Oldsmar holiday rentals

We found 6,038 holiday rentals — enter your dates for availability
Discover a selection of 11 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:18 Dec - 25 Dec

Bar (on property)
Pool and Hot tub
Exterior
Terrace/patio
Exceptional
(67 reviews)

NEW Fully renovated Gulf front home w/private resort style pool, outdoor kitchen

Crystal Beach

8% off
AU$11,786
for 7 nights, 1 home
AU$1,684 per night
includes taxes & fees
NEW Fully renovated Gulf front home w/private resort style pool, outdoor kitchen
Private kitchen
Interior
Private kitchen
Living area
Exceptional
(18 reviews)

Heated Pool, Hot Tub, Bikes, Minutes to Clearwater Beach & Honeymoon Island!

Dunedin

5% off
AU$5,861
for 7 nights, 1 home
AU$837 per night
includes taxes & fees
Heated Pool, Hot Tub, Bikes, Minutes to Clearwater Beach & Honeymoon Island!
Interior
Pool
Front of house in a quiet, manicured neighborhood
Cozy family room
Wonderful
(133 reviews)

Palm Harbor Paradise | Spacious Home with Pool & Hot Tub

Palm Harbor

6% off
AU$4,523
for 7 nights, 1 home
AU$646 per night
includes taxes & fees
Palm Harbor Paradise | Spacious Home with Pool & Hot Tub
Exterior
Beach
Private kitchen
Pool
Exceptional
(58 reviews)

*Pool* 8.5 miles to Honeymoon Island. 4 bdr

Palm Harbor

8% off
AU$5,640
for 7 nights, 1 home
AU$806 per night
includes taxes & fees
*Pool* 8.5 miles to Honeymoon Island. 4 bdr
Living area
Dining
Pool
Outdoor dining
Exceptional
(41 reviews)

Gorgeous private heated pool house, short drive to the beach!

Largo

8% off
AU$3,121
for 7 nights, 1 home
AU$446 per night
includes taxes & fees
Gorgeous private heated pool house, short drive to the beach!
Interior
Interior
Exterior
Interior
Exceptional
(9 reviews)

Lakefront Cabin #411, 10mins to Beach/Dog Friendly/Prime Location/BOOK TODAY

Seminole

7% off
AU$1,581
for 7 nights, 1 cabin
AU$226 per night
includes taxes & fees
Lakefront Cabin #411, 10mins to Beach/Dog Friendly/Prime Location/BOOK TODAY
Private kitchen
Firelight by the water makes evenings linger and memories settle in.
Dining
Fully screened outdoor space for lounging, dining, grilling, and relaxing.
Exceptional
(14 reviews)

Pelican Drift:Blue Jays Spring Training Retreat!Salt Pool,Hot Tub,Xbox,Game Room

Palm Harbor

5% off
AU$7,572
for 7 nights, 1 home
AU$1,082 per night
includes taxes & fees
Pelican Drift:Blue Jays Spring Training Retreat!Salt Pool,Hot Tub,Xbox,Game Room
Pool
Private kitchen
Room
Living area
Excellent
(56 reviews)

Casa de Corazon-A comfortable home with pool in a quiet neighborhood near beach.

Largo

14% off
AU$1,889
for 7 nights, 1 home
AU$270 per night
includes taxes & fees
Casa de Corazon-A comfortable home with pool in a quiet neighborhood near beach.
Living area
Property grounds
Terrace/patio
Interior
Wonderful
(22 reviews)

Cozy Coastal Tiny Home Retreat 🌴

Clearwater

8% off
AU$1,145
for 7 nights, 1 home
AU$164 per night
includes taxes & fees
Cozy Coastal Tiny Home Retreat 🌴
Dining
Full kitchen view
Dining
Screened porch
Exceptional
(16 reviews)

Holiday Retreat

Holiday

7% off
AU$2,639
for 7 nights, 1 home
AU$377 per night
includes taxes & fees
Holiday Retreat
Property grounds
Private kitchen
Room
Interior
Exceptional
(49 reviews)

Beautiful and comfortable room Apt # 2

Tampa

8% off
AU$1,001
for 7 nights, 1 apartment
AU$143 per night
includes taxes & fees
Beautiful and comfortable room Apt # 2
Bedroom #2 - Queen sized bed with a Smart TV for you to relax and watch a movie!
Full kitchen equipped for all of your culinary desires. Including coffee!
Free yourself from any stress in this beautiful private oasis!
Spend time with your group over a movie or a card game!
Exceptional
(30 reviews)

Tropical & Elegant l Pool, Bonfire, Outdoor Entertainment l Central Location

Tampa

13% off
AU$3,605
for 7 nights, 1 home
AU$515 per night
includes taxes & fees
Tropical & Elegant l Pool, Bonfire, Outdoor Entertainment l Central Location
Dining
Pool
Private kitchen
Outdoor dining
Exceptional
(8 reviews)

Private House with Heated Pool, Close to Attractions!

