Shired Island Vacations from $286
Book a Hotel + Flight or Car together to unlock savings
The Latest Shired Island Vacation Packages
- Palazzo Lakeside Hotel
Sep 15 - Sep 18Palazzo Lakeside Hotel + Flight
Kissimmee3 nights3.0 star property8.4/10 - Very Good (5,285 reviews)Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop - Westgate Towers Resort
Sep 28 - Oct 3Westgate Towers Resort + Flight
Kissimmee5 nights3.5 star property8.6/10 - Excellent (1,002 reviews)Roundtrip • New York (NYC) - Orlando (MCO)EWR - MCO • Nonstop MCO - EWR • Nonstop - Westgate Palace Hotel / Universal / I-Drive
Oct 29 - Nov 1Westgate Palace Hotel / Universal / I-Drive + Flight
International Drive District3 nights4.0 star property9.0/10 - Wonderful (1,303 reviews)"Very nice hotel and location was great. The staff was very helpful."Reviewed August 4, 2026Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop - Westgate Vacation Villas Resort
Oct 21 - Oct 25Westgate Vacation Villas Resort + Flight
Kissimmee4 nights4.0 star property8.2/10 - Very Good (2,031 reviews)"No cleaning service for a 6 day stay."Reviewed August 4, 2026Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop - Cedar Cove Resort and Cottages
Sep 14 - Sep 19Cedar Cove Resort and Cottages + Flight
Holmes Beach5 nights3.0 star property9.2/10 - Wonderful (568 reviews)"Will stay there again. Very convenient location near everything one might need while on vacation. Cottage was very clean and well equipped. Staff was very friendly and helpful."Reviewed August 3, 2026Roundtrip • Boston (BOS) - Tampa (TPA)BOS - SRQ • 1 stop SRQ - BOS • 1 stop
Shired Island Hotel Deals
"This place is like stepping back into history. You will love it."
Cross City Motel by Hotel O US 19
Cross City Motel by Hotel O US 19"Just not good all around sorry"
"It was okay I would stay there again..."
Dock & Fire Pit: Scenic Studio on Suwannee River!
Dock & Fire Pit: Scenic Studio on Suwannee River!"Great location!"
Lanai & Fire Pit: Riverfront Studio in Chiefland!
Lanai & Fire Pit: Riverfront Studio in Chiefland!"This is the perfect place to relax while enjoying the Suwannee River. A Boaters, fishermen, or hunters paradise, with all the basics, in a rustic setting. A great restaurant right next door puts the frosting on the Cake. The Suwannee River Cruise gives you extremely interesting insight into the history of the river, and views of manatees, alligators, otters and so much morel."
Frequently Asked Questions
How much does a Shired Island vacation package cost?
Offering great value package deals from $286 on Expedia, you'll be pleasantly surprised at how much a vacation to Shired Island costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Shired Island?
You can generally find reduced prices and greater availability in April, August and December. Browse our cheap Shired Island vacation packages and you could land some excellent off-season deals.
How many days is enough for Shired Island?
The ideal length of your Shired Island vacation depends on what you'd like to see and do. Typically, a handful of days to a week will give you enough time to hit all the top sights and discover some hidden gems along the way.
How to find the best Shired Island package deals?
Landing a cheap Shired Island package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget range, apply a few filters and see what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Shired Island package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Shired Island vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging hotels and flights individually. Better still, you can tailor your Shired Island getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Shired Island?
If you have your Shired Island vacation dates locked in, book as early as you can to score some outstanding deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Shired Island vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Shired Island vacation across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you see them.