House vacation rentals in Oldsmar

Find and book unique houses on Airbnb

Quick stats about house rentals in Oldsmar

  • Total vacation rentals

    Explore 100 vacation rentals in Oldsmar

  • Nightly prices starting at

    Oldsmar vacation rentals start at ﺩ.ﺇ 110 per night before taxes and fees

  • Verified guest reviews

    Over 2,970 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 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

    100 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 house rentals in Oldsmar

Guests agree: these houses are highly rated for location, cleanliness, and more.

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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
4.93 out of 5 average rating, 129 reviews

Lakefront home near beaches w/ waterview, pets ok

Imagine yourself waking up to a million-dollar view on Tampa Bay's largest lake - lake Tarpon. Close your eyes, relax and lose yourself to the sound of wind chimes, the caws and squeals of the birds, lapping of waves against the dock and fresh lake breeze. Watch an Osprey catch fish and other wildlife as you sip your morning coffee sitting on the dock. This is a quintessential lake house that one always desires in their dreams. Well that dream is attainable when you make this home your abode!

LocationFamilyHiking

Guest favorite
Home in Safety Harbor
4.88 out of 5 average rating, 125 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.

ValueLocationAmenities

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
4.91 out of 5 average rating, 171 reviews

Peaceful Pet friendly 2 BR cottage with hot tub.

Wellcome to our tranquil 2-bedroom, 1-bathroom farmhouse, nestled in the peaceful countryside of Palm Harbor. Whether you're seeking relaxation or adventure, this fully remodeled country cottage provides a serene and comfortable retreat. Whether you're relaxing with a movie, soaking in the hot tub, or exploring the nearby attractions, our farmhouse offers a serene and comfortable home away from home. Book your stay today! Please note that the minimum age requirement to book is 23.

ValueLocationHot tub

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
4.72 out of 5 average rating, 116 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.

FamilyValueBackyard

Top guest favorite
Home in Clearwater
4.98 out of 5 average rating, 231 reviews

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

Cozy, spacious home 🏡 w/ heated swimming 🏊‍♀️ pool, next to a golf ⛳️ course. Close to the famous beaches ⛱️, St.Pete and Tampa. This cozy open home has a large living room, big kitchen and pool deck patio. All 3 bedrooms have large TV's. The big back patio has a swimming 🏊‍♀️ pool, TV, fridge and BBQ for cook outs & R&R. Located in a quiet family-friendly neighborhood. Location! 15 min - Clearwater Beach, Dunedin, Safety Harbor 30 min from - St.Pete, TPA Airport, Tampa

ValueFamilyIndoor spaces

Guest favorite
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.
Home in Palm Harbor
4.93 out of 5 average rating, 156 reviews

Cozy Retreat! Walk to Crystal Beach/Park

Cozy Crystal Beach Retreat – Pet Friendly Enjoy this charming 2BR, 1BA home with queen beds and a pull-out sofa. Pets welcome with fee! Relax in the fully fenced backyard with picnic table, perfect for outdoor meals or your furry friend to play. Walk to the water or explore the nearby Pinellas Trail. Just minutes to downtown Dunedin (7 mi), Honeymoon Island (7.5 mi), Clearwater Beach (13 mi), and Tampa Intl Airport (22 mi). Ideal for couples, families, or a relaxing getaway!

ValueFamilySolo travel

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
4.91 out of 5 average rating, 236 reviews

Rooms with a Pool

Welcome to Tampa Bay! The home is central to everything Tampa Bay and is 1 hour 20 minutes from Orlando. This home includes a three guest rooms, 1.5 bathrooms, a living and a family room, kitchen, dining room, bar, office and a backyard lanai with a large heated pool area. You get the entire home and there is nobody else staying at the same time. It is in a quiet suburban neighborhood, about 40 minutes from downtown Tampa, Clearwater, and St. Petersburg.

LocationValueQuiet

Guest favorite
Home in Palm Harbor
4.94 out of 5 average rating, 200 reviews

Heated Pool 4 bed 7 miles to Honeymoon Island.

This stylish place is perfect for family vacation or work trip.. all brand new furnishing and appliances.. heated pool and 3 TVs for your enjoyment. The home is also conveniently located near many beaches, honeymoon island 6.9 miles Fred Howard park 11 miles ,Clearwater beach 14 miles ,Tampa and St. Pete . Please check house rules for more info. When you book, please put the exact number of guests that are going to be staying at the property.

FamilyValueAccess

Top guest favorite
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.
Home in Oldsmar
5 out of 5 average rating, 169 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

ValueFamilyLayout

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
4.84 out of 5 average rating, 149 reviews

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.

FamilyValueWifi

Top guest favorite
A heated pool is surrounded by lush palm trees, providing a sense of seclusion. A stone statue and decorative elements are featured along the pool's edge. Sunlight reflects off the water, creating a serene atmosphere in this private outdoor oasis.
Home in Palm Harbor
4.99 out of 5 average rating, 168 reviews

Tropical Oasis Retreat w/ Heated Pool

Welcome to your private backyard oasis. Relax by the heated pool, grill and dine outdoors, all within a fenced-in space. This home is ideally located—just a short drive to Crystal Beach, minutes from downtown Palm harbor, Dunedin and Tarpon Springs, and bike ride away to Pinellas Trail, golf courses, Honeymoon Island, and Clearwater Beach. Pets are welcome

FamilyLocationCleanliness

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
4.95 out of 5 average rating, 344 reviews

The perfect lake house getaway near the airport.

Relax with the whole family in this cozy residence in the Tampa Bay area. Enjoy the spacious backyard and unwind in the hot tub with peaceful views of the lake. Set in a centric location near the International Airport, Raymond James Stadium, Busch Gardens, Adventure Island, Citrus Park mall and Florida's best-rated beaches.

ValueLocationView

Popular amenities for Oldsmar house rentals

When is the best time to visit Oldsmar?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 735ﺩ.ﺇ 786ﺩ.ﺇ 812ﺩ.ﺇ 771ﺩ.ﺇ 665ﺩ.ﺇ 731ﺩ.ﺇ 643ﺩ.ﺇ 643ﺩ.ﺇ 617ﺩ.ﺇ 668ﺩ.ﺇ 698ﺩ.ﺇ 683
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