Pleasure Isles Vacation Packages
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Top Holiday Package Deals in Pleasure Isles
Price found within the past 48 hours. Click for updated prices.
St Pete Beach Suites
CA $1,549
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (1,003 reviews)
The location, cleanliness, and amenities were excellent! We had a great stay overall. There were just two issues that kept me from giving a full 5-star review:
1. Limited after-hours support: If you need assistance outside of normal business hours, you may have difficulty reaching someone. During our stay, there were no staff on-site, and I couldn't get a response by calling, text, or through the messaging portal until the following day. Fortunately, our issue wasn't an emergency, but it made me wonder what would happen if someone were locked out of their room or had another urgent problem. The AI phone assistant states that all calls and messages are answered between 8:00 a.m. and midnight, but that wasn't our experience. I completely understand not having on-site staff, but I do think the after-hours availability should be communicated more clearly.
2. Very slow hot water: In our suite, it took more than 15 minutes for the hot water to reach the shower. Once it got hot, it stayed hot, so it wasn't a major issue, especially if you know to plan ahead. I'm not sure if this was specific to our suite or a property-wide issue, but it's something I wish we'd known before our stay.
Despite these two issues, we enjoyed our stay and would absolutely consider staying here again.
Reviewed on Aug 10, 2026
Where to stay in Pleasure Isles
Find the best Pleasure Isles areas and neighborhoods for the activities you enjoy most. Learn more about Pleasure Isles
Gulf Shores
Gulf Shores might not have many top sights, but Hudson Beach and Beacon Woods Golf Course are two attractions nearby that you can check out.
Hudson Beach Estates
1 out of top 10 points of interest in this area
Though Hudson Beach Estates might not have many top sights, you can venture to the surrounding area to see attractions like Hudson Beach and Gulf View Square.
Bayonet Point
1 out of top 10 points of interest in this area
Shopping, waterfront views, and restaurants highlight some of the notable features of Bayonet Point. Make a stop by Beacon Woods Golf Course while you're exploring.
Sea Ranch
While Sea Ranch isn't home to many top sights, Hudson Beach and Gulf View Square are some notable places to visit nearby.
Gulf Coast Acres
2 out of top 10 points of interest in this area
While visiting Gulf Coast Acres, you might make a stop by sights like Colorama Music and Show Palace Dinner Theater.
Pleasure Isles Hotel Deals
Motel 6 Spring Hill, FL - Weeki Wachee
6172 Commercial Way Spring Hill FL
Fully refundableReserve now, pay when you stay
CA $74
CA $82 total
Sep 1 - Sep 2
includes taxes & fees
7.2/10 Good! (1,578 reviews)
"Darby was great , Chelsea was cool until her manager told her to call me down to the office and record me on camera asking to delete my other review because it was a honest review and I told it as I seen it, she made my friend go back to the room and come back to the office just to tell me that the ..."
Reviewed on Aug 10, 2026
Quality Inn & Suites Tarpon Springs South
38724 US Highway 19 North Tarpon Springs FL
Fully refundable
CA $118
CA $133 total
Sep 6 - Sep 7
includes taxes & fees
Innisbrook Resort
36750 Us Highway 19 N Palm Harbor FL
CA $166
CA $259 total
Aug 12 - Aug 13
includes taxes & fees
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
How much does a Pleasure Isles vacation package cost?
Choose from any combination of car rentals, flights and hotels, and you can be vacationing in Pleasure Isles from just CA $858. And the more you bundle, the more cash you save. Your dream escape has never been so affordable.
How do I get a cheap travel package to Pleasure Isles?
You'll save piles of cash if you combine your hotels, flights and car rentals into a Pleasure Isles travel package. Sometimes cheap packages mean fewer choices. But not with Expedia. We offer over 550 airlines and 1,000,000 hotels worldwide, which means you'll always have plenty of options to choose from. Want to save even more? Add some popular activities to your package deal and unlock even bigger discounts! After all, travel is about more than simply getting to your destination.
Where should I stay in Pleasure Isles?
With interesting attractions like Hudson Beach and Regional Medical Center Bayonet Point in this neighborhood, look for a hotel located near either of them. Cow Creek is another sight in Pleasure Isles that pulls the crowds.
How far in advance should I book my Pleasure Isles vacation?
Get rewarded with the biggest variety and the lowest prices by booking your Pleasure Isles vacation nice and early. Air carriers generally sell flights around 12 months prior to departure, so secure your spot ASAP. Having said that, Expedia is dedicated to providing you with the best bargains around, so there's never a bad time to book your dream vacation!
What does an Expedia Pleasure Isles travel package include?
Flights, hotels and a cool car for all your fun road trip adventures. Simply choose your favorite bundle and get access to incredible deals. Once you've made your booking, add on a couple of tours and experiences and watch your savings pile up. When it comes to creating your Pleasure Isles trip, the choice is all yours!
What should I know before booking a Pleasure Isles travel package?
A travel package can be customized for your budget and is a simple way to stretch your dollars further. How little or much you include is your call. Hotels, rental cars and flights — choose any combination that suits your plans.
Can I choose my airline with a Pleasure Isles Expedia vacation package?
You can. We offer more than 550 airline partners globally, so choose the carrier that fits your budget needs.
If I'm not able to travel, can I cancel my Pleasure Isles vacation package?
Yes you can, and we'll help you every step of the way. You may be able to cancel or amend your Pleasure Isles vacation package at no cost if you booked in the last 24 hours. But you may incur a fee from your airline, hotel or car rental company for older bookings. If life gets in the way of your vacation, visit our Customer Service Portal for more information.
Things to do
Clear Kayak Tours in Weeki Wachee
CA $127
per adult
100% of travellers recommend
Audio Guide to New Port Richey's History and Quirky People
CA $10
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.