Title: Pleasure Isles Vacation Packages 2026 from $500 | 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 $500

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

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

![Mar Bay Motel &Suites](https://images.trvl-media.com/lodging/24000000/23610000/23608800/23608750/d8e0ef7d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Mar Bay Motel &Suites

Save 100% on your flight

$500

per person

Mar 9 - Mar 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (60 reviews)

Excellent customer service

Reviewed on Dec 14, 2025

![ChartHouse Clearwater Beach Marina Hotel](https://images.trvl-media.com/lodging/115000000/114460000/114455200/114455182/48a8960b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### ChartHouse Clearwater Beach Marina Hotel

Save 100% on your flight

$722

per person

Mar 9 - Mar 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (531 reviews)

Excellent clean room with comfortable bed. Microwave, coffee maker and fridge available. Convenient parking across the street. Quiet yet convenient

Reviewed on Feb 3, 2026

![voco Sarasota by IHG](https://images.trvl-media.com/lodging/2000000/1580000/1577400/1577382/dc3c2bf5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$845

per person

Mar 20 - Mar 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,001 reviews)

Everything was great! Very friendly staff, room clean and comfortable! Front desk help went above and beyond. Will definitely be back!!

Reviewed on Feb 5, 2026

![FUSION Resort Waterfront Suites](https://images.trvl-media.com/lodging/37000000/36180000/36176500/36176495/bea713d0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### FUSION Resort Waterfront Suites

$1,940

per person

Apr 18 - Apr 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,097 reviews)

Great overall. The housekeeping is always behind but you just have to call multiple times.

Reviewed on Feb 4, 2026

![Plaza Beach Hotel Beachfront Resort](https://images.trvl-media.com/lodging/1000000/900000/894000/893981/196da8d7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Plaza Beach Hotel Beachfront Resort

Save 100% on your flight

$1,130

per person

Mar 9 - Mar 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,000 reviews)

We absolutely loved our stay! All the staff including Tanner, Liam, Judy, Crystal (just to name a few) were incredible! We will definitely be back!

Reviewed on Feb 5, 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)

![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 Werner Boyce Salt Springs State Park. 

[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)

![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 Werner Boyce Salt Springs State Park 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)

![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 Werner Boyce Salt Springs State Park 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 Werner Boyce Salt Springs State Park, 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/1000000/30000/22500/22426/3f000ab9_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

$51 nightly

$57 total

Feb 16 - Feb 17

Total with taxes and fees

7.2/10 Good! (1,365 reviews)

Friendly staff decent room for the price

Reviewed on Feb 1, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F16%2F2026&endDate=2%2F17%2F2026&selected=22426&PinnedHotelID=22426&HadPinnedHotel=true&regionId=553248635976479089)

![Quality Inn & Suites Tarpon Springs South](https://images.trvl-media.com/lodging/1000000/10000/2900/2801/a40a6433_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Quality Inn & Suites Tarpon Springs South

38724 US Highway 19 North Tarpon Springs FL

Fully refundableReserve now, pay when you stay

$104 nightly

$117 total

Feb 8 - Feb 9

Total with taxes and fees

8/10 Very Good! (1,027 reviews)

Clean room quiet area

Reviewed on Feb 4, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F8%2F2026&endDate=2%2F9%2F2026&selected=2801&PinnedHotelID=2801&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

$112 nightly

$125 total

Feb 15 - Feb 16

Total with taxes and fees

9.2/10 Wonderful! (1,154 reviews)

The entire experience was outstanding! Definitely will be back!

Reviewed on Feb 2, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F15%2F2026&endDate=2%2F16%2F2026&selected=92562405&PinnedHotelID=92562405&HadPinnedHotel=true&regionId=553248635976479089)

[See all 1,827 properties in Pleasure Isles](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F7%2F2026&endDate=2%2F8%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

![Florida’s gulf coast has some of the most beautiful sunsets. This picture was taken at Hudson Beach, luckily the weather has been beautiful all weekend and we were able to enjoy blue skies these weekend. #floridasunset #hudsonbeach #gulfofmexico #floridalifestyle #beachbum](https://images.trvl-media.com/place/177663/f0d9565a-be5a-4113-9f8b-bd4d85345637.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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. 

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

#### 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)

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