Oldsmar vacation rentals

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Best Oldsmar vacation rentals

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$103 - $366$366 - $629$629 - $892$892 - $1,155$1,155+ 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
$220+
Check availability
Pet-Friendly Tampa Bay Getaway Walk to the Water! - Oldsmar - Kitchen
Pet-Friendly Tampa Bay Getaway Walk to the Water!
Oldsmar, FL
10Wonderful(5)
Free Wi-Fi
Pet friendly
$279+
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
$202+
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
$413+
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Beautiful home in Oldsmar - Oldsmar - Dining room
Beautiful home in Oldsmar
Oldsmar, FL
9.8Wonderful(29)
$212+
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Peaceful getaway and Explore Tampa - Oldsmar - Living room
Peaceful getaway and Explore Tampa
Oldsmar, FL
9.3Wonderful(1)
Free Wi-Fi
$388+
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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
$406+
Check availability
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+
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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)
$156+
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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
$253+
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Idyllic Oldsmar Vacation Rental: 1 Mi to Beach! - Oldsmar - Living room
Idyllic Oldsmar Vacation Rental: 1 Mi to Beach!
Oldsmar, FL
Free Wi-Fi
$232+
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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)
$1,206+
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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
$281+
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Welcome to BonaVista Beach House great for couples and families - Oldsmar - Living room
Welcome to BonaVista Beach House great for couples and families
Oldsmar, FL
10Wonderful(8)
$250+
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(19)
Free Wi-Fi
$207+
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
$207+
Check availability
Useful Info

Good to know

Low season

High season

Average price (weeknight)

May
September
$338
Cheapest month to stay with an average 54% drop in price.
Most expensive month to stay with an average 52% 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 57% 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 Beautiful home in Oldsmar (9.8, 29 reviews), Beautifully, Renovated Home In Quiet Cul De Sac! Close To Everything! (9.7, 36), and family friendly, gated community, two pools, lake outside back door. (9.6, 31), 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.
  • The cheapest night for renting a vacation home in Oldsmar is Tuesday. In contrast, the most expensive is Sunday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Oldsmar for 5 days.
  • The cheapest Oldsmar vacation rental found on KAYAK in the last 2 weeks was $164, while the most expensive was $200.

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

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