Holiday

7% off
AU$2,523
for 7 nights, 1 home
AU$360 per night
includes taxes & fees
Private House with Heated Pool, Close to Attractions!
Room
Pool
Interior
Terrace/patio
Exceptional
(18 reviews)

101 · ☀Pool✔ Beach✔ Self Checkin✔ Free Parking✔

Clearwater Beach

8% off
AU$1,566
for 7 nights, 1 apartment
AU$224 per night
includes taxes & fees
101 · ☀Pool✔ Beach✔ Self Checkin✔ Free Parking✔
Need a book to read - help yourself to book stop across the street
Pool
Living area
Kitchen counter
Exceptional
(102 reviews)

Cozy Cottage, 1 minute walk to Beach

Clearwater Beach

8% off
AU$3,797
for 7 nights, 1 home
AU$542 per night
includes taxes & fees
Cozy Cottage, 1 minute walk to Beach
Pool
Private kitchen
Interior
Property grounds
Exceptional
(6 reviews)

2-bedroom beach condo, water views in beautiful Sand Key, 4 mins to Clearwater

Clearwater Beach

8% off
AU$5,198
for 7 nights, 1 apartment
AU$743 per night
includes taxes & fees
2-bedroom beach condo, water views in beautiful Sand Key, 4 mins to Clearwater
Primary king bedroom with ensuite.
Kitchen
adjacent to living room
Bonus room with 2 sofabeds.
Exceptional
(25 reviews)

Family Getaway - Relax, Enjoy, Adventure Sleeps 8

Tarpon Springs

8% off
AU$2,682
for 7 nights, 1 home
AU$383 per night
includes taxes & fees
Family Getaway - Relax, Enjoy, Adventure Sleeps 8
Living area
Beach
Private kitchen
Marina
Exceptional
(7 reviews)

Indulge in Waterfront Elegance: Stunning 4/3 Townhome - 2800 Square Feet

Clearwater Beach

8% off
AU$8,689
for 7 nights, 1 home
AU$1,241 per night
includes taxes & fees
Indulge in Waterfront Elegance: Stunning 4/3 Townhome - 2800 Square Feet
Interior
Dock across the street at Nautical Landings!
Marina
Exterior
Exceptional
(21 reviews)

Nautical Landings West close to Honeymoon Island and dock access!

Dunedin

7% off
AU$2,573
for 7 nights, 1 apartment
AU$368 per night
includes taxes & fees
Nautical Landings West close to Honeymoon Island and dock access!
Interior
Pool
Interior
Room
Wonderful
(19 reviews)

Condo On The Beach - Heated Pool - Self Check-in

Belleair Beach

8% off
AU$2,318
for 7 nights, 1 apartment
AU$331 per night
includes taxes & fees
Condo On The Beach - Heated Pool - Self Check-in
Outdoor dining
Pool
Exterior
Interior
Exceptional
(57 reviews)

Renovated condo at Avalon Clearwater

Clearwater

7% off
AU$1,871
for 7 nights, 1 apartment
AU$267 per night
includes taxes & fees
Renovated condo at Avalon Clearwater
60 inch Smart TV!
Private kitchen
Outdoor dining
Room
Exceptional
(59 reviews)

Perfect Location! Coral Sands Beach House II at Indian Rocks Beach!

Indian Rocks Beach

8% off
AU$3,254
for 7 nights, 1 home
AU$465 per night
includes taxes & fees
Perfect Location! Coral Sands Beach House II at Indian Rocks Beach!
CBC from the Gulf
Gulf of Mexico in front of CBC
Your private balcony
Sunset from your balcony
Exceptional
(71 reviews)

Gorgeous Hideaway on the Beach-Crescent Beach Club

Clearwater Beach

7% off
AU$3,083
for 7 nights, 1 apartment
AU$440 per night
includes taxes & fees
Gorgeous Hideaway on the Beach-Crescent Beach Club
Living area
Dining
Room
Exterior
Exceptional
(43 reviews)

Quaint Bungalow just off Main Street!

