Oldsmar Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Oldsmar holiday rentals

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

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

Palm Lake Retreat | Pool, Beaches, Near Tampa
Oldsmar
Palm Lake Retreat | Pool, Beaches, Near Tampa
A kitchen with dark wooden cabinets, a tiled backsplash, and a dining table set with plates, cups, and a kettle.

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

Oldsmar Oakleaf Villa! On Wildlife Area, Natural Privacy! Patio Garage. King Bed
Oldsmar
9.8 out of 10, Exceptional, (64 reviews)
"Roomy two BR two full bath house, beautifully maintained with nice lanai and backyard grill in quiet neighborhood. Perfect location for visiting Tampa Bay Downs horse track, Tarpon Springs & Dunedin. Would happily stay here again."
United States
Stephen W.
The price is AU$471
includes taxes & fees
9 Nov - 10 Nov
Oldsmar Oakleaf Villa! On Wildlife Area, Natural Privacy! Patio Garage. King Bed
A paved walkway with palm trees, a beach, and a clear sky.

3. Sailport Waterfront Suites

Sailport Waterfront Suites
3.5 star property
Rocky Point
8.4 out of 10, Very good, (5,310 reviews)
"Our favorite part was the on site bar and restaurant"
United States
Paula A
The price is AU$222
includes taxes & fees
22 Nov - 23 Nov
Sailport Waterfront Suites
A deck with lounge chairs and a hot tub, overlooking a body of water with a pier in the background.

4. Beso Del Sol Resort

Beso Del Sol Resort
2.5 star property
Dunedin
8.6 out of 10, Excellent, (786 reviews)
"Friendly staff, great location and wonderful views"
United States
Gina
The price is AU$232
includes taxes & fees
9 Nov - 10 Nov
Beso Del Sol Resort
Interior

5. Green Castle Suite in Tampa

Green Castle Suite in Tampa
Town 'n' Country
9.6 out of 10, Exceptional, (40 reviews)
"Great place to stay!"
United States
Stephanie S.
The price is AU$176
includes taxes & fees
12 Nov - 13 Nov
Green Castle Suite in Tampa
A hotel with a pool, palm trees, and a modern building in the background.

6. Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel
2.5 star property
Clearwater Beach
8.8 out of 10, Excellent, (1,177 reviews)
"Hotel was great!"
United States
Daniel
The price is AU$226
includes taxes & fees
2 Dec - 3 Dec
Pelican Pointe Clearwater Beach Hotel
A home entrance with a 'WELCOME' sign, a kitchen area visible through the doorway, and two potted plants.

7. Enchanting cottage with AC in Palm Harbor - 2 bedrooms, 1 bathroom & hot tub

Enchanting cottage with AC in Palm Harbor - 2 bedrooms, 1 bathroom & hot tub
Palm Harbor
9.8 out of 10, Exceptional, (23 reviews)
"Great place for my wife and I for a weekend getaway. Allison was an attentive host and replied promptly to our needs. Off the beaten path but close to everything, including the beaches. Will stay here again."
United States
Mike C.
The price is AU$403
includes taxes & fees
10 Nov - 11 Nov
Enchanting cottage with AC in Palm Harbor - 2 bedrooms, 1 bathroom & hot tub
A spacious living room with a large sliding glass door leading to a balcony, a ceiling fan, and a bookshelf.

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

Key West Style Cottage - with pool/hot-tub
Dunedin
9.4 out of 10, Exceptional, (36 reviews)
"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...
United States
Nayeli
The price is AU$280
includes taxes & fees
9 Nov - 10 Nov
Key West Style Cottage - with pool/hot-tub
A living room with a grey sofa, a patterned rug, a dining table with white chairs, and a potted plant.

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

Cozy Boho Guest House w/Patio - 6 min from the beach!
Town 'n' Country
9.0 out of 10, Wonderful, (40 reviews)
"Very clean, quiet. Safe surroundings if you are traveling by yourself."
United States
Deborah
The price is AU$165
includes taxes & fees
10 Nov - 11 Nov
Cozy Boho Guest House w/Patio - 6 min from the beach!
An outdoor patio with a dining table, chairs, and a sofa.

10. Mint House St. Petersburg Downtown by Kasa

Mint House St. Petersburg Downtown by Kasa
3.5 star property
Downtown St. Petersburg
9.4 out of 10, Exceptional, (1,113 reviews)
"Great place"
United States
Anonymous traveller
The price is AU$172
includes taxes & fees
22 Nov - 23 Nov
Mint House St. Petersburg Downtown by Kasa
Pool

11. Cozy Studio with Microwave, Mini Fridge & Coffee Maker, Perfect for Short Stays!

Cozy Studio with Microwave, Mini Fridge & Coffee Maker, Perfect for Short Stays!
Pinecrest West Park
9.6 out of 10, Exceptional, (42 reviews)
"Great room for the price!"
United States
S W.
The price is AU$115
includes taxes & fees
16 Nov - 17 Nov
Cozy Studio with Microwave, Mini Fridge & Coffee Maker, Perfect for Short Stays!
A garage with a number '16517' and a white door.

