Cypress Island Vacations from $260

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Your Cypress Island Vacation

Uncovering everything Cypress Island has to offer is simple with a Cypress Island vacation package. Known for its golfing and more, this captivating neighborhood is calling your name. When it's time to sightsee, you'll find loads of awesome attractions nearby including Promenade at Bonita Bay, Bonita Beach Dog Park and Little Hickory Island Beach Park. Visit one or all during your trip to Cypress Island. No matter your travel plans or the size of your budget, booking your perfect Cypress Island vacation is a cinch with Expedia.

The Latest Cypress Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Price was $439, price is now $260 per person
$260
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,006 reviews)
Safe and quiet place. Easy parking. Strongly recommend.

Reviewed on Aug 23, 2025

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 $1,900, price is now $1,057 per person
$1,057
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (1,003 reviews)
I loved the beachfront access

Reviewed on Aug 27, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $881, price is now $508 per person
$508
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (398 reviews)
Great property with welcoming staff

Reviewed on Aug 28, 2025

Innovation Hotel

Innovation Hotel

4 out of 5
Save 100% on your flight
Price was $851, price is now $513 per person
$513
per person
Nov 15 - Nov 19
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Fort Myers (RSW)
9.8/10 Exceptional! (512 reviews)
Everything was amazing except for the fan in the room continually blowing and making noise.

Reviewed on Aug 20, 2025

Hyatt Place Fort Myers/at The Forum

Hyatt Place Fort Myers/at The Forum

3 out of 5
The Forum
Price was $449, price is now $274 per person
$274
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.2/10 Very Good! (1,006 reviews)
There is not truly a restaurant or cafe in this hotel.

Reviewed on Aug 24, 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
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Bonita Shores

4.5/5(57 area reviews)

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
Fully refundable
$197 nightly
The price is $219 total per night from Sep 7 to Sep 8
$219 total
Sep 7 - Sep 8
Total with taxes and 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
$211 nightly
The price is $236 total per night from Sep 8 to Sep 9
$236 total
Sep 8 - Sep 9
Total with taxes and fees
8.8/10 Excellent! (1,411 reviews)
"Great hotel and facilities, late notice of a power cut annoying as lifts out of operation lugging suitcases up stairs and air con etc in rooms. Otherwise great stay"

Reviewed on Aug 27, 2025

Margaritaville Beach Resort Fort Myers
La Quinta Inn & Suites by Wyndham Naples Downtown

La Quinta Inn & Suites by Wyndham Naples Downtown

2.5 out of 5
1555 5th Ave S, Naples, FL
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $79 total per night from Sep 7 to Sep 8
$79 total
Sep 7 - Sep 8
Total with taxes and fees
8.2/10 Very Good! (1,606 reviews)
"The breakfast room is very small, which causes discomfort due to too many people."

Reviewed on Aug 25, 2025

La Quinta Inn & Suites by Wyndham Naples Downtown
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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Cypress Island

Bonita Springs Public Beach

Bonita Springs Public Beach

Why not spend a carefree afternoon at Bonita Springs Public Beach during your travels in Bonita Springs? Make time to visit the area's shops, or simply enjoy its top-notch restaurants.

Bonita Springs Public Beach
#Path to #BonitaSprings #DogBeach 🐕🌊☀🐬 Tons of #dolphins here!

Bonita Springs Dog Park

Enjoy the beautiful sunsets and explore Bonita Springs Dog Park, a lovely green space in Bonita Springs. Stroll along the beautiful beaches or seek out the golf courses.

Bonita Springs Dog Park
Pelicans

Everglades Wonder Gardens

See the exotic and native animals who call Everglades Wonder Gardens home during your trip to Bonita Springs. Wander the beautiful beaches and picturesque gardens in the area.

Everglades Wonder Gardens

Things to do

Dolphin, Manatee and Sea Turtle Adventure Tour

Dolphin, Manatee and Sea Turtle Adventure Tour

$65
per adult
Dolphin, Manatee and Sea Turtle Adventure Tour
Big Hickory Self Guided Kayaking Activity in Bonita Springs

Clear/Standard Kayak Self Guided Island EcoTour Bonita Springs!

$25
per adult
100% of travellers recommend
Clear/Standard Kayak Self Guided Island EcoTour Bonita Springs!
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.