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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Oldsmar vacation rentals

Pool

1. Luxury Bayfront Escape

Luxury Bayfront Escape
Oldsmar
$1,466 nightly
The price is $1,621
Sep 7 - Sep 8
Total with taxes and fees
Luxury Bayfront Escape
Exterior

2. 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
Sep 6 - Sep 7
Total with taxes and fees
Green Castle Suite in Tampa
Room

3. Escape By The Bay

Escape By The Bay
Town 'n' Country
9.8 out of 10, Exceptional, (43 reviews)
"Great value for space"
United States
Jake G.
$117 nightly
The price is $130
Sep 4 - Sep 5
Total with taxes and fees
Escape By The Bay
Living area

4. 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, (36 reviews)
"Very clean, quiet. Safe surroundings if you are traveling by yourself."
United States
Deborah
$108 nightly
The price is $120
Sep 7 - Sep 8
Total with taxes and fees
Cozy Boho Guest House w/Patio - 6 min from the beach!
Beach

5. 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, (108 reviews)
"Great location for our needs. Spring straining and Tampa Museums. Restaurant on premises is a plus. Great sunsets. "
United States
John S.
$356 nightly
The price is $399
Sep 7 - Sep 8
Total with taxes and fees
262-NEW! 3 beds x 2 baths. Amazing Waterfront Views!
Beach

6. 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.
$225 nightly
The price is $252
Sep 8 - Sep 9
Total with taxes and fees
Direct water view from Balcony-Pool
Pool

7. Waterfront view, Heated Pool, Private Balcony

Waterfront view, Heated Pool, Private Balcony
Rocky Point
9.6 out of 10, Exceptional, (95 reviews)
"The place was perfect, I would come back or recommend it in a heartbeat."
United States
Tony G.
$239 nightly
The price is $268
Sep 7 - Sep 8
Total with taxes and fees
Waterfront view, Heated Pool, Private Balcony
Beach

8. ☀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.
$215 nightly
The price is $240
Sep 14 - Sep 15
Total with taxes and fees
☀Oceanfront ☀Amazing Balcony view☀ WIFI Bar☀ Waterfront Heated Pool ☀
Beach

9. Waterfront! 10 min to airport/Near stadium

Waterfront! 10 min to airport/Near stadium
Rocky Point
9.4 out of 10, Exceptional, (75 reviews)
"Great location. Very clean and comfortable. I enjoyed the stay."
United States
Anthony L.
$230 nightly
The price is $258
Sep 29 - Sep 30
Total with taxes and fees
Waterfront! 10 min to airport/Near stadium
Private kitchen

10. 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 4 - Sep 5
Total with taxes and fees
Downtown Dunedin Walking District
Exterior

11. Sailport Waterfront Suites

Sailport Waterfront Suites
3.5 star property
Rocky Point
8.4 out of 10, Very Good, (5,211 reviews)
"Always welcoming atmosphere and the stay is always comforting."
United States
Patricia
$123 nightly
The price is $138
Sep 6 - Sep 7
Total with taxes and fees
Sailport Waterfront Suites
Exterior

12. Beso Del Sol Resort

Beso Del Sol Resort
2.5 star property
Dunedin
8.6 out of 10, Excellent, (762 reviews)
"Nice place, good people!"
United States
Johan
$115 nightly
The price is $128
Oct 4 - Oct 5
Total with taxes and fees
Beso Del Sol Resort
Room

13. 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, (77 reviews)
"Was really nice and price range good for accommodations "
United States
Alejandra
$87 nightly
The price is $96
Sep 11 - Sep 12
Total with taxes and fees
Welcome to our charming studio, perfectly located near Tampa Bay's attractions.
Interior

14. 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, (37 reviews)
"Will definitely use the property again! Really cozy and perfect for two!"
United States
Shey
$127 nightly
The price is $140
Sep 10 - Sep 11
Total with taxes and fees
Hideaway Haven: Cozy studio with WiFi, AC in charming Largo
Terrace/patio

15. Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!

Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!
Clearwater
10.0 out of 10, Exceptional, (171 reviews)
"Perfect location for the beach and restaurants. "
United States
Heather S.
$241 nightly
The price is $268
Sep 8 - Sep 9
Total with taxes and fees
Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!
Living area

16. The Purple Flower - 30 Second walk to the Beach. Free parking.

The Purple Flower - 30 Second walk to the Beach. Free parking.
Clearwater
9.8 out of 10, Exceptional, (224 reviews)
"I loved and enjoyed my stay will be booking again. Thank you Mary!"
United States
Amanda
$241 nightly
The price is $268
Sep 9 - Sep 10
Total with taxes and fees
The Purple Flower - 30 Second walk to the Beach. Free parking.
Property grounds

17. Great Studio - Under 2 minute walk to beach where dogs are welcome

Great Studio - Under 2 minute walk to beach where dogs are welcome
Clearwater Beach
10.0 out of 10, Exceptional, (162 reviews)
"Great location close to the beach and included chairs and an umbrella. Owner was great and helped out with anything needed. Would definitely stay there again."
United States
Paul W.
$310 nightly
The price is $345
Sep 4 - Sep 5
Total with taxes and fees
Great Studio - Under 2 minute walk to beach where dogs are welcome
Beach

18. 2/2 Penthouse, Clearwater Beach, 801 Avalon!

2/2 Penthouse, Clearwater Beach, 801 Avalon!
Clearwater
9.8 out of 10, Exceptional, (111 reviews)
"The place was clean and great location. Would love to stay again. Perfect"
United States
William M.
$446 nightly
The price is $490
Sep 7 - Sep 8
Total with taxes and fees
2/2 Penthouse, Clearwater Beach, 801 Avalon!
Grand Suite, 3 Bedrooms, Ocean View | Terrace/patio

19. The Avalon Club

The Avalon Club
4.0 star property
Clearwater Beach
9.4 out of 10, Exceptional, (597 reviews)
"4 or 5th time staying here . This place is by far the best place in Clearwater to stay . You don’t need to move your car once you check in . Everything right near you and the place is always clean !!"
United States
David
$237 nightly
The price is $267
Sep 13 - Sep 14
Total with taxes and fees
The Avalon Club
Outdoor dining

20. Spacious Gulf View Condo Hotel Suite

Spacious Gulf View Condo Hotel Suite
Clearwater
10.0 out of 10, Exceptional, (126 reviews)
"Great spot to enjoy Clearwater and the surrounding area."
United States
Ethan L.
$705 nightly
The price is $764
Sep 7 - Sep 8
Total with taxes and fees
Spacious Gulf View Condo Hotel Suite
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

10/10 Excellent
"Waiting for refund from dog deposit."
Don 1-night trip
Posted 4 hours 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 $105 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: 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 10 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.