Oldsmar Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Oldsmar vacation rentals

Grand Suite, 3 Bedrooms, Ocean View | Terrace/patio
The Avalon Club

Aparthotel in Clearwater Beach

The Avalon Club
4.0 star property
9.4 out of 10, Exceptional, (488)
"The room was clean and the size was very accommodating for the group we had"
United States
Hollie
The price is ₩338,470
₩440,421 total
includes taxes & fees
Dec 15 - Dec 16
The Avalon Club
On the beach
Surf Beach Treasure Island Resort

Aparthotel in Treasure Island

Surf Beach Treasure Island Resort
3.0 star property
9.2 out of 10, Wonderful, (853)
"Room was clean and the front desk was very nice. We would definitely stay here again!"
United States
Rebecca
The price is ₩250,849
₩558,508 total
includes taxes & fees
Dec 14 - Dec 15
Surf Beach Treasure Island Resort
Presidential Suite, 3 Bedrooms, Bay View | Water view
FUSION Resort Waterfront Suites

Aparthotel in Treasure Island

FUSION Resort Waterfront Suites
3.5 star property
9.2 out of 10, Wonderful, (1103)
"The property was so nice, clean, staff was extremely friendly."
United States
Tiffany
The price is ₩227,479
₩306,725 total
includes taxes & fees
Dec 14 - Dec 15
FUSION Resort Waterfront Suites
Outdoor pool
The BC Resort on the Water

Aparthotel in St. Petersburg

The BC Resort on the Water
2.5 star property
7.4 out of 10, Good, (16)
"Great location, great price, great customer service"
United States
Charles
The price is ₩184,115
₩439,817 total
includes taxes & fees
Dec 18 - Dec 19
The BC Resort on the Water
Sundeck
Provident Oceana Beachfront Suites

Condo in Treasure Island

Provident Oceana Beachfront Suites
3.5 star property
9.4 out of 10, Exceptional, (611)
"I believe the pool area the Jacuzzi should be open at least till 9:00 or 10:00 p.m."
United States
GARY
The price is ₩190,522
₩248,578 total
includes taxes & fees
Dec 18 - Dec 19
Provident Oceana Beachfront Suites
House | 2 bedrooms, desk, Internet
NEW Casa Fuente Ybor Bungalow Steps to 7th Ave

Vacation Home in Ybor City

NEW Casa Fuente Ybor Bungalow Steps to 7th Ave
2.0 star property
10.0 out of 10, Exceptional, (1)
"We had a wonderful experience at this house. It was clean, spacious, and beautifully maintained, with all the amenities we needed for a comfortable stay. We truly felt at home. Highly recommended!"
United States
Sean
The price is ₩374,316
₩822,059 total
includes taxes & fees
Dec 22 - Dec 23
NEW Casa Fuente Ybor Bungalow Steps to 7th Ave
Premium Condo, 1 Bedroom | In-room dining
Barefoot Beach Resort

Aparthotel in Indian Shores

Barefoot Beach Resort
3.5 star property
9.0 out of 10, Wonderful, (905)
"Was just as advertised, staff went out of their way to make sure both condos booked were close together. Smooth check in process, even arriving after hours. Great price to be as close to the beach as we were. Definitely would stay here again. "
United States
Dustin
The price is ₩189,016
₩235,112 total
includes taxes & fees
Dec 17 - Dec 18
Barefoot Beach Resort
Aerial view
Westwinds Waterfront Resort

Condo in Treasure Island

Westwinds Waterfront Resort
3.0 star property
9.0 out of 10, Wonderful, (692)
"AWESOME location! Right on the bay and 25 steps to the Gulf! 2 minute walk to Publix; 3 minute walk to Walgreens. 1.5 block to a Treasure Island Beach, where there was a sand castle festival for 3 days. "
United States
susan
Westwinds Waterfront Resort
Jade House at The Gemma | 6 bedrooms, premium bedding, memory foam beds, individually decorated
The Gemma by Brightwild

Vacation Home in Clearwater Beach

The Gemma by Brightwild
5.0 star property
10.0 out of 10, Exceptional, (2)
"Amazing property"
United States
Rusty
The price is ₩1,515,058
₩2,697,169 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Gemma by Brightwild
House (2 Bedrooms) | Interior
Family-friendly Tampa Home < 3 Mi to Ocean!

