Home in Town 'n' Country

The perfect lake house getaway near the airport.

A serene outdoor space is illuminated by string lights hanging from trees. A winding stone path leads to wooden steps ascending to a deck. Lush green grass surrounds a picnic table positioned on one side, enhancing the tranquil atmosphere of the lakefront setting.

4.98 out of 5 average rating, 43 reviews

Waterfront Gem Near Clearwater • Swim Spa + Nature

4.96 out of 5 average rating, 142 reviews

Home in Clearwater

Clearwater Gem! XL-Pool | Courts & More!

Family- and pet-friendly home rentals

A selection of woven storage baskets is displayed on a countertop, featuring neatly arranged napkins and two water bottles. A decorative sign reading 'HOME SWEET HOME' adds a personal touch to the arrangement, blending function with a welcoming aesthetic.

5 out of 5 average rating, 28 reviews

Palm Harbor Renovated Hideaway!

4.98 out of 5 average rating, 261 reviews

Two wooden Adirondack chairs are positioned on a deck overlooking a serene lake. A floating dock extends into the water, featuring two red lounge cushions. The clear blue sky enhances the tranquil atmosphere, with greenery visible along the shoreline.

Cottage in Tampa

Bay Lake Cottage

4.94 out of 5 average rating, 32 reviews

A screened-in balcony area is visible, showcasing views of a large pond surrounded by lush greenery. Bright blue skies and scattered clouds reflect a serene atmosphere. Two striped chairs are positioned for relaxation, set against the tiled floor surrounded by wooden railings.

Condo in Oldsmar

Guest Favorite Waterview- 2 bed/2 bath apt w/pool

5 out of 5 average rating, 102 reviews

The retro-style home is set back in a spacious driveway, framed by palm trees and lovely landscaping. A classic red pickup truck is parked in front, with a fenced yard visible to the side. A clear blue sky complements the inviting atmosphere of the property.

Home in Clearwater

Florida Retro AIRBnB

4.99 out of 5 average rating, 102 reviews

The spacious living area features a dark leather sectional sofa with decorative cushions and a low coffee table at the center. Light hardwood flooring extends throughout. Sliding barn doors lead to an adjoining room with television and dining space, while soft lighting enhances the inviting ambiance.

Villa in Safety Harbor

Villa at Harbor House "Villas by Christine"

4.92 out of 5 average rating, 115 reviews

A cozy kitchenette is featured with sleek white cabinetry, a compact refrigerator, and a granite countertop. Two seating areas are provided: a striped armchair and three bar stools positioned around a counter. Natural light filters in through a nearby window, illuminating the space.

Farm stay in Odessa

Cabin 1 - Marigold Moments

A comfortable living area is showcased with a beige sofa adorned with colorful pillows and two green accent chairs. A ceiling fan provides airflow, and natural light filters through large windows. The open layout connects to the kitchen area, creating a bright and inviting atmosphere.

4.93 out of 5 average rating, 149 reviews

Cozy Retreat! Walk to Crystal Beach/Park

A spacious house is shown from the front, featuring a well-manicured lawn and a driveway leading to a two-car garage. Soft lighting highlights the entrance, with palm trees and colorful garden features enhancing the inviting exterior against a vibrant sunset sky.

5 out of 5 average rating, 12 reviews

Oldsmar fully furnished home/ pet friendly

Family-friendly home rentals with a pool

4.89 out of 5 average rating, 96 reviews

The exterior of a single-story house is presented, featuring a two-car garage and a well-maintained lawn. Lush green shrubs frame the entrance, and a small American flag is placed near the mailbox. A partly cloudy sky adds depth to the welcoming scene.

Home in Safety Harbor

Nice Sparkling Clean Home with Pool.

A spacious living area features a large grey sectional sofa adorned with orange and blue accent pillows. A marble coffee table sits in front, while a ceiling fan is visible above. Light enters through large windows, illuminating the open layout connecting to a dining area.

4.96 out of 5 average rating, 46 reviews

The Coastal Calm - Entire Unit

The outdoor area features a heated pool with crystal-clear water, surrounded by a screened lanai. Comfortable lounge chairs are placed nearby, providing ideal spots for relaxation. Tropical plants enhance the space, framing a serene environment perfect for swimming and sunbathing.

4.91 out of 5 average rating, 140 reviews

Family Home with a Private Heated Pool

4.85 out of 5 average rating, 54 reviews

Sunny's Retreat

4.92 out of 5 average rating, 26 reviews

The exterior of a two-story condo is showcased, featuring a well-maintained entrance with a concrete pathway bordered by lush green grass. The building has multiple windows and a combination of beige and brown siding, along with a row of palm trees enhancing the tropical setting.

Apartment in Oldsmar

Cozy Private 2BR FL condo

5 out of 5 average rating, 48 reviews

A charming exterior of a townhome is presented, featuring a bright red front door. Lush greenery and colorful plants frame the pathway leading to the entrance, with a well-maintained lawn inviting guests to explore. The surrounding area is dotted with additional townhomes.

Villa in Palm Harbor

Coastal Cottage | Top 1% Airbnb Worldwide

4.99 out of 5 average rating, 116 reviews

Villa in Palm Harbor

The Palm Haus • Heated Pool • Near Beach • Games

A spacious living area is highlighted by a large wall-mounted television displaying vibrant underwater scenes. Two tall planters with decorative branches frame the television. A modern entertainment unit holds an electric fireplace, while a round coffee table sits at the center of the cozy seating arrangement.