Vacation rentals in Oldsmar
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Top-rated vacation rentals in Oldsmar
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Modern Private Estate | Central to Tampa & Beaches
Experience this private 1-acre, modern home designed for space, calm, and everyday comfort. Surrounded by mature oaks and palms, this serene property offers rare privacy just minutes from Tampa Airport, Clearwater Beach, Safety Harbor, St. Pete, and top attractions. Enjoy a chef’s kitchen with modern appliances, spacious living areas, and peaceful outdoor spaces with a patio, electric grill, and koi pond. Ideal for families, longer stays, & guests who value tranquility, and a thoughtful design!
Sunny Oasis: Villa Retreat
Welcome to a stunning 2-bedroom, 2-bathroom villa nestled in the heart of sunny Florida! Whether you're seeking a relaxing beach getaway or exploring all that Florida has to offer, this villa is your perfect destination. Located 15-20 minutes from the beach in a prime location, you'll find a plethora of dining, shopping, and entertainment options nearby, ensuring there's something for everyone to enjoy. Book your stay today and experience the ultimate in comfort, convenience, and coastal charm.
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
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.
Cozy 4BR Retreat|Near Busch Garden beach & TPA
Welcome to our beautiful newly built 2022 two-story home, perfect for families, business travelers, or group getaways. This spacious home features: ✔ 4 comfortable bedrooms ✔ 3.5 bathrooms ✔ Sleeps up to 8 guests ✔ Fully equipped modern kitchen ✔ Private patio with BBQ grill ✔ Fast WiFi ✔ Free parking Located in a peaceful neighborhood, only: 📍20 mins to Tampa Airport 📍30 mins to Clearwater Beach and Honeymoon Island beach 📍35 mins to Busch garden 📍Near shopping, restaurants & parks
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.
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.
Sunny's Retreat
Your vacation destination awaits at this 4 bedroom, 3 bath waterside Florida oasis! Enjoy this spacious home with a pool and all the amenities with your private view by the water and private dock for fishing and relaxing. Relax by the pool for the day! You are sure to see Sunny, the Egret, one of the native birds catching their share of fish. Sunny's Place is located in Oldsmar which is on the water of Tampa Bay and only 30 minutes from downtown Tampa!
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
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
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.
BeachBunkies Cottage 1. Four miles to the beach!
Welcome to the Beach Bunkies Cottages in historic Dunedin Fl. The cottages are located just 3 miles from charming downtown Dunedin, 4 miles from the stunning Honeymoon Island & Gulf coast. Both Cottages have fully accessorized kitchens and share some outside amenities.
Popular amenities for Oldsmar vacation rentals
Other great vacation rentals in Oldsmar
House in Oldsmar near Clearwater / Tampa Hot tub*
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Suite Sunshine - An Artist's Delight
Cozy 3/2 residential with free parking on premises
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 694 | ﺩ.ﺇ 720 | ﺩ.ﺇ 742 | ﺩ.ﺇ 602 | ﺩ.ﺇ 588 | ﺩ.ﺇ 569 | ﺩ.ﺇ 569 | ﺩ.ﺇ 606 | ﺩ.ﺇ 544 | ﺩ.ﺇ 577 | ﺩ.ﺇ 606 | ﺩ.ﺇ 613 |
| Avg. temp | 17°C | 18°C | 20°C | 23°C | 26°C | 28°C | 29°C | 29°C | 28°C | 25°C | 21°C | 18°C |
Frequently Asked Questions
What are the best places to stay in Oldsmar?
Accommodations near waterfront parks and in quiet residential neighborhoods are often preferred by visitors seeking a relaxing atmosphere. Many guests also look for stays that provide convenient access to local restaurants and recreation areas.
What are the best things to do in Oldsmar with kids?
Oldsmar has parks with playgrounds, shaded picnic areas, and walking trails where children can explore nature. Kids often enjoy interactive exhibits at local nature centers, as well as seasonal family-friendly events hosted around town.
What are some of the best things to do in Oldsmar?
Oldsmar has nature trails, waterfront parks, and local markets to explore. Outdoor recreation, birdwatching, and discovering nearby arts venues are frequently suggested by guests and residents alike.
How is the weather in Oldsmar?
