Pine Island Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Pine Island Vacation

With every last detail organized before you go away, our Pine Island vacation packages mean you can concentrate on enjoying your getaway. No matter if you're based in the neighborhood of Heritage Pines, which is great for golfing, or somewhere else, this exciting city promises a world of discoveries. There's loads to explore during a trip to Pine Island, including Pine Island Beach Park and Weeki Wachee Springs State Park. Check out Expedia's wide range of travel options and start organizing your ideal vacation to Pine Island today.

Top Pine Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was CA $813, price is now CA $528 per person
CA $528
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.6/10 Excellent! (80 reviews)
The room was clean, with one glaring exception. The carpet was stained throughout, with what looked like pet stains. After reading so many good reviews, this was totally unexpected and very disappointing. Also, the TV was entertaining, to say the least. It was apparently set to zoom mode, so part of the picture was missing. Also, there were captions in the middle of the screen that we couldn't get rid of and the TV actually spoke to us in a monotone computer voice from time to time. Not making this up. It was quite bizarre. We tried all of the settings, but to no avail. Parking was easy and getting in the room was no problem. Also, the location is good with close proximity to a nice park and not far from some nice restaurants.

Reviewed on Jul 19, 2026

ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was CA $2,007, price is now CA $1,130 per person
CA $1,130
per person
Sep 20 - Sep 27
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,249 reviews)
Clean rooms, exceptional views and onsite restaurant! Central location in Clearwater and near a lot of the boat tours.

Reviewed on Jul 20, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was CA $3,360, price is now CA $1,922 per person
CA $1,922
per person
Oct 3 - Oct 10
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.6/10 Exceptional! (1,087 reviews)
The staff and amenities, the room. The property was awesome.

Reviewed on Jul 21, 2026

CW Hotel

CW Hotel

4 out of 5
Price was CA $2,260, price is now CA $1,355 per person
CA $1,355
per person
Sep 20 - Sep 27
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
10/10 Exceptional! (6 reviews)
Hotel is new or renewed , very clean , the pool was las 120 degrees, could not swim, water was too hot. There was a bad smell in the pool area, there is no bar by the pool as the Expedia description says,I did not use the restaurant on the second floor. The room was very spacious and clean , it had kitchen appliances and washing machine with dryer. The parking is 40 dollars /day. Really clean hotel.

Reviewed on Jul 21, 2026

The Avalon Club

The Avalon Club

4 out of 5
Price was CA $2,482, price is now CA $1,566 per person
CA $1,566
per person
Sep 20 - Sep 27
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (564 reviews)
Just the parking fee is expensive I paid like almost 300 for two cars in 2 days

Reviewed on Jul 17, 2026

Ready to book your vacation to Pine Island?

 

Choose your dates

Pine Island Hotel Deals

Microtel Inn & Suites by Wyndham Spring Hill/Weeki Wachee

Microtel Inn & Suites by Wyndham Spring Hill/Weeki Wachee

2 out of 5
4881 Commercial Way Spring Hill FL
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from Aug 3 to Aug 4
CA $127
CA $142 total
Aug 3 - Aug 4
includes taxes & fees
Microtel Inn & Suites by Wyndham Spring Hill/Weeki Wachee
Rodeway Inn Homosassa

Rodeway Inn Homosassa

2 out of 5
4076 S Suncoast Blvd Homosassa FL
Fully refundable
The price is CA $95 per night from Aug 13 to Aug 14
CA $95
CA $108 total
Aug 13 - Aug 14
includes taxes & fees
7/10 Good! (1,004 reviews)
"The staff were great, we LOVED the onsite bar and grill and the pool was clean and a great escape from the heat."

Reviewed on Jul 21, 2026

Rodeway Inn Homosassa
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
The price is CA $84 per night from Jul 28 to Jul 29
CA $84
CA $94 total
Jul 28 - Jul 29
includes taxes & fees
Motel 6 Spring Hill, FL - Weeki Wachee
See all 1,315 properties in Pine Island
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
Family Vacations
Family Vacations

What to do in Pine Island

Clear Kayak Tours in Weeki Wachee

Clear Kayak Tours in Weeki Wachee

CA $128
per adult
100% of travellers recommend
Clear Kayak Tours in Weeki Wachee
90-Minute Guided Eco Airboat Tour in Homosassa

90-Minute Guided Eco Airboat Tour in Homosassa

CA $134
per adult
90-Minute Guided Eco Airboat Tour in Homosassa
Fast & More Airboat Tour

Fast & More Airboat Tour

CA $102
per adult
80% of travellers recommend
Fast & More Airboat Tour
See all activities in Pine Island

Frequently asked questions

How much does a Pine Island vacation package cost?
You can grab a vacation package to this destination from CA $528 on Expedia. But how much your vacation to Pine Island costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Pine Island?
Plan your trip for the off-peak season and you're likely to get cheap Pine Island vacation packages. Remember that school vacation periods and major festivals and events can impact prices, so do a little research before you go.
How many days is enough for Pine Island?
The ideal length of your Pine Island vacation depends on what you'd like to see. Typically, a handful of days to a week will give you time to tick off all the main sights and explore some hidden spots along the way.
How to find the best Pine Island package deals?
Landing a cheap Pine Island package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a few filters and browse what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most economical Pine Island package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Pine Island vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component individually. And you'll still get the flexibility to create a personalized Pine Island vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Pine Island?
If you're planning an impromptu Pine Island vacation, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Pine Island?

  1. Choose when to go: Check your schedule and pack your bags. Your favourite time of year and the type of activities on offer will also help you decide when to visit Pine Island.
  2. Work out your budget: Ensure you have enough money to cover everything from food and transportation to flights and activities. Your hotel will probably be the largest expense during your trip to Pine Island.
  3. Work out your trip length: Think about how long you want to spend exploring Pine Island. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to find a Pine Island vacation package that brings all your bookings together.

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