Oldsmar Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Oldsmar holiday rentals

A kitchen with dark wooden cabinets, a tiled backsplash, and a dining table set with plates, cups, and a kettle.

1. Oldsmar Oakleaf Villa! On Wildlife Area, Natural Privacy! Patio Garage. King Bed

Oldsmar Oakleaf Villa! On Wildlife Area, Natural Privacy! Patio Garage. King Bed
Oldsmar
9.8 out of 10, Exceptional, (64 reviews)
"Roomy two BR two full bath house, beautifully maintained with nice lanai and backyard grill in quiet neighborhood. Perfect location for visiting Tampa Bay Downs horse track, Tarpon Springs & Dunedin. Would happily stay here again."
United States
Stephen W.
Oldsmar Oakleaf Villa! On Wildlife Area, Natural Privacy! Patio Garage. King Bed
A beach with thatched umbrellas and lounge chairs, a sandy shore, and a sunset in the background.

2. Sailport Waterfront Suites

Sailport Waterfront Suites
3.5 star property
Rocky Point
8.4 out of 10, Very good, (5,316 reviews)
"Our favorite part was the on site bar and restaurant"
United States
Paula A
The price is HK$998
HK$1,274 total
includes taxes & fees
22 Nov - 23 Nov
Sailport Waterfront Suites
A wooden pier leading to a dock with several boats moored at the end.

3. Beso Del Sol Resort

Beso Del Sol Resort
2.5 star property
Dunedin
8.6 out of 10, Excellent, (790 reviews)
"Friendly staff, great location and wonderful views"
United States
Gina
The price is HK$847
HK$1,252 total
includes taxes & fees
12 Nov - 13 Nov
Beso Del Sol Resort
A balcony with wicker furniture overlooking a beach.

4. The Avalon Club

The Avalon Club
4.0 star property
Clearwater Beach
9.4 out of 10, Exceptional, (620 reviews)
"The room was spacious for my family and I. A close walk to the beach. Close to shopping and eating, great location."
United States
Courtney
The price is HK$1,839
HK$2,388 total
includes taxes & fees
15 Nov - 16 Nov
The Avalon Club
A hotel courtyard with a central fountain, palm trees, and a multi-story building with balconies.

5. Sunset Vistas Two Bedroom Beachfront Suites

Sunset Vistas Two Bedroom Beachfront Suites
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (3,781 reviews)
"I love staying here. This is my 3rd time staying here and I keep coming back because I love the property! The location is ideal, and the staff are amazing."
United States
Shelby
The price is HK$1,259
HK$1,644 total
includes taxes & fees
17 Nov - 18 Nov
Sunset Vistas Two Bedroom Beachfront Suites
A hotel with a pool area, palm trees, and a view of the ocean.

6. Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel
2.5 star property
Clearwater Beach
9.0 out of 10, Wonderful, (1,181 reviews)
"Hotel was great!"
United States
Daniel
The price is HK$735
HK$1,271 total
includes taxes & fees
2 Dec - 3 Dec
Pelican Pointe Clearwater Beach Hotel
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
3.5 star property
Downtown St. Petersburg
9.4 out of 10, Exceptional, (1,120 reviews)
"Great place"
United States
Anonymous traveller
The price is HK$753
HK$851 total
includes taxes & fees
22 Nov - 23 Nov
Mint House St. Petersburg Downtown by Kasa
A modern building with a flat roof and large windows.

8. Innisbrook 2BR Getaway With Balcony & Pool

Innisbrook 2BR Getaway With Balcony & Pool
Palm Harbor
9.6 out of 10, Exceptional, (30 reviews)
"Place was great and sits on hole 2 of Copperhead. The only catch is the property has no elevator, and the room is on the 3rd floor."
United States
Indy J.
The price is HK$710
HK$2,272 total
includes taxes & fees
12 Nov - 13 Nov
Innisbrook 2BR Getaway With Balcony & Pool
A spacious living room with a large sliding glass door leading to a balcony, a ceiling fan, and a bookshelf.

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

Key West Style Cottage - with pool/hot-tub
Dunedin
9.4 out of 10, Exceptional, (36 reviews)
"Had an amazing stay at this beautiful cottage! The place was very clean, spacious, and comfortable, making it the perfect spot to relax and enjoy our time away. I felt safe throughout the stay, and the location was excellent, with cafés and restaurants within walking distance. The host was wonderful (very easy to communicate back and forth with, even left an itinerary with recommendations, LOVEDDD THATTT) and truly, appreciated the opportunity to stay here. Would absolutely recommend this...
United States
Nayeli
The price is HK$681
HK$1,484 total
includes taxes & fees
15 Nov - 16 Nov
Key West Style Cottage - with pool/hot-tub
A living room with a grey sofa, a patterned rug, a dining table with white chairs, and a potted plant.

