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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Our top choices for Oldsmar vacation rentals

A tennis court with multiple courts, surrounded by trees and a building with a blue roof.

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

Oldsmar

$524 nightly

Oct 10 - Oct 11

Total with taxes and fees

2. Luxury Bayfront Escape

Oldsmar

$1,369 nightly

Oct 1 - Oct 2

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

Amy

$121 nightly

Oct 13 - Oct 14

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

$155 nightly

Sep 29 - Sep 30

Total with taxes and fees

A balcony with wicker furniture overlooking a beach.

5. The Avalon Club

Clearwater Beach

Robert

$270 nightly

Sep 30 - Oct 1

Total with taxes and fees

A modern kitchen with white cabinets, a large island with bar stools, stainless steel appliances, and pendant lighting.

6. Downtown Dunedin Walking District

Downtown Dunedin

Barbara B.

$370 nightly

Sep 29 - Sep 30

Total with taxes and fees

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

7. Mint House St. Petersburg Downtown by Kasa

Downtown St. Petersburg

Leah

$120 nightly

Sep 30 - Oct 1

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".

8. Escape By The Bay

Town 'n' Country

Denisa

$103 nightly

Sep 29 - Sep 30

Total with taxes and fees

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

9. Pelican Pointe Clearwater Beach Hotel

Clearwater Beach

Renee

$141 nightly

Sep 30 - Oct 1

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.

10. The Fold Hotels Indian Shores

Indian Shores

Karen

$158 nightly

Sep 29 - Sep 30

Total with taxes and fees

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

11. Barefoot Beach Resort

Indian Shores

HANNAH

$114 nightly

Sep 29 - Sep 30

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.

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

Dunedin

Sean

$173 nightly

Sep 29 - Sep 30

Total with taxes and fees

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

13. Green Castle Suite in Tampa

Town 'n' Country

Stephanie S.

$116 nightly

Sep 29 - Sep 30

Total with taxes and fees

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

14. Modern Heater pool house tampa. Close to the park and zoo

Lake Magdalene

David L.

$312 nightly

Sep 29 - Sep 30

Total with taxes and fees

A modern kitchen with a brick backsplash, a dining area with a large table and chairs, and a hanging light fixture.

15. Newly remodeled Bucs stadium home half mile walk, king bed master suite

Tampa

Tara H.

$255 nightly

Sep 29 - Sep 30

Total with taxes and fees

A beach with thatched umbrellas, lounge chairs, and palm trees.

16. 262-NEW! 3 beds x 2 baths. Amazing Waterfront Views!

Rocky Point

Tiffany m.

$334 nightly

Sep 29 - Sep 30

Total with taxes and fees

A modern building with a flat roof and large windows.

17. Beautiful condo on Copperhead. Beaches nearby!

Palm Harbor

Clive C.

$236 nightly

Sep 29 - Sep 30

Total with taxes and fees

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

18. Charming rental unit with separate entrance.

Tampa

Jorge H.

$133 nightly

Oct 6 - Oct 7

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.

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

Pinecrest West Park

Brandy

$96 nightly

Oct 5 - Oct 6

Total with taxes and fees

A beach with a pier extending into the ocean, a sandy beach lined with palm trees, and a row of beach umbrellas.

20. PROMO PRICES - POOL VIEW - CLEARWATER BEACH - FREE WI-FI/PARKING

Clearwater

James B.

$258 nightly

Sep 29 - Sep 30

Total with taxes and fees

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Top Oldsmar Hotel Reviews

Hyatt Regency Clearwater Beach Resort and Suites

10/10 Excellent

"Great trip! Can’t wait to go back!"

GALAXY HOTEL

10/10 Excellent

"This is NOT a 2 star hotel, don't let that rate fool you, it is excellent with beautiful view, clean, wonderful staff, wonderful environment, in an area full of things to do. It is bustling with life and yet so very VERY quiet. Slept like a baby here. The beds were comfy, the ac worked wonderful, if i have another event (which my brother and I went to anime st. Pete) we will definitely stay here. It's affordable as ever. The only flaw is parking. There is a parking garage very close by but the street parking is free but you have a 2 hour limit until nightfall where you can do your 2 hour parking and not need to move til the morning which restarts your 2 hour parking. They only do Valet for the hotel itself which is a bit pricey but honestly, this hotel is wonderful and worth it."

The Westin Tampa Bay

10/10 Excellent

"I recently stayed at the West Tampa Bay with a few girlfriends for a girls weekend. We were impressed from the start of our stay. The Bell hop in the carport greeted upon arrival with a smile and fantastic attitude. Welcoming and ready to help. Angel checked us. He too was welcoming, attentive, and ready to accommodate. He went a step behind calling to see if our room could be cleaned so we could get in early. He followed through and called as the room was available for hour earlier than expected. We all commented how impressed we were with the wonderful customer service. Leo waited on us at the pool and was friendly and very efficient. Just a joy! One of my girlfriends is a little high maintenance and called down to see if they possibly had a fan we could use in the room. They did and brought it right up to us. Wow! We really enjoyed our stay and I can’t say enough about how impressed we were with the staff and service. Gold star! Thank you.!"

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.

Oldsmar Vacation Rentals

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Check prices for these dates

Our top choices for Oldsmar vacation rentals

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

2. Luxury Bayfront Escape

3. Sailport Waterfront Suites

4. Beso Del Sol Resort

5. The Avalon Club

6. Downtown Dunedin Walking District

7. Mint House St. Petersburg Downtown by Kasa

8. Escape By The Bay

9. Pelican Pointe Clearwater Beach Hotel

10. The Fold Hotels Indian Shores

11. Barefoot Beach Resort

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

13. Green Castle Suite in Tampa

14. Modern Heater pool house tampa. Close to the park and zoo

15. Newly remodeled Bucs stadium home half mile walk, king bed master suite

16. 262-NEW! 3 beds x 2 baths. Amazing Waterfront Views!

17. Beautiful condo on Copperhead. Beaches nearby!

18. Charming rental unit with separate entrance.

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

20. PROMO PRICES - POOL VIEW - CLEARWATER BEACH - FREE WI-FI/PARKING

Find vacation rentals that suit your style

Top Oldsmar Hotel Reviews

Hyatt Regency Clearwater Beach Resort and Suites

Find out more about Oldsmar

Explore a world of travel with Expedia

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