Pine Island Vacations from $454

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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
Price was $705, price is now $454 per person
$454
per person
May 29 - Jun 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,006 reviews)
Room was very clean.

Reviewed on Mar 29, 2026

Voyager Beach Club

Voyager Beach Club

2.5 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,067, price is now $640 per person
$640
per person
May 9 - May 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (109 reviews)
Everything about this resort was perfect! Can't wait to go back!

Reviewed on Dec 30, 2025

Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $1,134, price is now $680 per person
$680
per person
Jun 23 - Jun 30
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (74 reviews)
Overall very good. Needs some updating but very good shower and bed, so I got everything I needed! Would use again

Reviewed on Apr 3, 2026

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was $1,743, price is now $1,155 per person
$1,155
per person
Jun 23 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,151 reviews)
The property is pretty, the view is amazing, I didn’t like that the kitchen cookware was extremely low quality (goodwill have better frying pan) no towel at the pool, they change resorts fee, but never a single towel to use, the price for room Was high, the free shuttle to beach was a joke, but overall the hotel was nice but I won’t stay again. To pricey for they offer.

Reviewed on Apr 4, 2026

Crystal Palms Beach Resort

Crystal Palms Beach Resort

3.5 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,494, price is now $1,026 per person
$1,026
per person
Jun 23 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (2,373 reviews)
Clean room very spacious staff friendly

Reviewed on Apr 6, 2026

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Discover the most popular places to visit in Pine Island

Coastal waterway near Spring Hill and Weeki Wachee, Florida

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
Kayaking the 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
Pine Island Beach Park

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

What to do in Pine Island

Clear Kayak Tours in Weeki Wachee

Clear Kayak Tours in Weeki Wachee

$90
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
$55 nightly
The price is $61 total per night from Apr 15 to Apr 16
$61 total
Apr 15 - Apr 16
Total with taxes and fees
7.4/10 Good! (1,453 reviews)
When you e arrive to our room I noticed the counters were not clean you could see cup ring and ketchup on the counter. Dirt on the shower. Not the cleanest place

Reviewed on Apr 8, 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
10/10 Exceptional! (313 reviews)
Living our best river life! 🛶 Between the kayaking, fishing, and tree-jumping, we didn't want the days to end. We even got lucky with the local wildlife—dolphins, otters, manatees, and turtles all made an appearance! Wish we had a few more days, but we’ll be back soon!

Reviewed on Mar 25, 2026

Get rates
Main River Mermaid Sleeps 8 kayaks for everyone. Gulf access for scalloping
Rodeway Inn Homosassa

Rodeway Inn Homosassa

2 out of 5
4076 S Suncoast Blvd Homosassa FL
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $74 total per night from Apr 16 to Apr 17
$74 total
Apr 16 - Apr 17
Total with taxes and fees
6.8/10 (1,007 reviews)
The room was very clean. The staff friendly and helpful. You could walk to the Manatee park. A 7/11 is right next door. And a Publix in in the next block. Overall a nice place to stay.

Reviewed on Apr 7, 2026

Rodeway Inn Homosassa
See all 1,278 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 $454 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.