A beach at sunset with birds flying and a person walking.

Oldsmar Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Oldsmar vacation rentals

1. Beso Del Sol Resort

Beso Del Sol Resort
2.5 star property
Dunedin
8.6 out of 10, Excellent, (784 reviews)
"Friendly staff, great location and wonderful views"
United States
Gina
The price is CA $138
CA $208 total
includes taxes & fees
Oct 29 - Oct 30
Beso Del Sol Resort

2. Sailport Waterfront Suites

Sailport Waterfront Suites
3.5 star property
Rocky Point
8.4 out of 10, Very good, (5,293 reviews)
"Me and my family loved this place ❤️"
United States
Alcendrea
The price is CA $161
CA $207 total
includes taxes & fees
Nov 25 - Nov 26
Sailport Waterfront Suites

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 $84
CA $179 total
includes taxes & fees
Nov 5 - Nov 6
Green Castle Suite in Tampa

4. Key West Style Cottage - with pool/hot-tub

Key West Style Cottage - with pool/hot-tub
Dunedin
9.4 out of 10, Exceptional, (35 reviews)
"It was perfect for what we needed. It was clean and maintained well. Great location close to the heart of town."
United States
Sean
The price is CA $116
CA $270 total
includes taxes & fees
Oct 28 - Oct 29
Key West Style Cottage - with pool/hot-tub

5. Beautiful condo on Copperhead. Beaches nearby!

Beautiful condo on Copperhead. Beaches nearby!
Palm Harbor
9.6 out of 10, Exceptional, (30 reviews)
"Place was great and sits on hole 2 of Copperhead. The only catch is the property has no elevator, and the room is on the 3rd floor."
United States
Indy J.
The price is CA $154
CA $460 total
includes taxes & fees
Oct 30 - Oct 31
Beautiful condo on Copperhead. Beaches nearby!

6. 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, (84 reviews)
"Great stay, very clean. The pool was very nice. And the scenery was amazing as well"
United States
Brandy
The price is CA $50
CA $149 total
includes taxes & fees
Oct 29 - Oct 30
Welcome to our charming studio, perfectly located near Tampa Bay's attractions.

7. Yude's Apartment

Yude's Apartment
Town 'n' Country
9.6 out of 10, Exceptional, (29 reviews)
"Had a very wonderful stay highly recommended "
United States
Thalia
The price is CA $105
CA $211 total
includes taxes & fees
Oct 31 - Nov 1
Yude's Apartment

8. Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel
2.5 star property
Clearwater Beach
9.0 out of 10, Wonderful, (1,159 reviews)
"Excellent remodeled and upgraded jewel on Clearwater Beach."
United States
Jamie Lawrence
The price is CA $144
CA $242 total
includes taxes & fees
Oct 29 - Oct 30
Pelican Pointe Clearwater Beach Hotel

9. 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
9.0 out of 10, Wonderful, (40 reviews)
"Very clean, quiet. Safe surroundings if you are traveling by yourself."
United States
Deborah
The price is CA $78
CA $168 total
includes taxes & fees
Nov 10 - Nov 11
Cozy Boho Guest House w/Patio - 6 min from the beach!

10. The Fold Hotels Indian Shores

The Fold Hotels Indian Shores
3.0 star property
Indian Shores
9.2 out of 10, Wonderful, (1,024 reviews)
"Great location"
United States
Karen
The price is CA $166
CA $228 total
includes taxes & fees
Nov 24 - Nov 25
The Fold Hotels Indian Shores

11. DFGmoments#2/Northdale/Citrus Park Mall

DFGmoments#2/Northdale/Citrus Park Mall
Greater Northdale
9.8 out of 10, Exceptional, (82 reviews)
"Comfortable stay"
United States
Patrick T.
The price is CA $68
CA $169 total
includes taxes & fees
Oct 28 - Oct 29
DFGmoments#2/Northdale/Citrus Park Mall

