Pine Island Vacations from $423

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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.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,007 reviews)
Excellent location, comfortable rooms..nice place!!!!

Reviewed on Aug 10, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (574 reviews)
This is our second time here, and it won't be our last. There's music and fun going on outside, but it's still very quiet in the rooms. Clean, comfortable and close to all our favorites.

Reviewed on Aug 10, 2025

The J Hotel & Suites

The J Hotel & Suites

2 out of 5
Save 100% on your flight
per person
Oct 20 - Oct 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (54 reviews)
It was a new hotel and I had not tried it before. I was very happy with my choice. The room sizes are some of the largest I have ever stayed it. Really well done.

Reviewed on Jul 29, 2025

The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,057 reviews)
Our experience at this hotel was exceptional from beginning to end. The property is beautiful, impeccably maintained, and offers a spectacular pool with a bar boasting stunning views. The à la carte breakfast was delicious and served with great care, and our room was always stocked with fresh, clean towels daily. Parking is valet only, and it is $50 per night (not $40 as stated on the Expedia listing). What truly made our stay unforgettable was the outstanding hospitality—especially from María Henderson, whose warm welcome and attention to detail made us feel at home from day one. This hotel is a true gem and we highly recommend it.

Reviewed on Aug 9, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (438 reviews)
Nice place...near the beach, would've rated it a 5 but I was denied a later checkout. Other than that a very nice place convenient to all the sites.

Reviewed on Aug 8, 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

WELCOME TO A PARADISE GETAWAY IN WEEKI WACHEE FLORIDA

WELCOME TO A PARADISE GETAWAY IN WEEKI WACHEE FLORIDA

Spring Hill
$452 nightly
The price is $498 total per night from Aug 13 to Aug 14
$498 total
Aug 13 - Aug 14
Total includes taxes and 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
$54 nightly
The price is $60 total per night from Aug 14 to Aug 15
$60 total
Aug 14 - Aug 15
Total includes taxes and fees
7.2/10 Good! (1,122 reviews)
Dont listen to bad reviews
"Wish they had a fridge. But understand that helps keep the cost down. Front desk was awesome."

Reviewed on Aug 6, 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! (287 reviews)
"Everything was perfect about this stay! The kitchen is well stocked for cooking and entertaining. Dogs allowed."

Reviewed on Aug 3, 2025

Get rates
Main River Mermaid Sleeps 8 kayaks for everyone. Gulf access for scalloping
See all 1,214 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 $423 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.