Title: Pleasure Isles Vacation Packages 2026 from $525 | Expedia.com

[Hotels in Pleasure Isles](https://expedia.com/Pleasure-Isles-Hudson-Hotels.0-n553248635976479089-0.Travel-Guide-Filter-Hotels)[Flights to Hudson](https://expedia.com/Cheap-Flights-To-Hudson.d177663.Travel-Guide-Flights)[Car Rentals in Pleasure Isles](https://expedia.com/Car-Rentals-In-Pleasure-Isles.d553248635976479089.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Pleasure Isles Vacations from $525

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
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Better together  
Save up to $1,045 when you book a flight and hotel together\*
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Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
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Rest easy  
Plan, book, and manage your trip all in one place

## 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](https://www.expedia.com/Hudson-Beach-Hudson-Beach-Estates.d553248621565061336.Vacation-Attraction) and [Cow Creek](https://www.expedia.com/Cow-Creek-Port-Richey.d553248635976197892.Vacation-Attraction). 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.

![Hilton Garden Inn Sarasota - Bradenton Airport](https://images.trvl-media.com/lodging/1000000/860000/851300/851284/1d90668b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Garden Inn Sarasota - Bradenton Airport

Save 100% on your flight

$525

per person

May 15 - May 20

found 2 days ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.2/10 Very Good! (1,000 reviews)

I did not order any drinks so I cannot comment on the bar. The breakfast was fine .

Reviewed on Apr 3, 2026

![Ocean Club Treasure Island Hotel](https://images.trvl-media.com/lodging/97000000/96160000/96150700/96150639/a3e54a35_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$1,224

per person

May 23 - May 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (846 reviews)

Great trip! Awesome place to stay.

Reviewed on Apr 3, 2026

![Kompose Boutique Hotel](https://images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/3006ffef_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Kompose Boutique Hotel

Save 100% on your flight

$642

per person

May 15 - May 20

found 2 days ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (5,207 reviews)

Great accommodations

Reviewed on Apr 4, 2026

![Hilton St. Petersburg Carillon Park](https://images.trvl-media.com/lodging/2000000/1370000/1364000/1363982/w3836h2555x3y3-ee13cfcf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton St. Petersburg Carillon Park

Save 100% on your flight

$843

per person

Jun 23 - Jun 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,009 reviews)

A little microwave in the room would have been very useful. Thanks

Reviewed on Mar 30, 2026

![SkyBeach Resort](https://images.trvl-media.com/lodging/1000000/20000/15200/15134/2093544e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### SkyBeach Resort

Greater Pinellas Point

Save 100% on your flight

$843

per person

Jun 23 - Jun 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (557 reviews)

Overall beautiful grounds. Hot tub was not working

Reviewed on Apr 3, 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](https://expedia.com/Port-Richey-Pleasure-Isles.dx553248635976479089)

![Pirate ship at St Andrews State Park](https://images.trvl-media.com/place/553248635976481436/9268ec32-a2bc-43c6-b9f7-858ff8d266f5.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Gulf Shores

 Gulf Shores might not have many top sights, but Hudson Beach and Cow Creek are two attractions nearby that you can check out. 

[Find hotel + flight trips in Gulf Shores](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Gulf%20Shores&DestID=553248635976481436&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Holmes Beach](https://images.trvl-media.com/place/553248635976471280/f18adeec-ced9-4fff-b172-f18e0a34fe37.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Hudson Beach Estates

1 out of top 10 points of interest in this area

4/5(9 area reviews)

 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 hotel + flight trips in Hudson Beach Estates](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Hudson%20Beach%20Estates&DestID=553248635976471280&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Boats2](https://images.trvl-media.com/place/553248635976480562/10ff41f8-d5b6-4a32-a57b-3dc1584047bc.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Sea Ranch

 While Sea Ranch isn't home to many top sights, Hudson Beach and Cow Creek are some notable places to visit nearby. 

[Find hotel + flight trips in Sea Ranch](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Sea%20Ranch&DestID=553248635976480562&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Dusk sunset above Gulf of Mexico ocean in Hudson Florida with orange sky](https://images.trvl-media.com/place/553248635976481017/6c2f5cf4-ade0-4535-b6b8-e7bed75b0eb6.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Gulf Coast Acres

2 out of top 10 points of interest in this area

 While visiting Gulf Coast Acres, you might make a stop by sights like Colorama Music and Show Palace Dinner Theater. 

[Find hotel + flight trips in Gulf Coast Acres](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Gulf%20Coast%20Acres&DestID=553248635976481017&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Signal Cove

 When in Signal Cove, you can plan a visit to Hudson Beach and Cow Creek, some noteworthy sights in the nearby area. 

