Oldsmar Vacation Rentals from $110: 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

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

1. Sailport Waterfront Suites

Rocky Point

Alcendrea

$125 nightly

Oct 28 - Oct 29

Total with taxes and fees

A stone pool surrounded by tropical plants and palm trees.

2. Vibrant 2BR 2BA w King Bed Pool Gym 11

Town 'n' Country

Kim Viola

$271 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

3. Beso Del Sol Resort

Dunedin

Tracey

$135 nightly

Oct 19 - Oct 20

Total with taxes and fees

A balcony with wicker furniture overlooking a beach.

4. The Avalon Club

Clearwater Beach

Robert

$270 nightly

Oct 19 - Oct 20

Total with taxes and fees

A beachside seating area with a fire pit and chairs, overlooking the ocean.

5. The Hemingway

Rocky Point

Michelle

$258 nightly

Oct 19 - Oct 20

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 8 - Nov 9

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

$152 nightly

Oct 20 - Oct 21

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

$167 nightly

Oct 19 - Oct 20

Total with taxes and fees

A beach with a large number of people, a seagull flying, and several high-rise buildings in the background.

9. Waterfront Resort Condo Gulf Sun Set

Dunedin

joe

$374 nightly

Oct 25 - Oct 26

Total with taxes and fees

A modern kitchen with a large island, white cabinetry, and a dining area with a table and chairs.

10. The Gemma by Brightwild

Clearwater Beach

William

$1,238 nightly

Oct 27 - Oct 28

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

$148 nightly

Nov 1 - Nov 2

Total with taxes and fees

A modern living room with a grey sofa, a round wooden coffee table, and a large mirror.

12. Modern 2BR Pool Gym Pet-friendly 12

Town 'n' Country

$296 nightly

Oct 20 - Oct 21

Total with taxes and fees

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

13. The Adaline

Hyde Park

Mihaela

$304 nightly

Oct 18 - Oct 19

Total with taxes and fees

A modern kitchen with white cabinetry, stainless steel appliances, and a central island.

14. 2631 Cedarglen Drive

Barrington Hills

$2,495 nightly

Oct 18 - Oct 19

Total with taxes and fees

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

15. Barefoot Beach Resort

Indian Shores

HANNAH

$132 nightly

Oct 18 - Oct 19

Total with taxes and fees

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

16. FUSION Resort Waterfront Suites

Treasure Island

Marilyn

$209 nightly

Oct 18 - Oct 19

Total with taxes and fees

A beach with numerous white tents and a sandy beach.

17. Surf Beach Treasure Island Resort

Treasure Island

Krishna

$327 nightly

Oct 19 - Oct 20

Total with taxes and fees

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

18. John's Pass Hotel

Madeira Beach

John

$97 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

19. Crystal Palms Beach Resort

Sunshine Beach

AMY

$112 nightly

Oct 25 - Oct 26

Total with taxes and fees

A hotel with a modern design, featuring a prominent 'South Beach' sign and a 'Beach' sign.

20. South Beach Oceanfront Resort

Sunshine Beach

Ronald

$247 nightly

Oct 19 - Oct 20

Total with taxes and fees

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Top Oldsmar Hotel Reviews

OASIS BAY SUITES, Tampa, Busch Gardens, USF

10/10 Excellent

"Property is well maintained, staff were nice and helpful, breakfast was yummy, room was absolutely perfect, minus the a/c being a bit loud. Only real downside was that the room keys repeatedly stopped working. Office staff were quick to replace them, though. Loved the pool and courtyard!!!"

Fairfield Inn & Suites by Marriott Clearwater Beach

10/10 Excellent

"The location is great. Walkable or they provided a golfcart shuttle to the beach 4 blocks away. They will also shuttle you to nearby restaurants. Friendly helpful staff. Only downfall is we upgraded to a water view room and the view was just a sliver out the window."

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!"

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 $110 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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Things to do in Palm Harbor

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.

Room 1

Check prices for these dates

Our top choices for Oldsmar vacation rentals

1. Sailport Waterfront Suites

2. Vibrant 2BR 2BA w King Bed Pool Gym 11

3. Beso Del Sol Resort

4. The Avalon Club

5. The Hemingway

6. Mint House St. Petersburg Downtown by Kasa

7. Pelican Pointe Clearwater Beach Hotel

8. Sunset Vistas Two Bedroom Beachfront Suites

9. Waterfront Resort Condo Gulf Sun Set

10. The Gemma by Brightwild

11. The Fold Hotels Indian Shores

12. Modern 2BR Pool Gym Pet-friendly 12

13. The Adaline

14. 2631 Cedarglen Drive

15. Barefoot Beach Resort

16. FUSION Resort Waterfront Suites

17. Surf Beach Treasure Island Resort

18. John's Pass Hotel

19. Crystal Palms Beach Resort

20. South Beach Oceanfront Resort

Find vacation rentals that suit your style

Top Oldsmar Hotel Reviews

OASIS BAY SUITES, Tampa, Busch Gardens, USF

Fairfield Inn & Suites by Marriott Clearwater Beach

Wyndham Grand Clearwater Beach

Quality Inn Tampa Airport - Cruise Port

Gulfview Hotel on the Beach

Ramada by Wyndham Temple Terrace/Tampa North

Four Points by Sheraton Suites Tampa Airport Westshore

The Barrymore Hotel Tampa Riverwalk

Hilton Tampa Airport Westshore

Find out more about Oldsmar

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