Pleasure Isles Vacations from $484

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Your Pleasure Isles Vacation

Make planning your travels stress-free by locking in a vacation package to Pleasure Isles. Let us handle the details, so you can concentrate on enjoying everything this neighborhood has to offer. Get your trip to Pleasure Isles off to a flying start by checking out some of its nearby attractions, such as Hudson Beach and Cow Creek. Don't just wish for it — take action! Secure your ultimate Pleasure Isles vacation with Expedia and get to where you're going your way.

The Latest Pleasure Isles Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $813, price is now $484 per person
$484
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (609 reviews)
looked brand new, absolutely beautiful inside As soon as you open the door, you can see down the hallway of a view of the Gulf. You are truly renting a 2bedroom, 2bath condo with a full kitchen and full size washer and dryer...everything you would need!

Reviewed on Aug 29, 2025

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,070, price is now $652 per person
$652
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (2,592 reviews)
Everything was great.

Reviewed on Aug 29, 2025

GALAXY HOTEL

GALAXY HOTEL

3.5 out of 5
Downtown St. Petersburg
Save 100% on your flight
Price was $1,048, price is now $650 per person
$650
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (362 reviews)
Randy was really nice and helpful

Reviewed on Aug 29, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,309, price is now $858 per person
$858
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (445 reviews)
Excellent place no word to explain how perfect everything was. We definitely go there from now on

Reviewed on Aug 24, 2025

Clearwater Suites

Clearwater Suites

2.5 out of 5
Save 100% on your flight
Price was $797, price is now $523 per person
$523
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (19 reviews)
Super convenient, clean, and right across the street from the beach. Staff was very friendly

Reviewed on Aug 25, 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(171 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
$60 nightly
The price is $67 total per night from Sep 7 to Sep 8
$67 total
Sep 7 - Sep 8
Total with taxes and fees
Motel 6 Spring Hill, FL - Weeki Wachee
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 refundableReserve now, pay when you stay
$89 nightly
The price is $101 total per night from Sep 7 to Sep 8
$101 total
Sep 7 - Sep 8
Total with taxes and fees
Quality Inn & Suites Tarpon Springs South
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
36750 Us Highway 19 N, Palm Harbor, FL
$199 nightly
The price is $225 total per night from Aug 31 to Sep 1
$225 total
Aug 31 - Sep 1
Total with taxes and 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

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

Show Palace Dinner Theater

You can enjoy a show at Show Palace Dinner Theater during your stay in Hudson. Amble around this family-friendly area's waterfront and enjoy its top-notch restaurants.

Show Palace Dinner Theater

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