Search Villas in Oldsmar

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

Villas in Oldsmar

#1 Tampa Waterfront Private Resort, 13BR Sleeps 40+, Heated Pool, Theater
Exterior

#1 Tampa Waterfront Private Resort, 13BR Sleeps 40+, Heated Pool, Theater

8.8 out of 10, Excellent, (11)
"Place looked amazing in person and there was so much to do while at our stay. Very clean and had little to no problems. Host was very nice to us. "
The price is AED 1,874
AED 4,916 total
includes taxes & fees
9 Oct - 10 Oct
#1 Tampa Waterfront Private Resort, 13BR Sleeps 40+, Heated Pool, Theater
CHARMING BEACH VILLA-HUGE ROOFTOP DECK-600 FEET FROM THE BEACH
Exterior

CHARMING BEACH VILLA-HUGE ROOFTOP DECK-600 FEET FROM THE BEACH

9.8 out of 10, Exceptional, (76)
"Great vacation rental"
CHARMING BEACH VILLA-HUGE ROOFTOP DECK-600 FEET FROM THE BEACH
Hidden Gem! Treasure Island Waterfront 2/2 with a pool and dock!
Outdoor pool

Hidden Gem! Treasure Island Waterfront 2/2 with a pool and dock!

10.0 out of 10, Exceptional, (83)
"Absolutely loved our stay! Great location, beautiful views and the pool was a huge bonus. Looking forward to returning again!"
Hidden Gem! Treasure Island Waterfront 2/2 with a pool and dock!
Sleeps 25 • Heated Pool • Indoor/Outdoor Games • Theater
Outdoor dining

Sleeps 25 • Heated Pool • Indoor/Outdoor Games • Theater

8.8 out of 10, Excellent, (13)
"There were 14 of us ranging from 63 to 2 years old. Everyone enjoyed the stay and we spent several days just staying at the home. I would recommend this property to anyone who has a large group."
Sleeps 25 • Heated Pool • Indoor/Outdoor Games • Theater
#1 Rated Mansion • Heated Pool/Spa • Theater • Peloton Gym • Game Room
Terrace/patio

#1 Rated Mansion • Heated Pool/Spa • Theater • Peloton Gym • Game Room

9.4 out of 10, Exceptional, (19)
"this was a great place to stay. The description is very accurate and the pictures show everything you need to enjoy your family vacation."
#1 Rated Mansion • Heated Pool/Spa • Theater • Peloton Gym • Game Room
Quite Paradise near Gulf of Mexico, Salt/Heated pool!!!!!,Port Richey
Exterior

Quite Paradise near Gulf of Mexico, Salt/Heated pool!!!!!,Port Richey

9.4 out of 10, Exceptional, (43)
"Overall it was a great stay "
The price is AED 731
AED 1,463 total
includes taxes & fees
3 Oct - 4 Oct
Quite Paradise near Gulf of Mexico, Salt/Heated pool!!!!!,Port Richey
Bikes, Beaches and Quaint Floridian Downtowns
Fridge, microwave, oven, stovetop

Bikes, Beaches and Quaint Floridian Downtowns

9.0 out of 10, Wonderful, (8)
"We have family that lives close by, so this was the perfect location for us to see them along with walking to different places off of the Pinellas Trail. Owners were super helpful with any questions we had!"
Bikes, Beaches and Quaint Floridian Downtowns
The Salty Pelican on the Pinellas Trail
Exterior

The Salty Pelican on the Pinellas Trail

10.0 out of 10, Exceptional, (8)
"Place is super easy to find and close to everything we wanted to do and see. Would definitely stay there again..."
The Salty Pelican on the Pinellas Trail
Charming 2-bedroom villa in Seminole with pool, WiFi and AC
Exterior

Charming 2-bedroom villa in Seminole with pool, WiFi and AC

10.0 out of 10, Exceptional, (3)
"Everything was perfect for our family of four. Cleanliness is a must for us and this place was extremely clean. It had everything we needed and more. We will definitely stay here again."
Charming 2-bedroom villa in Seminole with pool, WiFi and AC
Room in Studio - Villa La Esperanza 1
Room, 1 Bedroom, Accessible, Smoking | Front of property

Room in Studio - Villa La Esperanza 1

3.0 star property
Room in Studio - Villa La Esperanza 1
Lakeside Retreat-4plex Sleeps 20
A heated pool

