Oldsmar Holiday Rentals

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Holiday Rentals in Oldsmar

Beach nearby, beach volleyball, fishing
Sailport Waterfront Suites
3.5 star property
8.4 out of 10, Very good, (4099)
"Stayed for two nights here on a vacation. The balcony was overlooking the bay. Two beds and they were comfortable. Nice size TVs. Full kitchen. It was quiet and secluded. You could hear music from the restaurant across the bay by the sand but that wasn’t an issue. We saw dolphins swimming in the evening! Super cool! The staff at the front desk were nice. The guy at the front security gate was nice and helpful (younger kid with glasses). You can park anywhere once you get your parking pass....
The price is NZ$242
per night
14 May - 15 May
Sailport Waterfront Suites
Front of property
Chase Suite Hotel Rocky Point Tampa
3.0 star property
7.6 out of 10, Good, (4255)
"Complimentary bottle water will be nice"
The price is NZ$205
per night
26 May - 27 May
Chase Suite Hotel Rocky Point Tampa
Standard Studio, Kitchen, Corner | Terrace/patio
Mint House St. Petersburg - Downtown
3.5 star property
9.4 out of 10, Exceptional, (322)
"Loved everything about it "
The price is NZ$223
per night
27 May - 28 May
Mint House St. Petersburg - Downtown
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Studio (with Common Living Area (B))
ROOST Tampa
5.0 star property
9.4 out of 10, Exceptional, (287)
"Five stars"
The price is NZ$319
per night
9 Jun - 10 Jun
ROOST Tampa
Beach
Top Floor , Walk to Beach, Pool, Free Parking, #427, Sleeps 6
8.8 out of 10, Excellent, (24)
"Very quiet. Very comfortable and the staff were very informative and polite. I would highly recommend. .R.Talbert"
Top Floor , Walk to Beach, Pool, Free Parking, #427, Sleeps 6
2 outdoor pools, open 9:00 AM to 10:00 PM, pool umbrellas, sun loungers
Sunset Vistas Two Bedroom Beachfront Suites
3.5 star property
8.8 out of 10, Excellent, (2949)
"Enjoyed the amenities of home."
The price is NZ$389
per night
27 May - 28 May
Sunset Vistas Two Bedroom Beachfront Suites
Outdoor spa tub
FUSION Resort Two Bedroom Suites
3.5 star property
9.2 out of 10, Wonderful, (940)
"Newly updated. Great balcony with sunrise views. Pool was great. Kitchen super clean. "
The price is NZ$433
per night
13 May - 14 May
FUSION Resort Two Bedroom Suites
Deluxe Studio Suite, 2 Double Beds, Balcony, Ocean View | Balcony
Sands of Treasure Island
3.0 star property
7.4 out of 10, Good, (818)
"Great stay the staff was friendly and check in was quick. I love that's there no requirement for deposit and resort fees. This is a very old hotel. If you are expecting modern and 5 star accommodations for the price they charge skip this place you are not going to get it. They could do better with the cleaning. The floors were dirty and the kitchen stove and fridge were not wiped down properly. The location was ideal right on the beach and quick 5 min drive to Johns Pass . There's isnt much room...
The price is NZ$216
per night
29 May - 30 May
Sands of Treasure Island
Standard Suite, 2 Bedrooms, Ocean View | View from room
The Avalon Club
4.0 star property
9.6 out of 10, Exceptional, (294)
"Loved everything about our stay. The hotel was very nice and the staff was welcoming and friendly. Would stay again!"
The price is NZ$383
per night
15 May - 16 May
The Avalon Club
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
Exterior
Beso Del Sol Resort
2.5 star property
8.6 out of 10, Excellent, (415)
"It was good view and good location, we bike around Dunedin and there are so many seafood restaurants around. "
The price is NZ$354
per night
13 May - 14 May
Beso Del Sol Resort
Free WiFi
Studio in Clearwater Perfect for 2
2.0 star property
The price is NZ$161
per night
13 May - 14 May
Studio in Clearwater Perfect for 2
Aerial view
Dolphin Watch Beach & Dock
9.4 out of 10, Exceptional, (21)
"Very close to everything."
