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

Oldsmar Vacation Rentals

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  • Upfront pricing

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

Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Oldsmar vacation rentals

Room

1. Palm Lake Retreat | Pool, Beaches, Near Tampa

Palm Lake Retreat | Pool, Beaches, Near Tampa
Oldsmar
$432 nightly
The price is $455
Sep 20 - Sep 21
Total with taxes and fees
Palm Lake Retreat | Pool, Beaches, Near Tampa
Private kitchen

2. Luxury Bayfront Escape

Luxury Bayfront Escape
Oldsmar
$1,471 nightly
The price is $1,626
Oct 1 - Oct 2
Total with taxes and fees
Luxury Bayfront Escape
Exterior

3. 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 23 - Sep 24
Total with taxes and fees
Green Castle Suite in Tampa
Room

4. 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 17 - Sep 18
Total with taxes and fees
Escape By The Bay
Room

5. 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, (79 reviews)
"Was really nice and price range good for accommodations "
United States
Alejandra
$92 nightly
The price is $101
Sep 27 - Sep 28
Total with taxes and fees
Welcome to our charming studio, perfectly located near Tampa Bay's attractions.
Exterior

6. Sailport Waterfront Suites

Sailport Waterfront Suites
3.5 star property
Rocky Point
8.4 out of 10, Very good, (5,230 reviews)
"Great view and friendly staff"
United States
Torin
$120 nightly
The price is $134
Sep 29 - Sep 30
Total with taxes and fees
Sailport Waterfront Suites
Front of property

7. Beso Del Sol Resort

Beso Del Sol Resort
2.5 star property
Dunedin
8.6 out of 10, Excellent, (766 reviews)
"Every time I come to Florida this will be my home. Love this place"
United States
Jonathan
$127 nightly
The price is $142
Oct 4 - Oct 5
Total with taxes and fees
Beso Del Sol Resort
Living area

8. 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
9.2 out of 10, Wonderful, (37 reviews)
"Very clean, quiet. Safe surroundings if you are traveling by yourself."
United States
Deborah
$108 nightly
The price is $120
Sep 29 - Sep 30
Total with taxes and fees
Cozy Boho Guest House w/Patio - 6 min from the beach!
Private kitchen

9. Charming rental unit with separate entrance.

Charming rental unit with separate entrance.
Tampa
9.8 out of 10, Exceptional, (70 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.
$128 nightly
The price is $142
Sep 17 - Sep 18
Total with taxes and fees
Charming rental unit with separate entrance.
Pool

10. 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.
$110 nightly
The price is $122
Sep 24 - Sep 25
Total with taxes and fees
DFGmoments#2/Northdale/Citrus Park Mall
Private kitchen

11. Beautiful and comfortable room Apt # 2

Beautiful and comfortable room Apt # 2
Tampa
10.0 out of 10, Exceptional, (50 reviews)
"Amazing hosts and clean, quiet, super cute place to stay!"
United States
Angela W.
$133 nightly
The price is $148
Sep 17 - Sep 18
Total with taxes and fees
Beautiful and comfortable room Apt # 2
Property grounds

12. 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.
$257 nightly
The price is $286
Sep 22 - Sep 23
Total with taxes and fees
Beautiful condo on Copperhead. Beaches nearby!
Interior

13. Hideaway Haven: Cozy studio with WiFi, AC in charming Largo

Hideaway Haven: Cozy studio with WiFi, AC in charming Largo
Largo
9.8 out of 10, Exceptional, (38 reviews)
"Will definitely use the property again! Really cozy and perfect for two!"
United States
Shey
$127 nightly
The price is $140
Sep 26 - Sep 27
Total with taxes and fees
Hideaway Haven: Cozy studio with WiFi, AC in charming Largo
Private kitchen

14. Aileen Camping Space

Aileen Camping Space
East Tampa
9.6 out of 10, Exceptional, (79 reviews)
"The host was very welcoming and the accommodation was excellent!"
United States
daniel z.
$115 nightly
The price is $128
Sep 29 - Sep 30
Total with taxes and fees
Aileen Camping Space
Beach

15. ☀Oceanfront ☀Amazing Balcony view☀ WIFI Bar☀ Waterfront Heated Pool ☀

☀Oceanfront ☀Amazing Balcony view☀ WIFI Bar☀ Waterfront Heated Pool ☀
Rocky Point
9.4 out of 10, Exceptional, (51 reviews)
"Such a fantastic value. The location and the amenities were so fun and convince y!"
United States
Kasey J.
$193 nightly
The price is $216
Sep 24 - Sep 25
Total with taxes and fees
☀Oceanfront ☀Amazing Balcony view☀ WIFI Bar☀ Waterfront Heated Pool ☀
View from property

16. Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel
2.5 star property
Clearwater Beach
9.0 out of 10, Wonderful, (1,125 reviews)
"loved the stay"
United States
Carina Yamilet
$148 nightly
The price is $167
Sep 20 - Sep 21
Total with taxes and fees
Pelican Pointe Clearwater Beach Hotel
Exterior detail

17. 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
$119 nightly
The price is $130
Sep 17 - Sep 18
Total with taxes and fees
Experience the passion of hospitality, cleaning, and good location!
Pool

18. Waterfront view, Heated Pool, Private Balcony

Waterfront view, Heated Pool, Private Balcony
Rocky Point
9.6 out of 10, Exceptional, (96 reviews)
"The place was perfect, I would come back or recommend it in a heartbeat."
United States
Tony G.
$237 nightly
The price is $265
Sep 17 - Sep 18
Total with taxes and fees
Waterfront view, Heated Pool, Private Balcony
Beach

19. Direct water view from Balcony-Pool

Direct water view from Balcony-Pool
Rocky Point
9.4 out of 10, Exceptional, (76 reviews)
"Very nice for a quick relaxing getaway!"
United States
Stefanie M.
$228 nightly
The price is $255
Sep 22 - Sep 23
Total with taxes and fees
Direct water view from Balcony-Pool
Room

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

Experience the passion of hospitality, cleaning, and good location!
Westshore
9.4 out of 10, Exceptional, (144 reviews)
"Will stay again"
United States
Gary M.
$101 nightly
The price is $112
Sep 20 - Sep 21
Total with taxes and fees
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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Top Oldsmar Hotel Reviews

Barefoot Beach Club

Barefoot Beach Club

10/10 Excellent
"Amazing ocean view"
kerwin 2-night trip
Posted 2 hours ago
Barefoot Beach Club

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 $85 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.