Oldsmar vacation rentals

We found 5,955 vacation rentals — enter your dates for availability

Discover a selection of 11 homes and other vacation rentals in Oldsmar that are perfect for your trip. Whether you're staying in a vacation rental with family, friends, or just your furry companion, you'll have the best amenities for spending time at your home away from home, which might include WiFi and a fireplace. You'll be able to choose a rental to meet everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Oldsmar

Showing deals for:Mar 6 - Mar 13

Image gallery for 2 kitchens, Canoe, kayak on Sunset Lake + 700sqf apt Perfect for family getaways

Get our canoe for a peaceful short stroll to Sunset lake
8.4 out of 10, Very good, (24 reviews)
Very good
(24 reviews)

2 kitchens, Canoe, kayak on Sunset Lake + 700sqf apt Perfect for family getaways

Odessa, FL

10% off
Price is CA $1,259
CA $10,941 total
includes taxes & fees
2 kitchens, Canoe, kayak on Sunset Lake + 700sqf apt Perfect for family getaways

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Find out more about Oldsmar

Why visit Oldsmar

  • Outdoor Activities: Oldsmar boasts beautiful parks and nearby beaches, perfect for relaxation and family fun.
  • Charming Atmosphere: Experience a welcoming small-town vibe with friendly locals that enhance your visit.
  • Engaging Local Culture: Explore surrounding neighbourhoods that offer romantic excursions and vibrant cultural experiences.
  • Variety of Accommodations: Choose from spacious condos, private vacation homes, and apartments to suit your needs.
  • Family-Friendly Attractions: Enjoy a range of activities that cater to both adults and children for a memorable getaway.

Popular types of accommodation in Oldsmar

Planning a getaway to Oldsmar? You're in for a treat. Discover a range of spacious accommodations perfect for your needs, from cozy condos to houses and apartments. Whether you're searching for friendly places with multiple bedrooms or a relaxing retreat, Oldsmar rentals offer something for everyone. Enjoy your stay while experiencing the charm of this beautiful destination.

  • Condos: The top choice for vacation rentals in Oldsmar, offering modern amenities and often stunning views.
  • Houses: A fantastic option for families or groups, providing space and privacy for a comfortable stay.
  • Apartments: Ideal for solo travellers or couples, these offer a cozy and convenient home base.
  • Cottages: Quaint and charming, perfect for those seeking a relaxing retreat in a picturesque setting.
  • Villas: Luxurious and spacious, villas provide an upscale experience with plenty of room to unwind.**

Top attractions near Oldsmar

Oldsmar, Florida, is an ideal destination for outdoor and family vacations, offering a delightful mix of urban parks, beautiful beaches, and entertainment venues. Visitors can enjoy a variety of attractions that provide both city experiences and opportunities for relaxation. Whether you're travelling with family or friends, Oldsmar's charm and activities promise an enjoyable getaway for everyone.

  • Raymond James Stadium: Experience the thrill of live sports and entertainment at this iconic stadium, known for its vibrant atmosphere and family-friendly events, located 17.7km from Oldsmar.
  • Clearwater Beach: Enjoy sun-soaked days on one of Florida's most beautiful beaches, famous for its soft white sands and crystal-clear waters, just 17.7km away from Oldsmar.
  • Innisbrook Golf Club: Play a round at this stunning golf resort that caters to families and golfers alike, featuring lush greens and excellent amenities, located 11.3km from Oldsmar.

Things to do recommended for couples

For a romantic getaway in Oldsmar, enjoy a fun round of mini-golf at Congo River Golf in Clearwater, indulge in a lovely meal at 400 Beach, or savor exquisite wines at Tarpon Springs Castle Winery. Each experience offers a unique charm perfect for couples.

Things to do recommended for families

Families visiting Oldsmar can enjoy thrilling games at Celebration Station, unwind at the Eddie C. Moore Softball Complex, or catch a baseball game at BayCare Ballpark, all offering fantastic experiences just a short drive away.