Lakeside Retreat-4plex Sleeps 20

9.6 out of 10, Exceptional, (11)
"Great property with all amenities. Very nice layout that allows for large groups but also provides for privacy for each family. Love the pool, accessibility to the beach. Will definitely stay again."
Lakeside Retreat-4plex Sleeps 20
The Oasis Retreat | Pool + Game Room + Basketball + Massive Yard | Near Beach & Golf
Terrace/patio

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

9.0 out of 10, Wonderful, (33)
"We had a great time! The house was very accommodating. The beds were so comfortable and the pool/hot tub were the best we’ve had anywhere. The “Mother In Law” suite was a wonderful addition to this property! Thank you again for a great family vacation!!"
The price is AED 1,484
AED 4,244 total
includes taxes & fees
15 Oct - 16 Oct
The Oasis Retreat | Pool + Game Room + Basketball + Massive Yard | Near Beach & Golf
Great 6BR for All Ages/Heated Pool 5 Min to Beach by RedAwning
House, 6 Bedrooms | Exterior

Great 6BR for All Ages/Heated Pool 5 Min to Beach by RedAwning

3.5 star property
Great 6BR for All Ages/Heated Pool 5 Min to Beach by RedAwning
Backyard-1000mbs-WD-Updated-RainShower-AC-SmartTV-Workspace-10MinToBeach-Kitchen
Exterior detail

Backyard-1000mbs-WD-Updated-RainShower-AC-SmartTV-Workspace-10MinToBeach-Kitchen

2.0 star property
Backyard-1000mbs-WD-Updated-RainShower-AC-SmartTV-Workspace-10MinToBeach-Kitchen
MILOS Beach House-NEW Luxe Haven Steps from BEACH -NEW ROOFTOP POOL 36 FT LONG
Terrace/patio

MILOS Beach House-NEW Luxe Haven Steps from BEACH -NEW ROOFTOP POOL 36 FT LONG

10.0 out of 10, Exceptional, (25)
"We had a great stay at the property. We had over 20 people in the house , from babies to retired folks. The house was spotless and had so many top line amenities. We particularly liked waking up and starting the day with expressos. Only one block to the beach and lots of food options nearby. "
MILOS Beach House-NEW Luxe Haven Steps from BEACH -NEW ROOFTOP POOL 36 FT LONG
Chestnut Villas Down Town Tampa
Exterior

Chestnut Villas Down Town Tampa

3.0 star property
4.8 out of 10, (38)
"My family loved the clean and spacious rooms. The staff were so kind and made us feel right at home. The breakfast was amazing!"
Chestnut Villas Down Town Tampa
Blue Water Beach Rental #6 A little slice of beach paradise
Outdoor dining

Blue Water Beach Rental #6 A little slice of beach paradise

7.8 out of 10, Good, (15)
"Place was clean and exactly what we were looking for! Great location and a beautiful place to relax by the beach!"
Blue Water Beach Rental #6 A little slice of beach paradise
2,100sqf Villa · KING Beds · Heated Pool · Game Room · GYM · Beach 2miles
Exterior

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

2.0 star property
10.0 out of 10, Exceptional, (16)
"Our group of friends really enjoyed the house. "
The price is AED 694
AED 2,118 total
includes taxes & fees
6 Oct - 7 Oct
2,100sqf Villa · KING Beds · Heated Pool · Game Room · GYM · Beach 2miles
Luxury Cristiano Manor 8BR w Pool - 20 Guests
Exterior

Luxury Cristiano Manor 8BR w Pool - 20 Guests

9.4 out of 10, Exceptional, (12)
"Very nice and spacious."
Luxury Cristiano Manor 8BR w Pool - 20 Guests
Exclusive Resort-Style Villa – Luxury Pool Retreat, Sleep 26+ Guests
Exterior

Exclusive Resort-Style Villa – Luxury Pool Retreat, Sleep 26+ Guests

9.2 out of 10, Wonderful, (9)
"This was was perfect for a big group of friends visiting Tampa area. There were more than enough rooms/bathrooms and enough beds for everyone to sleep comfortably . Highly recommend if you're looking for a place that can sleep a big group!"
Exclusive Resort-Style Villa – Luxury Pool Retreat, Sleep 26+ Guests
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
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

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

10/10 Excellent
"The view was awesome, the staff was very professional and helpful. Thank you for a great stay! "
Keith 1-night trip
Posted 18 hours ago
Wyndham Grand Clearwater Beach

Frequently asked questions

How much do villas in Oldsmar cost?
Villas in Oldsmar cost between AED 1,463 and AED 4,916 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 146 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.