Oldsmar generally has mild winters around 53–74°F (12–23°C) and warm, humid summers near 77–91°F (25–33°C) with frequent afternoon showers. Rain tends to increase from late spring through early fall, while winter and spring see more sunshine.
When is the best time to visit Oldsmar?
Late fall through spring is often recommended for warm days and lower rainfall, with temperatures generally from 53–83°F (12–28°C). Summer brings high humidity and heavier rains, along with lush green landscapes.
What are the best places to visit in Oldsmar?
Nature lovers often explore Mobbly Bayou Wilderness Preserve and R.E. Olds Park, while local history enthusiasts visit interpretive centers or heritage museums. The area also has unique open-air markets and performance spaces.
What are some hiking trails in Oldsmar?
Guests frequently explore nature trails at Mobbly Bayou Wilderness Preserve, which features boardwalks along the bayou and forested paths. Other parks in Oldsmar have short walking loops suitable for various activity levels.
What are some family activities we can do in Oldsmar?
Families frequently explore waterfront parks, enjoy playgrounds, or visit nature preserves around Oldsmar. The area also has recreational facilities and community centers that host programs suitable for guests of all ages.
What are some of the best day trip ideas from Oldsmar?
Many visitors plan day trips to nearby Gulf beaches, botanical gardens, or lively art districts in neighboring cities. Exploring regional wildlife refuges and historic downtowns is also frequently suggested for a broader experience.
Are there any pet friendly accommodations available in Oldsmar?
Many accommodations in Oldsmar welcome pets, with hosts often providing amenities like fenced yards or easy access to parks. Checking individual listings for detailed pet policies can help find the right fit for your travel companions.
What are some local tips for visiting Oldsmar?
Locals suggest bringing sun protection, exploring early in the day during summer, and sampling fresh seafood at waterfront eateries. Attending a local market or festival is also a great way to experience the community’s welcoming spirit.
What is Oldsmar known for?
Oldsmar is known for its waterfront parks, nature preserves, and strong ties to automotive history, named after Ransom E. Olds. The city hosts community gatherings, outdoor activities, and is recognized for its welcoming, small-town feel.
What are the best hidden gems to explore in Oldsmar?
Hidden gems around Oldsmar include quiet nature preserves with birdwatching platforms, community gardens, and art spaces featuring local creators. Smaller waterfront parks offer a peaceful atmosphere for unwinding or photography.
What are the best foods to try in Oldsmar?
Fresh Gulf seafood, grouper sandwiches, and Southern-style barbecue are frequently suggested local flavors. Many visitors also sample Cuban sandwiches and key lime pie, reflecting Oldsmar’s mix of culinary influences.
What should I bring for a trip to Oldsmar?
Pack lightweight clothing, comfortable walking shoes, and sun protection such as hats or sunscreen. If visiting during summer, a rain jacket or umbrella is helpful, and insect repellent can make time outdoors more comfortable.
What is the nightlife in Oldsmar like?
Oldsmar’s nightlife tends to be relaxed, with casual pubs, live music venues, and restaurants featuring local musicians or karaoke nights. Around the city, guests sometimes find seasonal outdoor events and family-oriented evening gatherings.
What are the most popular events or festivals in Oldsmar?
Oldsmar celebrates with community festivals, outdoor concerts, and car shows, especially around late winter and early spring. Seasonal markets and multicultural heritage events are also frequently hosted in city parks.
Are there family friendly vacation rentals in Oldsmar?
You will find many family-friendly rentals in Oldsmar, often with features like multiple bedrooms, kitchens, and access to parks or playgrounds. Filtering for amenities such as outdoor space or cribs can help tailor your search.
Quick stats about vacation rentals in Oldsmar
Total vacation rentals
Explore 130 vacation rentals in Oldsmar
Nightly prices starting at
Oldsmar vacation rentals start at ﺩ.ﺇ 73 per night before taxes and fees
Verified guest reviews
Over 4,020 verified reviews to help you choose
Family-friendly vacation rentals
80 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 70 rentals that welcome pets
Vacation rentals with a pool
80 properties feature pools
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Wi-Fi availability
120 of Oldsmar vacation rentals include wi-fi access
Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across Oldsmar rentals
4.8 Average rating
Oldsmar stays are highly rated by guests—averaging 4.8 out of 5!
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- Family-friendly rentals Oldsmar
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