Oldsmar holiday lettings

We found 5,837 holiday rentals — enter your dates for availability

Discover a selection of 20 homes and other holiday rentals in Oldsmar that are perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll have the amenities that you expect and more, such as parking and air conditioning. What you'll find is a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Oldsmar

Showing deals for:20 Feb - 27 Feb

Image gallery for Sleeps 20+, 2 houses, Swim-Spa, hot tub, bachelor and party place

2 houses, Hot tub, Swimspa, minigolf, pole table, poker table, kajaks, canoes
10 out of 10, Exceptional, (35 reviews)
Exceptional
(35 reviews)

Sleeps 20+, 2 houses, Swim-Spa, hot tub, bachelor and party place

Tampa, FL

8% off
Price is £10,708
for 7 nights, 1 home
£1,530 per night
includes taxes & fees
Sleeps 20+, 2 houses, Swim-Spa, hot tub, bachelor and party place

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Friendly Oldsmar will entice you

The beaches and surrounding scenery provide a peaceful ambience to your holiday home in Oldsmar. This city's restaurants, theme park and golfing attract many visitors, as does its welcoming and romantic location. Raymond James Stadium and Port of Tampa are just a couple of the must-see attractions in the area. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Oldsmar

Do you want to find top things to see and do in the area? Venture out of your cosy holiday rental and check out everything that makes Oldsmar a one-of-a-kind holiday spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Busch Gardens Tampa Bay (14.9 mi / 23.9 km)
  • Tampa Bay Downs (1.5 mi / 2.4 km)
  • Innisbrook Golf Club (7.7 mi / 12.3 km)
  • Tampa Bay Grand Prix (10.5 mi / 16.9 km)
  • TPC of Tampa Bay (11.8 mi / 19 km)
  • ZooTampa at Lowry Park (12 mi / 19.3 km)

Exploring the natural features in Oldsmar

Whether you're an adventurous traveller or just want to take in the scenery, Oldsmar is a great place to get outside. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Tampa Bay (20.1 mi / 32.4 km)
  • Ben T. Davis Beach (6.8 mi / 11 km)
  • Coachman Park (9.6 mi / 15.5 km)
  • Al Lopez Park (10.3 mi / 16.5 km)
  • Clearwater Beach (10.6 mi / 17 km)
  • Pier 60 Park (10.7 mi / 17.3 km)

Seasonal weather averages in Oldsmar

If warm-weather activities are high on your list, August, July, September and June are the hottest months to visit, when temperatures average 28°C.

How to get to and around Oldsmar

Fly into Tampa, FL (TPA-Tampa Intl.), the closest airport, located 8.8 mi (14.2 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into St. Petersburg, FL (PIE-St. Petersburg-Clearwater Intl.), which is 9 mi (14.4 km) away.

Frequently asked questions

What is the best area to stay in Oldsmar when booking a holiday rental?
When considering a holiday rental in Oldsmar, Florida, a fantastic area to stay is the vicinity around Oldsmar Park. This neighbourhood not only offers a serene setting but also provides easy access to the beautiful Oldsmar City Hall and the scenic waterfront of Tampa Bay. With a selection of properties available, this area is ideal for those looking to immerse themselves in the local charm while enjoying nearby recreational activities.

Another delightful option is the area near the Tampa Bay Downs, which is superb for racing enthusiasts. The lively atmosphere of the nearby restaurants and shops adds to the appeal, making it an excellent spot for families and couples alike. There are numerous rental properties here, suiting various preferences, from cosy apartments to larger family homes.
How much does it cost to rent a holiday home in Oldsmar?
Prices for holiday rentals in Oldsmar vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Oldsmar to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Oldsmar holiday house rentals?
You can find great discounts on house rentals in Oldsmar on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Oldsmar?
For renting a beach house in Oldsmar, the picturesque vicinity of nearby Tampa Bay is an excellent choice. The area along the shores of the bay, specifically around the nearby beaches of Clearwater and Honeymoon Island State Park, offers a variety of holiday rentals that cater to different preferences. Many properties in this region feature amenities such as private pools, outdoor dining areas, and direct beach access, making them superb for families or groups seeking a relaxing seaside getaway.

