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

Oldsmar Vacation 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.

Where to?

Dates

November 2026

December 2026

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Our top choices for Oldsmar vacation rentals

A kitchen with dark wooden cabinets, a tiled backsplash, and a dining table set with plates, cups, and a kettle.

1. Oldsmar Oakleaf Villa! On Wildlife Area, Natural Privacy! Patio Garage. King Bed

Oldsmar

Stephen W.

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

2. Sailport Waterfront Suites

Rocky Point

Paula A

$134 nightly

Nov 25 - Nov 26

Total with taxes and fees

A wooden pier leading to a dock with several boats moored at the end.

3. Beso Del Sol Resort

Dunedin

Gina

$135 nightly

Nov 15 - Nov 16

Total with taxes and fees

A balcony with wicker furniture overlooking a beach.

4. The Avalon Club

Clearwater Beach

Courtney

$270 nightly

Nov 16 - Nov 17

Total with taxes and fees

A hotel courtyard with a central fountain, palm trees, and a multi-story building with balconies.

5. Sunset Vistas Two Bedroom Beachfront Suites

Sunshine Beach

Shelby

$173 nightly

Nov 18 - Nov 19

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

Daniel

$137 nightly

Dec 2 - Dec 3

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

Anonymous traveler

$99 nightly

Nov 19 - Nov 20

Total with taxes and fees

A modern building with a flat roof and large windows.

8. Innisbrook 2BR Getaway With Balcony & Pool

Palm Harbor

Indy J.

$258 nightly

Nov 12 - Nov 13

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.

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

Dunedin

"Had an amazing stay at this beautiful cottage! The place was very clean, spacious, and comfortable, making it the perfect spot to relax and enjoy our time away. I felt safe throughout the stay, and the location was excellent, with cafés and restaurants within walking distance. The host was wonderful (very easy to communicate back and forth with, even left an itinerary with recommendations, LOVEDDD THATTT) and truly, appreciated the opportunity to stay here. Would absolutely recommend this...

Nayeli

$169 nightly

Nov 15 - Nov 16

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.

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

Town 'n' Country

Deborah

$100 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

11. 262-NEW! 3 beds x 2 baths. Amazing Waterfront Views!

Rocky Point

Julie T.

$325 nightly

Nov 16 - Nov 17

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.

12. The Fold Hotels Indian Shores

Indian Shores

Karen

$140 nightly

Dec 10 - Dec 11

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.

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

Pinecrest West Park

Brandy

$79 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

14. Green Castle Suite in Tampa

Town 'n' Country

Stephanie S.

$107 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

15. FUSION Resort Waterfront Suites

Treasure Island

Andrew

$209 nightly

Nov 12 - Nov 13

Total with taxes and fees

A waterfront property with a paved walkway, benches, palm trees, and a white fence.

16. Barefoot Beach Resort

Indian Shores

HANNAH

$132 nightly

Nov 23 - Nov 24

Total with taxes and fees

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

17. John's Pass Hotel

Madeira Beach

Luis

$115 nightly

Nov 18 - Nov 19

Total with taxes and fees

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

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

Tampa

Angela W.

$125 nightly

Nov 13 - Nov 14

Total with taxes and fees

A bedroom with a large bed, a nightstand, a chair, and a view of the ocean.

19. Crystal Palms Beach Resort

Sunshine Beach

Joe

$125 nightly

Nov 18 - Nov 19

Total with taxes and fees

A house with a front door, a large potted plant, and a small white lantern on the porch.

20. Experience the passion of hospitality, cleaning, and good location!

Westshore

Anthony

$104 nightly

Nov 12 - Nov 13

Total with taxes and fees

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Find vacation rentals that suit your style

Top Oldsmar Hotel Reviews

Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

Oldsmar

10/10 Excellent

JESSICA

A hotel lobby with a bar area, seating arrangements, and a television mounted on the wall.

Hampton Inn & Suites Tampa Northwest/Oldsmar

Oldsmar

10/10 Excellent

The staff was friendly, the room was clean and comfortable - AND quiet! The only thing I noticed that they may want to change is when the lobby restrooms are cleaned. Both days this was during breakfast, which is of course the busiest time. This also happened while our seminar was going on, which meant when we had a break, the only restroom available to us was out of order. Other than that, this was one of the best hotel stays I've had in a long time. Continental breakfast had ample...

