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

Oldsmar Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Oldsmar holiday rentals

A tennis court with multiple courts, surrounded by trees and a building with a blue roof.

1. Palm Lake Retreat | Pool, Beaches, Near Tampa

Palm Lake Retreat | Pool, Beaches, Near Tampa
Oldsmar
The price is HK$2,379
HK$4,453 total
includes taxes & fees
10 Oct - 11 Oct
Palm Lake Retreat | Pool, Beaches, Near Tampa

2. Luxury Bayfront Escape

Luxury Bayfront Escape
Oldsmar
The price is HK$5,985
HK$11,951 total
includes taxes & fees
1 Oct - 2 Oct
Luxury Bayfront Escape
A beach with thatched umbrellas and lounge chairs, a sandy shore, and a sunset in the background.

3. Sailport Waterfront Suites

Sailport Waterfront Suites
3.5 star property
Rocky Point
8.4 out of 10, Very good, (5,246 reviews)
"Great location with fun pool and bar!"
United States
Amy
The price is HK$949
HK$1,218 total
includes taxes & fees
11 Oct - 12 Oct
Sailport Waterfront Suites
A waterfront hotel with multiple balconies, a dock, and a reflective water surface.

4. Beso Del Sol Resort

Beso Del Sol Resort
2.5 star property
Dunedin
8.6 out of 10, Excellent, (768 reviews)
"Loved the view, pool area very nice"
United States
Tracey
The price is HK$847
HK$1,252 total
includes taxes & fees
28 Sept - 29 Sept
Beso Del Sol Resort
A balcony with wicker furniture overlooking a beach.

5. The Avalon Club

The Avalon Club
4.0 star property
Clearwater Beach
9.4 out of 10, Exceptional, (607 reviews)
"Perfect location on the beach and close to many shops and restaurants."
United States
Robert
The price is HK$1,839
HK$2,389 total
includes taxes & fees
30 Sept - 1 Oct
The Avalon Club
A modern kitchen with white cabinets, a large island with bar stools, stainless steel appliances, and pendant lighting.

6. Downtown Dunedin Walking District

Downtown Dunedin Walking District
Downtown Dunedin
10.0 out of 10, Exceptional, (300 reviews)
"Great stay!"
United States
Barbara B.
The price is HK$1,922
HK$3,254 total
includes taxes & fees
28 Sept - 29 Sept
Downtown Dunedin Walking District
An outdoor patio with a dining table, chairs, and a sofa.

7. 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, (1,050 reviews)
"Nice stay, clean great location"
Australia
Leah
The price is HK$941
HK$1,064 total
includes taxes & fees
28 Sept - 29 Sept
Mint House St. Petersburg Downtown by Kasa
A neatly made bed with a quilted white and black bedspread, a wooden headboard, and a framed sign above reading "stay awhile".

8. Escape By The Bay

Escape By The Bay
Town 'n' Country
9.8 out of 10, Exceptional, (44 reviews)
"We had nice stay"
United States
Denisa
The price is HK$510
HK$825 total
includes taxes & fees
30 Sept - 1 Oct
Escape By The Bay
A hotel with a pool area, palm trees, and a view of the ocean.

9. Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel
2.5 star property
Clearwater Beach
9.0 out of 10, Wonderful, (1,139 reviews)
"Location, privacy, excellent staff- Hailey is wonderful.. We loved her attentiveness and willingness to answer any questions and assist us as needed.."
United States
Renee
The price is HK$784
HK$1,330 total
includes taxes & fees
28 Sept - 29 Sept
Pelican Pointe Clearwater Beach Hotel
A wooden dock with a fire feature and a 'Please be safe' sign, overlooking a lake with a building in the background.

10. The Fold Hotels Indian Shores

The Fold Hotels Indian Shores
3.0 star property
Indian Shores
9.2 out of 10, Wonderful, (1,018 reviews)
"Great location"
United States
Karen
The price is HK$1,042
HK$1,399 total
includes taxes & fees
30 Sept - 1 Oct
The Fold Hotels Indian Shores
A dining area with a round table, white chairs, a chandelier, and a window with blinds.

11. Barefoot Beach Resort

Barefoot Beach Resort
3.5 star property
Indian Shores
9.0 out of 10, Wonderful, (1,040 reviews)
"Loved our stay!"
United Kingdom
HANNAH
The price is HK$793
HK$1,012 total
includes taxes & fees
28 Sept - 29 Sept
Barefoot Beach Resort
A spacious living room with a large sliding glass door leading to a balcony, a ceiling fan, and a bookshelf.

12. Key West Style Cottage - with pool/hot-tub

Key West Style Cottage - with pool/hot-tub
Dunedin
9.4 out of 10, Exceptional, (30 reviews)
"It was perfect for what we needed. It was clean and maintained well. Great location close to the heart of town."
United States
Sean
The price is HK$651
HK$1,513 total
includes taxes & fees
28 Sept - 29 Sept
Key West Style Cottage - with pool/hot-tub
A hotel with a prominent 'Sheraton' sign, a waterfront location, and a modern bridge structure.