12. John's Pass Hotel

John's Pass Hotel
2.0 star property
Madeira Beach
8.6 out of 10, Excellent, (491 reviews)
"Love the location having shops around and how easy was to check in"
United States
Luis
The price is CA $119
CA $157 total
includes taxes & fees
Nov 2 - Nov 3
John's Pass Hotel

13. Mint House St. Petersburg Downtown by Kasa

Mint House St. Petersburg Downtown by Kasa
4.0 star property
Downtown St. Petersburg
9.4 out of 10, Exceptional, (1,093 reviews)
"Very good value, nice and clean and great space with a (nearly) full kitchen for longer stays."
United States
Ariel
The price is CA $150
CA $169 total
includes taxes & fees
Nov 15 - Nov 16
Mint House St. Petersburg Downtown by Kasa

14. "Romantic home with a hot tub, 10 minutes from Clearwater Beach

"Romantic home with a hot tub, 10 minutes from Clearwater Beach
Clearwater
9.8 out of 10, Exceptional, (21 reviews)
"Hot tub was very nice and so was my host. would definitely book again if im in the area!"
United States
richard s.
The price is CA $145
CA $314 total
includes taxes & fees
Oct 28 - Oct 29
"Romantic home with a hot tub, 10 minutes from Clearwater Beach

15. Charming rental with a separate entrance.

Charming rental with a separate entrance.
Tampa
9.8 out of 10, Exceptional, (72 reviews)
"This place was perfect for a quick over night trip. Just as described! Would definitely stay again!"
United States
Ken Y.
The price is CA $88
CA $208 total
includes taxes & fees
Oct 28 - Oct 29
Charming rental with a separate entrance.

16. A beautiful and comfortable room, Apartment No. 2

A beautiful and comfortable room, Apartment No. 2
Tampa
10.0 out of 10, Exceptional, (52 reviews)
"Amazing hosts and clean, quiet, super cute place to stay!"
United States
Angela W.
The price is CA $95
CA $207 total
includes taxes & fees
Oct 28 - Oct 29
A beautiful and comfortable room, Apartment No. 2

17. Barefoot Beach Resort

Barefoot Beach Resort
3.5 star property
Indian Shores
9.0 out of 10, Wonderful, (1,059 reviews)
"Loved our stay!"
United Kingdom
HANNAH
The price is CA $167
CA $209 total
includes taxes & fees
Oct 28 - Oct 29
Barefoot Beach Resort

18. Chic Cottage Walk to Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3

Chic Cottage Walk to Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3
Downtown Dunedin
10.0 out of 10, Exceptional, (33 reviews)
"Excellent location. The host pulled out all the stops - they had everything to make the stay amazing!!"
United States
Lori A.
The price is CA $192
CA $473 total
includes taxes & fees
Oct 28 - Oct 29
Chic Cottage Walk to Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3

19. Summer Breezes Holiday: A Charming Suite Near Florida's Best Beaches

Summer Breezes Holiday: A Charming Suite Near Florida's Best Beaches
Colonial Hills
9.8 out of 10, Exceptional, (37 reviews)
"This place was very clean and well thought out floor plan. Also was very convenient for going into town."
United States
Thomas
The price is CA $139
CA $207 total
includes taxes & fees
Oct 29 - Oct 30
Summer Breezes Holiday: A Charming Suite Near Florida's Best Beaches

20. Sunset Vistas Two Bedroom Beachfront Suites

Sunset Vistas Two Bedroom Beachfront Suites
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (3,767 reviews)
"Location was great close to everything. Cafe food was great for breakfast and lunch, Unit could use a little updating, linens definitely need to be replaced."
United States
Michele
The price is CA $212
CA $279 total
includes taxes & fees
Nov 2 - Nov 3
Sunset Vistas Two Bedroom Beachfront Suites
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.
Save an average of 15% on thousands of hotels when you're signed in

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.

Explore a world of travel with Expedia

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: Visitors like this Oldsmar vacation home rental. It 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 9 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.