Pine Island Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
St Pete Beach Suites
CA $1,549
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (1,003 reviews)
The location, cleanliness, and amenities were excellent! We had a great stay overall. There were just two issues that kept me from giving a full 5-star review:
1. Limited after-hours support: If you need assistance outside of normal business hours, you may have difficulty reaching someone. During our stay, there were no staff on-site, and I couldn't get a response by calling, text, or through the messaging portal until the following day. Fortunately, our issue wasn't an emergency, but it made me wonder what would happen if someone were locked out of their room or had another urgent problem. The AI phone assistant states that all calls and messages are answered between 8:00 a.m. and midnight, but that wasn't our experience. I completely understand not having on-site staff, but I do think the after-hours availability should be communicated more clearly.
2. Very slow hot water: In our suite, it took more than 15 minutes for the hot water to reach the shower. Once it got hot, it stayed hot, so it wasn't a major issue, especially if you know to plan ahead. I'm not sure if this was specific to our suite or a property-wide issue, but it's something I wish we'd known before our stay.
Despite these two issues, we enjoyed our stay and would absolutely consider staying here again.
Reviewed on Aug 10, 2026
Cedar Cove Resort and Cottages
CA $952
per person
Oct 2 - Oct 4
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (568 reviews)
Very charming small hotel, staff was extremely helpful, rooms were clean and had everything we needed for our stay. 10/10 will definitely stay there again
Reviewed on Aug 11, 2026
Ready to book your vacation to Pine Island?
Pine Island Hotel Deals
Motel 6 Spring Hill, FL - Weeki Wachee
6172 Commercial Way Spring Hill FL
Fully refundableReserve now, pay when you stay
CA $73
CA $82 total
Sep 10 - Sep 11
includes taxes & fees
7.2/10 Good! (1,579 reviews)
"All the staff was amazing"
Reviewed on Aug 11, 2026
Main River Mermaid Sleeps 8 kayaks for everyone. Gulf access for scalloping
Spring Hill FL
10/10 Exceptional! (325 reviews)
"The house was exactly as advertised, we had a group of 8, 2 adults and 6 children and we fit perfectly in the space. Everyone loved the kayaks and watching the manatees swim by. My son says he wants to come back to this house next summer. That’s high praise as he is pretty much impossible to please. ..."
Reviewed on Jul 22, 2026
Rodeway Inn Port Richey North
11810 Us Highway 19 Port Richey FL
Fully refundable
CA $82
CA $96 total
Aug 31 - Sep 1
includes taxes & fees
8/10 Very good! (1,014 reviews)
"This location"
Reviewed on Aug 11, 2026
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.
What to do in Pine Island
Clear Kayak Tours in Weeki Wachee
CA $127
per adult
100% of travellers recommend
90-Minute Guided Eco Airboat Tour in Homosassa
CA $132
per adult
Frequently asked questions
How much does a Pine Island vacation package cost?
You can grab a vacation package to this destination from CA $858 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?
- 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.
- 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.
- 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.
- 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.
