Search Oldsmar Villa Rentals from CA $309

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Oldsmar villas

Exterior

Boho Villa A

Boho Villa A
Drew Park
10.0 out of 10, Exceptional, (1 review)
"THANK YOU."
United States
Babette R.
The price is CA $121
CA $325 total
includes taxes & fees
Mar 15 - Mar 16
Boho Villa A
Dining

2-bedroom villa in tranquil Tampa with cool AC breeze

2-bedroom villa in tranquil Tampa with cool AC breeze
Carrollwood
The price is CA $168
CA $386 total
includes taxes & fees
Mar 3 - Mar 4
2-bedroom villa in tranquil Tampa with cool AC breeze
Exterior

Villa w/private pool & game room

Villa w/private pool & game room
Clearwater
10.0 out of 10, Exceptional, (2 reviews)
"Everything was great!! Decor was beautiful, pool was nice and all the outdoor activities was great!!"
United States
Rachel G.
The price is CA $183
CA $691 total
includes taxes & fees
Feb 18 - Feb 19
Villa w/private pool & game room
Living area

Wilderness Escape, by Breathtaking Natl Park

Wilderness Escape, by Breathtaking Natl Park
Town 'n' Country
8.8 out of 10, Excellent, (19 reviews)
"Great little house on the edge of the state park. It’s quiet and relaxing, but also less than a mile from any convenience you need. We would stay again. "
United States
Scott W.
The price is CA $320
CA $613 total
includes taxes & fees
Feb 23 - Feb 24
Wilderness Escape, by Breathtaking Natl Park
Outdoor pool

2,100sqf Villa · KING Beds · Heated Pool · Game Room · GYM · Beach 2miles

2,100sqf Villa · KING Beds · Heated Pool · Game Room · GYM · Beach 2miles
Largo
10.0 out of 10, Exceptional, (23 reviews)
"My best friend and I had a wonderful birthday get away here with our friends!! "
United States
Rebecca A.
The price is CA $271
CA $795 total
includes taxes & fees
Feb 18 - Feb 19
2,100sqf Villa · KING Beds · Heated Pool · Game Room · GYM · Beach 2miles
Property grounds

3-bedroom villa in enchanting St. Petersburg with AC comfort

3-bedroom villa in enchanting St. Petersburg with AC comfort
Childs Park
The price is CA $495
CA $945 total
includes taxes & fees
Feb 24 - Feb 25
3-bedroom villa in enchanting St. Petersburg with AC comfort
Exterior

NEW! Columbus Cabana | Modern & Spacious Home In Heart of Tampa w/ 95` Smart TV

NEW! Columbus Cabana | Modern & Spacious Home In Heart of Tampa w/ 95` Smart TV
MacFarlane Park
The price is CA $244
CA $777 total
includes taxes & fees
Feb 16 - Feb 17
NEW! Columbus Cabana | Modern & Spacious Home In Heart of Tampa w/ 95` Smart TV
Exterior

Boho- Minimalist villa

Boho- Minimalist villa
Drew Park
9.0 out of 10, Wonderful, (4 reviews)
"Great location within walking distance to the stadium. Super clean and comfortable."
United States
Melissa
The price is CA $163
CA $384 total
includes taxes & fees
Mar 1 - Mar 2
Boho- Minimalist villa
Exterior

Boho Villa B

Boho Villa B
Drew Park
10.0 out of 10, Exceptional, (1 review)
"It was a great location for the game but everything else was driving distance which we used uber. Communication was not as prompt as I was hoping and it always seemed a recording not a actual person very clean and cute thanks "
United States
Brenda C.
The price is CA $108
CA $309 total
includes taxes & fees
Feb 24 - Feb 25
Boho Villa B
Exterior

Luxury Tiny Home 1 Bed 1 Bath Unit C “Shelly”

Luxury Tiny Home 1 Bed 1 Bath Unit C “Shelly”
Downtown Dunedin
The price is CA $255
CA $503 total
includes taxes & fees
Mar 11 - Mar 12
Luxury Tiny Home 1 Bed 1 Bath Unit C “Shelly”
Exterior

NEW! Casa Doble On Columbus | 2 Stunning Townhomes by Ray-J & Steinbrenner Field

NEW! Casa Doble On Columbus | 2 Stunning Townhomes by Ray-J & Steinbrenner Field
MacFarlane Park
The price is CA $484
CA $1,616 total
includes taxes & fees
Feb 16 - Feb 17
NEW! Casa Doble On Columbus | 2 Stunning Townhomes by Ray-J & Steinbrenner Field
Pool

6BR Waterfront • Heated Pool • Hot Tub • Game Room

6BR Waterfront • Heated Pool • Hot Tub • Game Room
Largo
The price is CA $708
CA $1,334 total
includes taxes & fees
Feb 21 - Feb 22
6BR Waterfront • Heated Pool • Hot Tub • Game Room
Terrace/patio

Beachfront 3 Bedroom 2 Bath Penthouse Indian Shores Florida With A Pool

Beachfront 3 Bedroom 2 Bath Penthouse Indian Shores Florida With A Pool
Indian Shores
8.8 out of 10, Excellent, (86 reviews)
"Great! Everything was great."
United States
Marie P.
The price is CA $536
CA $1,072 total
includes taxes & fees
Feb 16 - Feb 17
Beachfront 3 Bedroom 2 Bath Penthouse Indian Shores Florida With A Pool
Smart TV