Things to do recommended for groups

Group travelers in Oldsmar can enjoy a shopping spree at Westfield Citrus Park, explore the vibrant Oldsmar Flea Market, or challenge each other at the scenic Westchase Golf Course, all while soaking in the local atmosphere and community spirit.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Oldsmar

When planning your trip, whether you're traveling with friends, family, pets, or seeking extended stays, it's important to apply the right filters based on your priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Oldsmar with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and many others on Vrbo.
  • Traveling to Oldsmar with young kids: Traveling with young children can present some challenges. It’s important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Oldsmar: For many, a family vacation wouldn't be the same without their furry companion by their side. If that resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring everyone feels comfortable and at home.
  • Planning for a long term stay visiting Oldsmar: If you're searching for vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By utilizing the appropriate filters, you can conveniently discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Oldsmar

Oldsmar, Florida, offers a delightful blend of outdoor adventures and family-friendly vibes, making it an ideal vacation spot. You can explore the beautiful nearby beaches, perfect for relaxation and fun. The charming small-town atmosphere, complemented by friendly locals, creates a warm welcome for visitors. Don’t miss the surrounding neighborhoods, where you can enjoy romantic excursions, engaging activities, and a vibrant local culture that truly embodies the essence of a memorable getaway.

  • Clearwater Beach: Located 17.7km from Oldsmar, Clearwater Beach is renowned for its stunning sandy shores and vibrant family-friendly atmosphere. This coastal gem offers various outdoor experiences, from sunbathing and swimming to water sports. The area features numerous resorts and shopping centres, making it an ideal spot for both relaxation and retail therapy. Must-visit attractions include the picturesque beach itself, a family beach perfect for children, and nearby theme parks that promise fun for all ages. Clearwater Beach is a destination where sun, sand, and family enjoyment come together beautifully.
  • Tampa: As a bustling metropolis, Tampa is situated right next to Oldsmar and offers visitors a dynamic blend of activities and attractions. Ideal for families and outdoor enthusiasts, Tampa boasts amusement parks, arena entertainment facilities, and luxurious resorts. Explore charming neighbourhoods, relax at the beach, or take in the stunning views of the bay. With a rich arts scene and diverse dining options, Tampa is a vibrant city that caters to all tastes, ensuring an exciting experience for every traveller.
  • Clearwater: Just 14.5km away from Oldsmar, Clearwater is another delightful destination that captures the essence of Florida’s coastal lifestyle. Known for its beautiful beaches and outdoor recreational activities, Clearwater is perfect for families looking for fun in the sun. The city features extensive resort options, shopping areas, and a welcoming atmosphere. Key attractions include the scenic beaches, a family beach ideal for kids, and charming local neighbourhoods that offer a taste of the community spirit. Clearwater promises a perfect blend of relaxation and adventure.

Best time to go to Oldsmar

If you're planning a trip to Oldsmar, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in March to April and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January61.0°F (16.1°C)Light RainMostly SunnyAverageSlightly Low
February63.7°F (17.6°C)No Rain (Dry)Mostly SunnyAverageAverage
March66.9°F (19.4°C)Light RainMostly SunnySlightly HighSlightly High
April72.5°F (22.5°C)Light RainSunnySlightly HighSlightly High
May77.4°F (25.2°C)Light RainSunnyAverageAverage
June81.9°F (27.7°C)Light RainMostly SunnyAverageAverage
July83.1°F (28.4°C)Light RainMostly SunnyAverageSlightly High
August83.7°F (28.7°C)Light RainMostly SunnyAverageAverage
September81.5°F (27.5°C)Light RainMostly SunnySlightly HighSlightly Low
October76.5°F (24.7°C)Light RainMostly SunnySlightly LowSlightly Low
November69.3°F (20.7°C)Light RainMostly SunnySlightly LowAverage
December64.9°F (18.3°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming getaway? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Vrbo property that suits your budget, feel free to use our filters to narrow your search by price, location, and type of vacation rental. We're here to support you in finding the perfect spot for your travels.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient place for you to plan new adventures, manage your travel arrangements, or review your bookings. Your saved and booked properties are thoughtfully organized into categories: Potential, Upcoming, or Current Trips. To start exploring your Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Friendly Oldsmar will entice you

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

Activities and attractions in Oldsmar

Are you searching for things to do while you're in town? Venture out of your vacation home and check out everything that makes Oldsmar a fun place to get away. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Feather Sound Country Club (9.4 mi / 15.1 km)
  • Tampa Bay Grand Prix (10.5 mi / 16.9 km)
  • TPC of Tampa Bay (11.8 mi / 19 km)

Exploring the natural features in Oldsmar

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Oldsmar is a great place to spend some time outside. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • 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 83°F.

