104+ Vacation Rentals & Holiday Homes in Oldsmar |
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Oldsmar Accommodations - Hotels & Rentals

About Oldsmar Vacation Rentals

Discover More than 104 Incredible Getaway Rentals Available in Oldsmar. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Oldsmar.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Oldsmar, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Oldsmar. The Average Size of Places to Stay Near Oldsmar is 553.17 ft², with Prices Averaging US $271 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Oldsmar. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Oldsmar

Type Count
Vacation Homes 45
Holiday Apartments 9
Villas 5

Use these Quick Filters to Find a Vacation Rental in Oldsmar

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Oldsmar with Online Reservations.

Weather in Oldsmar, FL

View the weather forecast for Oldsmar before booking your Oldsmar Vacation Rentals to confirm your best time to go.

December - February
High 75°F       Low 58°F
March - May
High 86°F       Low 61°F
June - August
High 91°F       Low 76°F
September - November
High 89°F       Low 63°F

Activities OldsmarGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World OldsmarGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


Oldsmar Flea Market
Oldsmar Historical Society Museum
Z - A Specialty Spa
Advanced Primary Care
Busch Gardens Tampa Bay
Port of Tampa
Tampa Riverwalk
University of South Florida
Seminole Hard Rock Casino Tampa
Tampa Convention Center
Raymond James Stadium
Florida Aquarium
Amalie Arena
Clearwater Marine Aquarium
Lowry Park Zoo
John's Pass Village & Boardwalk
Adventure Island
Sand Key Park
Tropicana Field
MacDill Air Force Base

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Z - A Specialty Spa 243 Properties
East Lake Woodlands 191 Properties
Elw Woods Landing 186 Properties
Quail Forest 182 Properties
Oldsmar Historical Society Museum 155 Properties
Advanced Primary Care 147 Properties
Oldsmar Flea Market 143 Properties
Turtle Creek 127 Properties

Frequently Asked Questions About Oldsmar?

What are the top hotels, lake houses & vacation rentals in Oldsmar?

We provide an array of great vacation destinations in Oldsmar. If you are looking to stay in or around the Oldsmar area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Oldsmar:

How many Hotels & Vacation Rentals have private pools in Oldsmar?

We have 2 Hotels & Vacation Rentals featuring a private pool in and near Oldsmar. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Oldsmar is best for families?

Searching for a family-friendly getaway in Oldsmar? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Oldsmar?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 104 in the Oldsmar area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Oldsmar.

Nearby Neighborhood (4) 
Neighborhood Property Count
East Lake Woodlands Vacation Rentals in Tampa, Florida 191
Quail Forest Vacation Rentals in Tampa, Florida 182
Elw Woods Landing Vacation Rentals in Tampa, Florida 186
Turtle Creek Vacation Rentals in Tampa, Florida 127

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