Cypress Island Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in Cypress Island

Price found within the past 48 hours. Click for updated prices.
Quality Inn Fort Myers Cape Coral

Quality Inn Fort Myers Cape Coral

2 out of 5
Price was CA $788, price is now CA $551 per person
CA $551
per person
Jan 11 - Jan 16
found 6 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Fort Myers (RSW)
7.6/10 Good! (465 reviews)
The room was clean and check in was easy. Shower had little to no hot water and toilet was not working properly. I wish there had been a guide for TV too.

Reviewed on Oct 27, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Save 100% on your flight
Price was CA $8,000, price is now CA $5,263 per person
CA $5,263
per person
Jan 11 - Jan 18
found 6 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) 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

Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Punta Rassa
Price was CA $3,324, price is now CA $2,370 per person
CA $2,370
per person
Dec 27 - Jan 3
found 17 hours ago
Roundtrip flight included
Ottawa (YOW) to Fort Myers (RSW)
8.6/10 Excellent! (1,002 reviews)

Edison Beach House

Edison Beach House

3.5 out of 5
Price was CA $3,597, price is now CA $2,603 per person
CA $2,603
per person
Dec 27 - Jan 3
found 17 hours ago
Roundtrip flight included
Ottawa (YOW) to Fort Myers (RSW)
9.4/10 Exceptional! (1,947 reviews)

Landing Apartments Fort Myers near Eastwood Village

Landing Apartments Fort Myers near Eastwood Village

3 out of 5
Price was CA $3,003, price is now CA $2,184 per person
CA $2,184
per person
Dec 27 - Jan 3
found 17 hours ago
Roundtrip flight included
Ottawa (YOW) to Fort Myers (RSW)
9.8/10 Exceptional! (31 reviews)
This place is as beautiful as the pictures. Welcome kit has essentials for a short stay. The place is clean and cozy. Highly recommended.

Reviewed on Sep 4, 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
A bridge over water at sunset with a clear sky.

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.

Find hotels in Bonita Shores

Cypress Island Hotel Deals

Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
17260 Harbour Pointe Dr Fort Myers FL
Fully refundableReserve now, pay when you stay
The price is CA $290 per night from Nov 11 to Nov 12
CA $290
CA $373 total
Nov 11 - Nov 12
includes taxes & fees
Marriott Sanibel Harbour Resort & Spa
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
The price is CA $237 per night from Oct 28 to Oct 29
CA $237
CA $334 total
Oct 28 - Oct 29
includes taxes & fees
Margaritaville Beach Resort Fort Myers
Fairways Inn of Naples

Fairways Inn of Naples

3 out of 5
103 Palm River Blvd Naples FL
Fully refundableReserve now, pay when you stay
The price is CA $125 per night from Oct 28 to Oct 29
CA $125
CA $139 total
Oct 28 - Oct 29
includes taxes & fees
9.4/10 Exceptional! (1,352 reviews)
"Such a wonderful stay. Everything was so nice. Very clean and well kept. The modern mid century style was so cute. The grounds were amazing. Other than a bit of a musty smell in the room (could use a dehumidifier) everything was fantastic."

Reviewed on Oct 26, 2026

Fairways Inn of Naples
See all 17,525 properties in Cypress 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
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $551. 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

Gulf of Mexico Sunset Cruise from Naples

CA $89
per adult
88% of travellers recommend
Gulf of Mexico Sunset Cruise from Naples
Guided Tour of Naples on a Vintage Trolley

Guided Tour of Naples on a Vintage Trolley (Hop on - Hop off)

CA $63
per adult
90% of travellers recommend
Guided Tour of Naples on a Vintage Trolley (Hop on - Hop off)
Sunset Cruise Fort Myers Beach

Sunset Cruise Fort Myers Beach

CA $68
per adult
100% of travellers recommend
Sunset Cruise Fort Myers Beach
See all activities in Bonita Springs
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.