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

Oldsmar Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Oldsmar vacation rentals

Exterior

1. Luxury Bayfront Escape

Luxury Bayfront Escape
Oldsmar
$1,435 nightly
The price is $1,590
Oct 5 - Oct 6
Total with taxes and fees
Luxury Bayfront Escape
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, (5,256 reviews)
"Me and my family loved this place ❤️"
United States
Alcendrea
$119 nightly
The price is $133
Oct 11 - Oct 12
Total with taxes and fees
Sailport Waterfront Suites
A neatly made bed with a quilted white and black bedspread, a wooden headboard, and a framed sign above reading "stay awhile".

3. 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
$103 nightly
The price is $114
Oct 5 - Oct 6
Total with taxes and fees
Escape By The Bay
A sign for Tampa International Airport with a logo and the name of the airport.

4. 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.
$115 nightly
The price is $128
Oct 5 - Oct 6
Total with taxes and fees
Green Castle Suite in Tampa
A spacious living room with a large sliding glass door leading to a balcony, a ceiling fan, and a bookshelf.

5. 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
$175 nightly
The price is $195
Oct 5 - Oct 6
Total with taxes and fees
Key West Style Cottage - with pool/hot-tub
A waterfront hotel with multiple balconies, a dock, and a reflective water surface.

6. Beso Del Sol Resort

Beso Del Sol Resort
2.5 star property
Dunedin
8.6 out of 10, Excellent, (772 reviews)
"Loved the view, pool area very nice"
United States
Tracey
$155 nightly
The price is $173
Oct 5 - Oct 6
Total with taxes and fees
Beso Del Sol Resort
A living room with a grey sofa, a patterned rug, a dining table with white chairs, and a potted plant.

7. 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
$108 nightly
The price is $120
Oct 30 - Oct 31
Total with taxes and fees
Cozy Boho Guest House w/Patio - 6 min from the beach!
A pool area with lounge chairs, palm trees, and a building with multiple windows.

8. It’s a "Shore" Thing; Hidden Gem, Vacation's Elixir

It’s a "Shore" Thing; Hidden Gem, Vacation's Elixir
Clearwater
9.8 out of 10, Exceptional, (39 reviews)
"We enjoyed everything this place had to offer"
United States
Pamela C.
It’s a "Shore" Thing; Hidden Gem, Vacation's Elixir
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, (1,144 reviews)
"Friendly staff great location rooms were clean and overall very positive"
United States
Bobbi
$145 nightly
The price is $164
Oct 5 - Oct 6
Total with taxes and fees
Pelican Pointe Clearwater Beach Hotel
A modern bedroom with a large bed, a bedside table, a nightstand, a small desk, a microwave, a coffee maker, and a sink.

10. 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, (83 reviews)
"Great stay, very clean. The pool was very nice. And the scenery was amazing as well"
United States
Brandy
$96 nightly
The price is $106
Oct 5 - Oct 6
Total with taxes and fees
Welcome to our charming studio, perfectly located near Tampa Bay's attractions.
A modern building with a flat roof and large windows.

11. Beautiful condo on Copperhead. Beaches nearby!

Beautiful condo on Copperhead. Beaches nearby!
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.
$247 nightly
The price is $275
Oct 5 - Oct 6
Total with taxes and fees
Beautiful condo on Copperhead. Beaches nearby!
A modern kitchen with a grey countertop, white cabinets, and a built-in microwave.

12. Yude's apartment

Yude's apartment
Town 'n' Country
9.6 out of 10, Exceptional, (29 reviews)
"Had a very wonderful stay highly recommended "
United States
Thalia
$135 nightly
The price is $151
Oct 5 - Oct 6
Total with taxes and fees
Yude's apartment
A water slide at Adventureland in Tampa, FL.

13. DFGmoments#2/Northdale/Citrus Park Mall

DFGmoments#2/Northdale/Citrus Park Mall
Greater Northdale
9.8 out of 10, Exceptional, (80 reviews)
"Comfortable stay"
United States
Patrick T.
$114 nightly
The price is $127
Oct 5 - Oct 6
Total with taxes and fees
DFGmoments#2/Northdale/Citrus Park Mall
A dining area with a round table, white chairs, a chandelier, and a window with blinds.

14. Barefoot Beach Resort

Barefoot Beach Resort
3.5 star property
Indian Shores
9.0 out of 10, Wonderful, (1,045 reviews)
"Loved our stay!"
United Kingdom
HANNAH
$114 nightly
The price is $129
Nov 1 - Nov 2
Total with taxes and fees
Barefoot Beach Resort
A two-story hotel with a balcony on the upper floor, a stop sign, and a parking area.

15. John's Pass Hotel

John's Pass Hotel
2.0 star property
Madeira Beach
8.6 out of 10, Excellent, (465 reviews)
"I love this place and will be spending more time there."
United States
John
$95 nightly
The price is $107
Nov 4 - Nov 5
Total with taxes and fees
John's Pass Hotel
A beach with a pier extending into the ocean, a sandy beach lined with palm trees, and a row of beach umbrellas.

16. 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.
$269 nightly
The price is $300
Oct 8 - Oct 9
Total with taxes and fees
PROMO PRICES - POOL VIEW - CLEARWATER BEACH - FREE WI-FI/PARKING
A beach with a pier, umbrellas, and palm trees.

17. Coastal Dunedin with GOLF CART!

Coastal Dunedin with GOLF CART!
Dunedin
10.0 out of 10, Exceptional, (137 reviews)
"Our stay was lovely and the hosts were extremely accommodating. Looking forward to staying again!!!"
United States
Karin
$252 nightly
The price is $281
Oct 6 - Oct 7
Total with taxes and fees
Coastal Dunedin with GOLF CART!
An outdoor patio with a dining table, chairs, and a sofa.

18. 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, (1,057 reviews)
"Nice stay, clean great location"
Australia
Leah
$120 nightly
The price is $136
Oct 11 - Oct 12
Total with taxes and fees
Mint House St. Petersburg Downtown by Kasa
A balcony with two blue and white chairs, a white railing, and a view of greenery and trees.

19. 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
$161 nightly
The price is $181
Nov 3 - Nov 4
Total with taxes and fees
The Fold Hotels Indian Shores
A modern kitchen with white cabinets, a black refrigerator, a microwave, and a granite countertop.

20. 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.
$133 nightly
The price is $148
Oct 6 - Oct 7
Total with taxes and fees
Charming rental unit with separate entrance.
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

OASIS BAY SUITES, Tampa, Busch Gardens, USF

OASIS BAY SUITES, Tampa, Busch Gardens, USF

8/10 Good
"Perfect"
Laura Ivey 5-night trip
Posted less than an hour ago
OASIS BAY SUITES, Tampa, Busch Gardens, USF

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 $107 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.