Oldsmar holiday lettings

We found 6,047 holiday rentals — enter your dates for availability
Discover a selection of 10 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 Nov - 27 Nov

Interior
Exterior
Dining
Private kitchen
Excellent
(18 reviews)

Riverside Castle With Large Pool by Tampa Zoo & Armature Works. NO POOL PARTIES

Tampa

16% off
£8,095
for 7 nights, 1 villa
£1,156 per night
includes taxes & fees
Riverside Castle With Large Pool by Tampa Zoo & Armature Works. NO POOL PARTIES
Living area
Beach
Private kitchen
Exterior
Exceptional
(56 reviews)

*Pool* 8.5 miles to Honeymoon Island. 4 bdr

Palm Harbor

7% off
£2,486
for 7 nights, 1 home
£355 per night
includes taxes & fees
*Pool* 8.5 miles to Honeymoon Island. 4 bdr
Interior
Interior
Living area
Private kitchen
Exceptional
(17 reviews)

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

Dunedin

5% off
£2,708
for 7 nights, 1 home
£387 per night
includes taxes & fees
Heated Pool, Hot Tub, Bikes, Minutes to Clearwater Beach & Honeymoon Island!
Pool
Private kitchen
Exterior
Room
Excellent
(56 reviews)

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

Largo

14% off
£942
for 7 nights, 1 home
£135 per night
includes taxes & fees
Casa de Corazon-A comfortable home with pool in a quiet neighborhood near beach.
Outdoor spa tub
Kitchen
Big Screen TV and electric fireplace
Pool
Wonderful
(42 reviews)

Clearwater Vacation Paradise Home Pool & Hot Tub, Outside Bar- TV, Pets welcome

Clearwater

7% off
£1,801
for 7 nights, 1 home
£257 per night
includes taxes & fees
Clearwater Vacation Paradise Home Pool & Hot Tub, Outside Bar- TV, Pets welcome
Living area
Living area
Room
Interior
Excellent
(25 reviews)

Wilderness Escape, by Breathtaking Natl Park

Tampa

12% off
£1,446
for 7 nights, 1 villa
£207 per night
includes taxes & fees
Wilderness Escape, by Breathtaking Natl Park
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
£3,084
for 7 nights, 1 home
£441 per night
includes taxes & fees
Pelican Drift:Blue Jays Spring Training Retreat!Salt Pool,Hot Tub,Xbox,Game Room
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!
Spend time with your group over a movie or a card game!
Hallway leading to bedrooms decorated with vibrant greenery.
Exceptional
(29 reviews)

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

Tampa

12% off
£1,536
for 7 nights, 1 home
£219 per night
includes taxes & fees
Tropical & Elegant l Pool, Bonfire, Outdoor Entertainment l Central Location
Marina
Exterior
Living area
Interior
Exceptional
(94 reviews)

Cozy Carriage House on Spring Bayou

Tarpon Springs

8% off
£774
for 7 nights, 1 home
£111 per night
includes taxes & fees
Cozy Carriage House on Spring Bayou
Living area
Beach
Pool
Private kitchen
Exceptional
(21 reviews)

Spacious & Fun Family Gem / Pool, Beach, Blue Jays

Palm Harbor

5% off
£1,787
for 7 nights, 1 home
£255 per night
includes taxes & fees
Spacious & Fun Family Gem / Pool, Beach, Blue Jays
Terrace/patio
Property grounds
Private kitchen
Interior
Wonderful
(22 reviews)

Cozy Coastal Tiny Home Retreat 🌴

Clearwater

8% off
£590
for 7 nights, 1 home
£84 per night
includes taxes & fees
Cozy Coastal Tiny Home Retreat 🌴
Dining
Private kitchen
Private kitchen
Outdoor dining
Exceptional
(7 reviews)

Home 3BR 2BA in Tampa-Saltwater Heated Pool-5min airport-5min Raymond James Stad

Tampa

8% off
£2,139
for 7 nights, 1 home
£306 per night
includes taxes & fees
Home 3BR 2BA in Tampa-Saltwater Heated Pool-5min airport-5min Raymond James Stad
Interior
Living area
Room
Private kitchen
Excellent
(5 reviews)

