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.
Hampton Inn Sarasota - I-75 Bee Ridge

Hampton Inn Sarasota - I-75 Bee Ridge

2.5 out of 5
Price was CA $935, price is now CA $641 per person
CA $641
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.6/10 Excellent! (433 reviews)
Newly updated. Clean rooms. Great staff.

Reviewed on Apr 23, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was CA $3,629, price is now CA $2,042 per person
CA $2,042
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (501 reviews)
We loved this hotel for a family trip. The beach is literally just steps away, which made everything so convenient. Everything was clean, the staff was good, and there are plenty of nearby restaurants.

Reviewed on Apr 24, 2026

Resort Sixty-Six

Resort Sixty-Six

2.5 out of 5
Price was CA $2,127, price is now CA $1,452 per person
CA $1,452
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.4/10 Very Good! (5 reviews)
I arrived 10 minutes late to check in and was not able to get in the first day.

Reviewed on Mar 14, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was CA $2,611, price is now CA $1,791 per person
CA $1,791
per person
Jul 14 - Jul 20
found 7 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Tampa (TPA)
9.6/10 Exceptional! (899 reviews)
Room was spotless, beds were comfortable, and everything needed was in the kitchen. The view from the balcony was amazing.

Reviewed on Apr 26, 2026

Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Downtown Tampa
Price was CA $1,407, price is now CA $975 per person
CA $975
per person
Jun 30 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
7/10 Good! (1,849 reviews)
The restaurant, gym and pool were all closed, the driveway was closed making it difficult for Uber drivers to pickup or drop off. This is all due to construction and renovations. I would recommend calling to find out the status of what appears to be major renovations. Even though this is on the river walk there are very few restaurants within walking distance

Reviewed on Apr 26, 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
Holmes Beach

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 Cow Creek.

Find hotels in Hudson Beach Estates

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 $80 per night from May 7 to May 8
CA $80
CA $89 total
May 7 - May 8
includes taxes & fees
7.4/10 Good! (1,470 reviews)
Other than some occasional noisy guests, the stay was everything one (2 of us) would want.

Reviewed on Apr 25, 2026

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 FL
10/10 Exceptional! (314 reviews)
This house is in the perfect location on the main river. The house and kitchen are well appointed for any length of stay. We saw so many manatees, a river otter and a pair of dolphins. The weather was rainy one day and the screened porch was the ideal location to sit and relax while still enjoying ...

Reviewed on Apr 12, 2026

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Main River Mermaid Sleeps 8 kayaks for everyone. Gulf access for scalloping
Rodeway Inn Port Richey North

Rodeway Inn Port Richey North

2 out of 5
11810 Us Highway 19 Port Richey FL
Fully refundableReserve now, pay when you stay
The price is CA $87 per night from May 22 to May 23
CA $87
CA $101 total
May 22 - May 23
includes taxes & fees
7.8/10 Good! (1,000 reviews)
Ample of parking, friendly reception staff, clean room and pool

Reviewed on Apr 27, 2026

Rodeway Inn Port Richey North
See all 1,832 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
Beach Vacations
Beach 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 $641. 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 $123
per adult
100% of travellers recommend
Clear Kayak Tours in Weeki Wachee
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.