Search Holiday Rentals in Oldsmar

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Tonight
27 Dec - 28 Dec
Tomorrow
28 Dec - 29 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan

Our top choices for Oldsmar holiday rentals

Aerial view
Sunset Vistas Two Bedroom Beachfront Suites

Sunset Vistas Two Bedroom Beachfront Suites

Sunset Vistas Two Bedroom Beachfront Suites
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (3417)
"The location is EXCELLENT, the staff was welcoming and accommodating, and our room had everything we needed to fulfill our goal of being beach bums and mermaids... We can't wait to come back!"
United States
Jaimie
The price is Rp2.600.714
Rp3.411.740 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sunset Vistas Two Bedroom Beachfront Suites
Beach nearby, beach volleyball, fishing
Sailport Waterfront Suites

Sailport Waterfront Suites

Sailport Waterfront Suites
3.5 star property
Rocky Point
8.4 out of 10, Very good, (4862)
"Great fishing spot,with a great view."
United States
Shanetta
The price is Rp1.863.719
Rp2.416.730 total
includes taxes & fees
28 Dec - 29 Dec
Sailport Waterfront Suites
Presidential Suite, 3 Bedrooms, Bay View | Egyptian cotton sheets, premium bedding, pillow-top beds
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites
3.5 star property
Treasure Island
9.2 out of 10, Wonderful, (1107)
"Clean and spacious"
United States
April
The price is Rp3.129.019
Rp4.103.312 total
includes taxes & fees
15 Jan - 16 Jan 2026
FUSION Resort Waterfront Suites
Standard Suite, 2 Bedrooms, Ocean View | View from room
The Avalon Club

The Avalon Club

The Avalon Club
4.0 star property
Clearwater Beach
9.4 out of 10, Exceptional, (492)
"We loved our stay here. Exceeded expectations"
United States
Anne
The price is Rp3.867.171
Rp5.032.011 total
includes taxes & fees
2 Jan - 3 Jan 2026
The Avalon Club
Premium Studio Suite | Terrace/patio
Mint House St. Petersburg - Downtown

Mint House St. Petersburg - Downtown

Mint House St. Petersburg - Downtown
4.5 star property
Downtown St. Petersburg
9.4 out of 10, Exceptional, (697)
"Very clean, conveniently located, and friendly staff."
United States
Carolyn
The price is Rp2.170.152
Rp2.452.271 total
includes taxes & fees
25 Jan - 26 Jan 2026
Mint House St. Petersburg - Downtown
Terrace/patio
The Fold Hotels Indian Shores

The Fold Hotels Indian Shores

The Fold Hotels Indian Shores
3.0 star property
Indian Shores
9.2 out of 10, Wonderful, (935)
"The room was spotless and staff so friendly and helpful. "
United States
Valerie
The price is Rp2.214.834
Rp2.748.521 total
includes taxes & fees
11 Jan - 12 Jan 2026
The Fold Hotels Indian Shores
Sun deck
Provident Oceana Beachfront Suites

Provident Oceana Beachfront Suites

Provident Oceana Beachfront Suites
3.5 star property
Treasure Island
9.4 out of 10, Exceptional, (611)
"I believe the pool area the Jacuzzi should be open at least till 9:00 or 10:00 p.m."
United States
GARY
The price is Rp2.818.347
Rp3.563.080 total
includes taxes & fees
12 Jan - 13 Jan 2026
Provident Oceana Beachfront Suites
Premier Studio, 2 Queen Beds, Balcony, Sea Facing | View from room
Shoreline Island Resort - Exclusively Adult

Shoreline Island Resort - Exclusively Adult

Shoreline Island Resort - Exclusively Adult
3.0 star property
Madeira Beach
9.2 out of 10, Wonderful, (1439)
"Super cute apartment and the view from the balcony, right on the beach and very close to restaurants and shops. "
United States
Walesca
The price is Rp3.616.056
Rp4.086.143 total
includes taxes & fees
16 Jan - 17 Jan 2026
Shoreline Island Resort - Exclusively Adult
Aerial view
Westwinds Waterfront Resort

Westwinds Waterfront Resort

Westwinds Waterfront Resort
3.0 star property
Treasure Island
9.0 out of 10, Wonderful, (693)
"AWESOME location! Right on the bay and 25 steps to the Gulf! 2 minute walk to Publix; 3 minute walk to Walgreens. 1.5 block to a Treasure Island Beach, where there was a sand castle festival for 3 days. "
United States
susan
Westwinds Waterfront Resort
Premium Condo, 1 Bedroom | In-room dining
Barefoot Beach Resort

Barefoot Beach Resort

Barefoot Beach Resort
3.5 star property
Indian Shores
9.0 out of 10, Wonderful, (908)
"Quiet, great location finally, staff management and the whole area was clean and well maintain"
United States
Harold
The price is Rp2.326.999
Rp2.875.434 total
includes taxes & fees
4 Jan - 5 Jan 2026
Barefoot Beach Resort
Lunch and dinner served, pool views
Beso Del Sol Resort

Beso Del Sol Resort

Beso Del Sol Resort
2.5 star property
Dunedin
8.8 out of 10, Excellent, (679)
"Hot tub was really nice, warm and clean"
United States
James
Beso Del Sol Resort
Coffee/tea maker
John's Pass Hotel

John's Pass Hotel

John's Pass Hotel
2.0 star property
Madeira Beach
8.6 out of 10, Excellent, (277)
"Great location, staff and room"
United States
Saori
John's Pass Hotel
View from property
Surf Beach Treasure Island Resort

Surf Beach Treasure Island Resort

Surf Beach Treasure Island Resort
3.0 star property
Treasure Island
9.2 out of 10, Wonderful, (855)
"Room was clean and the front desk was very nice. We would definitely stay here again!"
United States
Rebecca
The price is Rp3.120.522
Rp6.697.491 total
includes taxes & fees
8 Jan - 9 Jan 2026
Surf Beach Treasure Island Resort
Front of property – evening/night
South Beach Oceanfront Resort

South Beach Oceanfront Resort

South Beach Oceanfront Resort
3.0 star property
Sunshine Beach
9.2 out of 10, Wonderful, (1123)
"Great place to stay!"
United States
Angela
The price is Rp2.717.901
Rp5.440.339 total
includes taxes & fees
8 Jan - 9 Jan 2026
South Beach Oceanfront Resort
Front of property – evening/night
Crystal Palms Beach Resort

Crystal Palms Beach Resort

Crystal Palms Beach Resort
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (2362)
"Unit size was very nice and the linens were good quality. "
United States
Pamela
The price is Rp2.491.898
Rp3.099.604 total
includes taxes & fees
8 Jan - 9 Jan 2026
Crystal Palms Beach 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

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

10/10 Excellent
"Always the best"
shane 4-night trip
Posted 2 days ago
Wyndham Grand Clearwater Beach

Find out more about Oldsmar

Search for holiday rentals in Oldsmar on Expedia.co.id! You can easily find your home rentals, villas, holiday apartments in Oldsmar using one of the methods below:

  • View our selection of featured holiday rentals in Oldsmar
  • Use the map to find apartments and other holiday homes in the Oldsmar neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oldsmar while they last

Look no further and take a look at our great range of rental properties in Oldsmar!

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 11 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 Port of Tampa and Raymond James Stadium.

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.