Dunedin

8% off
AU$3,408
for 7 nights, 1 cottage
AU$487 per night
includes taxes & fees
Quaint Bungalow just off Main Street!

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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 Busch Gardens Tampa Bay 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)
  • Celebration Station (4.8 mi / 7.8 km)
  • Rocky Point Golf Course (7.6 mi / 12.2 km)
  • Innisbrook Golf Club (7.7 mi / 12.3 km)
  • Feather Sound Country Club (9.4 mi / 15.1 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)
  • Cypress Point Park (9.7 mi / 15.5 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, the area surrounding the city centre is particularly appealing. This neighbourhood offers a charming blend of accessibility and local attractions. One of the highlights nearby is the serene Oldsmar City Park, where visitors can enjoy a leisurely stroll or a picnic amidst lush greenery. Additionally, the nearby Mobbly Bayou Wilderness Preserve provides an excellent opportunity for nature enthusiasts to explore scenic trails and observe local wildlife.In terms of holiday rentals, the city centre area boasts a variety of properties, making it a convenient choice for families and couples alike. With diverse options available, you can find accommodations that suit different preferences and budgets.
Where are the best areas for renting a beach house in Oldsmar?
For renting a beach house in Oldsmar, the nearby coastal areas of Clearwater and Dunedin are excellent options. Clearwater Beach, known for its soft white sands and vibrant setting, offers a range of holiday rentals, including beachfront condos and charming cottages. Many properties come equipped with amenities such as outdoor patios or balconies with ocean views, full kitchens, and easy access to local attractions, including the famous Pier 60 and a variety of water sports activities.Dunedin, just a short drive away, provides a more laid-back vibe with its picturesque waterfront parks and a quaint downtown area filled with shops and restaurants. Here, visitors can find lovely beach houses and villas, often featuring private gardens, barbecues, and community amenities like swimming pools or direct access to the beach. Additionally, this area is known for its beautiful sunsets and proximity to the scenic Honeymoon Island State Park, where rentals may offer the chance to enjoy nature trails and unspoiled beaches.
What is the most popular type of holiday rental accomodation in Oldsmar?
In Oldsmar, holiday houses are the most popular type of holiday rental, with around 75 available throughout the area. These properties typically offer spacious layouts, featuring multiple bedrooms, fully equipped kitchens, and private outdoor spaces, making them ideal for families or groups looking for comfort and flexibility. Additionally, there are approximately 33 condos available, which provide a more compact living option, often with amenities such as swimming pools and fitness centres. For those seeking alternative accommodations, there are also 12 mobile homes and 12 villas, suiting various preferences and budgets.
Are there any family house rentals in Oldsmar?
In Oldsmar, Florida, there are numerous family-friendly house rentals—around 24 available throughout the area. This charming locale is known for its family-friendly atmosphere and proximity to various attractions. Many properties come equipped with spacious living areas, fully stocked kitchens great for preparing family meals, and outdoor spaces ideal for children to play.Visitors can also expect amenities such as Wi-Fi and air conditioning to ensure a comfortable stay. The area offers easy access to nearby parks, including the scenic Oldsmar Park, where families can enjoy picnicking, walking trails, and playgrounds. Additionally, the local community features a number of dining options and shopping centres, making it convenient for families to explore and enjoy their time together.
Can I rent a holiday home with a pool or hot tub in Oldsmar?
In Oldsmar, there are a variety of holiday homes available for rent that feature both pools and hot tubs, with around 21 options to choose from. This charming city is situated in the Tampa Bay area and offers a relaxed atmosphere, making it an excellent choice for families and groups looking to enjoy a getaway. Many of these properties come equipped with private pools, hot tubs, and outdoor spaces for lounging and dining, superb for soaking up the Florida sunshine.Travellers can expect amenities such as fully equipped kitchens for self-catering, spacious living areas, and sometimes even barbecue facilities to enhance their stay.
Are there pet-friendly house rentals in Oldsmar?
In Oldsmar, there are numerous pet-friendly house rentals available, with around twenty options for travellers seeking accommodations that welcome pets. The area offers a variety of properties, including spacious family homes with amenities such as fenced yards, modern kitchens, and comfortable living spaces, superb for both pets and their owners. Many rentals are conveniently located near local parks, providing great opportunities for walks and outdoor activities with pets.Oldsmar's proximity to the picturesque waterfront parks, such as the Oldsmar City Park and the nearby Upper Tampa Bay Park, allows for leisurely strolls and recreational activities. These parks often feature walking trails, picnic areas, and scenic views, making them ideal spots for enjoying time outdoors with your furry companions.
