Oldsmar Holiday Rentals

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

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Oldsmar holiday rentals

Aerial view
Sunset Vistas Two Bedroom Beachfront Suites

Condo resort in Sunshine Beach

Sunset Vistas Two Bedroom Beachfront Suites
3.5 star property
8.8 out of 10, Excellent, (3414)
"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 HK$1,136
HK$1,504 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sunset Vistas Two Bedroom Beachfront Suites
Water view
FUSION Resort Waterfront Suites

Aparthotel in Treasure Island

FUSION Resort Waterfront Suites
3.5 star property
9.2 out of 10, Wonderful, (1107)
"Clean and spacious"
United States
April
The price is HK$1,425
HK$1,874 total
includes taxes & fees
15 Jan - 16 Jan 2026
FUSION Resort Waterfront Suites
1 bedroom, WiFi
Welcome to our charming studio, perfectly located near Tampa Bay's attractions.

Apartment in Pinecrest West Park

Welcome to our charming studio, perfectly located near Tampa Bay's attractions.
2.0 star property
9.4 out of 10, Exceptional, (43)
"clean bed. Clean bathroom. "
United States
Juan
The price is HK$342
HK$897 total
includes taxes & fees
12 Jan - 13 Jan 2026
Welcome to our charming studio, perfectly located near Tampa Bay's attractions.
Outdoor dining
Mint House St. Petersburg - Downtown

Aparthotel in Downtown St. Petersburg

Mint House St. Petersburg - Downtown
4.5 star property
9.4 out of 10, Exceptional, (697)
"Very clean, conveniently located, and friendly staff."
United States
Carolyn
The price is HK$1,022
HK$1,155 total
includes taxes & fees
28 Dec - 29 Dec
Mint House St. Petersburg - Downtown
Exterior
Green Castle Suite in Tampa

Apartment in Town 'n' Country

Green Castle Suite in Tampa
9.8 out of 10, Exceptional, (36)
"internet and television options were great as well as the area was impeccably clean"
United States
Toasty
The price is HK$389
HK$906 total
includes taxes & fees
4 Jan - 5 Jan 2026
Green Castle Suite in Tampa
Exterior
Sailport Waterfront Suites

Aparthotel in Rocky Point

Sailport Waterfront Suites
3.5 star property
8.4 out of 10, Very good, (4862)
"Great fishing spot,with a great view."
United States
Shanetta
The price is HK$814
HK$1,064 total
includes taxes & fees
25 Dec - 26 Dec
Sailport Waterfront Suites
Sun deck
Provident Oceana Beachfront Suites

Condo in Treasure Island

Provident Oceana Beachfront Suites
3.5 star property
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 HK$1,283
HK$1,626 total
includes taxes & fees
12 Jan - 13 Jan 2026
Provident Oceana Beachfront Suites
Exterior
Loft Close to Downtown, Airport and Stadium

Apartment in MacFarlane Park

Loft Close to Downtown, Airport and Stadium
9.8 out of 10, Exceptional, (50)
"Great location close to Raymond James. "
United States
Drew F.
The price is HK$544
HK$1,321 total
includes taxes & fees
13 Jan - 14 Jan 2026
Loft Close to Downtown, Airport and Stadium
Pool
DFGmoments#2/Northdale/Citrus Park Mall

Apartment in Greater Northdale

DFGmoments#2/Northdale/Citrus Park Mall
9.8 out of 10, Exceptional, (64)
"Wonderful stay!"
United States
Jan P.
The price is HK$397
HK$959 total
includes taxes & fees
18 Jan - 19 Jan 2026
DFGmoments#2/Northdale/Citrus Park Mall
Terrace/patio
The Avalon Club

Aparthotel in Clearwater Beach

The Avalon Club
4.0 star property
9.4 out of 10, Exceptional, (492)
"We loved our stay here. Exceeded expectations"
United States
Anne
The price is HK$1,564
HK$2,076 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Avalon Club
1 bedroom, iron/ironing board, free WiFi, bed sheets
Rest apartament

