Cypress Lake Vacations from $601
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Your Cypress Lake Vacation
With plenty of highlights as well as some hidden gems, this city is best explored with a Cypress Lake vacation package. Look for places to stay in Hancock, which is great for watersports, views and walking. Edison Mall, CenturyLink Sports Complex and Bunche Beach are just a few of the attractions you'll want to explore during your trip to Cypress Lake. Whatever your travel plans or the size of your budget, organizing a tailored Cypress Lake vacation is easy with Expedia.
The Latest Cypress Lake Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Windward Passage Resort
Price was $889, price is now $601 per person
$601
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.4/10 Very Good! (22 reviews)
Location is amazing, being right on the beach.
Having access to beach chairs to take down to the beach and return is a major plus.
Gas grills on the property also give you the opportunity to grill up some dinner and watch the sunset while eating on your balcony!!
I would definitely recommend!
Reviewed on Oct 31, 2026
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Price was $2,243, price is now $1,308 per person
$1,308
per person
Dec 13 - Dec 19
found 2 days ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (1,003 reviews)
Overall, worth the stay. The place could use some updates.
Reviewed on Nov 5, 2026
GullWing Beach Resort
South Island
Price was $1,705, price is now $1,124 per person
$1,124
per person
Jan 12 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (982 reviews)
Beautiful property, generous size condos and all the amenities.
Reviewed on Nov 6, 2026
Where to stay in Cypress Lake
Find the best Cypress Lake areas and neighborhoods for the activities you enjoy most. Learn more about Cypress Lake
Iona
While visiting Iona, you might make a stop by sights like Estero Bay Preserve State Park and Tribby Arts Center.
Cypress Lake Hotel Deals
Marriott Sanibel Harbour Resort & Spa
17260 Harbour Pointe Dr Fort Myers FL
Fully refundableReserve now, pay when you stay
$255 nightly
The price is $284 total per night from Nov 22 to Nov 23
$284 total
Nov 22 - Nov 23
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
"Why does a hotel have to charge $25 a day for self parking? We had one of the hotel staff enter the room whilst we were half-dressed. This is totally unacceptable. The staff needs better training!"
Reviewed on Nov 6, 2026
Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
$212 nightly
The price is $237 total per night from Nov 29 to Nov 30
$237 total
Nov 29 - Nov 30
Total with taxes and fees
Lani Kai Beachfront Resort
1400 Estero Blvd Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $196 total per night from Dec 3 to Dec 4
$196 total
Dec 3 - Dec 4
Total with taxes and fees
8.8/10 Excellent! (2,184 reviews)
"Beautiful view but beds were terrible and uncomfortable."
Reviewed on Nov 7, 2026
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.
Stay near popular Cypress Lake attractions
Things to do
Fort Myers Beach Sunset and Dolphin Watching Cruise
$59
per adult
100% of travellers recommend
Parasailing Adventure on Fort Myers Beach (400 Foot Flight)
$105
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.