Oldsmar Vacation Rentals

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Our top choices for Oldsmar vacation rentals

Vacation Home w HOT TUB, 2 MASTER BEDROOMS, HEATED POOL NEAR BEACHES!

Vacation Home w HOT TUB, 2 MASTER BEDROOMS, HEATED POOL NEAR BEACHES!
Oldsmar
9.6 out of 10, Exceptional, (49 reviews)
"Nice Place!!!"
United States
Lulije A.
$615 nightly
The price is $686
May 28 - May 29
Total with taxes and fees
Vacation Home w HOT TUB, 2 MASTER BEDROOMS, HEATED POOL NEAR BEACHES!

Modern Private Estate - Central to Tampa & Beaches

Modern Private Estate - Central to Tampa & Beaches
Oldsmar
$519 nightly
The price is $579
May 7 - May 8
Total with taxes and fees
Modern Private Estate - Central to Tampa & Beaches

Aileen Camping Space

Aileen Camping Space
East Tampa
9.6 out of 10, Exceptional, (78 reviews)
"Aileen’s is cozy and private. The RV was very clean and comfortable. It is well decorated, too. "
United States
Loria
$119 nightly
The price is $132
May 3 - May 4
Total with taxes and fees
Aileen Camping Space

Sunset Vistas Two Bedroom Beachfront Suites

Sunset Vistas Two Bedroom Beachfront Suites
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (3,563 reviews)
"Loved our stay so close to the beach most beautiful sunsets!"
United States
Danielle
$251 nightly
The price is $284
May 11 - May 12
Total with taxes and fees
Sunset Vistas Two Bedroom Beachfront Suites

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, (787 reviews)
"Wonderful amenities…close to everything and an overall great experience! Looking forward to a return visit!"
United States
Donna
$94 nightly
The price is $106
May 10 - May 11
Total with taxes and fees
Mint House St. Petersburg Downtown by Kasa

Sailport Waterfront Suites

Sailport Waterfront Suites
3.5 star property
Rocky Point
8.4 out of 10, Very Good, (5,021 reviews)
"Great stay"
United States
Eric
$145 nightly
The price is $162
May 24 - May 25
Total with taxes and fees
Sailport Waterfront Suites

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites
3.5 star property
Treasure Island
9.2 out of 10, Wonderful, (1,162 reviews)
"I really liked the spaciousness of the environment, the cleanliness, and the view of the lake and the sunrise."
United States
LAURA
$229 nightly
The price is $259
May 25 - May 26
Total with taxes and fees
FUSION Resort Waterfront Suites

Surf Beach Treasure Island Resort

Surf Beach Treasure Island Resort
3.0 star property
Treasure Island
9.2 out of 10, Wonderful, (865 reviews)
"Clean room, convenient location and friendly staff"
United States
Jingjing
$352 nightly
The price is $397
May 7 - May 8
Total with taxes and fees
Surf Beach Treasure Island Resort

The Avalon Club

The Avalon Club
4.0 star property
Clearwater Beach
9.4 out of 10, Exceptional, (533 reviews)
"This place is very nice and clean, my entire family loves it..we enjoyed our stay..."
United States
marjane
$248 nightly
The price is $281
May 10 - May 11
Total with taxes and fees
The Avalon Club

Beso Del Sol Resort

Beso Del Sol Resort
2.5 star property
Dunedin
8.6 out of 10, Excellent, (718 reviews)
"Overall a nice place to stay"
Canada
Jerome
$148 nightly
The price is $166
May 13 - May 14
Total with taxes and fees
Beso Del Sol Resort

The Fold Hotels Indian Shores

The Fold Hotels Indian Shores
3.0 star property
Indian Shores
9.2 out of 10, Wonderful, (976 reviews)
"Absolutely love this hotel. It’s a short walk to the beach and a few restaurants. Very clean and updated. All the staff were helpful and friendly too. "
United States
Jared
$208 nightly
The price is $235
May 6 - May 7
Total with taxes and fees
The Fold Hotels Indian Shores

