Oldsmar Vacation Rentals from $112: Search Short-Term Rentals

Q: 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.

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Our top choices for Oldsmar vacation rentals

1. Luxury Bayfront Escape

Oldsmar

$1,435 nightly

Oct 14 - Oct 15

Total with taxes and fees

A modern kitchen with a central island, bar stools, and pendant lighting.

2. Palm Lake Retreat | Pool, Beaches, Near Tampa

Oldsmar

$456 nightly

Oct 16 - Oct 17

Total with taxes and fees

A beach with thatched umbrellas and lounge chairs, a sandy shore, and a sunset in the background.

3. Sailport Waterfront Suites

Rocky Point

Alcendrea

$131 nightly

Nov 2 - Nov 3

Total with taxes and fees

A waterfront hotel with multiple balconies, a dock, and a reflective water surface.

4. Beso Del Sol Resort

Dunedin

Tracey

$135 nightly

Nov 1 - Nov 2

Total with taxes and fees

A balcony with wicker furniture overlooking a beach.

5. The Avalon Club

Clearwater Beach

Robert

$270 nightly

Oct 14 - Oct 15

Total with taxes and fees

An outdoor patio with a dining table, chairs, and a sofa.

6. Mint House St. Petersburg Downtown by Kasa

Downtown St. Petersburg

Leah

$120 nightly

Nov 1 - Nov 2

Total with taxes and fees

A hotel with a pool area, palm trees, and a view of the ocean.

7. Pelican Pointe Clearwater Beach Hotel

Clearwater Beach

Bobbi

$145 nightly

Oct 19 - Oct 20

Total with taxes and fees

An aerial view of a coastal resort area with multiple buildings, a beach, and a marina.

8. Sunset Vistas Two Bedroom Beachfront Suites

Sunshine Beach

Rebecca

$176 nightly

Oct 26 - Oct 27

Total with taxes and fees

A dining table with a birthday cake, champagne, and a scenic waterfront view.

9. FUSION Resort Waterfront Suites

Treasure Island

Marilyn

$187 nightly

Oct 15 - Oct 16

Total with taxes and fees

A neatly made bed with a quilted white and black bedspread, a wooden headboard, and a framed sign above reading "stay awhile".

10. Escape By The Bay

Town 'n' Country

Denisa

$118 nightly

Oct 14 - Oct 15

Total with taxes and fees

A wooden dock with a fire feature and a 'Please be safe' sign, overlooking a lake with a building in the background.

11. The Fold Hotels Indian Shores

Indian Shores

Karen

$149 nightly

Nov 1 - Nov 2

Total with taxes and fees

A hotel with a prominent 'Sheraton' sign, a waterfront location, and a modern bridge structure.

12. Green Castle Suite in Tampa

Town 'n' Country

Stephanie S.

$115 nightly

Oct 14 - Oct 15

Total with taxes and fees

A modern building with a flat roof and large windows.

13. Beautiful condo on Copperhead. Beaches nearby!

Palm Harbor

Indy J.

$261 nightly

Oct 14 - Oct 15

Total with taxes and fees

A beach with clear blue water and a tree with white flowers.

14. Studio Apt w/ Private Balcony Overlooking Downtown Main St

Downtown Dunedin

Patrick M.

$262 nightly

Oct 14 - Oct 15

Total with taxes and fees

15. richon of love

Town 'n' Country

Francisco

$130 nightly

Oct 14 - Oct 15

Total with taxes and fees

A modern kitchen with a grey countertop, white cabinets, and a built-in microwave.

16. Yude's Apartment

Town 'n' Country

Thalia

$135 nightly

Oct 14 - Oct 15

Total with taxes and fees

A multi-story hotel with a curved entrance and balconies on each floor.

17. Crystal Palms Beach Resort

Sunshine Beach

AMY

$116 nightly

Oct 14 - Oct 15

Total with taxes and fees

A bright room with a round table, two chairs, and large windows.

18. The Adaline

Hyde Park

Mihaela

$304 nightly

Oct 14 - Oct 15

Total with taxes and fees

A two-story hotel with a balcony on the upper floor, a stop sign, and a parking area.

19. John's Pass Hotel

Madeira Beach

John

$99 nightly

Nov 10 - Nov 11

Total with taxes and fees

A dining area with a round table, white chairs, a chandelier, and a window with blinds.

20. Barefoot Beach Resort

Indian Shores

HANNAH

$132 nightly

Oct 18 - Oct 19

Total with taxes and fees

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Top Oldsmar Hotel Reviews

Ramada by Wyndham Temple Terrace/Tampa North

10/10 Excellent

"I had awesome good stay"

Hilton Tampa Airport Westshore

10/10 Excellent

"I really enjoyed my stay at this hotel! Everything was very clean, the air conditioning worked great and kept the room nice and cool, and the room was very comfortable. The hotel is also conveniently located, making it easy to get to nearby attractions and places of interest. I highly recommend this hotel!"

Wyndham Grand Clearwater Beach

10/10 Excellent

"This was my third time staying at the Wyndham Grand Clearwater Beach, and once again, it did not disappoint! Every visit reminds me why I keep coming back. From the moment we arrived, the check-in process was smooth, welcoming, and professional. The hotel is beautiful, exceptionally clean, and perfectly located right on the beachfront, offering a wonderful atmosphere for a relaxing getaway. The pool bar is absolutely amazing, with a fantastic atmosphere, and the lobby bar is just as impressive! Both are great places to unwind, enjoy a drink, and soak in the vacation vibes. The beachfront location is unbeatable, and the overall experience continues to exceed my expectations. It's clear that the hotel takes pride in providing a clean, comfortable, and enjoyable stay for its guests. Three visits and counting! Wyndham Grand Clearwater Beach continues to be one of my favorite places to stay in Clearwater. I look forward to returning for a fourth visit. Highly recommend!"

Hilton Clearwater Beach Resort & Spa

10/10 Excellent

"We have stayed here several times and it is consistently a great experience. Paying almost $40 a night to park our car is a bit extreme and more than it used to be, and then there is the additional $35/per night resort fee. That is our only complaint. Overall, a great time."

Find out more about Oldsmar

Everything you need to know about Oldsmar vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oldsmar vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oldsmar vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oldsmar vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oldsmar. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Oldsmar in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $112 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oldsmar rentals

At Expedia, we put the best Oldsmar vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Oldsmar rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oldsmar vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oldsmar. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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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: 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.

Oldsmar Vacation Rentals

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Check prices for these dates

Our top choices for Oldsmar vacation rentals

1. Luxury Bayfront Escape

2. Palm Lake Retreat | Pool, Beaches, Near Tampa

3. Sailport Waterfront Suites

4. Beso Del Sol Resort

5. The Avalon Club

6. Mint House St. Petersburg Downtown by Kasa

7. Pelican Pointe Clearwater Beach Hotel

8. Sunset Vistas Two Bedroom Beachfront Suites

9. FUSION Resort Waterfront Suites

10. Escape By The Bay

11. The Fold Hotels Indian Shores

12. Green Castle Suite in Tampa

13. Beautiful condo on Copperhead. Beaches nearby!

14. Studio Apt w/ Private Balcony Overlooking Downtown Main St

15. richon of love

16. Yude's Apartment

17. Crystal Palms Beach Resort

18. The Adaline

19. John's Pass Hotel

20. Barefoot Beach Resort

Find vacation rentals that suit your style

Top Oldsmar Hotel Reviews

Ramada by Wyndham Temple Terrace/Tampa North

Find out more about Oldsmar

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