Pine Island Vacations from $313

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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.

The Latest Pine Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Clearwater Suites

Clearwater Suites

2.5 out of 5
Save 100% on your flight
Price was $540, price is now $313 per person
$313
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
New York (LGA) to Tampa (TPA)
8.8/10 Excellent! (27 reviews)
Yes pool was very 😊

Reviewed on Sep 27, 2025

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $739, price is now $450 per person
$450
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,003 reviews)
Enjoyed our stay at the property. It was very clean and safe. Staff extremely helpful and friendly.

Reviewed on Sep 16, 2025

Holiday Inn Express & Suites Trinity by IHG

Holiday Inn Express & Suites Trinity by IHG

2.5 out of 5
Trinity
Save 100% on your flight
Price was $729, price is now $463 per person
$463
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (728 reviews)
Is great will stay again

Reviewed on Sep 20, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,030, price is now $656 per person
$656
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (456 reviews)
Excellent property! Wonderful staff and amenities. Would definitely stay again. As with the other feedback, the daily parking rate is expensive.

Reviewed on Sep 24, 2025

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Discover the most popular places to visit in Pine Island

Weeki Wachee River

Weeki Wachee River

Commune with nature and explore the great outdoors at Weeki Wachee River during your travels in Spring Hill. While in this family-friendly area, you can savor the top-notch restaurants.

Weeki Wachee River
End of sunset Pine Island Beach

Pine Island Beach Park

Why not spend a carefree afternoon at Pine Island Beach Park during your travels in Spring Hill? While in this family-friendly area, you can savor the top-notch restaurants.

Pine Island Beach Park

Weeki Wachee Springs

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

What to do in Pine Island

Clear Kayak Tours in Weeki Wachee

Clear Kayak Tours in Weeki Wachee

$73
per adult
100% of travellers recommend
Clear Kayak Tours in Weeki Wachee
See all activities in Pine Island

Pine Island Hotel Deals

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
$42 nightly
The price is $47 total per night from Sep 30 to Oct 1
$47 total
Sep 30 - Oct 1
Total with taxes and fees
7.2/10 Good! (1,193 reviews)
"Beautiful clean pool and affordable laundry facilities."

Reviewed on Sep 23, 2025

Motel 6 Spring Hill, FL - Weeki Wachee
Main River Mermaid Sleeps 8 kayaks for everyone. Gulf access for scalloping

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

Spring Hill
9.8/10 Exceptional! (292 reviews)
"Another enjoyable trip! So relaxing and perfect location for enjoying the springs by kayaking and swimming. Saw 12 manatees this time."

Reviewed on Sep 8, 2025

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Main River Mermaid Sleeps 8 kayaks for everyone. Gulf access for scalloping
DIRECT WEEKI WACHEE RIVERFRONT!! KEY WEST PARADISE!

DIRECT WEEKI WACHEE RIVERFRONT!! KEY WEST PARADISE!

Weeki Wachee
10/10 Exceptional! (222 reviews)
"Fabulous property, amazing view, great to see the manatees swimming past and having the use of the kayaks. We had a wonderful time staying here and I would highly recommend staying in this beautiful riverside house."

Reviewed on Sep 16, 2025

Get rates
DIRECT WEEKI WACHEE RIVERFRONT!! KEY WEST PARADISE!
See all 1,242 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.

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Frequently asked questions

How much does a Pine Island vacation package cost?
You'll find cheap prices from $313 on Expedia for your Pine Island getaway. However, a range of factors like the season, choice of hotel and length of stay will determine how much your vacation to Pine Island costs.
What are the cheapest months to go to Pine Island?
If you're looking to snag a cheap Pine Island vacation package, consider traveling in June, October and December. You'll usually find lower prices on flights and hotels during these months — perfect for travelers wishing to save money.
How many days is enough for Pine Island?
With a well-organized travel plan, you can easily visit the most popular Pine Island attractions in a few days. But if you'd like to venture off the beaten track or go on day tours, consider booking your Pine Island vacation for longer.
How to find the best Pine Island package deals?
Start your search for a Pine Island package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Pine Island package deal straight away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Pine Island escape off to a flying start.
Is it cheaper to book a Pine Island vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and accommodations individually. Better still, you can personalize your Pine Island getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Pine Island?
Land incredible discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Pine Island escape.
How to plan a trip to Pine Island?

  1. Pick the right time to travel: Your schedule, favorite season and the type of weather you like can all impact your decision on when to visit Pine Island.
  2. Plan your budget wisely: In addition to the price of your accommodations, you'll need to factor in other expenses too. These include transportation, flights and food. Also, put aside a little extra for unexpected costs that could crop up during your trip to Pine Island.
  3. Organize your Pine Island escape with our trip planning tool: Look for and book accommodations and experiences all in one place. You can also collaborate with your group to plan an unforgettable trip to Pine Island together.
  4. Decide how long to go away for: Now that you're up to speed on Pine Island, you can figure out the right length of your vacation. Pull together a rough plan and give yourself enough time for all the things you want to do.
  5. Combine your airfare and accommodations: After you've nailed down your dates and duration, lock in the right Pine Island vacation package for you.
  6. Book activities and experiences ahead of time: Whether it's a ticket to a major attraction or a day trip in nature, you won't have to worry about missing out on Pine Island's highlights. Find all the exciting things to do in Pine Island with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Pine Island vacation packages?
Your Pine Island break should be a relaxing escape from your busy life, not a source of money-related stress. So to allow you that extra flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.