Cypress Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Cypress Island

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Fort Myers/at The Forum

Hyatt Place Fort Myers/at The Forum

3 out of 5
The Forum
Price was CA $786, price is now CA $479 per person
CA $479
per person
Nov 17 - Nov 21
found 4 hours ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
8.2/10 Very Good! (1,006 reviews)
it was great, will definitely book here again

Reviewed on Aug. 31, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was CA $2,508, price is now CA $1,237 per person
CA $1,237
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.8/10 Excellent! (1,004 reviews)
The overall experience at the hotel was excellent.

Reviewed on Sep. 2, 2025

Casa Playa Beach Resort

Casa Playa Beach Resort

2.5 out of 5
Price was CA $2,062, price is now CA $1,327 per person
CA $1,327
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Fort Myers (RSW)
9.6/10 Exceptional! (85 reviews)
I had a great time there - staff was great - room was amazing on all levels . I will be back guaranteed

Reviewed on Aug. 31, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $1,329, price is now CA $888 per person
CA $888
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (398 reviews)
The Perry Hotel was amazing. A bit secluded but that made it even more special ! The service, the scent in the lobby, the free boat sunset tour was the highlight of the afternoon. We enjoyed the adult pool as well as the restaurants. The rooms were perfect and modern. Keep up the good work, highly recommended as a quick escape from Miami.

Reviewed on Sep. 2, 2025

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Price was CA $3,324, price is now CA $2,231 per person
CA $2,231
per person
Nov 8 - Nov 14
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Fort Myers (RSW)
9.4/10 Exceptional! (1,001 reviews)
Location, service and amenities are excellent

Reviewed on Aug. 31, 2025

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
Default Image

Bonita Shores

3/5(1 area review)

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

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
The price is CA $224 per night from Sep 9 to Sep 10
CA $224
CA $318 total
Sep 9 - Sep 10
includes taxes & fees
Naples Grande Beach Resort
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 $179 per night from Sep 9 to Sep 10
CA $179
CA $254 total
Sep 9 - Sep 10
includes taxes & fees
Margaritaville Beach Resort Fort Myers
Hyatt House Naples/5th Avenue

Hyatt House Naples/5th Avenue

3.5 out of 5
1345 5th Avenue South, Naples, FL
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Sep 14 to Sep 15
CA $162
CA $180 total
Sep 14 - Sep 15
includes taxes & fees
Hyatt House Naples/5th Avenue
See all 16,267 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 $479. 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.

Discover the most popular places to visit in Cypress Island

Little Hickory Island Beach Park

Little Hickory Island Beach Park is just one of the places to see in Bonita Springs, so why not enjoy the other things to explore during your travels? Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.

Little Hickory Island Beach Park

Raptor Bay Golf Club

Enjoy a round of golf in Bonita Springs at Raptor Bay Golf Club. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.

Raptor Bay Golf Club

Things to do

Lovers Key Guided Eco Tour-Mangrove Estuary

Lovers Key Guided Eco Tour-Mangrove Estuary

CA $92
per adult
96% of travellers recommend
Lovers Key Guided Eco Tour-Mangrove Estuary
Shelling Tours - Fort Myers Beach / Estero Bay

Shelling Tours - Fort Myers Beach / Naples

CA $482
per traveller
Shelling Tours - Fort Myers Beach / Naples
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.