12. DFGmoments#2/Northdale/Citrus Park Mall

DFGmoments#2/Northdale/Citrus Park Mall
Greater Northdale
9.8 out of 10, Exceptional, (82 reviews)
"Great place and great host"
United States
Melinda K.
The price is AU$153
includes taxes & fees
14 Nov - 15 Nov
DFGmoments#2/Northdale/Citrus Park Mall
Room

13. Full of Love

Full of Love
Town 'n' Country
9.4 out of 10, Exceptional, (39 reviews)
"Very comfortable setting, reliable price, and great communication with the host!, totally recommendable for those looking a place to book for their weekend vacations in Tampa."
United States
Francisco
The price is AU$201
includes taxes & fees
25 Nov - 26 Nov
Full of Love
A hotel room with a bed, a chair, a lamp, and a window with curtains.

14. John's Pass Hotel

John's Pass Hotel
2.0 star property
Madeira Beach
8.6 out of 10, Excellent, (501 reviews)
"Love the location having shops around and how easy was to check in"
United States
Luis
The price is AU$163
includes taxes & fees
15 Nov - 16 Nov
John's Pass Hotel
A large building surrounded by parking, trees, and a small lake.

15. Innisbrook 2BR Getaway With Balcony & Pool

Innisbrook 2BR Getaway With Balcony & Pool
Palm Harbor
9.6 out of 10, Exceptional, (30 reviews)
"Place was great and sits on hole 2 of Copperhead. The only catch is the property has no elevator, and the room is on the 3rd floor."
United States
Indy J.
The price is AU$421
includes taxes & fees
9 Nov - 10 Nov
Innisbrook 2BR Getaway With Balcony & Pool
A wooden dock with a fire feature and a 'Please be safe' sign, overlooking a lake with a building in the background.

16. The Fold Hotels Indian Shores

The Fold Hotels Indian Shores
3.0 star property
Indian Shores
9.2 out of 10, Wonderful, (1,025 reviews)
"Great location"
United States
Karen
The price is AU$272
includes taxes & fees
8 Dec - 9 Dec
The Fold Hotels Indian Shores
A waterfront property with a paved walkway, benches, palm trees, and a white fence.

17. Barefoot Beach Resort

Barefoot Beach Resort
3.5 star property
Indian Shores
9.0 out of 10, Wonderful, (1,068 reviews)
"Loved our stay!"
United Kingdom
HANNAH
The price is AU$205
includes taxes & fees
9 Dec - 10 Dec
Barefoot Beach Resort
A hotel courtyard with a central fountain, palm trees, and a multi-story building with balconies.

18. Sunset Vistas Two Bedroom Beachfront Suites

Sunset Vistas Two Bedroom Beachfront Suites
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (3,780 reviews)
"I love staying here. This is my 3rd time staying here and I keep coming back because I love the property! The location is ideal, and the staff are amazing."
United States
Shelby
The price is AU$287
includes taxes & fees
29 Nov - 30 Nov
Sunset Vistas Two Bedroom Beachfront Suites
A modern kitchen with white cabinets, a black refrigerator, a microwave, and a granite countertop.

19. Charming rental with a separate entrance.

Charming rental with a separate entrance.
Tampa
9.8 out of 10, Exceptional, (73 reviews)
"This place was perfect for a quick over night trip. Just as described! Would definitely stay again!"
United States
Ken Y.
The price is AU$206
includes taxes & fees
9 Nov - 10 Nov
Charming rental with a separate entrance.
A wooden pergola with a hammock, patio furniture, and a covered seating area.

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

Experience the passion of hospitality, cleaning, and good location!
Westshore
9.4 out of 10, Exceptional, (85 reviews)
"Location, location, location! We had a very early arrival time at the airport the day after our stay. It only took us about 6 minutes to get to the airport to turn in our rental car. The size was just fine for what we needed. There were plenty of private parking spots to choose from. Our bed was more comfortable than the Comfort Suites we stayed in the previous two nights in another town. We arrived after 9 pm and had no difficulty using the directions we had been given to get into the unit....
United States
michelle
The price is AU$166
includes taxes & fees
9 Nov - 10 Nov
Experience the passion of hospitality, cleaning, and good location!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Find holiday rentals that suit your style

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Top Oldsmar Hotel Reviews

A patio area with a circular fire pit surrounded by wicker chairs and a table.
Residence Inn by Marriott Tampa Oldsmar

Residence Inn by Marriott Tampa Oldsmar

Residence Inn by Marriott Tampa Oldsmar
Oldsmar

8/10 Good

Excellent hotel for an overnight stay during transit elsewhere in the state.
Australia
Chenoa
Reviewed July 31, 2023
Residence Inn by Marriott Tampa Oldsmar

Find out more about Oldsmar

Everything you need to know about Oldsmar holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oldsmar holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Oldsmar holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oldsmar holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oldsmar holiday rentals we have selected for you start as low as AU$129 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Oldsmar rentals

At Expedia, we put the best Oldsmar holiday 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 holiday.

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 holiday rentals in Oldsmar?

Yes, we have holiday rentals where you'll be only 14.9 mi (23.9 km) from Busch Gardens Tampa Bay, offering you a more remote option if you want a quieter place to stay. Visitors like the top-notch restaurants and beaches in Oldsmar. Make sure you have time to check out the theme park and cafés during your trip.

What are some of the best holiday rentals that Oldsmar has to offer?

The Gemma by Brightwild: This holiday home rental outside of Oldsmar is located on the beach, and has an outdoor pool, a private balcony and a BBQ 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 that you can cook with friends or family. It offers a terrace, a private garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Oldsmar?

Expedia has 9 holiday 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 wider area, you’ll find popular places such as Raymond James Stadium and Port Tampa Bay.

What are holiday rentals like in Oldsmar?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oldsmar. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips or small group gatherings.