Choose from 90 vacation rentals located in Oldsmar, Florida. Top filters in Oldsmar include Air conditioner, Internet / Wifi, and Kitchen or Kitchenette. Prices range from $121 to $2,216 per night. Our most popular vacation rental types near Oldsmar are Hotel and RV.

Top vacation rentals in Oldsmar

Beach towels
4.7
Outstanding(118 Reviews)
Centrally located to beaches, Close to Bush Gardens Pets Welcome Free Wifi
Villa
 in Tampa
7 guests · 3 bedrooms · 2 baths
Garden · Pool · Pets allowed

Looking for a memorable stay in Oldsmar? Our Villa might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.

$$$$
vrbo logo
View deal
Property grounds
5.0
Outstanding(244 Reviews)
You Are Closer to Your Own Private Paradise on Beautiful Tampa Bay!
House
 in Safety Harbor
6 guests · 3 bedrooms · 2 baths
Garden · Pool · Kitchen or Kitchenette

This attractive House in Oldsmar, $545 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
vrbo logo
View deal
Property building
4.4
Excellent(471 Reviews)
Holiday Inn Express Hotel & Suites Tampa-Oldsmar, an IHG Hotel
Hotel
 in Oldsmar
2star
1 king bed
Pool · Pets allowed · Kitchen or Kitchenette

Nestled in Oldsmar, this Hotel is perfect for your next vacation. Enjoy Holiday Inn Express Hotel & Suites Tampa-Oldsmar, an IHG Hotel's top-rated amenities, including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
booking logo
View deal
Property building
4.1
Excellent(124 Reviews)
Hilton Garden Inn Tampa Northwest/Oldsmar
Hotel
 in Oldsmar
3star
1 king bed
Pool · Pets allowed · Kitchen or Kitchenette

Enjoy the best of Oldsmar in our Hotel, Hilton Garden Inn Tampa Northwest/Oldsmar. A stunning property with amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
booking logo
View deal

Vacation rentals with air conditioning in Oldsmar

Fridge, microwave, oven, stovetop
4.8
Outstanding(79 Reviews)
Beautifully, Renovated Home in Quiet Cul de Sac! Close to EVERYTHING!
House
 in Oldsmar
5 guests · 2 bedrooms · 2 baths
Garden · Pool · Kitchen or Kitchenette

Are you ready to indulge in a relaxing getaway? Our House in Oldsmar has everything you need for a rejuvenating stay. Treat yourself to Beautifully, Renovated Home in Quiet Cul de Sac! Close to EVERYTHING! 's exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.

$$$$
vrbo logo
View deal
Interior
4.8
Outstanding(100 Reviews)
family friendly, gated community, two pools, lake outside back door.
Apartment
 in Oldsmar
4 guests · 2 bedrooms · 2 baths
Garden · Pool · Kitchen or Kitchenette

This attractive Apartment in Oldsmar, $211 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
vrbo logo
View deal
Fridge, microwave, oven, stovetop
4.8
Outstanding(62 Reviews)
Beautiful Condo in prime Florida location within premier gated community.
Apartment
 in Oldsmar
4 guests · 2 bedrooms · 2 baths
Garden · Pool · Kitchen or Kitchenette

Indulge in a peaceful retreat at Beautiful Condo in prime Florida location within premier gated community., our elegant Apartment in Oldsmar. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
vrbo logo
View deal
Swimming pool
4.1
Excellent(79 Reviews)
Courtyard Tampa Oldsmar
Hotel
 in Oldsmar
3star
1 king bed, 1 sofa bed
Pool · Kitchen or Kitchenette · Air conditioner

This attractive Hotel in Oldsmar, $152 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
booking logo
View deal
city photo
Oldsmar

Oldsmar travel guide

Let us help you plan your perfect Oldsmar vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Oldsmar, and more.

Frequently asked questions

What are the most popular vacation rental amenities in Oldsmar?

  • Air conditioner
  • Internet / Wifi
  • Kitchen or Kitchenette

What are the must-visit tourist attractions in Oldsmar, FL?

Oldsmar, FL is a great place to visit for tourists. There are a number of attractions that you should not miss while visiting. These include:

  • Upper Tampa Bay Trail
  • John Chesnut Sr. Park
  • Oldsmar Flea Market
  • Escape Room Adventure

The Upper Tampa Bay Trail offers stunning views of the Tampa Bay area, while John Chesnut Sr. Park is a great place to explore nature. Oldsmar Flea Market is a great spot to find unique souvenirs, and Escape Room Adventure is a fun and exciting way to spend an afternoon.

