Cypress Island Vacations from $295

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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
per person
Sep 10 - Sep 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,004 reviews)
Everything was great, but last night I found a roach behind the curtains by the windows and I couldnt sleep.

Reviewed on Jun 29, 2025

Hyatt Place Fort Myers/at The Forum

Hyatt Place Fort Myers/at The Forum

3 out of 5
The Forum
Save 100% on your flight
per person
Sep 10 - Sep 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.2/10 Very Good! (1,008 reviews)
We like it not love but liked

Reviewed on Jul 1, 2025

Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
Save 100% on your flight
per person
Sep 10 - Sep 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,005 reviews)
I like that the rooms were nice and clean. The view is amazing I like how it is close to everything. I however didn’t understand why there were no microwaves. In the standard rooms. I feel like that would be a very good thing to have in every room. As well as a broom and dust pan. Being that it is on the beach. My a/c united is very load when coming on. And I feel like the doors should have something on a spring to stop them from slamming from the wind. Also I believe that everyone working here should know the times and rules for the pool and other facilities on property. The first night the guy said the pool closed at 8. But the next night the lady was trying to tell us that the pool was closing at 6:30. However the sign says from dusk till dawn. Other than that it was overall an amazing fun time.

Reviewed on Jul 6, 2025

Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
per person
Sep 10 - Sep 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,385 reviews)
Perfect spot for watching 4th of July fireworks

Reviewed on Jul 5, 2025

South Seas Resort

South Seas Resort

3.5 out of 5
Save 100% on your flight
per person
Sep 10 - Sep 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.4/10 Very Good! (1,001 reviews)
Good please to stay with family

Reviewed on May 26, 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 Bay

1 out of top 10 points of interest in this area
4.5/5(66 area reviews)

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.

Find hotels in Bonita Bay

Cypress Island Hotel Deals

Naples Grande Beach Resort
Naples Grande Beach Resort
4.5 out of 5
475 Seagate Drive, Naples, FL
Fully refundable
$217 nightly
The price is $241 total per night from Jul 14 to Jul 15
$241 total
Jul 14 - Jul 15
Total includes taxes and fees
9/10 Wonderful! (1,565 reviews)
"We have been coming to Naples grande for years! We finally made it to the adult pool and loved it! The service and food was amazing!"

Reviewed on Jul 5, 2025

Naples Grande Beach Resort
Lani Kai Beachfront Resort
Lani Kai Beachfront Resort
3.5 out of 5
1400 Estero Blvd, Fort Myers Beach, FL
Fully refundableReserve now, pay when you stay
$229 nightly
The price is $256 total per night from Jul 7 to Jul 8
$256 total
Jul 7 - Jul 8
Total includes taxes and fees
8.4/10 Very Good! (1,006 reviews)
"Amazing view, beautifully updated room. No microwave and very small fridge. The food downstairs can be expensive, but overall it is a nice place. The pool is very relaxing and the resort is worth the price."

Reviewed on Jul 4, 2025

Lani Kai Beachfront Resort
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
$159 nightly
The price is $176 total per night from Aug 3 to Aug 4
$176 total
Aug 3 - Aug 4
Total includes taxes and fees
8.8/10 Excellent! (1,294 reviews)
4 night stay
"On vacation from Scotland. Enjoyable 4 night stay. This is our 3rd time staying at the Hyatt with no major complaints. Friendly and courteous staff. Breakfast did not have as much of a choice as previously but adequate. Pool area good, no problem getting sun beds. Great third floor room, overlooking ..."

Reviewed on Jul 4, 2025

Hyatt House Naples/5th Avenue
See all 15,888 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
Clear Kayak Guided Eco Tour in North Naples

Clear Kayak Guided Eco Tour in North Naples

$84
per adult
100% of travellers recommend
Clear Kayak Guided Eco Tour in North Naples
Shelling Tours - Fort Myers Beach / Estero Bay

Shelling Tours - Fort Myers Beach / Naples

$350
per traveler
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.