Vacation Villa in Tampa 17 Guest

Vacation Villa in Tampa 17 Guest
Town 'n' Country
The price is CA $681
CA $1,286 total
includes taxes & fees
Feb 23 - Feb 24
Vacation Villa in Tampa 17 Guest
Terrace/patio

The Belleair Estate - Breathtaking Waterfront Home w/ Heated Pool

The Belleair Estate - Breathtaking Waterfront Home w/ Heated Pool
Clearwater
9.6 out of 10, Exceptional, (51 reviews)
"Very clean and had everything needed for our stay."
United States
Roxana J.
The price is CA $705
CA $1,902 total
includes taxes & fees
Feb 16 - Feb 17
The Belleair Estate - Breathtaking Waterfront Home w/ Heated Pool
Exterior

Riverside Castle With Large Pool by Tampa Zoo & Armature Works

Riverside Castle With Large Pool by Tampa Zoo & Armature Works
Old Seminole Heights
10.0 out of 10, Exceptional, (4 reviews)
"Massive property and host was very accommodating. Great value for price!"
United States
Tabish C.
The price is CA $1,021
CA $1,739 total
includes taxes & fees
Feb 16 - Feb 17
Riverside Castle With Large Pool by Tampa Zoo & Armature Works
Property grounds

Beachside Bliss | Rooftop Gulf Views & Fun Vibes

Beachside Bliss | Rooftop Gulf Views & Fun Vibes
Madeira Beach
10.0 out of 10, Exceptional, (1 review)
"Could not have asked for a better place to stay. Everyone in our party commented on how amazing it was. We were just a few steps from beach access and felt pampered. They provided everything we needed for an amazing stay! You won’t be disappointed with this place. Thank you "
United States
stacy w.
The price is CA $662
CA $1,709 total
includes taxes & fees
Feb 18 - Feb 19
Beachside Bliss | Rooftop Gulf Views & Fun Vibes
A heated pool

The Oasis Retreat | Pool + Game Room + Basketball + Massive Yard | Near Beach & Golf

The Oasis Retreat | Pool + Game Room + Basketball + Massive Yard | Near Beach & Golf
Walsingham
9.0 out of 10, Wonderful, (37 reviews)
"it was a great place to stay, so big, really good for big group. the in law suite was so nice too. pool is an added plus points.the house is clean.the man cave was awesome, we didn't expect that.the carpet above smells nice, no musty smell. am allergic to carpet but not that. good job. "
United States
Roniel P.
The price is CA $1,133
CA $2,348 total
includes taxes & fees
Mar 10 - Mar 11
The Oasis Retreat | Pool + Game Room + Basketball + Massive Yard | Near Beach & Golf
Property grounds

OCEANFRONT 5⭐3BR/2BA/6BED_Heated Pool_180 View Patio_ Beach Gear

OCEANFRONT 5⭐3BR/2BA/6BED_Heated Pool_180 View Patio_ Beach Gear
Madeira Beach
9.0 out of 10, Wonderful, (7 reviews)
"Beautiful view. Enjoyed our stay and appreciated the quickness of our host to respond to messages."
United States
Amy R.
The price is CA $771
CA $1,181 total
includes taxes & fees
Mar 11 - Mar 12
OCEANFRONT 5⭐3BR/2BA/6BED_Heated Pool_180 View Patio_ Beach Gear
Outdoor dining

Villa Valentino Luxury 8br Villa With Heated Pool 8 Bedroom Villa

Villa Valentino Luxury 8br Villa With Heated Pool 8 Bedroom Villa
3.0 star property
Allen's Ridge
The price is CA $1,651
CA $3,065 total
includes taxes & fees
Feb 18 - Feb 19
Villa Valentino Luxury 8br Villa With Heated Pool 8 Bedroom Villa
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.
View all properties

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oldsmar Hotel Reviews

Quality Inn Airport - Cruise Port

Quality Inn Airport - Cruise Port

10/10 Excellent
"Clean room, friendly staff "
Dianne M 1-night trip
Posted 2 days ago
Quality Inn Airport - Cruise Port

Find out more about Oldsmar

Oldsmar Villas information

Number of reviews
222
Accommodation
184 Villas
Lowest Price
CA $309
Highest Price
CA $3,065

Frequently asked questions

How much do villas in Oldsmar cost?
Villas in Oldsmar cost between CA $309 and CA $3,065 per night. These getaways offer the privacy of your own space at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Oldsmar?
Use up your vacation days and pick from 184 villas in Oldsmar. For a vacation with the family, a romantic break and everything in between, Expedia can help you find the perfect place in a few easy clicks.
Why book your villa in Oldsmar with Expedia?
Booking a villa in Oldsmar is as easy as deciding on your travel dates and choosing a place that satisfies your needs. Searching for something inexpensive or upscale, or a stay that also features WiFi and a hot tub? Use Expedia's search filters to narrow your results and find your ideal pad.
How can I find cheap villas in Oldsmar?
Expedia can help you locate cheap villas in Oldsmar. Use our filter tool to choose amenities, star rating and budget to refine your search and find a fantastic place to stay in a matter of clicks.
What is there to do near my villa in Oldsmar?
If you'd like to explore the sights of Oldsmar, be sure to stop by Oldsmar Flea Market. It's popular with tourists and locals alike.

Explore a world of travel with Expedia