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Family-friendly vacation rentals in Oldsmar

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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.ﺇ 184 per night before taxes and fees

  • Verified guest reviews

    Over 2,690 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Vacation rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    40 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

  • 4.9 Average rating

    Oldsmar stays are highly rated by guests—averaging 4.9 out of 5!

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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Top guest favorite
A charming Florida bungalow features a turquoise exterior with natural stone accents. The front porch is accessed by a concrete pathway lined with greenery, including tropical plants. A small entry door and window allow for natural light, framed by neatly placed shutters and landscaping.
Home in Dunedin

Wonderful family friendly home in Dunedin FL

Comfy Kid & Pet friendly Florida home, 15 minutes to Honeymoon Island, Caladesi State park & Clearwater Beach and Clearwater Aquarium. Large kitchen, dining area, & nice screened in back porch. Shopping malls, grocery store and pharmacies two blocks away. Take a stroll in fun Downtown Dunedin, go for a bike ride on the Pinellas Trail or play foosball and table games with the family. Short drive to Busch Gardens, Lowry Park Zoo or the Florida Aquarium. The yard is fenced in and quite spacious.

4.92 out of 5 average rating, 285 reviews
Top guest favorite
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.
Home in Palm Harbor

Coastal Escape: Heated Pool, Playground&Family fun

★ 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

5.0 out of 5 average rating, 177 reviews
Top guest favorite
Villa in Palm Harbor

Palm Haus • Heated Pool • Near Beach • Game Room

Charming home with stylish baths & bedrooms. Heated pool included in the price. Gas fire-pit, outdoor games, large secluded backyard! Game room! Near Honeymoon Beach & Caladesi Island open for sunbathing & water sports; historic downtown Dunedin with cute shops, cafes, restaurants & cultural events. The area has a number of top-notch golf courses and trails. Palm Harbor's welcoming community & mild climate make it an ideal getaway for outdoor adventures, cultural experiences, and coastal views.

4.99 out of 5 average rating, 133 reviews
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

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

4.96 out of 5 average rating, 205 reviews
Top guest favorite
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.

4.99 out of 5 average rating, 108 reviews
Guest favorite
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.

Spacious family-friendly retreat. Three comfortable bedrooms and a cozy sitting room within the Master Bedroom, our home offers ample space for the entire family. With two full bathrooms, everyone can enjoy their own privacy and convenience. Step outside to the inviting pool area with a spacious enclosed patio. A Fully stocked kitchen is equipped with everything for preparing and enjoying delicious meals together. Plate settings for six to a comprehensive array of utensils and pots/pans.

4.89 out of 5 average rating, 103 reviews
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

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.

4.84 out of 5 average rating, 170 reviews
Guest favorite
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.
Home in Oldsmar

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.

4.73 out of 5 average rating, 117 reviews
Guest favorite
Vacation home in Safety Harbor

Heated Pool • 4BR • Near Clearwater Beach

Welcome to your private Safety Harbor getaway—perfect for families and groups of up to 8. Enjoy 4 comfortable bedrooms, 2 baths, a private heated pool maintained around 86°F, fast Wi-Fi, a fully equipped kitchen, spacious living areas, and free driveway parking. About 15–20 minutes from St. Pete–Clearwater Airport, 20–25 minutes from Tampa International Airport, and convenient to Clearwater Beach, shopping, dining, and local attractions. Easy self check-in with a smart lock.

4.84 out of 5 average rating, 101 reviews
Top guest favorite
A serene outdoor space features a heated pool, reflecting the colorful sky during sunset. Strands of lights are draped above, enhancing the inviting atmosphere. Comfortable loungers are placed beside the pool, with dining areas visible in the background, surrounded by lush greenery.
Home in Dunedin

Heated saltwater pool|Spacious 4BR/3BA|

Welcome to Cerulean Cottage, our coastal home centrally located in Dunedin, Florida. Whatever brings you to this area, you will find yourself right at home in our comfortable beds, cozy couch, and functionally designed spaces. Have a blast in the pool and game room and wind down in our new 4D massage chair. We are close to conveniences, including grocery stores and many favorite local restaurants and just a short drive from our quaint downtown and beaches.