Anonymous traveler

A poolside area with lounge chairs, a fire pit, and outdoor seating.

Hyatt House Tampa Airport Westshore

Westshore

10/10 Excellent

Madison

A hotel with multiple floors, a covered entrance, and palm trees in the foreground.

Holiday Inn Express & Suites St. Petersburg - Madeira Beach by IHG

St. Petersburg

10/10 Excellent

Agustin

A hotel pool area with sun loungers and a clear blue pool.

ChartHouse Clearwater Beach Marina Hotel

Clearwater Beach

10/10 Excellent

Jessica

An outdoor seating area with fire pits and lounge chairs, a stone wall, and a view of the interior through large windows.

Home2 Suites By Hilton Clearwater St. Petersburg Ulmerton Rd

Clearwater

10/10 Excellent

Michael

A restaurant with wooden ceiling and walls, hanging pendant lights, and a long wooden bar.

Hollander Boutique Hotel

Downtown St. Petersburg

10/10 Excellent

Paul

A modern lobby with seating areas, a flat-screen TV, and a reception desk.

Holiday Inn Express & Suites Tampa Stadium – Airport Area by IHG

MacFarlane Park

10/10 Excellent

Lorraine

A spacious lobby with a large white sofa, several armchairs, a coffee table, and a patterned rug. There are multiple doors leading outside, and a potted plant is visible.

Crystal Bay Historic Hotel

La Vista

10/10 Excellent

This hotel definately exceeded our expectations. Even though it is an old building (built in the early 1900s), the staff is very proud of its heritage and previous famous guests. They have done an outstanding job renovating and upkeeping this place. The hotel areas and rooms were impecably clean and the ambiance was from an old high vintage high class hotel. But the most noteworthy thing was their outstanding customer service. They treated us like family from the moment we checked in up to a...

Luis

A hotel with a central courtyard, palm trees, and a well-lit entrance.

Holiday Inn Express Hotel & Suites Clearwater North-Dunedin by IHG

Downtown Dunedin

10/10 Excellent

Gary

A multi-story hotel with a covered entrance, outdoor seating area, and a staircase leading to the upper levels.

The Grant Street Inn Dunedin Downtown Historic District, an Ascend Collection Hotel

Downtown Dunedin

10/10 Excellent

KEVIN

A swimming pool with lounge chairs and umbrellas, surrounded by trees and a clear sky.

SpringHill Suites by Marriott Tampa Westshore Airport

Westshore

10/10 Excellent

Michael

A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

Wyndham Grand Clearwater Beach

Clearwater Beach

10/10 Excellent

Ernesto

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 $87 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.

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.

Explore a world of travel with Expedia

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Oldsmar Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Oldsmar vacation rentals

1. Oldsmar Oakleaf Villa! On Wildlife Area, Natural Privacy! Patio Garage. King Bed

2. Sailport Waterfront Suites

3. Beso Del Sol Resort

4. The Avalon Club

5. Sunset Vistas Two Bedroom Beachfront Suites

6. Pelican Pointe Clearwater Beach Hotel

7. Mint House St. Petersburg Downtown by Kasa

8. Innisbrook 2BR Getaway With Balcony & Pool

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

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

11. 262-NEW! 3 beds x 2 baths. Amazing Waterfront Views!

12. The Fold Hotels Indian Shores

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

14. Green Castle Suite in Tampa

15. FUSION Resort Waterfront Suites

16. Barefoot Beach Resort

17. John's Pass Hotel

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

19. Crystal Palms Beach Resort

20. Experience the passion of hospitality, cleaning, and good location!

Find vacation rentals that suit your style

Top Oldsmar Hotel Reviews

Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

10/10 Excellent

Find out more about Oldsmar

Everything you need to know about Oldsmar vacation rentals

Oldsmar vacation rentals: An excellent choice for every season

How to find incredible deals on Oldsmar rentals

Frequently Asked Questions

Can I find vacation rentals in Oldsmar?

What are some of the best vacation home rentals in Oldsmar?

How many vacation rentals will I find in Oldsmar?

What can I see and do in Oldsmar?

What are vacation rentals like in Oldsmar?

Explore a world of travel with Expedia