Book Holiday Homes in Oldsmar
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Featured Holiday Homes in Oldsmar
1950s Retro Beach Bungalow directly on the Beach! Spectacular Views! John's Pass
Treasure Island FL
The price is AU$596 per night from 6 Jan to 7 Jan
AU$596
6 Jan - 7 Jan 2026
includes taxes & fees
With a stay at this vacation home in Treasure Island (Sunshine Beach), you'll be steps from St. Petersburg - Clearwater Beaches and 8 minutes by foot from John's ...
1950s Retro Inspired 3 Bedroom/2 Bath Beach House w/Amazing Deck! John's Pass
Treasure Island FL
The price is AU$544 per night from 5 Jan to 6 Jan
AU$544
5 Jan - 6 Jan 2026
includes taxes & fees
With a stay at this vacation home in Treasure Island (Sunshine Beach), you'll be steps from St. Petersburg - Clearwater Beaches and 8 minutes by foot from John's ...
Spacious Tampa Pool Home with 5 Bedrooms. 5 minutes from Downtown Tampa.
Tampa FL
With a stay at this vacation home in Tampa (Davis Islands), you'll be within a 5-minute drive of Tampa Bay and Tampa Convention Center.
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Charming 2-Bedroom Home in the Heart of St. Petersburg
St. Petersburg FL
With a stay at this vacation home in St. Petersburg (Disston Heights), you'll be within a 10-minute drive of Tampa Bay and Salvador Dali Museum.
Bush Gardens, USF, Hard Rock group stay!
Tampa FL
With a stay at this vacation home in Tampa (Temple Crest), you'll be within a 5-minute drive of Busch Gardens Tampa Bay and University of South Florida.
Modern Heater pool house tampa. Close to the park and zoo
Tampa FL
The price is AU$544 per night from 5 Jan to 6 Jan
AU$544
5 Jan - 6 Jan 2026
includes taxes & fees
With a stay at this vacation home in Tampa (Lake Magdalene), you'll be within a 15-minute drive of University of South Florida and Raymond James Stadium.
Wonderful bungalow completely remodeled in St. Petersburg
St. Petersburg FL
With a stay at this vacation home in St. Petersburg, you'll be a 3-minute drive from Tampa Bay and 9 minutes from Vinoy Park.
Cozy Home with Heated pool near Clearwater Beach
Clearwater FL
With a stay at this vacation home in Clearwater, you'll be near the beach, within a 10-minute drive of Tampa Bay and Eagle Lake Park.
Zoo House Down Town Tampa
818 W Sligh Ave Tampa FL
The price is AU$478 per night from 27 Dec to 28 Dec
AU$478
27 Dec - 28 Dec
includes taxes & fees
With a stay at this vacation home in Tampa (Riverbend), you'll be a 2-minute drive from ZooTampa at Lowry Park and 7 minutes from Raymond James Stadium.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Oldsmar Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Oldsmar vacation homes are the perfect way for you to wing it.
Holiday houses in Oldsmar let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Oldsmar in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Oldsmar adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Oldsmar with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Oldsmar vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Oldsmar Holiday Homes essential information
Accommodation | 5730 Holiday Homes |
|---|---|
Lowest Price | AU$180 |
Highest Price | AU$596 |
Popular accommodation | 1950s Retro Beach Bungalow directly on the Beach! Spectacular Views! John's Pass, 1950s Retro Inspired 3 Bedroom/2 Bath Beach House w/Amazing Deck! John's Pass, Spacious Tampa Pool Home with 5 Bedrooms. 5 minutes from Downtown Tampa., Charming 2-Bedroom Home in the Heart of St. Petersburg, Bush Gardens, USF, Hard Rock group stay!, Modern Heater pool house tampa. Close to the park and zoo, Wonderful bungalow completely remodeled in St. Petersburg, Cozy Home with Heated pool near Clearwater Beach, Zoo House Down Town Tampa |
Top trending hotels in Oldsmar
Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG
3990 Tampa Rd Oldsmar FL
Fully refundable
The price is AU$199 per night from 28 Dec to 29 Dec
AU$199
28 Dec - 29 Dec
includes taxes & fees
Located in Oldsmar, Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG is in the suburbs, within a 5-minute drive of Oldsmar Flea Market and ...
Courtyard by Marriott Tampa Oldsmar
4014 Tampa Rd Oldsmar FL
Fully refundableReserve now, pay when you stay
The price is AU$180 per night from 28 Dec to 29 Dec
AU$180
28 Dec - 29 Dec
includes taxes & fees
When you stay at Courtyard by Marriott Tampa Oldsmar in Oldsmar, you'll be in the suburbs, within a 15-minute drive of Tampa Bay and Innisbrook Golf Club.
Wyndham Grand Clearwater Beach
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
The price is AU$405 per night from 1 Jan to 2 Jan
AU$405
1 Jan - 2 Jan 2026
includes taxes & fees
With a stay at Wyndham Grand Clearwater Beach in Clearwater Beach, you'll be on the beach, a 3-minute walk from St. Petersburg - Clearwater Beaches and 10 minutes ...
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Hilton Clearwater Beach Resort & Spa
400 Mandalay Ave Clearwater Beach FL
Fully refundableReserve now, pay when you stay
The price is AU$320 per night from 11 Jan to 12 Jan
AU$320
11 Jan - 12 Jan 2026
includes taxes & fees
When you stay at Hilton Clearwater Beach Resort & Spa in Clearwater Beach, you'll be on the beach, just steps from Beach Walk and Pier 60 Park.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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^Subject to availability and chosen travel dates.