Cottage in Port Tampa City

Family-friendly Tampa Home < 3 Mi to Ocean!
3.0 star property
10.0 out of 10, Exceptional, (4)
"Located in a quiet, Safe area. The Duplex was clean and had adequate amenities."
United States
David
The price is ₩197,807
₩539,501 total
includes taxes & fees
Dec 15 - Dec 16
Family-friendly Tampa Home < 3 Mi to Ocean!
Aerial view
Sunset Vistas Two Bedroom Beachfront Suites

Condo resort in Sunshine Beach

Sunset Vistas Two Bedroom Beachfront Suites
3.5 star property
8.8 out of 10, Excellent, (3409)
"The location is EXCELLENT, the staff was welcoming and accommodating, and our room had everything we needed to fulfill our goal of being beach bums and mermaids... We can't wait to come back!"
United States
Jaimie
The price is ₩190,522
₩256,900 total
includes taxes & fees
Dec 18 - Dec 19
Sunset Vistas Two Bedroom Beachfront Suites
Front of property - evening/night
South Beach Oceanfront Resort

Aparthotel in Sunshine Beach

South Beach Oceanfront Resort
3.0 star property
9.2 out of 10, Wonderful, (1121)
"Great place to stay!"
United States
Angela
The price is ₩235,390
₩473,064 total
includes taxes & fees
Dec 14 - Dec 15
South Beach Oceanfront Resort
Family Cottage | Terrace/patio
BeachTrail Lodging

Condo in Indian Rocks Beach

BeachTrail Lodging
3.0 star property
9.8 out of 10, Exceptional, (96)
"Great location to walk to the water park or the beach."
United States
Leslie
The price is ₩255,183
₩621,237 total
includes taxes & fees
Dec 17 - Dec 18
BeachTrail Lodging
Junior Apartment, 1 Queen Bed with Sofa bed, Patio | Living area
Treasure Island

Apartment in Isle of Palms

Treasure Island
2.0 star property
The price is ₩169,681
₩472,624 total
includes taxes & fees
Dec 13 - Dec 14
Treasure Island
House | 2 bedrooms
The Tarpon Treasure - Family Home 5 Mins to Beach

Vacation Home in Tarpon Springs

The Tarpon Treasure - Family Home 5 Mins to Beach
2.0 star property
9.6 out of 10, Exceptional, (4)
"Chill Place great vibes"
United States
Crissie
The Tarpon Treasure - Family Home 5 Mins to Beach
Front of property - evening/night
Crystal Palms Beach Resort

Aparthotel in Sunshine Beach

Crystal Palms Beach Resort
3.5 star property
8.8 out of 10, Excellent, (2359)
"Unit size was very nice and the linens were good quality. "
United States
Pamela
The price is ₩180,005
₩228,241 total
includes taxes & fees
Dec 15 - Dec 16
Crystal Palms Beach Resort
Beach
Waterfront Resort Condo Gulf Sun Set

Condo resort in Dunedin

Waterfront Resort Condo Gulf Sun Set
3.0 star property
10.0 out of 10, Exceptional, (3)
"Great place"
United States
Daniel
The price is ₩347,772
₩661,576 total
includes taxes & fees
Dec 15 - Dec 16
Waterfront Resort Condo Gulf Sun Set
Panoramic Apartment, Fireplace, Bay View | Living area | 55-inch Smart TV with digital channels
The Hemingway

Apartment in Rocky Point

The Hemingway
4.0 star property
7.6 out of 10, Good, (18)
"Great"
United States
elvis
The price is ₩130,553
₩376,773 total
includes taxes & fees
Dec 14 - Dec 15
The Hemingway
The Adaline #6 - 2nd Floor Suite | Dining room
The Adaline

Apartment in Hyde Park

The Adaline
5.0 star property
9.6 out of 10, Exceptional, (58)
"4th time staying here. Amazing stay."
United States
Dawn
The price is ₩218,321
₩538,826 total
includes taxes & fees
Dec 14 - Dec 15
The Adaline
House (1 Bedroom) | Interior
Cozy St Pete Home ~ 2 Mi to Madeira Beach!

Cottage in Bay Pines

Cozy St Pete Home ~ 2 Mi to Madeira Beach!
3.0 star property
10.0 out of 10, Exceptional, (1)
"Spacious for a one bedroom flat. Exceptionally quiet. Would stay there again. A good value. "
United States
HELEN
The price is ₩117,219
₩356,229 total
includes taxes & fees
Dec 25 - Dec 26
Cozy St Pete Home ~ 2 Mi to Madeira Beach!
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

Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

10/10 Excellent
"All good"
nadia 3-night trip
Posted 18 hours ago
Hilton Clearwater Beach Resort & Spa

Find out more about Oldsmar

Search for Vacation rentals in Oldsmar on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Oldsmar using one of the methods below:

  • View our selection of featured Vacation rentals in Oldsmar
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  • Enter your travel dates to view the best deals on Vacation rentals in Oldsmar while they last

Look no further and take a look at our great range of rental properties in Oldsmar!

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 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.