Best Resorts in Oldsmar

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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Compare 95 Resorts in Oldsmar with updated reviews, rates, and availability.

Hilton Clearwater Beach Resort & Spa
Exterior

Hilton Clearwater Beach Resort & Spa

4.0 star property
8.0 out of 10, Very Good, (1843)
"Great location , Great STAFF"
The price is $305
includes taxes & fees
$269 per night
Jun 1 - Jun 2
Hilton Clearwater Beach Resort & Spa
Bilmar Beach Resort
On the beach, white sand, beach towels, beach bar

Bilmar Beach Resort

4.0 star property
8.8 out of 10, Excellent, (1006)
"Great location"
The price is $240
includes taxes & fees
$213 per night
May 26 - May 27
Bilmar Beach Resort
Opal Sands Resort
Outdoor pool, sun loungers

Opal Sands Resort

4.0 star property
9.4 out of 10, Exceptional, (1001)
"Great family resort"
The price is $435
includes taxes & fees
$385 per night
May 4 - May 5
Opal Sands Resort
Hyatt Regency Clearwater Beach Resort & Spa
Outdoor pool, open 8:00 AM to 10:00 PM, cabanas (surcharge)

Hyatt Regency Clearwater Beach Resort & Spa

4.0 star property
9.2 out of 10, Wonderful, (1860)
"Such a beautiful spot on the gulf."
The price is $401
includes taxes & fees
$355 per night
Jun 1 - Jun 2
Hyatt Regency Clearwater Beach Resort & Spa
JW Marriott Clearwater Beach Resort & Spa
On the beach, white sand

JW Marriott Clearwater Beach Resort & Spa

4.0 star property
9.4 out of 10, Exceptional, (220)
"Beautiful property, loved the private beach. "
The price is $445
includes taxes & fees
$394 per night
May 26 - May 27
JW Marriott Clearwater Beach Resort & Spa
Sandpearl Resort
Exterior

Sandpearl Resort

4.0 star property
9.2 out of 10, Wonderful, (1003)
"Very nice place to stay "
The price is $474
includes taxes & fees
$420 per night
May 11 - May 12
Sandpearl Resort
The Vinoy Resort & Golf Club, Autograph Collection
Lobby

The Vinoy Resort & Golf Club, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (1001)
"The room was beautiful, breakfast bar was lovely, Pool was great and e bikes were fun"
The price is $403
includes taxes & fees
$357 per night
May 11 - May 12
The Vinoy Resort & Golf Club, Autograph Collection
Clearwater Beach Marriott Resort on Sand Key
Outdoor pool, cabanas (surcharge), pool umbrellas

Clearwater Beach Marriott Resort on Sand Key

4.0 star property
9.2 out of 10, Wonderful, (1001)
"Great stay"
The price is $307
includes taxes & fees
$272 per night
May 5 - May 6
Clearwater Beach Marriott Resort on Sand Key
The Hiatus Clearwater Beach, Curio Collection By Hilton
Outdoor pool

The Hiatus Clearwater Beach, Curio Collection By Hilton

4.0 star property
9.2 out of 10, Wonderful, (129)
"So close to the beach it was perfect"
The price is $310
includes taxes & fees
$275 per night
May 11 - May 12
The Hiatus Clearwater Beach, Curio Collection By Hilton
DoubleTree Beach Resort by Hilton Tampa Bay - North Redingto
On the beach, beach towels, beach volleyball, beach bar

DoubleTree Beach Resort by Hilton Tampa Bay - North Redingto

4.0 star property
9.0 out of 10, Wonderful, (1002)
"Great Beach front stay."
The price is $233
includes taxes & fees
$206 per night
May 4 - May 5
DoubleTree Beach Resort by Hilton Tampa Bay - North Redingto
Sheraton Sand Key Resort
View from property

Sheraton Sand Key Resort

4.0 star property
8.4 out of 10, Very Good, (1001)
"The place was clean, nice, modern and the people very polite "
The price is $446
includes taxes & fees
$395 per night
May 11 - May 12
Sheraton Sand Key Resort
Palihouse Hyde Park Village
Bar (on property)

Palihouse Hyde Park Village

3.5 star property
9.6 out of 10, Exceptional, (248)
"Lovely rooms and staff very helpful. "
The price is $253
includes taxes & fees
$225 per night
Jun 1 - Jun 2
Palihouse Hyde Park Village
Innisbrook Resort
6 outdoor pools, pool umbrellas, sun loungers

Innisbrook Resort

3.5 star property
8.2 out of 10, Very Good, (1000)
"Nice surroundings, nice staff, enjoyable stay"
The price is $180
includes taxes & fees
$159 per night
May 20 - May 21
Innisbrook Resort
Treasure Island Beach Resort
Property amenity

Treasure Island Beach Resort

4.0 star property
9.6 out of 10, Exceptional, (1000)
"Great hotel and very quiet .Clean, and the room with full kitchen, plates and full fridge is very convenient. "
The price is $411
includes taxes & fees
$364 per night
May 18 - May 19
Treasure Island Beach Resort
Saint Petersburg/ Treasure Island Ocean Front Beach Resort
Outdoor pool, a heated pool

Saint Petersburg/ Treasure Island Ocean Front Beach Resort

10.0 out of 10, Exceptional, (47)
"Great room"
Saint Petersburg/ Treasure Island Ocean Front Beach Resort
Paradise Oasis
Beach nearby

Paradise Oasis

9.8 out of 10, Exceptional, (76)
"Clean, affordable, nice. Would stay there again."
Paradise Oasis
Water View Apartment Suite on the Beach!
On the beach

Water View Apartment Suite on the Beach!

