Oldsmar Holiday Rentals

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Holiday Rentals in Oldsmar

Outdoor dining
Right on the BEACH! Exclusive Lighthouse Towers, Sand Key, Clearwater Beach
10.0 out of 10, Exceptional, (89)
"Vince is a very attentive owner/caring. As the listing says, there is a major project going on with the building. One must be prepared for some days it is very loud and distracting. Not all days, but some days were very loud . It’s not anything to blame the owner for and we knew the patio wasn’t available. Having said that it’s a very nice place , beautiful pool and spa. Beaches in the area are stellar. Nice trolley to Clearwater Beach , about a 5 minute ride . Nice Shopping area a 5 min walk...
Right on the BEACH! Exclusive Lighthouse Towers, Sand Key, Clearwater Beach
Sun-loungers, beach towels
75 Steps to the beach, 1-2 minute walk
10.0 out of 10, Exceptional, (26)
"First off, the lack of a 5th star has absolutely nothing to do with Joe. He was incredibly nice, communicative every step of the way and did a fantastic job of welcoming us and being a resource. If your goal is to be on the quieter side of Clearwater Beach, very close to the beach and don't plan on spending much time in the room, this place is perfect. The only reason I knocked off a star is because the place is REALLY small, even smaller than the pictures make it seem. It was just me and my...
The price is NZ$529
per night
2 Jun - 3 Jun
75 Steps to the beach, 1-2 minute walk
Beach
Great Studio - Only 75 Steps to Clearwater Beach
10.0 out of 10, Exceptional, (110)
"cozy studio apartment ,quiet neighborhood a few steps from beach. Nice restaurants on beach nearby. Great time!"
Great Studio - Only 75 Steps to Clearwater Beach
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Property grounds
Beautiful Treasure Island and Directly on Sunset Beach! Location, Location!!!!!
9.8 out of 10, Exceptional, (215)
"We had a wonderful time staying at this beautiful condo. The owner has made sure that anything you could possibly need is there. It was nicely decorated and very clean. The owner was quick to answer any questions. I would definitely return to this unit. Sunset Beach is a spectacular location. We hated to leave. 🏖️"
Beautiful Treasure Island and Directly on Sunset Beach! Location, Location!!!!!
View from property
Bayside Condos Studio 23 Pool, Bay Views. Walk to Beach
9.8 out of 10, Exceptional, (8)
"Simple clean space with enough amenities for an extended stay."
Bayside Condos Studio 23 Pool, Bay Views. Walk to Beach
View from property
BEACHFRONT-6 Bedroom/5 Bathroom House with Rooftop Deck
9.8 out of 10, Exceptional, (46)
"We've had the privilege of enjoying this home in Indian Rocks Beach twice now, and we're eagerly looking forward to returning in the future. The meticulous cleanliness of the property is noteworthy, providing a comfortable and welcoming environment from the moment we stepped in. The location is truly perfect, offering convenient access to the stunning beach and a variety of local restaurants and activities. Communication with the owner was excellent, ensuring a peaceful and hassle-free stay. We...
The price is NZ$1,563
per night
28 May - 29 May
BEACHFRONT-6 Bedroom/5 Bathroom House with Rooftop Deck
A heated pool
606S-Penthouse-Beach View,Top Floor, 2/2 on Beach
9.8 out of 10, Exceptional, (127)
"We loved our stay here! Great location, nice and clean, good set up for a family and wonderful views from unit!"
The price is NZ$1,046
per night
2 Jun - 3 Jun
606S-Penthouse-Beach View,Top Floor, 2/2 on Beach
Standard Suite, 2 Bedrooms, Ocean View | View from room
The Avalon Club
4.0 star property
9.6 out of 10, Exceptional, (299)
"No free parking in theyre garage. "
The price is NZ$338
per night
27 May - 28 May
The Avalon Club
On the beach
Beach View, Private Plunge Pool, Charming 1938 Bungalow Madeira Beach Johns Pass
9.6 out of 10, Exceptional, (194)
"Clean with everything you need to make your stay seamless. No frill, classy cozy place! Checking was without issues as was checking out. Bob was super responsive. Easy access to the beach - time of the year was great for our stay. Would definitely stay again in the future."
The price is NZ$746
per night
21 Jun - 22 Jun
Beach View, Private Plunge Pool, Charming 1938 Bungalow Madeira Beach Johns Pass
Standard Studio, Kitchen, Corner | Terrace/patio
Mint House St. Petersburg - Downtown
3.5 star property
9.4 out of 10, Exceptional, (339)
"Quiet, clean, comfortable, convenient."
The price is NZ$240
per night
2 Jun - 3 Jun
Mint House St. Petersburg - Downtown
Studio (with Common Living Area (B))
ROOST Tampa
5.0 star property
9.4 out of 10, Exceptional, (295)
"Place is very clean from the front desk to the room. I love this hotel"
The price is NZ$314
per night
9 Jun - 10 Jun
ROOST Tampa
Aerial view
Dolphin Watch Beach & Dock
9.4 out of 10, Exceptional, (21)
"Very close to everything."
The price is NZ$627
per night
11 Jun - 12 Jun
Dolphin Watch Beach & Dock
Outdoor spa tub
FUSION Resort Two Bedroom Suites
3.5 star property
9.2 out of 10, Wonderful, (944)
"Great place to stay. Our 1st room had a funky smell so we asked for another room. Front staff was very accomodating. Was able to get fresh coffee from the registration area as the coffee maker wasn't really a coffee pot. Loved having a full size kitchen, 2 bathrooms and deck. Would stay again. "
The price is NZ$369
per night
5 Jun - 6 Jun
FUSION Resort Two Bedroom Suites
BBQ/picnic area
The Pointe Condos by Barsala
4.5 star property
9.2 out of 10, Wonderful, (82)
"We enjoyed everything about the property and the room. We wished we would have got three bedroom because it came with a garage. Parking was a little bit of an adventure but other than that we can't complain about anything on the grounds."
The price is NZ$450
per night
19 Jun - 20 Jun
The Pointe Condos by Barsala
Outdoor pool
Legacy Vacation Resorts - Indian Shores
3.0 star property
9.2 out of 10, Wonderful, (816)
"Great location and had everything we needed. Will definitely stay here again "
The price is NZ$306
per night
9 Jun - 10 Jun
Legacy Vacation Resorts - Indian Shores
View from property
Surf Beach Resort by Sunsational Beach Rentals
3.0 star property
9.2 out of 10, Wonderful, (745)
"Great property, great area. Friendly/helpfull staff"
The price is NZ$723
per night
23 May - 24 May
Surf Beach Resort by Sunsational Beach Rentals
Snow and ski sports
Historic Beach Cottage steps from beach. Pet friendly!
9.2 out of 10, Wonderful, (109)
"Had the best time for the weekend! Capt Al is an amazing host who spent time visiting and offered suggestions of where to eat and what to do. Highly recommend and hope to be back soon! Don’t miss out on this treasure"
The price is NZ$827
per night
26 May - 27 May
Historic Beach Cottage steps from beach. Pet friendly!
Outdoor pool
Barefoot Beach Resort
3.5 star property
9.0 out of 10, Wonderful, (818)
"The bed was not the most comfortable. Housekeeping barged in 15 minutes before we were supposed to be out, did not even knock. But the unit was clean and it was a quick walk to the beach which is just across the street. Plenty of other things within walking distance too. "
The price is NZ$331
per night
23 May - 24 May
Barefoot Beach Resort
Snow and ski sports
Sleeps 6 Daily Rentals, Pets OK, Hot Tub
9.0 out of 10, Wonderful, (38)
"The old Florida cottage was old Florida. It was clean with history and very friendly property management. I grew up in this area and this is what vacation was before all the resorts cluttered the beach. I mis booked our cottage and the manager met me and fixed it without argument. Close to the beach and far enough from south beach that you had some peaceful time off. Would definitely go back and have already recommended to several friends and family."
The price is NZ$519
per night
23 May - 24 May
Sleeps 6 Daily Rentals, Pets OK, Hot Tub
Front of property - evening/night
Crystal Palms Beach Resort
3.5 star property
9.0 out of 10, Wonderful, (2232)
"Everything was nice "
The price is NZ$347
per night
6 Jun - 7 Jun
Crystal Palms Beach Resort
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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.