4.96 out of 5 average rating, 135 reviews
Guest favorite
Home in Palm Harbor

Chic|Pool|PuttingGreen|Beaches

Enjoy a relaxing family getaway in the Sunshine State! Spend days relaxing on the beach and enjoying outdoor fun for the whole group with a bounce house, putting green, and more at this stylish home. Whether you’re traveling with family and friends or on business, this is a great place to discover the beautiful. Clearwater Beach area. 8 Min Walk to Saint George Lake 12 Min Drive to Wall Springs Park 22 Min Drive to Clearwater Beach.

4.78 out of 5 average rating, 107 reviews
Guest favorite
The illuminated pool takes center stage under the night sky, emitting a tranquil green glow. Surrounding the pool is a spacious deck, featuring lounge chairs and a table for outdoor gatherings, complemented by well-maintained landscaping in the background.
Home in Oldsmar

Hot Tub, Heated Pool, 2 Master Suites, Beach

Minutes from the beach is this fully renovated home with brand-new furniture. Enjoy an extra-large backyard with a hot tub, heated pool & plus a bonfire pit! Relax in the sunny Florida sunroom or park in the private double garage. Located in a quiet neighborhood, just minutes from Honeymoon Island and shopping centers. Strict no parties or events policy. Perfect for families and small groups seeking a peaceful, luxury getaway.

4.84 out of 5 average rating, 149 reviews

Popular amenities for Oldsmar family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favorite
Home in Palm Harbor

FREE Heated Pool & Spa l Book your Winter Vacation

4.93 out of 5 average rating, 136 reviews
Guest favorite
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.

4.95 out of 5 average rating, 349 reviews
Guest favorite
A heated pool is enclosed by a screened lanai, featuring a unique shape with a brick border. Lounge seating is present around the pool, while a hammock is visible in the background. The tranquil area is surrounded by high wooden fencing for privacy.
Home in Town 'n' Country

Rooms with a Pool

4.91 out of 5 average rating, 236 reviews
Guest favorite
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.
Home in Palm Harbor

Peaceful Pet friendly 2 BR cottage with hot tub.

4.9 out of 5 average rating, 176 reviews
Top guest favorite
A tranquil lagoon pool is surrounded by lush tropical foliage and colorful flowers. A shaded seating area is visible, along with a light-colored house in the background. Multiple palm trees contribute to the serene atmosphere of this private oasis.
Apartment in Dunedin

Tropical Paradise

4.99 out of 5 average rating, 276 reviews
Guest favorite
A screened-in outdoor area features a heated pool and spa accompanied by a spacious dining table set for eight. Vibrant glassware and dining plates are arranged, capturing bright colors against the backdrop of lush greenery and a clear sky.
Home in Dunedin

Luxury home ~ Heated pool, hot tub, TWO kitchens

4.92 out of 5 average rating, 132 reviews
Superhost
A foosball table occupies the foreground with a clear view of the private pool shimmering in the sunlight. The surrounding area is enclosed with mesh screens, featuring lush greenery in the background, complementing the inviting water and a beach ball floating on the surface.
Home in Town 'n' Country

Ultimate Getaway: w/ Pool, Patio, Pool Table & BBQ

4.85 out of 5 average rating, 115 reviews
Top guest favorite
Home in Clearwater

Clearwater Gem! XL-Pool | Courts & More!.

4.97 out of 5 average rating, 153 reviews

Family- and pet-friendly home rentals

Guest favorite
Home in Palm Harbor

Heated Pool 4 bed 7 miles to Honeymoon Island.

4.94 out of 5 average rating, 203 reviews
Top guest favorite
A wooden dock extends over the calm waters of Lake Tarpon, surrounded by lush greenery. The expansive blue sky and gentle waves create a serene ambiance, ideal for enjoying nature. The space offers direct access to the lake, enhancing the outdoor experience.
Home in Palm Harbor

Lakefront home near beaches w/ waterview, pets ok

4.93 out of 5 average rating, 132 reviews
Top guest favorite
The exterior of a retro home is highlighted by a red vintage truck parked in the driveway. Lush greenery, including palm and flowering plants, surrounds the property, while two distinct pathways lead toward the entrance. The warm concrete driveway complements the inviting atmosphere.
Home in Clearwater

Sleeps 10, pet friendly/ fenced yard, near beaches

5.0 out of 5 average rating, 121 reviews
Top guest favorite
The exterior of a coastal cottage is shown, featuring a gravel driveway and tropical landscaping with palm trees. Two wicker chairs are positioned under a covered porch, inviting relaxation. Large windows allow natural light to brighten the welcoming facade.
Cottage in Dunedin

