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Oldsmar Vacation Rentals

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Our top choices for Oldsmar vacation rentals

1. Luxury Bayfront Escape

Luxury Bayfront Escape
Oldsmar
The price is CA $1,056
CA $2,249 total
includes taxes & fees
Sep 14 - Sep 15
Luxury Bayfront Escape

2. Escape By The Bay

Escape By The Bay
Town 'n' Country
9.8 out of 10, Exceptional, (43 reviews)
"Great value for space"
United States
Jake G.
The price is CA $85
CA $180 total
includes taxes & fees
Sep 13 - Sep 14
Escape By The Bay

3. Green Castle Suite in Tampa

Green Castle Suite in Tampa
Town 'n' Country
9.6 out of 10, Exceptional, (40 reviews)
"Great place to stay!"
United States
Stephanie S.
The price is CA $83
CA $177 total
includes taxes & fees
Sep 14 - Sep 15
Green Castle Suite in Tampa

4. Cozy Boho Guest House w/Patio - 6 min from the beach!

Cozy Boho Guest House w/Patio - 6 min from the beach!
Town 'n' Country
9.2 out of 10, Wonderful, (37 reviews)
"Very clean, quiet. Safe surroundings if you are traveling by yourself."
United States
Deborah
The price is CA $77
CA $166 total
includes taxes & fees
Sep 29 - Sep 30
Cozy Boho Guest House w/Patio - 6 min from the beach!

5. Welcome to our charming studio, perfectly located near Tampa Bay's attractions.

Welcome to our charming studio, perfectly located near Tampa Bay's attractions.
Pinecrest West Park
9.2 out of 10, Wonderful, (78 reviews)
"Was really nice and price range good for accommodations "
United States
Alejandra
The price is CA $50
CA $147 total
includes taxes & fees
Sep 14 - Sep 15
Welcome to our charming studio, perfectly located near Tampa Bay's attractions.

6. Beso Del Sol Resort

Beso Del Sol Resort
2.5 star property
Dunedin
8.6 out of 10, Excellent, (765 reviews)
"Every time I come to Florida this will be my home. Love this place"
United States
Jonathan
The price is CA $149
CA $221 total
includes taxes & fees
Sep 13 - Sep 14
Beso Del Sol Resort

7. Sailport Waterfront Suites

Sailport Waterfront Suites
3.5 star property
Rocky Point
8.4 out of 10, Very good, (5,223 reviews)
"Great view and friendly staff"
United States
Torin
The price is CA $146
CA $190 total
includes taxes & fees
Sep 22 - Sep 23
Sailport Waterfront Suites

8. DFGmoments#2/Northdale/Citrus Park Mall

DFGmoments#2/Northdale/Citrus Park Mall
Greater Northdale
9.8 out of 10, Exceptional, (80 reviews)
"Comfortable stay"
United States
Patrick T.
The price is CA $69
CA $169 total
includes taxes & fees
Sep 24 - Sep 25
DFGmoments#2/Northdale/Citrus Park Mall

9. Beautiful and comfortable room Apt # 2

Beautiful and comfortable room Apt # 2
Tampa
10.0 out of 10, Exceptional, (49 reviews)
"Amazing hosts and clean, quiet, super cute place to stay!"
United States
Angela W.
The price is CA $93
CA $204 total
includes taxes & fees
Sep 14 - Sep 15
Beautiful and comfortable room Apt # 2

10. Charming rental unit with separate entrance.

Charming rental unit with separate entrance.
Tampa
9.8 out of 10, Exceptional, (69 reviews)
"Great and safe location! Lots of restaurants nearby. It is an ideal place to stay if planning on attending a Tampa bay buccaneers game or planning to go to Clearwater beach and not drive back home . I would definitely stay again . "
United States
Jorge H.
The price is CA $80
CA $197 total
includes taxes & fees
Sep 13 - Sep 14
Charming rental unit with separate entrance.

