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

Oldsmar Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Oldsmar vacation rentals

A paved walkway with palm trees, a beach, and a clear sky.

1. Sailport Waterfront Suites

Sailport Waterfront Suites
3.5 star property
Rocky Point
8.4 out of 10, Very good, (5,300 reviews)
"Me and my family loved this place ❤️"
United States
Alcendrea
$131 nightly
The price is $147
Nov 22 - Nov 23
Total with taxes and fees
Sailport Waterfront Suites
A stone pool surrounded by tropical plants and palm trees.

2. Vibrant 2BR 2BA w King Bed Pool Gym 11

Vibrant 2BR 2BA w King Bed Pool Gym 11
3.0 star property
Town 'n' Country
10.0 out of 10, Exceptional, (1 review)
"Sehr groß und sauber. Alle Möbel waren sauber und funktionsfähig."
Germany
Kim Viola
$286 nightly
The price is $325
Nov 2 - Nov 3
Total with taxes and fees
Vibrant 2BR 2BA w King Bed Pool Gym 11
A deck with lounge chairs and a hot tub, overlooking a body of water with a pier in the background.

3. Beso Del Sol Resort

Beso Del Sol Resort
2.5 star property
Dunedin
8.6 out of 10, Excellent, (785 reviews)
"Friendly staff, great location and wonderful views"
United States
Gina
$132 nightly
The price is $147
Nov 23 - Nov 24
Total with taxes and fees
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, (617 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
$254 nightly
The price is $287
Nov 30 - Dec 1
Total with taxes and fees
The Avalon Club
An outdoor patio with a dining table, chairs, and a sofa.

5. 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, (1,101 reviews)
"Very good value, nice and clean and great space with a (nearly) full kitchen for longer stays."
United States
Ariel
$113 nightly
The price is $128
Dec 1 - Dec 2
Total with taxes and fees
Mint House St. Petersburg Downtown by Kasa
An aerial view of a coastal resort area with multiple buildings, a beach, and a marina.

6. Sunset Vistas Two Bedroom Beachfront Suites

Sunset Vistas Two Bedroom Beachfront Suites
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (3,772 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
$169 nightly
The price is $192
Nov 29 - Nov 30
Total with taxes and fees
Sunset Vistas Two Bedroom Beachfront Suites
A wooden dock with a fire feature and a 'Please be safe' sign, overlooking a lake with a building in the background.

7. The Fold Hotels Indian Shores

The Fold Hotels Indian Shores
3.0 star property
Indian Shores
9.2 out of 10, Wonderful, (1,024 reviews)
"Great location"
United States
Karen
$136 nightly
The price is $154
Nov 29 - Nov 30
Total with taxes and fees
The Fold Hotels Indian Shores
A hotel with a pool, palm trees, and a modern building in the background.

8. Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel
2.5 star property
Clearwater Beach
8.8 out of 10, Excellent, (1,163 reviews)
"We loved our stay here"
United States
Manpreet Kaur
$150 nightly
The price is $169
Nov 10 - Nov 11
Total with taxes and fees
Pelican Pointe Clearwater Beach Hotel
A fountain with multiple tiers, surrounded by well-maintained hedges and flowering plants, with a clear blue sky and a building in the background.

9. Waterfront Resort Condo Gulf Sun Set

Waterfront Resort Condo Gulf Sun Set
3.0 star property
Dunedin
10.0 out of 10, Exceptional, (3 reviews)
"The place was nice quiet and clean. Nice little tiki bar on site also. Good communication before arrival also. "
United States
joe
$304 nightly
The price is $343
Nov 1 - Nov 2
Total with taxes and fees
Waterfront Resort Condo Gulf Sun Set
A bright room with a round table, two chairs, and large windows.

10. The Adaline

The Adaline
5.0 star property
Hyde Park
9.6 out of 10, Exceptional, (77 reviews)
"The best part about this apartment is its location: right by Bayshore, 10 min walking distance from Hyde Park, and in short driving distance from everything S Tampa. The apartment is cute, spacious, quiet, and well equipped. The host provided comprehensive info ahead of check-in so getting in the apartment was smooth."
United States
Mihaela
$316 nightly
The price is $359
Nov 2 - Nov 3
Total with taxes and fees
The Adaline
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, (1,062 reviews)
"Loved our stay!"
United Kingdom
HANNAH
$121 nightly
The price is $137
Dec 1 - Dec 2
Total with taxes and fees
Barefoot Beach Resort
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with seating.

12. NEW Canopy Cabana Luxury Downtown Apt

NEW Canopy Cabana Luxury Downtown Apt
2.0 star property
Safety Harbor
8.0 out of 10, Very good, (1 review)
"Todo fue muy fácil, la propiedad muy limpia y el lugar fue muy bonito una bonita experiencia"
United States
Maria
$411 nightly
The price is $464
Nov 15 - Nov 16
Total with taxes and fees
NEW Canopy Cabana Luxury Downtown Apt
A living room with a sofa, two armchairs, a lamp, and a TV.