Apartment in Holiday

Rest apartament
9.6 out of 10, Exceptional, (55)
"Very nice place, looked exactly like the photos, Great Hospitality also."
United States
Marcael Y.
The price is HK$389
HK$1,027 total
includes taxes & fees
26 Dec - 27 Dec
Rest apartament
Terrace/patio
The Fold Hotels Indian Shores

Aparthotel in Indian Shores

The Fold Hotels Indian Shores
3.0 star property
9.2 out of 10, Wonderful, (935)
"The room was spotless and staff so friendly and helpful. "
United States
Valerie
The price is HK$1,029
HK$1,277 total
includes taxes & fees
11 Jan - 12 Jan 2026
The Fold Hotels Indian Shores
Dining
Aileen Camping Space

Mobile Home in East Tampa

Aileen Camping Space
9.6 out of 10, Exceptional, (70)
"Great stay, will stay again."
United States
Holly D.
The price is HK$343
HK$942 total
includes taxes & fees
4 Jan - 5 Jan 2026
Aileen Camping Space
View from room
Shoreline Island Resort - Exclusively Adult

Aparthotel in Madeira Beach

Shoreline Island Resort - Exclusively Adult
3.0 star property
9.2 out of 10, Wonderful, (1437)
"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 HK$1,630
HK$1,842 total
includes taxes & fees
16 Jan - 17 Jan 2026
Shoreline Island Resort - Exclusively Adult
On the beach
Surf Beach Treasure Island Resort

Aparthotel in Treasure Island

Surf Beach Treasure Island Resort
3.0 star property
9.2 out of 10, Wonderful, (854)
"Room was clean and the front desk was very nice. We would definitely stay here again!"
United States
Rebecca
The price is HK$1,435
HK$3,094 total
includes taxes & fees
4 Jan - 5 Jan 2026
Surf Beach Treasure Island Resort
Marina
The M’s Cozy Corner

Apartment in Ybor City

The M’s Cozy Corner
9.8 out of 10, Exceptional, (73)
"Great Host & Great location!"
Canada
Todd V.
The price is HK$513
HK$1,180 total
includes taxes & fees
30 Dec - 31 Dec
The M’s Cozy Corner
In-room dining
Barefoot Beach Resort

Aparthotel in Indian Shores

Barefoot Beach Resort
3.5 star property
9.0 out of 10, Wonderful, (906)
"Quiet, great location finally, staff management and the whole area was clean and well maintain"
United States
Harold
The price is HK$1,081
HK$1,336 total
includes taxes & fees
4 Jan - 5 Jan 2026
Barefoot Beach Resort
Front of property – evening/night
South Beach Oceanfront Resort

Aparthotel in Sunshine Beach

South Beach Oceanfront Resort
3.0 star property
9.2 out of 10, Wonderful, (1123)
"Great place to stay!"
United States
Angela
The price is HK$1,263
HK$2,527 total
includes taxes & fees
5 Jan - 6 Jan 2026
South Beach Oceanfront Resort
Exterior
John's Pass Hotel

Aparthotel in Madeira Beach

John's Pass Hotel
2.0 star property
8.6 out of 10, Excellent, (277)
"Great location, staff and room"
United States
Saori
John's Pass Hotel
Aerial view
Westwinds Waterfront Resort

Condo in Treasure Island

Westwinds Waterfront Resort
3.0 star property
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
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

Hilton Tampa Airport Westshore

Hilton Tampa Airport Westshore

10/10 Excellent
"Room was clean. Loved the shower pressure, just wish there would have been a bath tub. Excellent shuttle service for nearby locations. Rob was great."
melissa 1-night trip
Posted 1 day ago
Hilton Tampa Airport Westshore

Find out more about Oldsmar

Search for holiday rentals in Oldsmar on Expedia! 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!

Explore a world of travel with Expedia

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.