Book Holiday Homes in Oldsmar
More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)
We keep it easy with the option to pay now or later on select accommodation
Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Oldsmar
Luxurious Downtown Pool Retreat - St. Petersburg - Pets Welcome
St. Petersburg, FL
With a stay at this vacation home, you'll be centrally located in St. Petersburg, within a 5-minute drive of Tampa Bay and Vinoy Park.
Clearwater Beach House - Right On The Beach
Clearwater
The price is AU$975 per night from 29 Sept to 30 Sept
AU$975
29 Sept - 30 Sept
includes taxes & fees
With a stay at this vacation home, you'll be centrally located in Clearwater Beach, a 1-minute drive from Clearwater Beach and 12 minutes from Sand Key ...
Beach View, Private Plunge Pool, Charming 1938 Bungalow Madeira Beach Johns Pass
Madeira Beach
The price is AU$597 per night from 29 Sept to 30 Sept
AU$597
29 Sept - 30 Sept
includes taxes & fees
When you stay at this vacation home in Madeira Beach, you'll be on the beach, within a 10-minute walk of John's Pass Village & Boardwalk and Hubbards ...
Save an average of 15% on thousands of hotels when you're signed in
Charming 3-bedroom house with pool, AC, WiFi in pleasant Tampa
Tampa
With a stay at this vacation home in Tampa (Citrus Park), you'll be within a 10-minute drive of Westfield Citrus Park and Lake Rogers Park.
Sunset Beach Getaway – Steps to the Beach, Walk to Restaurants, Sleeps 8!
Treasure Island
With a stay at this vacation home in Treasure Island (Sunset Beach), you'll be within a 10-minute drive of John's Pass Village & Boardwalk and St. Petersburg ...
Tampa Bay Perfect location for a safe vacation! 5 bedrooms, ,3.5 bath ,sleeps14
Tampa
With a stay at this vacation home in Tampa (Lake Magdalene), you'll be within a 10-minute drive of University of South Florida and H. Lee Moffitt Cancer ...
Resort style pool with lazy river, grotto, and hot tub! Dog-Friendly!
Lutz
Located in Lutz (Greater Northdale), this vacation home is within a 5-minute drive of Brooker Creek Headwaters Nature Preserve and St. Joseph's Hospital - ...
Fun & Cheerful - 4009 W Pearl Ave · Fun & Cheerful Mini Golf Pool Home
Tampa
The price is AU$519 per night from 30 Sept to 1 Oct
AU$519
30 Sept - 1 Oct
includes taxes & fees
With a stay at this vacation home, you'll be centrally located in Tampa, within a 5-minute drive of Tampa Bay and MacDill Air Force Base.
Fantastic Family/Friends Getaway - 6' deep Heated Pool & Spa close to Beaches!
Largo
With a stay at this vacation home in Seminole, you'll be by the sea, within a 15-minute drive of John's Pass Village & Boardwalk and Treasure Island Fun ...
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 | 5648 Holiday Homes |
|---|---|
Lowest Price | AU$253 |
Highest Price | AU$975 |
Popular accommodation | Luxurious Downtown Pool Retreat - St. Petersburg - Pets Welcome, Clearwater Beach House - Right On The Beach, Beach View, Private Plunge Pool, Charming 1938 Bungalow Madeira Beach Johns Pass, Charming 3-bedroom house with pool, AC, WiFi in pleasant Tampa, Sunset Beach Getaway – Steps to the Beach, Walk to Restaurants, Sleeps 8!, Tampa Bay Perfect location for a safe vacation! 5 bedrooms, ,3.5 bath ,sleeps14 , Resort style pool with lazy river, grotto, and hot tub! Dog-Friendly!, Fun & Cheerful - 4009 W Pearl Ave · Fun & Cheerful Mini Golf Pool Home, Fantastic Family/Friends Getaway - 6' deep Heated Pool & Spa close to Beaches! |
Top trending hotels in Oldsmar
Hilton Clearwater Beach Resort & Spa
400 Mandalay Ave, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
The price is AU$353 per night from 5 Oct to 6 Oct
AU$353
5 Oct - 6 Oct
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.
Hotel Tampa Riverwalk
200 N Ashley Dr, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is AU$253 per night from 29 Sept to 30 Sept
AU$253
29 Sept - 30 Sept
includes taxes & fees
A stay at Hotel Tampa Riverwalk places you in the heart of Tampa, within a 15-minute walk of Tampa Convention Center and Tampa Riverwalk.
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
4860 West Kennedy Boulevard, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is AU$259 per night from 3 Oct to 4 Oct
AU$259
3 Oct - 4 Oct
includes taxes & fees
With a stay at The Westshore Grand, A Tribute Portfolio Hotel, Tampa in Tampa (Beach Park), you'll be a 5-minute drive from Raymond James Stadium and 6 minutes ...
Save an average of 15% on thousands of hotels when you're signed in
The Westin Tampa Bay
7627 W Courtney Campbell Cswy, Tampa, FL
Fully refundable
The price is AU$280 per night from 3 Oct to 4 Oct
AU$280
3 Oct - 4 Oct
includes taxes & fees
With a stay at The Westin Tampa Bay in Tampa (Rocky Point), you'll be a 1-minute drive from Tampa Bay and 8 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.
More ways to explore Oldsmar
Top picks
Hotels
- Accommodation in Lorne
- Accommodation in Port Fairy
- Adelaide Rockford
- Hotels around Royal Prince Alfred Hospital
- Accommodation in Kingston SE
- Caravan Parks Waratah Bay
- Pompano Beach Boutique Hotels
- The Langham, Gold Coast and Jewel Residences
- Accommodation in Kingscote
- Accommodation in Clearwater Beach
- Accommodation in Byron Bay
- Accommodation in Sunshine Coast
- Accommodation in Strahan
- Accommodation in Stanley
- Accommodation in Wallan
- Accommodation in Ipswich
- Miami Beach All Inclusive Hotels
- Accommodation in Swan Hill
- Courtyard By Marriott Bali Seminyak Resort
- Batemans Bay Pet Friendly Hotels
Flights
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.