The price is NZ$618
per night
11 Jun - 12 Jun
Dolphin Watch Beach & Dock
Outdoor pool
Barefoot Beach Resort
3.5 star property
9.0 out of 10, Wonderful, (809)
"This is our 2nd time staying here. It is a great location with beach access right across the street. The pool is very nice with plenty of lounge chairs. The rooms are a bit old but quite comfortable and roomy. One small complaint is they don't provide tissues for the room, just paper towels. "
The price is NZ$335
per night
14 May - 15 May
Barefoot Beach Resort
Property grounds
Beautiful Treasure Island and Directly on Sunset Beach! Location, Location!!!!!
9.8 out of 10, Exceptional, (212)
"Beautiful sunsets every night we stayed. Beach was quiet and not over crowded. Had all the basics we needed."
Beautiful Treasure Island and Directly on Sunset Beach! Location, Location!!!!!
Snow and ski sports
Sleeps 6 Daily Rentals, Pets OK, Hot Tub
9.0 out of 10, Wonderful, (37)
"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$582
per night
22 May - 23 May
Sleeps 6 Daily Rentals, Pets OK, Hot Tub
Interior
Beach house
2.0 out of 10, (2)
"I reached out to the owner Christian P before and after booking the house with VRBO. I never heard from him no received any information about how to access the house. An hour away from our arrival time on Day 1, I still hadn’t heard so I called the phone number listed with the property. It disconnected every time I called it. I reached out to VRBO who was also unable to contact the owner so VRBO cancelled the reservation and assisted us with finding a new place. It was very frustrating and a...
Beach house
BBQ/picnic area
The Pointe Condos by Barsala
4.5 star property
9.2 out of 10, Wonderful, (79)
"The Pointe in Tampa was an amazing stay! Tons of amenities, beautiful decor, secure, and all the neighbors were welcoming. They definitely accommodated our needs for the full week we stayed. I recommend Barsala! Great customer service. "
The Pointe Condos by Barsala
Sun-loungers, beach towels
75 Steps to the beach, 1-2 minute walk
10.0 out of 10, Exceptional, (25)
"Property just steps to beach and short walk to restaurants. Host responded quickly to a minor issue and was a pleasure to deal with. No complaints. Two thumbs up."
The price is NZ$496
per night
13 May - 14 May
75 Steps to the beach, 1-2 minute walk
On the beach
Beach View, Private Plunge Pool, Charming 1938 Bungalow Madeira Beach Johns Pass
9.6 out of 10, Exceptional, (193)
"Five childhood friends turning 60, long weekend getaway and this was the perfect location. Short walk to shopping and dining, great weather and this house had everything we needed for the beach."
The price is NZ$705
per night
22 May - 23 May
Beach View, Private Plunge Pool, Charming 1938 Bungalow Madeira Beach Johns Pass
Don't see what you're looking for?
See all available properties in Oldsmar
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, (1904)
"We had a fabulous stay from check-in to check-out! Everything from staff to the fun at the pool was just perfect. "
The price is NZ$328
per night
2 Jun - 3 Jun
Wyndham Grand Clearwater Beach
Exterior
Hilton Clearwater Beach Resort & Spa
4.0 star property
7.4 out of 10, Good, (1639)
"Beautiful beach"
The price is NZ$475
per night
14 May - 15 May
Hilton Clearwater Beach Resort & Spa
Outdoor pool, free pool cabanas, pool loungers
Hotel Alba, Tapestry Collection by Hilton
4.0 star property
8.8 out of 10, Excellent, (1206)
"Very friendly staff and clean environment. You could hear everything outside of the room. Also there was no fridge or microwave inside the room. But other than that very nice place to stay. "
The price is NZ$302
per night
19 May - 20 May
Hotel Alba, Tapestry Collection by Hilton
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.

How many holiday rentals will I find in Oldsmar?

Expedia has 35 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