Pleasure Isles Vacations from $451

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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 $751, price is now $451 per person
$451
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (618 reviews)
We were very pleased with our 3 night stay at the hotel. The staff graciously offered us an umbrella and chairs to take to the beach from the donation stash. We really appreciated that and returned the items when we left for future guests.

Reviewed on Sep 8, 2025

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $858, price is now $466 per person
$466
per person
Oct 27 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,017 reviews)
Loved it Voco hotel was great clean and quiet great place to just sit back and relax place was not busy at all kids are all back in school thank god . Beach’s all near by 10 to 20 minute drive to any beach u wana go too.

Reviewed on Sep 2, 2025

The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,178, price is now $703 per person
$703
per person
Oct 25 - Oct 31
found 2 days ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,069 reviews)
$50 a night parking _ had no option

Reviewed on Sep 9, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,318, price is now $802 per person
$802
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (446 reviews)
Karen is the best and her staff makes you feel safe and welcomed

Reviewed on Sep 9, 2025

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,033, price is now $650 per person
$650
per person
Oct 25 - Oct 31
found 2 days ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (4,320 reviews)
Everything was wonderful accept for the noisy AC

Reviewed on Sep 8, 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
$45 nightly
The price is $50 total per night from Sep 16 to Sep 17
$50 total
Sep 16 - Sep 17
Total with taxes and 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
$199 nightly
The price is $225 total per night from Sep 10 to Sep 11
$225 total
Sep 10 - Sep 11
Total with taxes and fees
Innisbrook Resort
See all 1,704 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

4/5(32 reviews)

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.