Awesome 2-bedroom house with AC in sunny Tampa

Tampa

8% off
£761
for 7 nights, 1 home
£109 per night
includes taxes & fees
Awesome 2-bedroom house with AC in sunny Tampa
Living area
Pool
Room
Property grounds
Exceptional
(17 reviews)

Ground Floor Condo in Avalon of Clearwater 3 miles from Clearwater beach

Clearwater

7% off
£807
for 7 nights, 1 apartment
£115 per night
includes taxes & fees
Ground Floor Condo in Avalon of Clearwater 3 miles from Clearwater beach
Exterior
Private kitchen
Room
Dining
Exceptional
(9 reviews)

Modern 4BR 2 Bath Home • Near TPA & Beaches • Sleeps 8

Tampa

8% off
£1,596
for 7 nights, 1 home
£228 per night
includes taxes & fees
Modern 4BR 2 Bath Home • Near TPA & Beaches • Sleeps 8
Interior
Pool
Terrace/patio
Interior
Exceptional
(18 reviews)

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

Clearwater Beach

7% off
£720
for 7 nights, 1 apartment
£103 per night
includes taxes & fees
101 · ☀Pool✔ Beach✔ Self Checkin✔ Free Parking✔
Private kitchen
Dock across the street at Nautical Landings!
Exterior
Interior
Wonderful
(20 reviews)

Nautical Landings West close to Honeymoon Island and dock access!

Dunedin

7% off
£1,347
for 7 nights, 1 apartment
£192 per night
includes taxes & fees
Nautical Landings West close to Honeymoon Island and dock access!
Screened porch
Full kitchen view
Dining
Room
Exceptional
(15 reviews)

Holiday Retreat

Holiday

7% off
£1,404
for 7 nights, 1 home
£201 per night
includes taxes & fees
Holiday Retreat
Kitchen area with island table and chairs.
Private kitchen
Outside shower area
Salty Bloom Oasis
Exceptional
(29 reviews)

Relax Home with Pool and near Beaches in Largo, FL

Largo

8% off
£1,507
for 7 nights, 1 home
£215 per night
includes taxes & fees
Relax Home with Pool and near Beaches in Largo, FL
Pool
Private kitchen
Living area
Property grounds
Exceptional
(6 reviews)

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

Clearwater Beach

7% off
£2,558
for 7 nights, 1 apartment
£365 per night
includes taxes & fees
2-bedroom beach condo, water views in beautiful Sand Key, 4 mins to Clearwater
Interior
Exterior
Private kitchen
Clearwater Beach
Exceptional
(46 reviews)

New & Luxurious 4/3 Townhouse with boat slip- 2,800 Square Feet

Clearwater Beach

8% off
£4,716
for 7 nights, 1 home
£674 per night
includes taxes & fees
New & Luxurious 4/3 Townhouse with boat slip- 2,800 Square Feet
Pool
Private kitchen
Living area
Interior
Exceptional
(81 reviews)

Charming, newly reno 1Bdrm condo, minutes from beautiful Clearwater Beach

Clearwater

7% off
£731
for 7 nights, 1 apartment
£104 per night
includes taxes & fees
Charming, newly reno 1Bdrm condo, minutes from beautiful Clearwater Beach
Private kitchen
Property grounds
Master bedroom has a King bed with a very comfortable mattress.
Cable TV and Stereo for your entertainment
Exceptional
(87 reviews)

1 step and you are on the BEACH! Watch amazing sunsets from 3 decks! PremierHost

Indian Rocks Beach

8% off
£3,734
for 7 nights, 1 home
£533 per night
includes taxes & fees
1 step and you are on the BEACH! Watch amazing sunsets from 3 decks! PremierHost
Living area
Private kitchen
Outdoor dining
60 inch Smart TV!
Exceptional
(57 reviews)

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

Indian Rocks Beach

7% off
£1,785
for 7 nights, 1 home
£255 per night
includes taxes & fees
Perfect Location! Coral Sands Beach House II at Indian Rocks Beach!

  • 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, 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)
  • 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)

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.
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 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.
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 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 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 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.
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.
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.
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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