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

Oldsmar Vacation Rentals

Check prices for these dates

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

Our top choices for Oldsmar vacation rentals

1. Luxury Bayfront Escape

Luxury Bayfront Escape
Oldsmar
$1,435 nightly
The price is $1,590
Oct 1 - Oct 2
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, (5,244 reviews)
"Great location with fun pool and bar!"
United States
Amy
$122 nightly
The price is $136
Oct 1 - Oct 2
Total with taxes and fees
Sailport Waterfront Suites
A waterfront hotel with multiple balconies, a dock, and a reflective water surface.

3. 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
$155 nightly
The price is $173
Sep 27 - Sep 28
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, (606 reviews)
"Perfect location on the beach and close to many shops and restaurants."
United States
Robert
$270 nightly
The price is $305
Sep 30 - Oct 1
Total with taxes and fees
The Avalon Club
A wooden dock with a fire feature and a 'Please be safe' sign, overlooking a lake with a building in the background.

5. 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
$155 nightly
The price is $175
Sep 28 - Sep 29
Total with taxes and fees
The Fold Hotels Indian Shores
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, (1,136 reviews)
"loved the stay"
United States
Carina Yamilet
$147 nightly
The price is $166
Sep 28 - Sep 29
Total with taxes and fees
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
4.0 star property
Downtown St. Petersburg
9.4 out of 10, Exceptional, (1,045 reviews)
"Great stay"
United States
Brittany
$110 nightly
The price is $125
Sep 27 - Sep 28
Total with taxes and fees
Mint House St. Petersburg Downtown by Kasa
A modern kitchen with white cabinets, a large island with bar stools, stainless steel appliances, and pendant lighting.

8. Downtown Dunedin Walking District

Downtown Dunedin Walking District
Downtown Dunedin
10.0 out of 10, Exceptional, (300 reviews)
"Great stay!"
United States
Barbara B.
$394 nightly
The price is $439
Sep 25 - Sep 26
Total with taxes and fees
Downtown Dunedin Walking District
A dining area with a round table, white chairs, a chandelier, and a window with blinds.

9. Barefoot Beach Resort

Barefoot Beach Resort
3.5 star property
Indian Shores
9.0 out of 10, Wonderful, (1,038 reviews)
"Loved our stay!"
United Kingdom
HANNAH
$114 nightly
The price is $129
Sep 27 - Sep 28
Total with taxes and fees
Barefoot Beach Resort
An aerial view of a coastal resort area with multiple buildings, a beach, and a marina.

10. Sunset Vistas Two Bedroom Beachfront Suites

Sunset Vistas Two Bedroom Beachfront Suites
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (3,745 reviews)
"Great spacious rooms, clean. Friendly staff"
United States
Rebecca
$170 nightly
The price is $192
Oct 5 - Oct 6
Total with taxes and fees
Sunset Vistas Two Bedroom Beachfront Suites
A dining table with a birthday cake, champagne, and a scenic waterfront view.

11. FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites
3.5 star property
Treasure Island
9.2 out of 10, Wonderful, (1,256 reviews)
"Overall the resort is nice."
United States
Michelle
$186 nightly
The price is $210
Oct 20 - Oct 21
Total with taxes and fees
FUSION Resort Waterfront Suites
A neatly made bed with a quilted white and black bedspread, a wooden headboard, and a framed sign above reading "stay awhile".

12. 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
$117 nightly
The price is $130
Sep 25 - Sep 26
Total with taxes and fees
Escape By The Bay
A beach with thatched umbrellas, lounge chairs, and palm trees.

13. 262-NEW! 3 beds x 2 baths. Amazing Waterfront Views!

262-NEW! 3 beds x 2 baths. Amazing Waterfront Views!
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.
$354 nightly
The price is $397
Sep 29 - Sep 30
Total with taxes and fees
262-NEW! 3 beds x 2 baths. Amazing Waterfront Views!
A modern building with a flat roof and large windows.

14. 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.
$262 nightly
The price is $292
Sep 28 - Sep 29
Total with taxes and fees
Beautiful condo on Copperhead. Beaches nearby!
A beach with numerous white tents and a sandy beach.

15. Surf Beach Treasure Island Resort

Surf Beach Treasure Island Resort
3.0 star property
Treasure Island
9.2 out of 10, Wonderful, (902 reviews)
"Clean room, close to beach"
United States
Krishna
$352 nightly
The price is $398
Sep 27 - Sep 28
Total with taxes and fees
Surf Beach Treasure Island Resort
A hotel with a prominent 'Sheraton' sign, a waterfront location, and a modern bridge structure.

16. 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.
$116 nightly
The price is $129
Sep 25 - Sep 26
Total with taxes and fees
Green Castle Suite in Tampa
A hotel with a modern design, featuring a prominent 'South Beach' sign and a 'Beach' sign.

17. South Beach Oceanfront Resort

South Beach Oceanfront Resort
3.0 star property
Sunshine Beach
9.2 out of 10, Wonderful, (1,173 reviews)
"Close to a lot of amenities"
Canada
Erika
$273 nightly
The price is $309
Sep 27 - Sep 28
Total with taxes and fees
South Beach Oceanfront Resort
A spacious living room with a large sliding glass door leading to a balcony, a ceiling fan, and a bookshelf.

18. 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
$173 nightly
The price is $193
Sep 28 - Sep 29
Total with taxes and fees
Key West Style Cottage - with pool/hot-tub
A wide sandy beach with footprints and a few beachgoers.

19. PRIVATE COTTAGE OCEAN VIEW 44 PACES TO BEACH, CLOSE TO RESTAURANTS AND SHOPS

PRIVATE COTTAGE OCEAN VIEW 44 PACES TO BEACH, CLOSE TO RESTAURANTS AND SHOPS
clearwater beach
10.0 out of 10, Exceptional, (234 reviews)
"Enjoyed our stay at this lovely cottage! Almost right on the beach and an easy walk to downtown and pier 60."
United States
Michael H.
PRIVATE COTTAGE OCEAN VIEW 44 PACES TO BEACH, CLOSE TO RESTAURANTS AND SHOPS
A multi-story hotel with a curved entrance and balconies on each floor.

20. Crystal Palms Beach Resort

Crystal Palms Beach Resort
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (2,406 reviews)
"Less than 5 minute walk to the beach. Property is well maintained. Condo was clean. I would highly recommend it"
United States
Vladimir
$131 nightly
The price is $148
Sep 27 - Sep 28
Total with taxes and fees
Crystal Palms Beach 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.
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Top Oldsmar Hotel Reviews

Hyatt Regency Clearwater Beach Resort and Suites

Hyatt Regency Clearwater Beach Resort and Suites

10/10 Excellent
"Clean room, beautiful beaches"
Svetlana 3-night trip
Posted less than an hour ago
Hyatt Regency Clearwater Beach Resort and Suites

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 $106 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 11 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.