Are there any remote work holiday rentals in Oldsmar?
In Oldsmar, Florida, there are a significant number of remote work-friendly holiday rentals available, with around 126 options to choose from. This charming city, located near the Gulf Coast, offers a variety of properties that cater to those needing a productive environment while away from home. Many rentals come equipped with high-speed internet and Wi-Fi, ensuring that guests can stay connected for work purposes.Travellers can expect amenities such as dedicated workspaces, comfortable seating areas, and sometimes even outdoor spaces to enjoy breaks in the Florida sunshine. The area features a mix of townhomes, apartments, and single-family homes, often providing additional comforts like fully equipped kitchens, laundry facilities, and private patios or balconies.Oldsmar itself is known for its parks and proximity to the beautiful beaches of Tampa Bay, making it an appealing location for remote workers who want to balance work with leisure. Visitors can take advantage of local parks, trails, and recreational activities while enjoying the convenience of their home office setup. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Oldsmar?
In Oldsmar, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties feature decks or patios, providing an inviting outdoor space to relax or dine al fresco. Onsite parking is also a common amenity, making it convenient for those travelling by car. Additionally, some rentals permit pets, suiting travellers who wish to bring their furry companions along. Amenities like blenders are often provided, enhancing the home-like experience by enabling guests to whip up smoothies or other refreshments.
When is the best time to visit Oldsmar for a holiday rental?
September is a delightful time to visit Oldsmar for a holiday rental, as the summer crowds begin to thin out and the weather remains pleasantly warm. During this month, you can enjoy outdoor activities, such as exploring the scenic trails at the nearby Upper Tampa Bay Trail or relaxing at the picturesque parks that dot the area.The peak season in Oldsmar typically runs from February to April, attracting visitors who are eager to take advantage of the temperate climate and vibrant local events. With temperatures hovering around 20 to 30 degrees Celsius, it's an ideal period for sightseeing, participating in festivals, and enjoying the beautiful Florida sunshine.If you're looking for a more budget-friendly option, consider planning your visit in October. This month offers a quieter atmosphere while still presenting opportunities for enjoyable outdoor adventures. The weather remains warm, and you can experience the beauty of Oldsmar without the hustle and bustle of peak tourist activity.Ultimately, your choice of when to visit Oldsmar will depend on whether you prefer the lively energy of the peak season or the more relaxed vibe of the shoulder months.
What are the top attractions in Oldsmar?
In Oldsmar, visitors can enjoy a range of attractions that highlight the area's natural beauty and recreational opportunities. One of the main draws is the picturesque Oldsmar Park, which features walking trails, picnic areas, and a lovely pond, making it an ideal spot for outdoor activities. Nearby, the Mobbly Bayou Wilderness Preserve offers a unique chance to explore mangroves and wetlands, with opportunities for birdwatching and kayaking.For those interested in sports, the Oldsmar Sports Complex provides facilities for various activities, including baseball and soccer, and often hosts local events. Additionally, the nearby Tampa Bay Downs is a popular destination for horse racing enthusiasts.Oldsmar's proximity to the Gulf Coast means that beautiful beaches are just a short drive away, with places like Caladesi Island State Park offering pristine shorelines and nature trails. The area also boasts a selection of local dining options, where visitors can indulge in fresh seafood and regional cuisine.
Are all fees included in the Oldsmar holiday homes prices shown on Stayz?
Stayz 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.
Are there any Oldsmar holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Oldsmar holiday homes?
You can find great discounts on holiday homes in Oldsmar on Stayz, 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.
Can I change or cancel my Oldsmar holiday home booking on Stayz?
To find Oldsmar holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Oldsmar?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Oldsmar holiday home?
Book your Oldsmar holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Oldsmar?
Prices for holiday homes 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. Stayz offers something for every taste and budget, from affordable homes in Oldsmar to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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