Holiday rentals in Oldsmar

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.

4.91 out of 5 average rating, 382 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.

Guest house 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.

4.96 out of 5 average rating, 237 reviews

"Chic/cozy Petite Studio •"Spa-Inspired Shower. 1”

Welcome to your serene hideaway in Citrus Park, where modern comfort meets thoughtful design. Just 11 minutes from Tampa International Airport, and free parking on premises this stylish and private studio is the perfect spot for couples, solo travelers, or business guests seeking a peaceful and rejuvenating stay. Located in a quiet, safe, and central neighborhood, you’ll enjoy a private entrance, free on-site parking, and easy access to restaurants, grocery stores, and major Tampa attractions.

4.99 out of 5 average rating, 142 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

4.87 out of 5 average rating, 165 reviews

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.

Flat in Tampa

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

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.

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’

5 out of 5 average rating, 146 reviews

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

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

Superhost

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.

Flat 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.

4.96 out of 5 average rating, 303 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.

4.91 out of 5 average rating, 235 reviews

A well-furnished bedroom features a spacious bed layered with patterned bedding. A large mirror reflects the room's layout, while a sleek television is mounted on the wall. A small workstation and closet space are visible in the background, providing a modern and functional atmosphere.

Flat in Tampa

Cozy 1 bedroom apartment 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.

4.98 out of 5 average rating, 264 reviews

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

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).

Guest suite in Timberlane Woodlake

A cozy bedroom is highlighted by a spacious bed covered with a soft throw. Mirrored closet doors reflect natural light, while a wooden desk and chair offer a functional workspace. A ceiling fan and flat-screen TV enhance the comfort of the space.

4.92 out of 5 average rating, 124 reviews

Cozy Red Door Studio

Keep it simple at this peaceful and centrally located place. Very cozy and private with a carport parking spot. Close to beaches, shopping, Tampa International Airport, Busch Gardens and more!

Popular amenities for Oldsmar holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Oldsmar

4.94 out of 5 average rating, 70 reviews

An outdoor patio area features a shaded table surrounded by four adirondack chairs. A tropical palm tree adds greenery, and a grilling station is positioned nearby. The space is enclosed by a white fence and showcases a well-maintained lawn.

Home in Oldsmar

Sunny Oasis: Villa Retreat

Guest house in Clearwater

A well-lit living area features a comfortable sofa with decorative pillows, a cozy bed with patterned bedding, and a modern kitchenette equipped with stainless steel appliances. Large sliding doors provide access to an outdoor patio, enhancing the space's openness.

4.97 out of 5 average rating, 39 reviews

Cozy In-Law Suite Near Beach

4.88 out of 5 average rating, 16 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.

Flat in Oldsmar

Cozy Private 2BR FL condo

Guest house in Safety Harbor

A cozy interior space is highlighted by light wood paneling and textured wall decor. A comfortable bed with dark bedding is positioned near a wooden accent wall, featuring a mounted television. Natural light fills the room through a nearby window, enhancing the inviting atmosphere.

4.93 out of 5 average rating, 288 reviews

Tiny House Oasis | Best Location | Outdoor Shower

5 out of 5 average rating, 15 reviews

A winding driveway leads up to a modern home nestled among lush landscaping. Towering oak trees create shade, and manicured greenery enhances the sense of privacy. The expansive grounds are tranquil, inviting visitors to explore the serene outdoor environment.

Home in Oldsmar

Luxury Modern Retreat I Spacious, Private & Serene

4.79 out of 5 average rating, 38 reviews

A comfortable living area features a stylish brown couch, complemented by decorative cushions. A ceiling fan provides airflow. Nearby, a dining setup showcases plates and glasses arranged on a textured placemat. Natural light enters through the door leading to an outdoor space.

Guest house in Oldsmar

Hidden Cottage

A well-equipped kitchen area is paired with a modern dining space featuring two red stools at a granite island. The cozy sleeping area showcases a neatly made bed with a blue and white patterned coverlet. Artwork adorns the walls, adding a pop of color.

4.9 out of 5 average rating, 117 reviews

Entire Adorable guest room place