Walk Downtown and to Waterfront, Mins to Beaches

4.97 out of 5 average rating, 392 reviews
Guest favorite
Home in Safety Harbor

Modern Paradise home near Clearwater Dunedin Beach

4.88 out of 5 average rating, 125 reviews
Top guest favorite
Home in Clearwater

Artsy oasis in Clearwater

4.95 out of 5 average rating, 150 reviews
Guest favorite
An inviting living room showcases ample seating with a gray sectional couch and plush ottoman. A cozy dining area is visible outdoors, furnished with a table and chairs under a shaded canopy. The sparkling pool, surrounded by lounge chairs, is highlighted by vibrant tropical landscaping.
Home in Dunedin

3BR Oasis | Sleeps 11 | Heated Pool | Ping Pong!

4.93 out of 5 average rating, 106 reviews
Guest favorite
Home in Clearwater

Clearwater-Pickleball/SltPool/Golf/Theatre/Arcade

4.93 out of 5 average rating, 123 reviews

Family-friendly home rentals with a pool

Top guest favorite
A screened-in patio features a heated swimming pool, surrounded by white decking. The pool offers a view of the canal with palm trees and neighboring properties beyond. The tranquil outdoor space is complemented by a backyard with swings and a dock visible in the background.
Home in Town 'n' Country

Waterfront Resort with HEATED POOL!

4.93 out of 5 average rating, 152 reviews
Guest favorite
A comfortable living area features a gray sectional sofa, accompanied by a matching armchair. A light wooden coffee table sits in the center, topped with decor. Large windows allow natural light to fill the space, complemented by light-colored walls and polished wooden flooring.
Cottage in Palm Harbor

Palm Paradise

4.92 out of 5 average rating, 107 reviews
Guest favorite
A spacious outdoor area features a heated pool surrounded by a screened enclosure. Two lounge chairs are positioned beside the pool, and a barbecue grill is visible near the edge, providing an ideal setting for relaxation and meals.
Home in Clearwater

Heated Pool Home | Close to Clearwater Beach

4.85 out of 5 average rating, 141 reviews
Guest favorite
The kitchen features wooden cabinetry, a central island with seating, and modern appliances. Natural light enters through the glass doors, illuminating the granite countertops. A coffee maker and dishwasher are visible, and the tiled floor adds a polished finish to the overall space.
Home in Town 'n' Country

Entire residential home, Tampa. 3/2, Pool.

4.88 out of 5 average rating, 220 reviews
Guest favorite
An outdoor area features a private pool surrounded by a concrete deck. Lounge chairs and a dining table are visible beneath a covered patio, while tropical landscaping adds greenery. A path of stepping stones leads toward the pool, inviting relaxation and leisure.
Home in Palm Harbor

Private pool, Golf Cart, Completely Renovated!

4.94 out of 5 average rating, 122 reviews
Top guest favorite
The charming guest house exterior is framed by a lush green lawn. A walkway leads to a welcoming front door, with two comfortable chairs positioned by the entrance. Large windows allow natural light into the space, complemented by a well-maintained garden area.
Guesthouse in Palm Harbor

Guesthouse with Pool in Palm Harbor

4.98 out of 5 average rating, 117 reviews
Top guest favorite
The spacious living area features a comfortable sofa and a unique hanging chair. Light streams through glass doors leading to a patio. Coastal-themed artwork adorns the walls, while a patterned area rug adds warmth to the tile floor. A ceiling fan provides air circulation.
Home in Oldsmar

Sunny Oasis: Villa Retreat

4.96 out of 5 average rating, 99 reviews
Top guest favorite
Home in Oldsmar

Modern Tropical Oasis • Heated Pool & Firepit

4.96 out of 5 average rating, 57 reviews

When is the best time to visit Oldsmar?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 786ﺩ.ﺇ 815ﺩ.ﺇ 863ﺩ.ﺇ 797ﺩ.ﺇ 735ﺩ.ﺇ 738ﺩ.ﺇ 690ﺩ.ﺇ 716ﺩ.ﺇ 639ﺩ.ﺇ 668ﺩ.ﺇ 698ﺩ.ﺇ 731
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