Oldsmar Vacation Rentals from $118: 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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In two weeks

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Our top choices for Oldsmar vacation rentals

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

1. Beso Del Sol Resort

Dunedin

Gina

$124 nightly

Oct 25 - Oct 26

Total with taxes and fees

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

2. Sailport Waterfront Suites

Rocky Point

Alcendrea

$133 nightly

Nov 2 - Nov 3

Total with taxes and fees

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

3. Green Castle Suite in Tampa

Town 'n' Country

Stephanie S.

$115 nightly

Oct 21 - Oct 22

Total with taxes and fees

A spacious living room with a large sliding glass door leading to a balcony, a ceiling fan, and a bookshelf.

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

Dunedin

Sean

$174 nightly

Oct 25 - Oct 26

Total with taxes and fees

5. Full of Love

Town 'n' Country

Francisco

$130 nightly

Oct 21 - Oct 22

Total with taxes and fees

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

6. Pelican Pointe Clearwater Beach Hotel

Clearwater Beach

Bobbi

$152 nightly

Oct 28 - Oct 29

Total with taxes and fees

A modern bedroom with a large bed, a bedside table, a nightstand, a small desk, a microwave, a coffee maker, and a sink.

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

Pinecrest West Park

Brandy

$96 nightly

Oct 25 - Oct 26

Total with taxes and fees

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

8. Yude's Apartment

Town 'n' Country

Thalia

$135 nightly

Oct 21 - Oct 22

Total with taxes and fees

A modern building with a flat roof and large windows.

9. Beautiful condo on Copperhead. Beaches nearby!

Palm Harbor

Indy J.

$267 nightly

Oct 26 - Oct 27

Total with taxes and fees

A water slide at Adventureland in Tampa, FL.

10. DFGmoments#2/Northdale/Citrus Park Mall

Greater Northdale

Patrick T.

$114 nightly

Oct 21 - Oct 22

Total with taxes and fees

A living room with a grey sofa, a patterned rug, a dining table with white chairs, and a potted plant.

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

Town 'n' Country

Deborah

$108 nightly

Nov 10 - Nov 11

Total with taxes and fees

A hot tub with a waterfall backdrop, a bottle of wine, and two glasses.

12. "Romantic home with jacuzzi, 10 minutes from Clearwater Beach

Clearwater

richard s.

$204 nightly

Oct 22 - Oct 23

Total with taxes and fees

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

13. John's Pass Hotel

Madeira Beach

John

$104 nightly

Nov 19 - Nov 20

Total with taxes and fees

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

14. Mint House St. Petersburg Downtown by Kasa

Downtown St. Petersburg

Leah

$120 nightly

Nov 8 - Nov 9

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.

15. The Fold Hotels Indian Shores

Indian Shores

Karen

$147 nightly

Nov 2 - Nov 3

Total with taxes and fees

A modern kitchen with white cabinets, a black refrigerator, a microwave, and a granite countertop.

16. Charming rental with a separate entrance.

Tampa

Ken Y.

$133 nightly

Oct 21 - Oct 22

Total with taxes and fees

A kitchen with teal walls, white cabinets, and a white refrigerator.

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

Tampa

Angela W.

$133 nightly

Oct 21 - Oct 22

Total with taxes and fees

A wooden swing with metal chains, overlooking a beach with clear turquoise water and a cloudy sky.

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

Colonial Hills

Thomas

$134 nightly

Oct 21 - Oct 22

Total with taxes and fees

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

19. Barefoot Beach Resort

Indian Shores

HANNAH

$142 nightly

Oct 22 - Oct 23

Total with taxes and fees

A balcony with wicker furniture overlooking a beach.

20. The Avalon Club

Clearwater Beach

Robert

$248 nightly

Nov 19 - Nov 20

Total with taxes and fees

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Top Oldsmar Hotel Reviews

The Westin Tampa Bay

10/10 Excellent

"Very nice hotel rooms were clean. Staff is always there and helpful. They had a very nice little Starbucks and a very good restaurant in the hotel"

GALAXY HOTEL

10/10 Excellent

"This has been the best stay we ever had. We went to celebrate our wedding anniversary and we also found out we are having a baby. They were so kind and helpful. Reserved us a parking spot in the garage, extended our checkout time till later in the day since we were doing the museum before we left. They accommodated everything and we had the best stay. We 100% recommend to stay here and we will definitely stay here again when we visit. For it being our first time in ST. Pete this was by far the best stay."

Gulfview Hotel on the Beach

10/10 Excellent

"My family and I enjoyed our stay here. The staff were gracious and welcoming. The hotel is basic but a great value and includes on site parking, a private beach and beach towels. There is a 7 Eleven across the street and several restaurants are within walking distance. I especially liked how we weren't nickel and dimed like the last hotel we stayed at a few doors down with added resort and parking fees. We could hear the band from the hotel next door but the music was great and the a/c drowned it out. We look forward to returning."

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 $118 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. Beso Del Sol Resort

2. Sailport Waterfront Suites

3. Green Castle Suite in Tampa

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

5. Full of Love

6. Pelican Pointe Clearwater Beach Hotel

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

8. Yude's Apartment

9. Beautiful condo on Copperhead. Beaches nearby!

10. DFGmoments#2/Northdale/Citrus Park Mall

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

12. "Romantic home with jacuzzi, 10 minutes from Clearwater Beach

13. John's Pass Hotel

14. Mint House St. Petersburg Downtown by Kasa

15. The Fold Hotels Indian Shores

16. Charming rental with a separate entrance.

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

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

19. Barefoot Beach Resort

20. The Avalon Club

Find vacation rentals that suit your style

Top Oldsmar Hotel Reviews

The Westin Tampa Bay

OASIS BAY SUITES, Tampa, Busch Gardens, USF

GALAXY HOTEL

Hilton Clearwater Beach Resort & Spa

Gulfview Hotel on the Beach

Hyatt Regency Clearwater Beach Resort and Suites

Hotel Haya

Four Points by Sheraton Suites Tampa Airport Westshore

Hotel South Tampa & Suites

Find out more about Oldsmar

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