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

Search Holiday Rentals in Oldsmar

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Oldsmar holiday rentals

Outdoor dining

Mint House St. Petersburg Downtown by Kasa

Mint House St. Petersburg Downtown by Kasa
4.0 star property
Downtown St. Petersburg
9.4 out of 10, Exceptional, (893 reviews)
"Loved the room And great location will be going back"
United States
Benjamin
The price is 3.049.831 ₫
3.446.310 ₫ total
includes taxes & fees
9 Aug - 10 Aug
Mint House St. Petersburg Downtown by Kasa
Exterior

Sailport Waterfront Suites

Sailport Waterfront Suites
3.5 star property
Rocky Point
8.4 out of 10, Very good, (5,118 reviews)
"Location was great. Loved having extra space and a full kitchen! The food at the pool restaurant was fantastic."
United States
Natalie Alice
The price is 2.863.452 ₫
3.722.859 ₫ total
includes taxes & fees
26 Jul - 27 Jul
Sailport Waterfront Suites
Exterior

John's Pass Hotel

John's Pass Hotel
2.0 star property
Madeira Beach
8.6 out of 10, Excellent, (387 reviews)
"Love this place one of my favorite hotels!"
United States
angela
The price is 2.226.489 ₫
2.937.446 ₫ total
includes taxes & fees
2 Aug - 3 Aug
John's Pass Hotel
Lunch and dinner served

Beso Del Sol Resort

Beso Del Sol Resort
2.5 star property
Dunedin
8.6 out of 10, Excellent, (749 reviews)
"Excellent accommodations for the price point"
United States
Yvette
The price is 3.546.315 ₫
4.995.051 ₫ total
includes taxes & fees
12 Jul - 13 Jul
Beso Del Sol Resort
Aerial view

Sunset Vistas Two Bedroom Beachfront Suites

Sunset Vistas Two Bedroom Beachfront Suites
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (3,657 reviews)
"This was the perfect place for our beach getaway!"
United States
Christi
The price is 4.964.841 ₫
6.352.369 ₫ total
includes taxes & fees
9 Aug - 10 Aug
Sunset Vistas Two Bedroom Beachfront Suites
Terrace/patio

The Fold Hotels Indian Shores

The Fold Hotels Indian Shores
3.0 star property
Indian Shores
9.2 out of 10, Wonderful, (997 reviews)
"Great hotel!"
United States
Stefano
The price is 3.999.459 ₫
5.261.488 ₫ total
includes taxes & fees
6 Aug - 7 Aug
The Fold Hotels Indian Shores
Presidential Suite, 3 Bedrooms, Bay View | Water view

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites
3.5 star property
Treasure Island
9.2 out of 10, Wonderful, (1,210 reviews)
"The views were incredible!! Everything was modern and clean and the staff at checkin and check out were very helpful! It was close to the beach and restaurants."
United States
Pamela
The price is 5.232.785 ₫
6.803.566 ₫ total
includes taxes & fees
5 Aug - 6 Aug
FUSION Resort Waterfront Suites
House (3 Bedrooms) | Interior

3 Mi to Botanical Gardens: Sun-kissed Largo Escape

3 Mi to Botanical Gardens: Sun-kissed Largo Escape
3.0 star property
Largo
8.6 out of 10, Excellent, (7 reviews)
"Everything. The space was great for my family of 5! The pool area was nice and the use of a grill, washer and dryer made our trip even more enjoyable. Will definitely rent again when we come back down from Maine."
United States
Krystal
3 Mi to Botanical Gardens: Sun-kissed Largo Escape
Front of property – evening/night

Crystal Palms Beach Resort

Crystal Palms Beach Resort
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (2,387 reviews)
"Clean rooms... nice big kitchen...2 big bathrooms.. 4 min wall to the beach"
United States
debbie
The price is 3.341.416 ₫
4.221.061 ₫ total
includes taxes & fees
4 Aug - 5 Aug
Crystal Palms Beach Resort
The Adaline #6 - 2nd Floor Suite | Dining room

The Adaline

The Adaline
5.0 star property
Hyde Park
9.6 out of 10, Exceptional, (71 reviews)
"Very clean and great location to Hyde park. Would definitely stay again"
United States
Shane
The price is 4.413.192 ₫
10.226.654 ₫ total
includes taxes & fees
13 Jul - 14 Jul
The Adaline
On the beach

Surf Beach Treasure Island Resort

Surf Beach Treasure Island Resort
3.0 star property
Treasure Island
9.2 out of 10, Wonderful, (885 reviews)
"Pool & spa very nice !"
United States
Richard
The price is 5.127.709 ₫
10.796.654 ₫ total
includes taxes & fees
9 Aug - 10 Aug
Surf Beach Treasure Island Resort
Exclusive Studio | Living area

Swann Avenue Central Tampa Homes

Swann Avenue Central Tampa Homes
2.0 star property
SoHo
5.0 out of 10, (2 reviews)
"Terrible Decision – Do Not Recommend We booked this Studio for 3 nights but only stayed for one. A strong, overwhelming mildew odor filled the unit and actually made us feel physically ill. We also noticed significant water buildup on the toilet seat and cover, which we believe was contributing to the persistent mildew smell. The listing photos are very misleading — they clearly don’t reflect the current condition and appear to have been taken many years ago. In reality, the property is quite...
United States
Donnell
The price is 1.513.094 ₫
6.442.492 ₫ total
includes taxes & fees
13 Jul - 14 Jul
Swann Avenue Central Tampa Homes
Premium Condo, 1 Bedroom | In-room dining