10. Cozy Boho Guest House w/Patio - 6 min from the beach!

Cozy Boho Guest House w/Patio - 6 min from the beach!
Town 'n' Country
9.0 out of 10, Wonderful, (40 reviews)
"Very clean, quiet. Safe surroundings if you are traveling by yourself."
United States
Deborah
The price is HK$439
HK$878 total
includes taxes & fees
12 Nov - 13 Nov
Cozy Boho Guest House w/Patio - 6 min from the beach!
A beach with thatched umbrellas, lounge chairs, and palm trees.

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

Amazing Waterfront Views Resort, Enjoy Heated Pool & Sunset!
Rocky Point
9.6 out of 10, Exceptional, (114 reviews)
"This place was so cute and large! Great pool area and views! Very clean and would highly recommend!!"
United States
Julie T.
The price is HK$1,687
HK$2,882 total
includes taxes & fees
16 Nov - 17 Nov
Amazing Waterfront Views Resort, Enjoy Heated Pool & Sunset!
A wooden dock with a fire feature and a 'Please be safe' sign, overlooking a lake with a building in the background.

12. The Fold Hotels Indian Shores

The Fold Hotels Indian Shores
3.0 star property
Indian Shores
9.2 out of 10, Wonderful, (1,026 reviews)
"Great location"
United States
Karen
The price is HK$874
HK$1,209 total
includes taxes & fees
9 Dec - 10 Dec
The Fold Hotels Indian Shores
A modern bedroom with a large bed, a bedside table, a nightstand, a small desk, a microwave, a coffee maker, and a sink.

13. 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, (86 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$686 total
includes taxes & fees
16 Nov - 17 Nov
Welcome to our charming studio, perfectly located near Tampa Bay's attractions.
A hotel with a prominent 'Sheraton' sign, a waterfront location, and a modern bridge structure.

14. 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$471
HK$940 total
includes taxes & fees
12 Nov - 13 Nov
Green Castle Suite in Tampa
A dining table with a birthday cake, champagne, and a scenic waterfront view.

15. FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites
3.5 star property
Treasure Island
9.2 out of 10, Wonderful, (1,277 reviews)
"Nice place at a reasonable price. Great amenities. Beautiful views"
United States
Andrew
The price is HK$1,405
HK$1,853 total
includes taxes & fees
15 Nov - 16 Nov
FUSION Resort Waterfront Suites
A waterfront property with a paved walkway, benches, palm trees, and a white fence.

16. Barefoot Beach Resort

Barefoot Beach Resort
3.5 star property
Indian Shores
9.0 out of 10, Wonderful, (1,069 reviews)
"Loved our stay!"
United Kingdom
HANNAH
The price is HK$933
HK$1,170 total
includes taxes & fees
30 Nov - 1 Dec
Barefoot Beach Resort
A two-story hotel with a balcony on the upper floor, a stop sign, and a parking area.

17. John's Pass Hotel

John's Pass Hotel
2.0 star property
Madeira Beach
8.6 out of 10, Excellent, (504 reviews)
"Love the location having shops around and how easy was to check in"
United States
Luis
The price is HK$667
HK$880 total
includes taxes & fees
17 Nov - 18 Nov
John's Pass Hotel
A kitchen with teal walls, white cabinets, and a white refrigerator.

18. A beautiful and comfortable room, Apartment No. 2

A beautiful and comfortable room, Apartment No. 2
Tampa
10.0 out of 10, Exceptional, (53 reviews)
"Amazing hosts and clean, quiet, super cute place to stay!"
United States
Angela W.
The price is HK$530
HK$1,096 total
includes taxes & fees
13 Nov - 14 Nov
A beautiful and comfortable room, Apartment No. 2
A bedroom with a large bed, a nightstand, a chair, and a view of the ocean.

19. Crystal Palms Beach Resort

Crystal Palms Beach Resort
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (2,416 reviews)
"Always a great stay"
United States
Joe
The price is HK$935
HK$1,189 total
includes taxes & fees
18 Nov - 19 Nov
Crystal Palms Beach Resort
A house with a front door, a large potted plant, and a small white lantern on the porch.

20. Experience the passion of hospitality, cleaning, and good location!

Experience the passion of hospitality, cleaning, and good location!
Westshore
9.2 out of 10, Wonderful, (94 reviews)
"Staff was really nice!"
United States
Anthony
The price is HK$518
HK$899 total
includes taxes & fees
12 Nov - 13 Nov
Experience the passion of hospitality, cleaning, and good location!
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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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 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 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.