11. Aileen Camping Space

Aileen Camping Space
East Tampa
9.6 out of 10, Exceptional, (79 reviews)
"The host was very welcoming and the accommodation was excellent!"
United States
daniel z.
The price is CA $62
CA $177 total
includes taxes & fees
Sep 14 - Sep 15
Aileen Camping Space

12. Direct water view from Balcony-Pool

Direct water view from Balcony-Pool
Rocky Point
9.4 out of 10, Exceptional, (76 reviews)
"Very nice for a quick relaxing getaway!"
United States
Stefanie M.
The price is CA $149
CA $348 total
includes taxes & fees
Sep 30 - Oct 1
Direct water view from Balcony-Pool

13. Waterfront view, Heated Pool, Private Balcony

Waterfront view, Heated Pool, Private Balcony
Rocky Point
9.6 out of 10, Exceptional, (95 reviews)
"The place was perfect, I would come back or recommend it in a heartbeat."
United States
Tony G.
The price is CA $166
CA $371 total
includes taxes & fees
Sep 14 - Sep 15
Waterfront view, Heated Pool, Private Balcony

14. Experience the passion of hospitality, cleaning, and good location!

Experience the passion of hospitality, cleaning, and good location!
Westshore
9.2 out of 10, Wonderful, (94 reviews)
"Staff was really nice!"
United States
Anthony
The price is CA $101
CA $180 total
includes taxes & fees
Sep 14 - Sep 15
Experience the passion of hospitality, cleaning, and good location!

15. Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel
2.5 star property
Clearwater Beach
9.0 out of 10, Wonderful, (1,121 reviews)
"Clean property with very close proximity to the beach. Close to all attractions."
United States
Therezabeth
The price is CA $134
CA $230 total
includes taxes & fees
Sep 13 - Sep 14
Pelican Pointe Clearwater Beach Hotel

16. ☀Oceanfront ☀Amazing Balcony view☀ WIFI Bar☀ Waterfront Heated Pool ☀

☀Oceanfront ☀Amazing Balcony view☀ WIFI Bar☀ Waterfront Heated Pool ☀
Rocky Point
9.4 out of 10, Exceptional, (51 reviews)
"Such a fantastic value. The location and the amenities were so fun and convince y!"
United States
Kasey J.
The price is CA $137
CA $324 total
includes taxes & fees
Sep 14 - Sep 15
☀Oceanfront ☀Amazing Balcony view☀ WIFI Bar☀ Waterfront Heated Pool ☀

17. Experience the passion of hospitality, cleaning, and good location!

Experience the passion of hospitality, cleaning, and good location!
Westshore
9.4 out of 10, Exceptional, (144 reviews)
"Will stay again"
United States
Gary M.
The price is CA $93
CA $172 total
includes taxes & fees
Sep 14 - Sep 15
Experience the passion of hospitality, cleaning, and good location!

18. Powhatan suite 3 just 5 mins away from Raymond James Stadium

Powhatan suite 3 just 5 mins away from Raymond James Stadium
Tampa
9.8 out of 10, Exceptional, (42 reviews)
"very clean/ efficient check in/out"
United States
Leisa J.
The price is CA $137
CA $262 total
includes taxes & fees
Sep 13 - Sep 14
Powhatan suite 3 just 5 mins away from Raymond James Stadium

19. Waterfront! 10 min to airport/Near stadium

Waterfront! 10 min to airport/Near stadium
Rocky Point
9.4 out of 10, Exceptional, (75 reviews)
"Great location. Very clean and comfortable. I enjoyed the stay."
United States
Anthony L.
The price is CA $158
CA $358 total
includes taxes & fees
Sep 15 - Sep 16
Waterfront! 10 min to airport/Near stadium

20. La Casita Blanca Ybor City Tampa

La Casita Blanca Ybor City Tampa
Ybor City
9.8 out of 10, Exceptional, (142 reviews)
"Very clean, great a/c, good location and nice host!"
Canada
Aimee
The price is CA $104
CA $279 total
includes taxes & fees
Sep 15 - Sep 16
La Casita Blanca Ybor City Tampa
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.
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Top Oldsmar Hotel Reviews

Find out more about Oldsmar

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Oldsmar. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find vacation rentals in Oldsmar?

Yes, we have vacation rentals where you'll be just 14.9 mi (23.9 km) from Busch Gardens Tampa Bay, giving you a secluded option to escape the hustle and bustle. Visitors like the top-notch restaurants and beaches in Oldsmar. Make sure you have time to check out the theme park and cafes during your trip.

What are some of the best vacation home rentals in Oldsmar?

The Gemma by Brightwild: You might want to consider this vacation home rental near Oldsmar, which is located on the beach and has an outdoor pool, a private balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family. It offers a terrace, a private yard, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals will I find in Oldsmar?

Expedia has 11 vacation rentals for your stay in Oldsmar.

What can I see and do in Oldsmar?

Explore the area and family-friendly sights such as Busch Gardens Tampa Bay, or get out into nature at a spot like Tampa Bay. In the larger area, you’ll find popular places like Raymond James Stadium and Port Tampa Bay.

What are vacation rentals like in Oldsmar?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Oldsmar. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.