Pine Island Vacation Packages

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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.
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.2/10 Wonderful! (1,040 reviews)
The property was quiet, clean and comfortable. The customer service was professional and above average. I would not hesitate to book again. Two bedrooms and two bathrooms, living room and full kitchen was plenty room for husband and I. Only stayed one night but wished it was longer.

Reviewed on Jun. 26, 2025

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

4 out of 5
Wesley Chapel South
Save 100% on your flight
per person
Aug 17 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
6.2/10 (1,003 reviews)
Wish the big pool was open

Reviewed on Jul. 11, 2025

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (2,352 reviews)
Great location with convenient stores, restaurants,very clean the hotel with excellent guest service. Overall everything was great at our stay.

Reviewed on Jul. 13, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Aug 29 - Aug 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.4/10 Exceptional! (430 reviews)
Beautiful property I would highly recommend this place to anyone looking for clean,friendly,convenience with a beautiful view.

Reviewed on Jul. 10, 2025

Clearwater Beach Hotel Suites

Clearwater Beach Hotel Suites

2.5 out of 5
Save 100% on your flight
per person
Oct 5 - Oct 12
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
No reviews

Ready to book your vacation to Pine Island?

 

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Pine Island Hotel Deals

WELCOME TO A PARADISE GETAWAY IN WEEKI WACHEE FLORIDA
WELCOME TO A PARADISE GETAWAY IN WEEKI WACHEE FLORIDA
Spring Hill
The price is CA $272 per night from Jul 16 to Jul 17
CA $272
CA $656 total
Jul 16 - Jul 17
includes taxes & fees
9.6/10 Exceptional! (122 reviews)
"Cute little cottage on the bay. Was great for one night. Beds weren't very comfortable and there was no way to get to a beach because the park was closed. But the porch was great for coffee in the morning, kitchen was well stocked, and had everything we needed for a quick stop over."

Reviewed on Jun. 15, 2025

WELCOME TO A PARADISE GETAWAY IN WEEKI WACHEE FLORIDA
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 $59 per night from Jul 21 to Jul 22
CA $59
CA $65 total
Jul 21 - Jul 22
includes taxes & fees
7.2/10 Good! (1,092 reviews)
"Very friendly staff easy and quick checking"

Reviewed on Jul. 11, 2025

Motel 6 Spring Hill, FL - Weeki Wachee
La Vista Inn
La Vista Inn
2 out of 5
11736 US HIGHWAY 19, Port Richey, FL
Fully refundableReserve now, pay when you stay
The price is CA $72 per night from Jul 26 to Jul 27
CA $72
CA $81 total
Jul 26 - Jul 27
includes taxes & fees
5.2/10 (1,007 reviews)
You get what you pay for
"The staff was gracious and dexterous with my check-in. My room was what I paid for and decently kept and clean. Overall a great experience 10/10 would stay here again"

Reviewed on Jul. 10, 2025

La Vista Inn
See all 1,211 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

Discover the most popular places to visit in Pine Island

Weeki Wachee Springs

4.5/5(5 reviews)

Explore the great outdoors at Weeki Wachee Springs, a lovely green space in Spring Hill. Wander the riverfront in this family-friendly area.

Weeki Wachee Springs

Bayport Park Boat Ramp

Explore the great outdoors at Bayport Park Boat Ramp, a lovely green space in Bayport. Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.

Bayport Park Boat Ramp

Silverthorn Country Club

Enjoy a round of golf in Spring Hill at Silverthorn Country Club. While in this family-friendly area, you can savor the top-notch restaurants.

Silverthorn Country Club

What to do in Pine Island

Clear Kayak Tours in Weeki Wachee

Clear Kayak Tours in Weeki Wachee

CA $124
per adult
100% of travellers recommend
Clear Kayak Tours in Weeki Wachee
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 $475 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.