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.
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Downtown Tampa
Price was CA $1,822, price is now CA $1,282 per person
CA $1,282
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.6/10 Excellent! (2,636 reviews)
very good location, well kept public areas and nice bar and pool

Reviewed on Jun 21, 2026

CW Hotel

CW Hotel

4 out of 5
Price was CA $2,719, price is now CA $1,602 per person
CA $1,602
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
No reviews
Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn

3 out of 5
Price was CA $2,079, price is now CA $1,465 per person
CA $1,465
per person
Sep 9 - Sep 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (453 reviews)
Great little place, very small rooms but very clean and nice. Having to check in at a different location was a bit odd but overall a good place.

Reviewed on Jun 15, 2026

The Avalon Club

The Avalon Club

4 out of 5
Price was CA $4,782, price is now CA $3,405 per person
CA $3,405
per person
Jul 27 - Aug 3
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Tampa (TPA)
9.4/10 Exceptional! (552 reviews)
The staff was very kind and accommodating. We will definitely look to book again.

Reviewed on Jun 19, 2026

The Marker

The Marker

2 out of 5
Price was CA $3,861, price is now CA $2,828 per person
CA $2,828
per person
Jul 27 - Aug 3
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Tampa (TPA)
6/10 (3 reviews)
There was no staff due to it being brand new! The owner Jeff was great and very polite and went out of his way to make us feel welcome and valued! It was very quiet and comfortable for my family. Only about a two block walk to the beach but being in the bay was beautiful to wake up to!

Reviewed on Apr 12, 2026

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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
The price is CA $83 per night from Jun 29 to Jun 30
CA $83
CA $92 total
Jun 29 - Jun 30
includes taxes & fees
7.2/10 Good! (1,525 reviews)
"The room was just dirty and run down, the grounds were not kept up well, and the staff was odd"

Reviewed on Jun 20, 2026

Motel 6 Spring Hill, FL - Weeki Wachee
Rodeway Inn Port Richey North

Rodeway Inn Port Richey North

2 out of 5
11810 Us Highway 19 Port Richey FL
Fully refundableReserve now, pay when you stay
The price is CA $90 per night from Jul 5 to Jul 6
CA $90
CA $105 total
Jul 5 - Jul 6
includes taxes & fees
7.8/10 Good! (1,003 reviews)
"Everything is good 👍"

Reviewed on Jun 20, 2026

Rodeway Inn Port Richey North
Rodeway Inn Homosassa

Rodeway Inn Homosassa

2 out of 5
4076 S Suncoast Blvd Homosassa FL
Fully refundableReserve now, pay when you stay
The price is CA $90 per night from Jun 28 to Jun 29
CA $90
CA $103 total
Jun 28 - Jun 29
includes taxes & fees
7/10 Good! (1,005 reviews)
"All good"

Reviewed on Jun 21, 2026

Rodeway Inn Homosassa
See all 1,305 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
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Beach Vacations
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Discover the most popular places to visit in Pine Island

A calm water body with tall palm trees and a metal bridge.

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

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 $125
per adult
100% of travellers recommend
Clear Kayak Tours in Weeki Wachee
See all activities in Pine Island

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.