The Clearwater Beach area is particularly popular, known for its vibrant atmosphere and stunning sunsets. Here, travellers can find beachfront houses and condos equipped with modern kitchens, spacious living areas, and balconies that offer panoramic views of the Gulf of Mexico. Nearby, Honeymoon Island State Park provides a more tranquil setting, with opportunities for nature walks and birdwatching. Rentals in this area often come with outdoor showers and easy access to the park's pristine beaches.
What is the most popular type of holiday rental accomodation in Oldsmar?
In Oldsmar, holiday houses are the most popular rental choice, with around 47 available throughout the area. These houses typically offer spacious living arrangements, featuring multiple bedrooms, fully equipped kitchens, and private outdoor spaces—ideal for families or groups looking to enjoy the sunny Florida climate. Additionally, travellers can find several condos, mobile homes, villas, and cottages, providing a variety of options to suit different preferences.
Are there any family house rentals in Oldsmar?
In Oldsmar, Florida, there are numerous family-friendly house rentals available, with around 22 options to choose from. This charming area is greatly situated between Tampa Bay and the Gulf of Mexico, making it an excellent base for families seeking both relaxation and adventure. Many of these homes offer spacious living areas, well-equipped kitchens for preparing family meals, and outdoor spaces where children can play and enjoy the Florida sunshine.
Can I rent a holiday home with a pool or hot tub in Oldsmar?
In Oldsmar, there are many holiday homes available for rent with pools and hot tubs, with approximately 35 options to choose from. This charming city, located in the Tampa Bay area, offers a variety of neighbourhoods where these properties can be found, including the picturesque areas surrounding Oldsmar Park and the waterfront along the Old Tampa Bay.
Can I find long-stay holiday rentals in Oldsmar?
A long-stay holiday rental in Oldsmar is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Oldsmar?
In Oldsmar, there are several pet-friendly house rentals available, offering a variety of options for travellers with furry companions. Many of these properties feature amenities such as spacious backyards, which are great for pets to roam and play. You can expect to find rentals equipped with modern kitchens, comfortable living areas, and often outdoor spaces like patios or decks where you can relax with your pet.

The neighbourhood is also conveniently located near parks that welcome pets, such as the nearby Oldsmar Sports Complex, which provides ample green space for walking and exercising your dog. Additionally, the scenic shoreline along Old Tampa Bay offers beautiful views and walking trails that are pet-friendly, allowing for enjoyable outings with your four-legged friends.
Are there any remote work holiday rentals in Oldsmar?
In Oldsmar, Florida, there are numerous options for remote work holiday rentals, with around 60 available throughout the area. Travellers can expect properties that cater specifically to remote workers, featuring amenities such as high-speed Wi-Fi, dedicated workspaces with desks and chairs, and even safe storage for valuables. Many rentals also come equipped with computer monitors and laptop workspaces, ensuring a comfortable and productive environment for those balancing work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Oldsmar holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Oldsmar with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Oldsmar?
In Oldsmar, popular rental amenities include free in-room Wi-Fi, heated pools, and access to swimming pools, making it a pleasant choice for travellers looking to relax and unwind. Additionally, many rentals come equipped with kitchens, allowing guests to prepare their own meals, and often feature dishwashers for convenient clean-up.
When is the best time to visit Oldsmar for a holiday rental?
September is a fantastic time to visit Oldsmar, as the summer crowds begin to thin out and the weather remains pleasantly warm. This month typically features temperatures in the low 30s Celsius, creating ideal conditions for outdoor activities and exploration. Visitors can enjoy the region's beautiful parks, such as the serene John Chesnut Senior Park, where you can stroll along scenic trails and observe local wildlife.

The peak travel season in Oldsmar runs from February to April, when tourists flock to the area to enjoy the vibrant local culture and partake in various festivals and events. During this period, the pleasant climate and lively atmosphere make it great for those seeking a blend of relaxation and adventure. The stunning waterfront views and proximity to Tampa Bay allow for convenient day trips filled with sightseeing and outdoor fun.

For those looking for more affordable options, October provides a wonderful alternative. The weather remains warm, and the fewer crowds allow you to enjoy the local attractions at a more leisurely pace. It's an excellent time for families and solo travellers who appreciate the tranquillity of the off-peak season while still having access to Oldsmar's amenities.
How early should I book a Oldsmar holiday rental?
Book your Oldsmar holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Oldsmar home rental booking on Vrbo?
To find Oldsmar holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Oldsmar holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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