Cypress Island Vacations from $305

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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
Save 100% on your flight
Price was $603, price is now $305 per person
$305
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,003 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
Price was $2,502, price is now $1,090 per person
$1,090
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (1,004 reviews)
Ants in room-service was just okay-place needs updating-prices very high for what you get. Lack of attention to detail-Balleen was just fair-signature grouper dish highly recommended by server was warm (not hot) and risotto cake was undercooked (and for $65 per portion ????? ) overall price for value received was WAY TO HIGH).

Reviewed on Aug 29, 2025

Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $1,089, price is now $586 per person
$586
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,474 reviews)
The staff was so kind and very helpful. The beach and views were amazing. Alot of places to shop and eat were in walking distance. We will definitely be back.

Reviewed on Aug 31, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,231, price is now $669 per person
$669
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (398 reviews)
Amazing experience. Will definitely come back!

Reviewed on Aug 30, 2025

Casa Playa Beach Resort

Casa Playa Beach Resort

2.5 out of 5
Save 100% on your flight
Price was $978, price is now $588 per person
$588
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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

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
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.