Discover a selection of 2,500 vacation rentals in Oldsmar, FL that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and kitchens. Prices start at $66 per night, and condos and houses are popular options for a stay in Oldsmar. Either way, you'll find a rental for everyone's needs.
Destination guide

Friendly Oldsmar will entice you

The beaches and other outdoor surroundings create an inviting atmosphere in Oldsmar. Well-liked for its restaurants, theme park and golfing, this city is both welcoming and romantic. Big Cat Rescue and Clearwater Marine Aquarium are just a couple of the must-sees in the area. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.


Activities and attractions in Oldsmar

Are you hoping to discover top things to see and do during your stay? Venture out of your cozy vacation rental and experience everything that makes Oldsmar a fun place to get away. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Big Cat Rescue (6.4 mi / 10.4 km)
  • Clearwater Marine Aquarium (9.9 mi / 16 km)
  • Lowry Park Zoo (12.9 mi / 20.8 km)
  • Florida Aquarium (15.7 mi / 25.2 km)
  • Adventure Island (15.8 mi / 25.4 km)
  • Chi Chi Rodriguez Golf Club (2.4 mi / 3.8 km)

Seasonal weather in Oldsmar

If you're planning a vacation around warm-weather activities, August, July, June and September are the hottest months to visit, when temperatures average 91°F.

Natural features

Exploring the natural features in Oldsmar

Whether you're an active traveler or just want to take in the scenery, Oldsmar is a great spot to appreciate mother nature. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Pier 60 Park (10.4 mi / 16.8 km)
  • Sand Key Park (11.1 mi / 17.9 km)
  • Upper Tampa Bay Park (3 mi / 4.8 km)
  • John Chesnut Sr Park (3.3 mi / 5.4 km)
  • Moccasin Lake Nature Park (5.6 mi / 9 km)
  • Lake Rogers Park (7 mi / 11.3 km)
How to get there

Transportation options to and around Oldsmar

Fly into St. Petersburg, FL (PIE-St. Petersburg-Clearwater Intl.), the closest airport, located 9.7 mi (15.6 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Tampa, FL (TPA-Tampa Intl.), which is 9.7 mi (15.7 km) away.

How many vacation rentals are available around Oldsmar, FL?

Our 2020 property listings offer a large selection of 2,468 vacation rentals around Oldsmar. From 1,154 condo and apartment rentals to 844 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a seaside property in Oldsmar?

Oh I do like to be beside the seaside... said... absolutely everyone. Find the perfect locale for the whole gang and you'll be well on your way to basking in beachy bliss! Luckily, there are 591 beachside vacation properties to cast yourself away to. Open to more suggestions? Vrbo has loads of other options to explore, including:

  • 517 water-view vacation rentals.
  • 403 shore-front vacation rentals.
  • 356 beach-view vacation rentals.

Can I rent a condo in Oldsmar?

Sharing is good. But sharing bunk beds and bathrooms with a bunch of strangers can be a bit tiring. Make the most of the time you've got with your loved ones in a condo vacation rental. The space and convenience is hard to beat. In this destination, Vrbo has 945 to choose from. Book now and you could be spending as little as $32 per night. If that doesn't agree with your squad's style, we've got a number of different rental options to select from, such as:

  • House: 893 vacation homes. Prices start from $39 per night.
  • Apartment: 206 vacation homes. Prices start from $35 per night.
  • Hotel: 136 vacation homes. Prices start from $30 per night.

Can I stay in Oldsmar in a large group?

Nothing compares to getting together with old work colleagues or spending a couple of weeks with extended family in a terrific new place. And the best thing is Vrbo has places big enough for everyone. Condo vacation homes are the top choice here for big groups of travelers. Our extensive database presently has 328 available. If you're traveling in a large group, the vacation rental options that are suitable for you include:

  • If yours is a group of 6, we have 733 vacation homes perfectly suited for that size. Spend a night for as little as $45.
  • Need a vacation property for 8 guests? We have 325 that will serve you well. The starting price is $73 per night.
  • Arranging a trip away with a group of 5? We've got 179 vacation homes that will meet your needs. Prices start from $55 per night.

You and your crew will be more than satisfied when you arrange your Oldsmar escape through us!

Where are the cheapest rentals in Oldsmar?

Forget those soulless chain-hotel rooms! Cherish the charm of living like a local in a budget-friendly rental instead. Have a look at the great options available now on Vrbo. Turtle Creek is perfect for bargain hunters. And with 8 Vrbo rentals at an average price of $70 a night, it isn't hard to see why. Another 70 Vrbo rentals are on offer in or around South Tampa. With an average price of $133 a night, you're sure to grab a deal worth bragging to your friends about.

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