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.
Clearwater Suites

Clearwater Suites

2.5 out of 5
Price was CA $1,493, price is now CA $872 per person
CA $872
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
8.8/10 Excellent! (19 reviews)
Estuvimos dos noches en el hotel y nos gustó mucho, todo muy limpio lo mismo dentro de la habitación que en la piscina, la atención excelente, la playa super serca del hotel es solo cruzar la calle, está ubicado céntrico, una experiencia satisfactoria la esatacia, lo volvería a repetir!!!

Reviewed on Aug. 31, 2025

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was CA $2,259, price is now CA $1,136 per person
CA $1,136
per person
Nov 15 - Nov 22
found 18 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Tampa (TPA)
9.2/10 Wonderful! (1,056 reviews)
The room was fantastic with a big wrap around balcony. Even though the weather did not cooperate, we all enjoyed chilling on the balcony with many trips to the pool. Beach was great. My only disappointment was they did not have any type of grill anywhere. I brought some really expensive steaks, burgers,hot dogs, which we had to cook in a pan. The staff was fantastic and made sure we had everything we needed

Reviewed on Aug. 24, 2025

The Avalon Club

The Avalon Club

4 out of 5
Price was CA $2,375, price is now CA $1,487 per person
CA $1,487
per person
Oct 12 - Oct 18
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Tampa (TPA)
9.4/10 Exceptional! (445 reviews)
Place was very clean loved how large it was and was in a great location, could walk to everything The only negative thing was the pool seemed to be pictured different on the website and was very small and the rooftop bar really cannot be called a bar. They were out of most of the beers didn’t sell liquor and really was not a bar at all.

Reviewed on Sep. 1, 2025

Inn on the Beach

Inn on the Beach

2.5 out of 5
Pass-a-Grille
Price was CA $1,678, price is now CA $1,060 per person
CA $1,060
per person
Nov 15 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Tampa (TPA)
9.8/10 Exceptional! (330 reviews)
Convenient beach access, good amenities - beach chairs, umbrella, ice, cooler. Complimentary bikes as well. Easy walk to restaurants and shops.

Reviewed on Sep. 2, 2025

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Price was CA $2,650, price is now CA $1,687 per person
CA $1,687
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
8.8/10 Excellent! (1,002 reviews)
Awesome boutique hotel! With the best staff ever! Can’t wait to go back in October- and unlike all the other family owned properties on the beach who sold out to corporate interests they are still family owned! Best price on this sandbar! And no gouging- even at their beach bar!

Reviewed on Aug. 21, 2025

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
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Bayonet Point

1 out of top 10 points of interest in this area
3.5/5(5 area reviews)

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.

Find hotels in Bayonet Point

Pleasure Isles Hotel Deals

Motel 6 Spring Hill, FL - Weeki Wachee

Motel 6 Spring Hill, FL - Weeki Wachee

2 out of 5
6172 Commercial Way, Spring Hill, FL
Fully refundableReserve now, pay when you stay
The price is CA $62 per night from Sep 9 to Sep 10
CA $62
CA $69 total
Sep 9 - Sep 10
includes taxes & fees
Motel 6 Spring Hill, FL - Weeki Wachee
Main River Mermaid Sleeps 8 kayaks for everyone. Gulf access for scalloping

Main River Mermaid Sleeps 8 kayaks for everyone. Gulf access for scalloping

Spring Hill
Get rates
Main River Mermaid Sleeps 8 kayaks for everyone. Gulf access for scalloping
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
36750 Us Highway 19 N, Palm Harbor, FL
The price is CA $219 per night from Sep 3 to Sep 4
CA $219
CA $309 total
Sep 3 - Sep 4
includes taxes & fees
Innisbrook Resort
See all 1,683 properties in Pleasure Isles
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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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 $872. 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.

Discover the most popular places to visit in Pleasure Isles

Hudson Beach

Why not spend a carefree afternoon at Hudson Beach during your travels in Hudson? Amble around the area's parks or visit its shops.

Hudson Beach

Beacon Woods Golf Course

Enjoy a round of golf in Hudson at Beacon Woods Golf Course. Amble around this family-friendly area's waterfront and enjoy its top-notch restaurants.

Beacon Woods Golf Course

Colorama Music

You can make plans for a show at Colorama Music during your stay in Hudson. Amble around this family-friendly area's waterfront and enjoy its top-notch restaurants.

Colorama Music
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.