Pine Island Vacations from $595

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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.
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Save 100% on your flight
Price was $1,081, price is now $595 per person
$595
per person
Feb 24 - Mar 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
No reviews
The resort is absolutely beautiful.We will definitely be staying here again.We actually decided to stay another night. What definitely recommended

Reviewed on Jan 1, 2026

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was $1,809, price is now $980 per person
$980
per person
Mar 16 - Mar 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,097 reviews)
The room was spotless and staff was so friendly and polite!

Reviewed on Jan 9, 2026

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Price was $1,888, price is now $1,127 per person
$1,127
per person
Mar 16 - Mar 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,000 reviews)
We were pleasantly surprised with how clean the room was when we arrived and had everything we needed. The walk from our room to the beach was about 4 seconds... perfect.

Reviewed on Jan 10, 2026

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $1,063, price is now $639 per person
$639
per person
Mar 16 - Mar 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (4,624 reviews)
Clean room, quiet, great location for us (meeting friends at a local restaurant), all the desired amenities - pool, lounge, games, restaurant, bar, free parking.

Reviewed on Jan 10, 2026

Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Belle Vista
Price was $1,152, price is now $693 per person
$693
per person
Mar 16 - Mar 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (496 reviews)
Staff courteous and a fun place.

Reviewed on Jan 9, 2026

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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

$79
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 FL
$440 nightly
The price is $486 total per night from Jan 12 to Jan 13
$486 total
Jan 12 - Jan 13
Total with 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
$37 nightly
The price is $41 total per night from Jan 20 to Jan 21
$41 total
Jan 20 - Jan 21
Total with taxes and fees
7.2/10 Good! (1,333 reviews)
It was easy to find. The front desk lady was kind and helpful. She appeared to care and enjoyed helpimg guest. The room was large and clean. The bath tub faucet leaked water so badly that it wasn't dripping, it was a continuous stream from the spigot to the tub bottom. It had been doing it a while ...

Reviewed on Jan 9, 2026

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 FL
9.8/10 Exceptional! (297 reviews)
Absolutely amazing with lots of wildlife - otters manatees turtles dolphins and monkeys. We felt no need to go anywhere else our entire stay. One of the few places I’d book again.

Reviewed on Dec 25, 2025

Get rates
Main River Mermaid Sleeps 8 kayaks for everyone. Gulf access for scalloping
See all 1,277 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.

Find the Best Pine Island Vacation Packages

Pine Island Essential Information

Language
English
Currency
U.S dollars
Top Sights
Pine Island Beach Park, Weeki Wachee Springs State Park and Weeki Wachee Springs

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Frequently asked questions

How much does a Pine Island vacation package cost?
You'll find cheap prices from $595 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.