How can I get around in Oldsmar, FL?

You can get around in Oldsmar, FL in a variety of ways:

  • Walking
  • Biking
  • Public Transportation
  • Rideshare Services

Oldsmar also offers plenty of parking, making it easy to get around by car as well.

Where can I find affordable accommodation in Oldsmar, FL?

Oldsmar, FL offers a variety of affordable accommodation options. Here are some of the top picks:

  • The Holiday Inn Express Oldsmar Tampa
  • Hampton Inn Tampa East/Ybor City
  • Suburban Extended Stay Hotel Oldsmar
  • Extended Stay America - Tampa - Oldsmar

These hotels offer comfortable rooms at competitive prices, making them ideal for those looking for an affordable stay in Oldsmar, FL.

What is the culture like in Oldsmar, FL?

Oldsmar, FL is a small town located in the Tampa Bay area of Florida. It is known for its vibrant culture and friendly atmosphere. Here are five points about the culture in Oldsmar, FL:

  • The town is very family-friendly, with lots of activities for kids and adults alike.
  • The town has a strong sense of community, with many local events and festivals.
  • The town is known for its beautiful beaches, parks, and outdoor activities.
  • The town is home to a thriving arts and culture scene, with galleries, museums, and performing arts groups.
  • The town is known for its diverse population, with people from all backgrounds and walks of life.

Is Oldsmar, FL safe to travel to?

Oldsmar, FL is generally considered a safe place to travel to. Here are a few safety tips for travelers:

  • Be aware of your surroundings and who is around you.
  • Don't leave your belongings unattended.
  • Keep your valuables secure and out of sight.

What are the popular shopping destinations in Oldsmar, FL?

Oldsmar, FL is home to some of the most popular shopping destinations in the area. Here are some of the must-visit places:

  • Tampa Premium Outlets
  • Oldsmar Flea Market
  • Oldsmar Shopping Center

Whether you’re looking for a great bargain or the latest fashion trends, Oldsmar has something for everyone!

What are the best neighborhoods to visit in Oldsmar, FL?

The best neighborhoods to visit in Oldsmar, FL are:

  • East Lake Woodlands
  • Tampa Bay Golf & Country Club
  • Tarpon Woods Golf Club

These neighborhoods offer a variety of activities, such as golfing, biking, and walking trails, as well as plenty of shopping and dining options.

Where is Oldsmar, FL?

Oldsmar, FL is a city located in Pinellas County, Florida. It is situated about 15 miles northwest of Tampa and is known for its many parks, trails, and recreational activities. The population of the city was 13,591 as of the 2010 census, making it the 15th most populous city in Pinellas County.

What are the most popular vacation rental amenities in Oldsmar, FL?

The most popular vacation rental amenities in Oldsmar, FL include:

  • Fully equipped kitchens
  • Modern appliances
  • Spacious living areas
  • High-speed internet
  • On-site swimming pools

These amenities provide guests with the comforts of home, as well as the convenience of a hotel. Fully equipped kitchens allow guests to prepare meals in the comfort of their own home, while modern appliances and high-speed internet provide the necessary tools for a modern lifestyle. Spacious living areas provide plenty of room to relax and unwind, while on-site swimming pools provide a great way to cool off in the Florida heat.

What are the top things to do in Oldsmar, FL?

Oldsmar, FL is a great place to explore and enjoy the outdoors. Here are some of the top things to do in Oldsmar:

  • Visit the Oldsmar Flea Market
  • Go for a hike in Brooker Creek Preserve
  • Check out the Tampa Bay Skating Academy
  • Attend the Oldsmar Art Festival

Take in the views at the R.E. Olds Park, or take a boat tour of Tampa Bay. There's something for everyone in Oldsmar, FL!

What do I need to know before visiting Oldsmar, FL?

Oldsmar is a small city located in Pinellas County, Florida. It is known for its beautiful parks, outdoor activities, and vibrant downtown area. Before visiting Oldsmar, here are a few things to keep in mind:
  • The weather in Oldsmar is typically hot and humid year-round.
  • The city has many parks and outdoor activities to enjoy.
  • Be sure to check out the vibrant downtown area.
Oldsmar is also a great place to shop, dine, and explore. Before visiting, make sure to research the local attractions and restaurants to make the most of your trip.

What is the price range for rentals in Oldsmar?

Vacation rentals in Oldsmar have a price range between $121-$2,216. The average price for rentals in Oldsmar is $204 per night.

Explore near Oldsmar

Rentals near top attractions

Related vacation destinations

Nearby vacation destinations

Travel inspiration