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.
Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn

3 out of 5
Price was CA $2,079, price is now CA $1,465 per person
CA $1,465
per person
Sep 9 - Sep 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (453 reviews)
Great little place, very small rooms but very clean and nice. Having to check in at a different location was a bit odd but overall a good place.

Reviewed on Jun 15, 2026

CW Hotel

CW Hotel

4 out of 5
Price was CA $2,719, price is now CA $1,602 per person
CA $1,602
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
No reviews
The Avalon Club

The Avalon Club

4 out of 5
Price was CA $4,304, price is now CA $3,106 per person
CA $3,106
per person
Aug 3 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Tampa (TPA)
9.4/10 Exceptional! (552 reviews)
Hotel cerca de la playa y con muy buenas condiciones.

Reviewed on Jun 21, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was CA $3,148, price is now CA $2,314 per person
CA $2,314
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (526 reviews)
Beautiful facility. Perfect for families close to all the beaches and fun. Can't wait to return for our next visit!

Reviewed on Jun 18, 2026

The Marker

The Marker

2 out of 5
Price was CA $3,768, price is now CA $2,780 per person
CA $2,780
per person
Aug 3 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Tampa (TPA)
6/10 (3 reviews)
There was no staff due to it being brand new! The owner Jeff was great and very polite and went out of his way to make us feel welcome and valued! It was very quiet and comfortable for my family. Only about a two block walk to the beach but being in the bay was beautiful to wake up to!

Reviewed on Apr 12, 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
Pirate ship at St Andrews State Park

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.

Find hotels in Gulf Shores

Pleasure Isles Hotel Deals

Quality Inn & Suites Tarpon Springs South

Quality Inn & Suites Tarpon Springs South

2.5 out of 5
38724 US Highway 19 North Tarpon Springs FL
Fully refundable
The price is CA $120 per night from Jun 25 to Jun 26
CA $120
CA $135 total
Jun 25 - Jun 26
includes taxes & fees
8/10 Very Good! (1,114 reviews)
"At 230 am. Heard car horn a couple times. Then loud banging on front and back patio door. Right below us . Called front desk. Told them. It still went on for over a half hour. Never heard front desk clerk."

Reviewed on Jun 19, 2026

Quality Inn & Suites Tarpon Springs South
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
36750 Us Highway 19 N Palm Harbor FL
The price is CA $234 per night from Jun 29 to Jun 30
CA $234
CA $336 total
Jun 29 - Jun 30
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
"Have stayed at Innisbrook several times and always had great experiences. Although there were a couple of minute issues with the room they weren’t noteworthy. The rooms we had were very clean, comfortable and quiet. We had our son and his family with us so having rooms just a short walk to the Lochness ..."

Reviewed on Jun 21, 2026

Innisbrook Resort
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 $83 per night from Jun 29 to Jun 30
CA $83
CA $92 total
Jun 29 - Jun 30
includes taxes & fees
7.2/10 Good! (1,525 reviews)
"The room was just dirty and run down, the grounds were not kept up well, and the staff was odd"

Reviewed on Jun 20, 2026

Motel 6 Spring Hill, FL - Weeki Wachee
See all 1,853 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.
All Inclusive Vacations
All Inclusive Vacations
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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 $1,465. 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

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

Things to do

Clear Kayak Tours in Weeki Wachee

Clear Kayak Tours in Weeki Wachee

CA $125
per adult
100% of travellers recommend
Clear Kayak Tours in Weeki Wachee
Audio Guide to New Port Richey's History and Quirky People

Audio Guide to New Port Richey's History and Quirky People

CA $10
per adult
Audio Guide to New Port Richey's History and Quirky People
See all activities in Hudson
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.