Oldsmar vacation rentals

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Best Oldsmar vacation rentals

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$99 - $473$473 - $846$846 - $1,220$1,220 - $1,593$1,593+ per night

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Most recommended vacation rentals in Oldsmar

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2 Bedroom , 2 Bath , Villa - Oldsmar - Beach
2 Bedroom , 2 Bath , Villa
Oldsmar, FL
9.5Wonderful(51)
Parking
Free Wi-Fi
Pool
Pet friendly
$315+
Check availability
Pond front groundfloor 2/2 condo - Oldsmar - Dining room
Pond front groundfloor 2/2 condo
Oldsmar, FL
9.5Wonderful(14)
Free Wi-Fi
$201+
Check availability
DOG friendly pool home close to the BEACH! - Oldsmar - Living room
DOG friendly pool home close to the BEACH!
Oldsmar, FL
8.4Very good(18)
Free Wi-Fi
$401+
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Beautiful home in Oldsmar - Oldsmar - Dining room
Beautiful home in Oldsmar
Oldsmar, FL
9.8Wonderful(29)
$215+
Check availability
Peaceful getaway and Explore Tampa - Oldsmar - Living room
Peaceful getaway and Explore Tampa
Oldsmar, FL
9.3Wonderful(1)
Free Wi-Fi
$376+
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family friendly, gated community, two pools, lake outside back door. - Oldsmar - Living room
family friendly, gated community, two pools, lake outside back door.
Oldsmar, FL
9.6Wonderful(31)
Free Wi-Fi
$164+
Check availability
Vacation Home W/ Hot Tub, 2 Master Bedrooms, Heated Pool Near Beaches! - Oldsmar - Patio
Vacation Home W/ Hot Tub, 2 Master Bedrooms, Heated Pool Near Beaches!
Oldsmar, FL
9.5Wonderful(29)
Free Wi-Fi
$409+
Check availability
Cozy Two Bedroom Condo Tucked Away In The Serene Settings Of East Lake Woodlands - Oldsmar - Living room
Cozy Two Bedroom Condo Tucked Away In The Serene Settings Of East Lake Woodlands
Oldsmar, FL
9.6Wonderful(11)
$157+
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Amazing Private Beach Home - Oldsmar - Living room
Amazing Private Beach Home
Oldsmar, FL
10Wonderful(4)
Parking
Free Wi-Fi
Pet friendly
$414+
Check availability
Idyllic Oldsmar Vacation Rental: 1 Mi to Beach! - Oldsmar - Living room
Idyllic Oldsmar Vacation Rental: 1 Mi to Beach!
Oldsmar, FL
Free Wi-Fi
$239+
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Modern Condo on the lake Oldsmar FL - Oldsmar - Bedroom
Modern Condo on the lake Oldsmar FL
Oldsmar, FL
Free Wi-Fi
$393+
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Executive Home With Resort Pool In The Heart Of Tampa Bay - Oldsmar - Living room
Executive Home With Resort Pool In The Heart Of Tampa Bay
Oldsmar, FL
9.6Wonderful(13)
$1,630+
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Beautiful Condo in prime Florida location within premier gated community. - Oldsmar - Kitchen
Beautiful Condo in prime Florida location within premier gated community.
Oldsmar, FL
9.5Wonderful(20)
$111+
Check availability
Beautifully, Renovated Home In Quiet Cul De Sac! Close To Everything! - Oldsmar - Bedroom
Beautifully, Renovated Home In Quiet Cul De Sac! Close To Everything!
Oldsmar, FL
9.7Wonderful(36)
Free Wi-Fi
$226+
Check availability
Spectacular Like New House, Close to Safety Harbor, Dunedin, Beaches & Shopping! - Oldsmar - Beach
Spectacular Like New House, Close to Safety Harbor, Dunedin, Beaches & Shopping!
Oldsmar, FL
10Wonderful(20)
Free Wi-Fi
$210+
Check availability
Entire House -Private Pool 3 Bedrooms 2 Baths - Oldsmar - Living room
Entire House -Private Pool 3 Bedrooms 2 Baths
Oldsmar, FL
9.0Wonderful(12)
Free Wi-Fi
$258+
Check availability
Useful Info

Good to know

Low season

High season

Average price (weeknight)

May
September
$338
Cheapest month to stay with an average 56% drop in price.
Most expensive month to stay with an average 45% rise in price.
Average Sun - Thu price over the last 2 weeks.

KAYAK's top tips for finding Oldsmar vacation rental deals

  • Vacation rentals in Oldsmar are around 52% more expensive than hotels on average. Search here to compare prices for all accommodation types in Oldsmar.
  • The best vacation rental properties in Oldsmar are Spectacular Like New House, Close to Safety Harbor, Dunedin, Beaches & Shopping! (10.0, 20 reviews), Beautiful home in Oldsmar (9.8, 29), and Beautifully, Renovated Home In Quiet Cul De Sac! Close To Everything! (9.7, 36), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Oldsmar, you should consider visiting during the low season. The cheapest vacation homes in Oldsmar can be found in May and August.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Oldsmar for 4 days.
  • The cheapest Oldsmar vacation rental found on KAYAK in the last 2 weeks was $164, while the most expensive was $200.

FAQs when booking a vacation home in Oldsmar

  • What types of vacation rentals are available in Oldsmar?

    There are loads of different property types that you can make your vacation home in Oldsmar. You’ll find apartments, condos, cottages, houses and villas.

  • Are there any pet-friendly vacation rentals in Oldsmar?

    There are a number of dog and pet-friendly Oldsmar vacation rentals, with around 7% allowing you to bring your pet along with you.

  • How much is a vacation rental in Oldsmar for tonight?

    In the last 72 hours, users have found Oldsmar vacation rentals for tonight for as low as $317. Search here for similar prices

  • How can I find vacation rentals near me in Oldsmar?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Oldsmar?

Our map will help you find the perfect place to stay in Oldsmar by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Oldsmar