9.6 out of 10, Exceptional, (102)
"Inside was so cute and clean. "
Water View Apartment Suite on the Beach!
Entire Private Resort! Heated Pool! Sleeps 24 Comfortably!
Beach

Entire Private Resort! Heated Pool! Sleeps 24 Comfortably!

Entire Private Resort! Heated Pool! Sleeps 24 Comfortably!
WELCOME to the best beach anywhere
On the beach

WELCOME to the best beach anywhere

9.6 out of 10, Exceptional, (56)
"We really enjoyed our stay! So glad we picked this condo for our trip!"
WELCOME to the best beach anywhere
262-NEW! 3 beds x 2 baths. Amazing Waterfront Views!
Beach

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

9.8 out of 10, Exceptional, (75)
"Great property to stay at and the restaurant and bar is outstanding. "
The price is $423
includes taxes & fees
$381 per night
May 4 - May 5
262-NEW! 3 beds x 2 baths. Amazing Waterfront Views!
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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Other property types in Oldsmar

Sailport Waterfront Suites
Beach nearby, beach volleyball, fishing

Sailport Waterfront Suites

3.5 star property
8.4 out of 10, Very Good, (4495)
"This is a very nice resort. We really enjoyed our stay."
The price is $140
includes taxes & fees
$126 per night
Jun 1 - Jun 2
Sailport Waterfront Suites
Sunset Vistas Two Bedroom Beachfront Suites
2 outdoor pools, open 9:00 AM to 10:00 PM, pool umbrellas, sun loungers

Sunset Vistas Two Bedroom Beachfront Suites

3.5 star property
8.8 out of 10, Excellent, (3198)
"Amazing location views gorgeous!!!!"
The price is $227
includes taxes & fees
$203 per night
May 19 - May 20
Sunset Vistas Two Bedroom Beachfront Suites
Chase Suite Hotel Rocky Point Tampa
Front of property

Chase Suite Hotel Rocky Point Tampa

3.0 star property
7.6 out of 10, Good, (4923)
"Great stay"
The price is $199
includes taxes & fees
$177 per night
May 2 - May 3
Chase Suite Hotel Rocky Point Tampa
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.

Frequently asked questions

What can I expect from a resort vacation in Oldsmar?
You deserve a break, and a resort is the ideal place to indulge in all the services and amenities you need for a relaxing stay in Oldsmar. One of the 8 comfortable resort hotels in the surrounding area might be just what you’re searching for, whether you want great restaurants on site, blissful spa treatments, or nightly entertainment options.
What's the best resort in Oldsmar?
Our highest-rated resorts around Oldsmar: Hilton Clearwater Beach Resort & Spa - Beach resort, 5-minute walk from St. Petersburg - Clearwater Beaches. 10.6 mi (17.1 km) from Oldsmar. Features 2 outdoor pools, 3 restaurants, and a private beach. Highly rated for its pool. Hyatt Regency Clearwater Beach Resort & Spa - Beach resort steps from Beach Walk. 10.8 mi (17.4 km) from Oldsmar. Has 2 restaurants, 2 bars, and a full-service spa. Popular for its pool. Opal Sands Resort - Beach resort, 5-minute walk from Beach Walk. 11 mi (17.7 km) from Oldsmar. Highly rated for its pool. Enjoy the spa, fitness center, and terrace. Sandpearl Resort - Beach resort steps from Clearwater Beach. 10.5 mi (16.9 km) from Oldsmar. Amenities include a private beach, a full-service spa, and a health club. JW Marriott Clearwater Beach Resort & Spa - Beach resort, 5-minute walk from St. Petersburg - Clearwater Beaches. 10.8 mi (17.4 km) from Oldsmar. Guests love the great beach location. Access to 3 restaurants, 2 bars, and a full-service spa.
What can I do in Oldsmar?
Travelers enjoy exploring the beaches, and also have good things to say about the dining options here. Check out the interesting exhibits at Oldsmar Historical Society Museum, or discover the shopping possibilities at Oldsmar Flea Market. You’ll also find top attractions like Port of Tampa and Busch Gardens Tampa Bay in the area.
What's the seasonal weather like in Oldsmar?
The hottest months are usually August and July with an average temp of 83°F, while the coldest months are January and February with an average of 64°F. Average annual precipitation for Oldsmar is 45 inches.
What's the best way to get to and around Oldsmar?
Fly into Tampa Intl. Airport (TPA), which is located 8.8 mi (14.2 km) away from the heart of the city. Otherwise, look for flights into St. Petersburg-Clearwater Intl. Airport (PIE), which is 9 mi (14.4 km) away. If you’d like to explore around the area, consider renting a car to take in more sights.