Other types of properties in Oldsmar you may be interested in

Outdoor pool, pool umbrellas, pool loungers
Wyndham Grand Clearwater Beach
4.0 star property
9.2 out of 10, Wonderful, (1872)
"Front desk guy that checked us in was not very friendly or helpful….some of your staff need more hospitality training…we had a great time in your beautiful resort "
The price is NZ$313
per night
2 Jun - 3 Jun
Wyndham Grand Clearwater Beach
Outdoor pool, open 8:00 AM to 10:00 PM, pool cabanas (surcharge)
Hyatt Regency Clearwater Beach Resort & Spa
4.0 star property
9.0 out of 10, Wonderful, (1644)
"I like that the staff asked about what type of housekeeping you prefer and what times (morning/afternoon) Shor grille had amazing food! The pool was nice with great bar! It was nice to have beach towels available! "
The price is NZ$568
per night
9 Jun - 10 Jun
Hyatt Regency Clearwater Beach Resort & Spa
Outdoor banquet area
The Westin Tampa Bay
4.0 star property
8.0 out of 10, Very good, (1002)
"Nice location "
The price is NZ$251
per night
27 May - 28 May
The Westin Tampa Bay
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oldsmar holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oldsmar. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Oldsmar. Seeing all the best attractions is bound to make you fall in love with Oldsmar. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Oldsmar short-term rentals, that won’t be hard to do.

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?

Studio in Clearwater Perfect for 2: This holiday home rental outside Oldsmar comes with WiFi so that you can feel at home during your trip. Kitchen amenities such as a fridge and an oven can make your holiday run smoothly.

How many holiday rentals will I find in Oldsmar?

Expedia has 34 holiday rentals for your stay in Oldsmar.

What can I see and do in Oldsmar?

Cultural attractions include Oldsmar Historical Society Museum, whereas Tampa Bay is a spot to enjoy nature. In the wider area, you’ll find popular places such as Raymond James Stadium and Port of Tampa.

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.

Recent reviews of Oldsmar properties
Expedia verified reviews