How to get to and around Oldsmar

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

Frequently asked questions

What is the best area to stay in Oldsmar when booking a vacation rental?
When considering a vacation rental in Oldsmar, Florida, a great area to stay in is the East Lake Woodlands neighbourhood. This picturesque community is known for its lush landscapes and tranquil environment, making it an ideal spot for relaxation. With numerous properties available, you can expect a wide range of options, from spacious family homes to charming villas.
How much does it cost to rent a vacation home in Oldsmar?
Prices for vacation 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 travelling 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.
Are there any discounts for Oldsmar vacation 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, Florida, the nearby coastal areas of Clearwater and Dunedin are excellent choices. Clearwater Beach, renowned for its powdery white sands and vibrant atmosphere, is just a short drive away. Here, travellers can find beach houses that offer a range of amenities, including private pools, outdoor grilling areas, and spacious decks for sunbathing or enjoying sunset views. Many properties also come equipped with full kitchens, allowing guests to prepare meals after a day spent on the beach.

Dunedin, with its charming waterfront and relaxed vibe, presents additional options for those seeking a beach retreat. Rentals in this area often feature lush outdoor spaces, some with easy access to the beach and proximity to the picturesque Dunedin Marina. Guests can expect amenities such as bicycles for local exploring, kayaks for water activities, and cozy living rooms great for family gatherings.
What is the most popular type of vacation rental accomodation in Oldsmar?
In Oldsmar, vacation houses are the most popular type of accommodation, with around 47 available throughout the area. These houses typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and private outdoor spaces, making them ideal for families or larger groups. Additionally, several condos, mobile homes, villas, and cottages can be found, offering travellers a variety of choices to suit different preferences. Many of these rentals are located near local parks, such as the serene John Chesnut Sr. Park, providing easy access to nature trails and recreational activities.
Are there any family house rentals in Oldsmar?
In Oldsmar, Florida, there are numerous family-friendly house rentals available—around 22 options to choose from. This vibrant area is great for those looking to enjoy both relaxation and adventure. Many properties boast spacious living areas, fully equipped kitchens ideal for family meals, and outdoor spaces where children can play safely. Amenities such as Wi-Fi and air conditioning are typically included, ensuring comfort throughout your stay.
Can I rent a vacation home with a pool or hot tub in Oldsmar?
In Oldsmar, travellers can find a variety of vacation homes available for rent that feature pools or hot tubs, with around 35 options to choose from. This charming city, located near the picturesque Gulf Coast, offers a range of neighbourhoods that cater to different preferences. Many properties come equipped with private pools, hot tubs, and outdoor spaces ideal for relaxation and entertainment. Guests can also expect amenities such as fully equipped kitchens, spacious living areas, and sometimes even outdoor grills, making it great for family gatherings or social events.
Can I find long-stay vacation rentals in Oldsmar?
A long-stay vacation 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 a variety of pet-friendly house rentals available, with around 25 options to choose from. Many of these properties come equipped with amenities such as private backyards, spacious living areas, and fully stocked kitchens, making them ideal for families or groups travelling with pets.
Are there any remote work vacation rentals in Oldsmar?
In Oldsmar, Florida, there are numerous remote work vacation rentals available, with around 60 options to choose from. This charming community, situated conveniently between Tampa and Clearwater, offers a variety of properties well-suited for those looking to work remotely. Many rentals feature dedicated workspaces, including desks and ergonomic chairs, ensuring a comfortable environment for productivity. Travellers can also expect amenities such as Wi-Fi, laptop workspaces, and even computer monitors in some properties, suiting the needs of digital nomads. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Oldsmar vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 vacation rental?
The best time to visit Oldsmar for a vacation rental is during the peak season, which spans from February to April. This period is particularly popular among travellers seeking to enjoy the sunny Florida weather and partake in a variety of outdoor activities. With temperatures typically ranging from the mid to high 20s Celsius, it's an ideal time for leisurely strolls, sightseeing, and exploring the nearby parks and nature reserves.

As the region experiences a vibrant atmosphere, visitors can indulge in water sports along the beautiful coastline or relax at local attractions, such as the nearby Tampa Bay. This season attracts a diverse crowd, making it easy to connect with fellow adventure enthusiasts and families alike.

If you're looking for a more budget-friendly option, consider visiting in October. This month offers a quieter experience with fewer tourists, allowing you to savour the natural beauty of Oldsmar at a more relaxed pace. The weather remains pleasant, and you can still enjoy outdoor activities without the crowds.
How early should I book a Oldsmar vacation rental?
Book your Oldsmar vacation 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 vacation 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 vacation 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 vacation 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.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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