
Vacation rentals in Oldsmar
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Oldsmar
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Oldsmar vacation rentals
Other great vacation rentals in Oldsmar

SouthTampa-Family&Group Oasis-3K bd, private pool
Great house in a wonderful neighborhood. Recommend for families looking to check out a game or do any of the wonderful things available to do in Tampa!

Vintage Florida Beach Cottage B
This place was exactly what the description states. It was very clean and great location if you want to be just a little off the main road. Would definitely stay again.

Enjoy brand new vacation 2/2 condo & water park!
Host was very responsive to questions before and during our stay. This was our first time renting an Airbnb so that was so helpful. This is a great condo with easy access to the beach, restaurants, shops and more.

Luxurious holiday home
really modern place, very clean. comfy beds, cool shower and good pool. Aircon really good and quiet. only negative was there could be more plates and utensils. would stay again.

Bring your family and friends to our luxury airbnb
I was in town celebrating my 45th birthday with family, and this home was the perfect accommodation. We enjoyed the jacuzzi and pool the most! The home was clean, warm and inviting. Our host Leon was quickly responsive and extremely accommodating...he was able to grant us a last minute late check out, which we greatly appreciated. We'd definitely stay again if we ever find ourselves back in Tampa.

2min walk to the beach/pool, BBQ/great area, RO110
We’ve stayed here the last few vacations and as always, the place never disappoints. Great location with all beach amenities you could possibly need. We unfortunately needed to evacuate from Hurricane Helene and John was gracious and concerned for our safety. The town of Redington is a family and we’re praying for their safety and quick turn around to their paradise again.

Luxury Home centrally located in Tampa Bay!
This place was perfect for me and my family. The location was great for all the places we planned to attend. I would definitely booked this again!!! Thank you Ray for allowing us to stay!!!

Mini-Golf 2/1 with Heated pool.
The place is as described. Pool area was fantastic. Could use more silverware. Close to the beach. restaurants and stores.
Quick stats about vacation rentals in Oldsmar
Total rentals
130 properties
Nightly prices starting at
ﺩ.ﺇ73 before taxes and fees
Total number of reviews
3.8K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
70 properties have a pool
Frequently Asked Questions
Where should I stay in Oldsmar?
Make yourself at home in Oldsmar by choosing from our most frequently booked neighborhoods. We have over 200 vacation rentals in Tarpon Woods, over 530 vacation rentals in The Grove Of Laforest, over 200 vacation rentals in East Lake Woodlands, and over 200 vacation rentals in Bridlewood.
Are there vacation rentals with a dedicated workspace in Oldsmar?
Yes! Work meets play with ease at over 70 vacation rentals in Oldsmar featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Oldsmar?
Four-legged friends are welcome in Oldsmar. Choose from more than 60 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Oldsmar?
Experience the best of Oldsmar with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there Oldsmar vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 70 vacation homes with pools in Oldsmar, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Oldsmar have a bbq area?
Absolutely! We offer over 20 house rentals with a bbq area in Oldsmar. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oldsmar have air conditioning?
Absolutely! We offer over 80 house rentals with air conditioning in Oldsmar. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oldsmar have wireless internet?
Absolutely! We offer over 80 house rentals with wireless internet in Oldsmar. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Oldsmar?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a bbq area, over 80 homes with air conditioning, over 80 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly house rentals in Oldsmar?
Oldsmar has more than 60 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Destinations to explore
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- John's Pass
- Bean Point Beach
- Cortez Beach
- Busch Gardens Tampa Bay
- Amalie Arena
- Raymond James Stadium
- North Beach
- Clearwater Beach
- Vinoy Park
- Coquina Beach
- Tampa Theatre
- Fort De Soto Park
- Curtis Hixon Waterfront Park
- Jannus Live
- ZooTampa at Lowry Park
- Adventure Island
- Splash Harbour Water Park
- River Strand Golf and Country Club
- Clearwater Marine Aquarium
- Fred Howard Park
- Lakewood National Golf Club
- Alafia River State Park
- Tropicana Field
- Van Wezel Performing Arts Hall