103+ Private Villas and Holiday Rentals in Oldsmar |
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Oldsmar Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Oldsmar

Discover more than 103 vacation rentals available in Oldsmar. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Oldsmar.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Oldsmar, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Oldsmar. On average, places to stay near Oldsmar offer 540.06 ft², with nightly prices averaging US $272.

With Casai, finding and comparing holiday rentals in Oldsmar is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Oldsmar

Type Count
Vacation Homes 67
Holiday Apartments 9
Villas 5

Use these Quick Filters to Find a Holiday Rental in Oldsmar

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Oldsmar.

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

Top Attractions Around Oldsmar, FL

Casai offers a large selection of top attractions around Oldsmar . Research things to do on your vacation before you visit Oldsmar.


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

Other Places to Stay in Oldsmar, FL


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 holiday rentals in Oldsmar?

With numerous options available in Oldsmar, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Oldsmar:

How many holiday rentals have private pools in Oldsmar?

Discover a selection of holiday rentals with private pools near Oldsmar with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Oldsmar are best for families?

If you're searching for a family-friendly holiday home in Oldsmar, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Oldsmar:

How many Casai.com holiday rentals are available in Oldsmar?

As of 2025, Casai boasts over 103 properties listed in the Oldsmar area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties 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

People Also Ask

There are 103 Oldsmar, FL Holiday Rentals

Recently Booked Holiday Rentals in Oldsmar