Provident Oceana Beachfront Suites

Provident Oceana Beachfront Suites
3.5 star property
Treasure Island
9.4 out of 10, Exceptional, (630 reviews)
"Great View, Clean Rooms. Would stay again"
Canada
Connor
$230 nightly
The price is $260
May 4 - May 5
Total with taxes and fees
Provident Oceana Beachfront Suites

South Beach Oceanfront Resort

South Beach Oceanfront Resort
3.0 star property
Sunshine Beach
9.2 out of 10, Wonderful, (1,136 reviews)
"Great staff always helpful and knowledgeable about the area. Enjoy the size of the one bedroom condo "
United States
Bob
$290 nightly
The price is $328
May 4 - May 5
Total with taxes and fees
South Beach Oceanfront Resort

Barefoot Beach Resort

Barefoot Beach Resort
3.5 star property
Indian Shores
9.0 out of 10, Wonderful, (946 reviews)
"Great place right on the beach!"
United States
Tom
$162 nightly
The price is $183
May 13 - May 14
Total with taxes and fees
Barefoot Beach Resort

Luxurious Waterfront Holiday Home with Fully Encompassing Lakeview

Luxurious Waterfront Holiday Home with Fully Encompassing Lakeview
Holiday
9.8 out of 10, Exceptional, (130 reviews)
"We stayed on the property while working in the area and found it warm and welcoming. The host was responsive and helpful, especially when we needed to extend our stay. We really enjoyed our time here and would gladly return if work brings us back"
United States
Rick L.
$304 nightly
The price is $336
May 1 - May 2
Total with taxes and fees
Luxurious Waterfront Holiday Home with Fully Encompassing Lakeview

John's Pass Hotel

John's Pass Hotel
2.0 star property
Madeira Beach
8.4 out of 10, Very Good, (331 reviews)
"Parking was easy and the shops are right there."
United States
Denice
$168 nightly
The price is $190
May 3 - May 4
Total with taxes and fees
John's Pass Hotel

SUNNY DELIGHT! pets ok! UPDATED HEATED POOL VACATION CONDO. Safe gated community

SUNNY DELIGHT! pets ok! UPDATED HEATED POOL VACATION CONDO. Safe gated community
Seminole
10.0 out of 10, Exceptional, (101 reviews)
"Everything was covered and host went over and beyond for us."
United States
Deborah C.
$241 nightly
The price is $269
May 2 - May 3
Total with taxes and fees
SUNNY DELIGHT! pets ok! UPDATED HEATED POOL VACATION CONDO. Safe gated community

BeachTrail Lodging

BeachTrail Lodging
3.0 star property
Indian Rocks Beach
9.8 out of 10, Exceptional, (100 reviews)
"The location was the perfect distance to the beach, and the provided beach chairs were very much appreciated. Clean accommodations. Perfect home away from home. "
United States
Shelbie
$425 nightly
The price is $480
May 4 - May 5
Total with taxes and fees
BeachTrail Lodging

Beach View, Private Plunge Pool, Charming 1938 Bungalow Madeira Beach Gulf-Blvd

Beach View, Private Plunge Pool, Charming 1938 Bungalow Madeira Beach Gulf-Blvd
Madeira Beach
9.6 out of 10, Exceptional, (258 reviews)
"This charming bungalow was perfect for a weekend getaway with friends. Fantastic beach access and easy walking distance to the strand of local shops and restaurants. Would stay again!"
United States
Lanie C.
$443 nightly
The price is $493
May 10 - May 11
Total with taxes and fees
Beach View, Private Plunge Pool, Charming 1938 Bungalow Madeira Beach Gulf-Blvd

Beautiful suite with separate entrance.

Beautiful suite with separate entrance.
North Park
9.4 out of 10, Exceptional, (29 reviews)
"Enjoyed the simply, straight forward layout and the convenient location"
United States
Thomas D.
$120 nightly
The price is $132
May 1 - May 2
Total with taxes and fees
Beautiful suite 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.
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Top Oldsmar Hotel Reviews

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.

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: You might want to consider this vacation home rental near Oldsmar, which 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 13 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 of Tampa.

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.