Cypress Island Vacation Packages
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Top Holiday Package Deals in Cypress Island
Price found within the past 48 hours. Click for updated prices.
Sunsuites Villas At Sunseeker Resort, Curio By Hilton
CA $1,559
per person
Jan 2 - Jan 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (135 reviews)
We scheduled our stay for my wife's 60th birthday party. We had spoken to the hotel staff about how we were looking forward to celebrating by the rooftop pool..
THE ROOFTOP POOL WAS CLOSED THE ENTIRE TIME WE WERE THERE FOR A PRIVATE COMPANY PARTY.
EXTREMELY DISAPPOINTED!!
Reviewed on Oct 25, 2026
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
CA $5,136
per person
Dec 28 - Jan 2
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9/10 Wonderful! (1,003 reviews)
Very helpful staff, great Gulf side room. Undergoing some renovation so only one elevator working but didn’t create too much of a problem. Great location, nice people.
Reviewed on Oct 25, 2026
Where to stay in Cypress Island
Find the best Cypress Island areas and neighborhoods for the activities you enjoy most. Learn more about Cypress Island
Bonita Shores
Bonita Shores might not have many top sights, but Barefoot Beach and Promenade at Bonita Bay are two attractions nearby that you can check out.
Bonita Bay
1 out of top 10 points of interest in this area
When in Bonita Bay, you can plan a visit to Promenade at Bonita Bay and Bonita Springs Public Beach, some noteworthy sights in the nearby area.
Estero Bay Shores
When in Estero Bay Shores, you can plan a visit to Saltleaf Golf Preserve and Bonita Beach Dog Park, some noteworthy sights in the nearby area.
Village Walk of Bonita Springs
While Village Walk of Bonita Springs isn't home to many top sights, Arrowhead Golf Course and Bonita Springs Dog Park are some notable places to visit nearby.
Burning Tree
Burning Tree might not have many top sights, but Promenade at Bonita Bay and Bonita Fairways Golf Course are two attractions nearby that you can check out.
Cypress Island Hotel Deals
Marriott Sanibel Harbour Resort & Spa
17260 Harbour Pointe Dr Fort Myers FL
Fully refundableReserve now, pay when you stay
CA $290
CA $373 total
Nov 8 - Nov 9
includes taxes & fees
Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
CA $237
CA $334 total
Oct 27 - Oct 28
includes taxes & fees
Fairways Inn of Naples
103 Palm River Blvd Naples FL
Fully refundableReserve now, pay when you stay
CA $118
CA $131 total
Oct 27 - Oct 28
includes taxes & fees
9.4/10 Exceptional! (1,349 reviews)
"It was our second time staying here for vacation. It was a pleasure staying here. Will definitely book again if we come to Florida."
Reviewed on Oct 26, 2026
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.
Frequently asked questions
How much does a Cypress Island vacation package cost?
Choose from any combination of car rentals, flights and hotels, and you can be vacationing in Cypress Island from just CA $291. And the more you bundle, the more dollars you save. The getaway of your dreams has never been more affordable.
How do I get a cheap travel package to Cypress Island?
It's easy. Just bundle everything together. Hotels, flights and rental cars — combine whatever you need into a Cypress Island vacation package to save tons of cash. Score even more deals when you add extras such as sightseeing tours to your booking. But that's not the only impressive part. You have the flexibility to customize your vacation your way. We offer over 550 air carriers and 1,000,000 hotels in all corners of the globe, so that everyone has an opportunity to travel and fulfill those vacation fantasies.
Where should I stay in Cypress Island?
It makes sense to stay near the action. Many visitors book hotels in the vicinity of top sights, such as Promenade at Bonita Bay, Bonita Beach Dog Park and Little Hickory Island Beach Park.
How far in advance should I book my Cypress Island vacation?
Be rewarded with the biggest variety at the lowest prices by booking your Cypress Island adventure nice and early. Air carriers tend to advertise flights around a year before departure, so secure your spot as soon as possible. Having said that, Expedia is dedicated to giving you the best bargains around, so there's never a bad time to book your dream vacation!
What does an Expedia Cypress Island travel package include?
Rental cars, flights and hotels — we've got them all. With Expedia, you can create your Cypress Island travel package just the way you want. All you have to do is decide what you need. Once you've made your booking, you can add on extras like activities and tours. The more you bundle, the more you save!
What should I know before booking a Cypress Island travel package?
Discover deals to match your budget with an Expedia package. Airfares, hotels, rental cars — we've got them all. You'll save a packet just by bundling your bookings. Whether you're heading away on a winter snow adventure or venturing someplace warm, your dream getaway is only clicks away.
Can I choose my airline with a Cypress Island Expedia vacation package?
With a vacation package, you're in control. Whether you're eager to fly to Cypress Island in economy or first class, simply pick from the available airline options. Expedia has access to more than 550 partner airlines all over the world.
If I'm not able to travel, can I cancel my Cypress Island vacation package?
Yes you can, and we'll help you every step of the way. You may be able to amend or cancel your Cypress Island vacation package for free if you booked in the last 24 hours. But you may incur a fee from your hotel, airline or car rental company if your booking is older than that. If life gets in the way of your vacation, browse our Customer Service Portal for further information.
Things to do
Gulf of Mexico Sunset Cruise from Naples
CA $89
per adult
88% of travellers recommend
Guided Tour of Naples on a Vintage Trolley (Hop on - Hop off)
CA $63
per adult
90% of travellers recommend
Sunset Cruise Fort Myers Beach
CA $68
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.