Barefoot Beach Resort

Barefoot Beach Resort
3.5 star property
Indian Shores
9.0 out of 10, Wonderful, (992 reviews)
"The apartment is in good condition overall for the price. Great location right across the beach and close to restaurants. Great resort overall!"
United States
Luis
The price is 3.388.701 ₫
4.215.125 ₫ total
includes taxes & fees
20 Jul - 21 Jul
Barefoot Beach Resort
Exterior

Voyager Beach Club

Voyager Beach Club
2.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (117 reviews)
"Very pleasant stay"
United States
Pamela
The price is 5.201.262 ₫
8.372.981 ₫ total
includes taxes & fees
15 Jul - 16 Jul
Voyager Beach Club
Aerial view

Westwinds Waterfront Resort

Westwinds Waterfront Resort
3.0 star property
Treasure Island
9.0 out of 10, Wonderful, (720 reviews)
"The room was spacious and clean with a great view of the water. The location is great. Enjoyed my stay!"
United States
Karen
The price is 3.749.674 ₫
8.066.363 ₫ total
includes taxes & fees
10 Aug - 11 Aug
Westwinds Waterfront Resort
Apartment, 2 Bedrooms, Non Smoking, Kitchen | Terrace/patio

The Westshore by Stylish Stays

The Westshore by Stylish Stays
3.5 star property
Beach Park
8.4 out of 10, Very good, (5 reviews)
"This property leaves a lot be desired. please see what was shared with property management. Foul smell of mold and smoking was present towels were unclean communication was thru email only Bathrooms showed it age and lack of cleanliness. This is aged and run down apartment unit dressed up to hide the short coming."
United States
Pedros
The price is 1.891.368 ₫
5.426.386 ₫ total
includes taxes & fees
12 Jul - 13 Jul
The Westshore by Stylish Stays
House, Accessible | 1 bedroom, Internet

Sunny Tampa Home Near Downtown Stadiums

Sunny Tampa Home Near Downtown Stadiums
2.0 star property
MacFarlane Park
9.4 out of 10, Exceptional, (3 reviews)
"Location was good, close to the airport, downtown, and major attractions. Quiet neighborhood, allowing good night rest. "
United States
Lusine
The price is 1.576.603 ₫
3.658.865 ₫ total
includes taxes & fees
13 Jul - 14 Jul
Sunny Tampa Home Near Downtown Stadiums
Signature Studio, Pets allowed | Living area

St Conrad Bungalow House

St Conrad Bungalow House
2.0 star property
MacFarlane Park
The price is 1.158.463 ₫
4.451.575 ₫ total
includes taxes & fees
13 Jul - 14 Jul
St Conrad Bungalow House
Apartment (1 Bedroom) | Interior

Walk to Madeira Beach: Family Resort Condo

Walk to Madeira Beach: Family Resort Condo
3.0 star property
Madeira Beach
6.0 out of 10, (5 reviews)
"We didnt stay there, we were told that the accommodations were comprised because the repairs that had to be done were not up to code. Thus we were diverted to a different facility further away from where we wanted to stay. Stop putting this place on your website as a viable option."
United States
Thomas
Walk to Madeira Beach: Family Resort Condo
Front of property – evening/night

South Beach Oceanfront Resort

South Beach Oceanfront Resort
3.0 star property
Sunshine Beach
9.2 out of 10, Wonderful, (1,153 reviews)
"Everything you need and want for a nice relaxing or adventurous beach vacation"
United States
Mitchell
The price is 4.161.010 ₫
8.407.687 ₫ total
includes taxes & fees
9 Aug - 10 Aug
South Beach Oceanfront Resort
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oldsmar Hotel Reviews

OASIS BAY SUITES, Tampa, Busch Gardens, USF

OASIS BAY SUITES, Tampa, Busch Gardens, USF

10/10 Excellent
"We loved our room, with the private bedroom & other area for table & chairs microwave , refrigerator & couch with another TV as well as another sink and large full mirror. The bed was very comfy, the shower worked perfectly. My only issue was the AC kept kicking on/off & was quite loud and it got hot when it turned off. We took the room right outside the pool which was cool. They kept the pool open later which I appreciated as we were out most of the day.. unfortunately there were many kids jumping all over & off the fountain ect. We tried to just go toward an area where they weren't literally jumping on top of us. Eventually they were told to leave. Nobody told us, but we assumed it meant everyone should go. The pool felt very soft and was clean. The breakfast was typical hotel buffet food. I enjoyed a pancake...I'm not a fan of those eggs. Everything was clean & well stocked. It's very roomy with many tables and it had everything needed... The toaster worked well . The staff were professional and the overall hotel was excellent and well maintained. They were constantly cleaning every area. There were plenty of luggage carts to carry your stuff to the room. I'm very happy we found this hotel and would stay again. Thank you"
Dolores 2-night trip
Posted less than an hour ago
OASIS BAY SUITES, Tampa, Busch Gardens, USF

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 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 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.