13. Green Castle Suite in Tampa

Green Castle Suite in Tampa
Town 'n' Country
9.6 out of 10, Exceptional, (40 reviews)
"Great place to stay!"
United States
Stephanie S.
The price is HK$480
HK$1,013 total
includes taxes & fees
29 Sept - 30 Sept
Green Castle Suite in Tampa
A modern kitchen with white cabinetry, stainless steel appliances, and a marble island.

14. Modern Heater pool house tampa. Close to the park and zoo

Modern Heater pool house tampa. Close to the park and zoo
Lake Magdalene
9.8 out of 10, Exceptional, (185 reviews)
"Fnatastic place and fantastic host!"
United States
David L.
The price is HK$1,267
HK$2,752 total
includes taxes & fees
28 Sept - 29 Sept
Modern Heater pool house tampa. Close to the park and zoo
A modern kitchen with a brick backsplash, a dining area with a large table and chairs, and a hanging light fixture.

15. Newly remodeled Bucs stadium home half mile walk, king bed master suite

Newly remodeled Bucs stadium home half mile walk, king bed master suite
Tampa
10.0 out of 10, Exceptional, (29 reviews)
"Property was in a great location, very comfortable and we would stay there again."
United States
Tara H.
The price is HK$1,059
HK$2,249 total
includes taxes & fees
28 Sept - 29 Sept
Newly remodeled Bucs stadium home half mile walk, king bed master suite
A beach with thatched umbrellas, lounge chairs, and palm trees.

16. Amazing Waterfront Views Resort, Enjoy Heated Pool & Sunset!

Amazing Waterfront Views Resort, Enjoy Heated Pool & Sunset!
Rocky Point
9.6 out of 10, Exceptional, (110 reviews)
"Great view of the bay. The condo was clean and has a cute and cozy beach vibe. The cafe down stairs was super convenient and made a great breakfast sandwich. We really enjoyed our stay."
United States
Tiffany m.
The price is HK$1,687
HK$2,953 total
includes taxes & fees
29 Sept - 30 Sept
Amazing Waterfront Views Resort, Enjoy Heated Pool & Sunset!
A modern building with a flat roof and large windows.

17. Beautiful condo on Copperhead. Beaches nearby!

Beautiful condo on Copperhead. Beaches nearby!
Palm Harbor
9.6 out of 10, Exceptional, (29 reviews)
"Very nice view onto copperhead course from the balcony. Spacious condo. Perfect for our stay."
United States
Clive C.
The price is HK$526
HK$2,072 total
includes taxes & fees
28 Sept - 29 Sept
Beautiful condo on Copperhead. Beaches nearby!
A modern kitchen with white cabinets, a black refrigerator, a microwave, and a granite countertop.

18. Charming rental unit with separate entrance.

Charming rental unit with separate entrance.
Tampa
9.8 out of 10, Exceptional, (71 reviews)
"Great and safe location! Lots of restaurants nearby. It is an ideal place to stay if planning on attending a Tampa bay buccaneers game or planning to go to Clearwater beach and not drive back home . I would definitely stay again . "
United States
Jorge H.
The price is HK$494
HK$1,163 total
includes taxes & fees
28 Sept - 29 Sept
Charming rental unit with separate entrance.
A modern bedroom with a large bed, a bedside table, a nightstand, a small desk, a microwave, a coffee maker, and a sink.

19. Welcome to our charming studio, perfectly located near Tampa Bay's attractions.

Welcome to our charming studio, perfectly located near Tampa Bay's attractions.
Pinecrest West Park
9.2 out of 10, Wonderful, (80 reviews)
"Great stay, very clean. The pool was very nice. And the scenery was amazing as well"
United States
Brandy
The price is HK$247
HK$793 total
includes taxes & fees
28 Sept - 29 Sept
Welcome to our charming studio, perfectly located near Tampa Bay's attractions.
A beach with a pier extending into the ocean, a sandy beach lined with palm trees, and a row of beach umbrellas.

20. PROMO PRICES - POOL VIEW - CLEARWATER BEACH - FREE WI-FI/PARKING

PROMO PRICES - POOL VIEW - CLEARWATER BEACH - FREE WI-FI/PARKING
Clearwater
9.8 out of 10, Exceptional, (53 reviews)
"This is a great place"
United States
James B.
The price is HK$690
HK$2,266 total
includes taxes & fees
28 Sept - 29 Sept
PROMO PRICES - POOL VIEW - CLEARWATER BEACH - FREE WI-FI/PARKING
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.
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Top Oldsmar Hotel Reviews

Mint House St. Petersburg Downtown by Kasa

Mint House St. Petersburg Downtown by Kasa

10/10 Excellent
"The best fairly priced place I’ve ever stayed! The pool was the perfect temperature."
Kaitlyn 2-night trip
Posted 15 hours ago
Mint House St. Petersburg Downtown by Kasa

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
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  • 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 Raymond James Stadium and Port Tampa Bay.

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.