Oldsmar vacation rentals
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
Get the amount of space that is right for you
Popular amenities for Oldsmar vacation rentals
Other great vacation rentals in Oldsmar
Home in Oldsmar
4.94 out of 5 average rating, 17 reviewsSunny Oasis: Villa Retreat
Dec 30 – Jan 6
Home in Oldsmar
4.85 out of 5 average rating, 67 reviewsPrivate In-Law Suite with Beautiful Bay View
Nov 29 – Dec 6
Home in Oldsmar
4.89 out of 5 average rating, 96 reviewsCoastal themed home near beach and airport
Jun 17 – 24
Guest suite in Oldsmar
4.91 out of 5 average rating, 95 reviewsQuiet Bay Getaway-Hot Tub-Dog friendly-Bikes
Apr 26 – May 3
Apartment in Oldsmar
4.92 out of 5 average rating, 59 reviewsModern 2nd Floor Two Bedroom Apt with Pool
Jun 21 – 28
Guesthouse in Palm Harbor
4.93 out of 5 average rating, 40 reviewsHome away from home
Oct 23 – 30
Guesthouse in Clearwater
5.0 out of 5 average rating, 23 reviewsCozy In-Law Suite Near Beach
May 30 – Jun 6
Cottage in Dunedin
4.95 out of 5 average rating, 97 reviewsBeachBunkies Cottage 2. Four miles to the beach!
Aug 7 – 14
Other great vacation rentals in Oldsmar
Barn in Odessa
5.0 out of 5 average rating, 26 reviewsCypress Lakes Barndominium
Jan 20 – 27
Home in Oldsmar
4.99 out of 5 average rating, 71 reviewsFountain House On Timberbay Lake
Sep 18 – 25
Home in Oldsmar
4.86 out of 5 average rating, 50 reviewsModern & Spacious Retreat with Private Pool!
Oct 17 – 24
Condo in Palm Harbor
5.0 out of 5 average rating, 22 reviewsClassy Resort Condo w/ 75 inch TV & Patio
Aug 9 – 16
Camper/RV in Oldsmar
4.91 out of 5 average rating, 11 reviewsRv Experience
Dec 24 – 31
Guest suite in Odessa
5.0 out of 5 average rating, 73 reviewsGREAT ESCAPE for the Road Warrior.
Jun 13 – 20
Guesthouse in Dunedin
4.83 out of 5 average rating, 54 reviewsGuest House in prime location!
Oct 29 – Nov 5
Apartment in Clearwater
5.0 out of 5 average rating, 22 reviewsWelcome to your cozy studio!
Nov 22 – 29
Quick stats about vacation rentals in Oldsmar
Total rentals
120 properties
Rentals with a pool
60 properties have a pool
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
70 properties are a good fit for families
Total number of reviews
3.7K reviews
Nightly prices starting at
$20 before taxes and fees
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 520 vacation rentals in The Grove Of Laforest, over 170 vacation rentals in East Lake Woodlands, and over 170 vacation rentals in Bridlewood.
Are there pet-friendly vacation rentals in Oldsmar?
Four-legged friends are welcome in Oldsmar. Choose from more than 50 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Oldsmar?
Yes! Work meets play with ease at over 60 vacation rentals in Oldsmar featuring dedicated workspaces. Stay connected and productive 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 60 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 30 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 70 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 70 house rentals with wireless internet in Oldsmar. Enjoy a tailored experience with all the comforts you desire.
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 family-friendly house rentals in Oldsmar?
Oldsmar has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Oldsmar?
Enhance your stay in our House Rentals with the most popular amenities: over 70 homes with wireless internet, over 70 homes with air conditioning, over 30 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
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