[Find hotel + flight trips in Signal Cove](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Signal%20Cove&DestID=553248635976472041&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Pleasure Isles Hotel Deals

![Motel 6 Spring Hill, FL - Weeki Wachee](https://images.trvl-media.com/lodging/1000000/30000/22500/22426/b1bcd6ce_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Motel 6 Spring Hill, FL - Weeki Wachee

6172 Commercial Way Spring Hill FL

Fully refundableReserve now, pay when you stay

$65 nightly

$72 total

May 3 - May 4

Total with taxes and fees

7.4/10 Good! (1,446 reviews)

No refrigerator or microwave in room. They were partying in the parking lot. Smoking and drinking and loud. Mattress was worn out.

Reviewed on Apr 3, 2026

[](https://expedia.com/Hotel-Search?startDate=5%2F3%2F2026&endDate=5%2F4%2F2026&selected=22426&PinnedHotelID=22426&HadPinnedHotel=true&regionId=553248635976479089)

![Main River Mermaid Sleeps 8 kayaks for everyone. Gulf access for scalloping](https://images.trvl-media.com/lodging/100000000/99030000/99029500/99029488/0af077ac_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Main River Mermaid Sleeps 8 kayaks for everyone. Gulf access for scalloping

 Spring Hill FL

10/10 Exceptional! (313 reviews)

Living our best river life! 🛶 Between the kayaking, fishing, and tree-jumping, we didn't want the days to end. We even got lucky with the local wildlife—dolphins, otters, manatees, and turtles all made an appearance! Wish we had a few more days, but we’ll be back soon!

Reviewed on Mar 25, 2026

[Get rates](https://expedia.com/Hotel-Search?startDate=4%2F18%2F2026&endDate=4%2F19%2F2026&selected=99029488&PinnedHotelID=99029488&HadPinnedHotel=true&regionId=553248635976479089)

[](https://expedia.com/Hotel-Search?startDate=4%2F18%2F2026&endDate=4%2F19%2F2026&selected=99029488&PinnedHotelID=99029488&HadPinnedHotel=true&regionId=553248635976479089)

![Comfort Inn & Suites New Port Richey Downtown District](https://images.trvl-media.com/lodging/93000000/92570000/92562500/92562405/9d4d4c1c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Comfort Inn & Suites New Port Richey Downtown District

6206 US HWY 19 New Port Richey FL

Fully refundableReserve now, pay when you stay

$105 nightly

$118 total

May 4 - May 5

Total with taxes and fees

9.2/10 Wonderful! (1,254 reviews)

Reservation reception person was vibrate, informative and committed to our comfort. Breakfast area was very roomy and comfortable. Room was was very comfortable.

Reviewed on Apr 2, 2026

[](https://expedia.com/Hotel-Search?startDate=5%2F4%2F2026&endDate=5%2F5%2F2026&selected=92562405&PinnedHotelID=92562405&HadPinnedHotel=true&regionId=553248635976479089)

[See all 1,826 properties in Pleasure Isles](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&regionId=553248635976479089)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Kid Friendly Vacations

[](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.com/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.com/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.com/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

LGBTQ Friendly Vacations

[](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Adventure Vacations

[](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click)

![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Where to go when

[](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Honeymoon Vacations

[](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Mountain Vacations

[](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Fishing Vacations

[](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Adults Only Vacations

[](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Waterpark Vacations

[](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Scuba Diving Vacations

[](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Yoga Vacations

[](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Cheap Vacations

[](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Solo Vacations

[](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click)

### Discover the most popular places to visit in Pleasure Isles

![Hudson Beach](https://images.trvl-media.com/place/177663/f0d9565a-be5a-4113-9f8b-bd4d85345637.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Hudson Beach

4/5(33 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. 

[](https://expedia.com/Hudson-Beach-Hudson-Beach-Estates.d553248621565061336.Vacation-Attraction)

#### 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. 

[](https://expedia.com/Beacon-Woods-Golf-Course-Bayonet-Point.d553248621561885264.Vacation-Attraction)

#### 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. 

[](https://expedia.com/Show-Palace-Dinner-Theater-Gulf-Coast-Acres.d553248621532653842.Vacation-Attraction)

### Things to do

![Clear Kayak Tours in Weeki Wachee](https://mediaim.expedia.com/localexpert/3655017/238e91f1-0a7d-429e-8f0c-8939572449da.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Clear Kayak Tours in Weeki Wachee

$90

per adult

**100%** of travellers recommend

[](https://expedia.com/things-to-do/clear-kayak-tours-in-weeki-wachee.a3655017.activity-details)

![Audio Guide to New Port Richey's History and Quirky People](https://mediaim.expedia.com/localexpert/49362992/b1a9e4dd-8b72-460f-8948-c37e422c3132.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

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

$7

per adult

[](https://expedia.com/things-to-do/audio-guide-to-new-port-richeys-history-and-quirky-people.a49362992.activity-details)

[See all activities in Hudson](https://expedia.com/things-to-do/search?rid=553248635976479089)

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