13. John's Pass Hotel

John's Pass Hotel
2.0 star property
Madeira Beach
8.6 out of 10, Excellent, (496 reviews)
"Love the location having shops around and how easy was to check in"
United States
Luis
$100 nightly
The price is $113
Nov 30 - Dec 1
Total with taxes and fees
John's Pass Hotel
A dining table with a birthday cake, champagne, and a scenic waterfront view.

14. FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites
3.5 star property
Treasure Island
9.2 out of 10, Wonderful, (1,274 reviews)
"Nice place at a reasonable price. Great amenities. Beautiful views"
United States
Andrew
$209 nightly
The price is $236
Nov 1 - Nov 2
Total with taxes and fees
FUSION Resort Waterfront Suites
A multi-story hotel with a curved entrance and balconies on each floor.

15. Crystal Palms Beach Resort

Crystal Palms Beach Resort
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (2,413 reviews)
"Always a great stay"
United States
Joe
$146 nightly
The price is $165
Nov 1 - Nov 2
Total with taxes and fees
Crystal Palms Beach Resort
A modern kitchen with a large island, white cabinetry, and a dining area with a table and chairs.

16. The Gemma by Brightwild

The Gemma by Brightwild
5.0 star property
Clearwater Beach
9.8 out of 10, Exceptional, (7 reviews)
"The house was beautiful and the location was perfect for our family."
United States
William
$1,253 nightly
The price is $1,415
Nov 22 - Nov 23
Total with taxes and fees
The Gemma by Brightwild
A beach with a curved pathway, palm trees, and a view of the ocean.

17. Surf Beach Treasure Island Resort

Surf Beach Treasure Island Resort
3.0 star property
Treasure Island
9.2 out of 10, Wonderful, (908 reviews)
"We vacation about four times a year at different places, and this was the first time that we stayed here and will not be the last. Staff was friendly, and the whole place was every bit as advertised. Thank you!"
United States
Tobias
$313 nightly
The price is $353
Nov 16 - Nov 17
Total with taxes and fees
Surf Beach Treasure Island Resort
A modern kitchen with white cabinetry, stainless steel appliances, and a central island.

18. 2631 Cedarglen Drive

2631 Cedarglen Drive
3.0 star property
Barrington Hills
$2,755 nightly
The price is $3,113
Nov 3 - Nov 4
Total with taxes and fees
2631 Cedarglen Drive
A hotel with a modern design, featuring a prominent 'South Beach' sign and a 'Beach' sign.

19. South Beach on Treasure Island Oceanfront Resort

South Beach on Treasure Island Oceanfront Resort
3.0 star property
Sunshine Beach
9.2 out of 10, Wonderful, (1,184 reviews)
"Second year staying there this time we stayed 10 days, clean property ,beautiful view, staff was friendly."
United States
Ronald
$259 nightly
The price is $293
Dec 1 - Dec 2
Total with taxes and fees
South Beach on Treasure Island Oceanfront Resort
A multi-story hotel with balconies, a palm tree in front, and a clear sky.

20. Voyager Beach Club

Voyager Beach Club
2.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (120 reviews)
"Great location on the beach very clean, free barking recommend"
United States
Walid
$293 nightly
The price is $331
Nov 1 - Nov 2
Total with taxes and fees
Voyager Beach Club
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

Fairfield Inn & Suites by Marriott Clearwater Beach

Fairfield Inn & Suites by Marriott Clearwater Beach

10/10 Excellent
"Very good customer services"
Ahmed 2-night trip
Posted 9 hours ago
Fairfield Inn & Suites by Marriott Clearwater Beach

Find out more about Oldsmar

Everything you need to know about Oldsmar vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oldsmar vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oldsmar vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oldsmar vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oldsmar. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Oldsmar in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $113 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oldsmar rentals

At Expedia, we put the best Oldsmar vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Oldsmar rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oldsmar vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oldsmar. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Oldsmar?

Yes, we have vacation rentals where you'll be just 14.9 mi (23.9 km) from Busch Gardens Tampa Bay, giving you a secluded option to escape the hustle and bustle. Visitors like the top-notch restaurants and beaches in Oldsmar. Make sure you have time to check out the theme park and cafes during your trip.

What are some of the best vacation home rentals in Oldsmar?

The Gemma by Brightwild: Visitors like this Oldsmar vacation home rental. It is located on the beach and has an outdoor pool, a private balcony, and a barbecue grill 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 you can cook with friends or family. It offers a terrace, a private yard, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals will I find in Oldsmar?

Expedia has 9 vacation 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 larger area, you’ll find popular places like Raymond James Stadium and Port Tampa Bay.

What are vacation rentals like in Oldsmar?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Oldsmar. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.