Pleasure Isles Vacations from $468

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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.
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $842, price is now $468 per person
$468
per person
Jan 7 - Jan 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (4,624 reviews)
Super clean, comfortable beds, good rooms, and polite staff. The hotel is really good!

Reviewed on Nov 29, 2025

Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Price was $1,542, price is now $723 per person
$723
per person
Feb 21 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.2/10 Very Good! (1,002 reviews)
Staff was very friendly and happy to help. The room was clean. The front area was organized, and plenty of snack items were available to purchase.

Reviewed on Nov 24, 2025

Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
Price was $1,612, price is now $863 per person
$863
per person
Jan 20 - Jan 27
found 21 hours ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
9.4/10 Exceptional! (40 reviews)
Room was a little outdated but very clean, and comfy!

Reviewed on Nov 27, 2025

Holiday Inn Express Lake Wales N-Winter Haven by IHG

Holiday Inn Express Lake Wales N-Winter Haven by IHG

2.5 out of 5
Price was $904, price is now $486 per person
$486
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,002 reviews)
The hotel was very clean. We were rather pleased.. The breakfast choices left something to be desired. The lady's servicingThe breakfast cafe was wonderful.

Reviewed on Nov 28, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,224, price is now $674 per person
$674
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (481 reviews)
Room was great. Reception awesome. Location awesome. However, the washer stopped working middle of night - resulting in our laundry being stuck (door locked, would not release as water error). We couldn't get fixed. By time maintenance got fixed, we had to check out. TO credit, they mailed our laundry to us, but we needed it the for the next 3 days of our vacaction, and didn't have it available.

Reviewed on Nov 26, 2025

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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
$49 nightly
The price is $55 total per night from Dec 8 to Dec 9
$55 total
Dec 8 - Dec 9
Total with taxes and fees
7.2/10 Good! (1,259 reviews)
Great

Reviewed on Nov 27, 2025

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
$77 nightly
The price is $86 total per night from Dec 7 to Dec 8
$86 total
Dec 7 - Dec 8
Total with taxes and fees
8/10 Very Good! (1,007 reviews)
Courtesy from The staff, clean room

Reviewed on Nov 19, 2025

Quality Inn & Suites Tarpon Springs South
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
9.8/10 Exceptional! (296 reviews)
The host is more than welcoming! She is very thoughtful and helpful. The home is beautiful and has everything you could ever need! We are already planning our next visit.

Reviewed on Nov 13, 2025

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Main River Mermaid Sleeps 8 kayaks for everyone. Gulf access for scalloping
See all 1,771 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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All Inclusive Vacations
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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.