Cranberry Crossing Vacation Packages
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Top Holiday Package Deals in Cranberry Crossing
Price found within the past 48 hours. Click for updated prices.
Landing Apartments Fort Myers near Eastwood Village
CA $849
per person
Oct 10 - Oct 17
found 14 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Fort Myers (RSW)
9.6/10 Exceptional! (30 reviews)
This place is as beautiful as the pictures. Welcome kit has essentials for a short stay. The place is clean and cozy. Highly recommended.
Reviewed on Sep 4, 2026
Tween Waters Island Resort & Spa
CA $1,069
per person
Oct 16 - Oct 20
found 4 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Fort Myers (RSW)
8.6/10 Excellent! (1,005 reviews)
Great location for get unique island travel experience . Beautiful ocean view on Restaurant to see incredible sunset. Food was delicious also. Property needs to be maintained . Total price includes resort fee is a bit higher for current property conditions.
Reviewed on Sep 4, 2026
Casa Ybel Resort
Mid Island
CA $934
per person
Nov 13 - Nov 16
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Fort Myers (RSW)
8.8/10 Excellent! (417 reviews)
The property is super convenient the beaches across the street a volleyball pool and then a huge lighted pool. The rooms were very clean older but clean and very comfortable. Mine felt like a little apartment tiki bar downstairs is great. The food is good. The drinks were good. They do play music until about midnight so if you don’t like music till that time, this isn’t the place for you lol. We will definitely stay here again.
Reviewed on Aug 30, 2026
Where to stay in Cranberry Crossing
Find the best Cranberry Crossing areas and neighborhoods for the activities you enjoy most. Learn more about Cranberry Crossing
Central Naples
1 out of top 10 points of interest in this area
If you're spending some time in Central Naples, Naples Zoo at Caribbean Gardens and Naples Grande Golf Club are top sights worth seeing.
East Naples
Beaches, shopping, and restaurants are just a few things travelers enjoy about East Naples. Check out Fifth Avenue South or Naples Botanical Garden while you're exploring the area.
Old Naples
3 out of top 10 points of interest in this area
The stunning beaches and popular shops are just a few highlights of Old Naples. Make a stop by Fifth Avenue South or Naples Beach while you're exploring the area.
Naples Park
Located in North Naples, Naples Park is bounded by U.S. Route 41 and offers easy access to Vanderbilt Lagoon. Enjoy shopping at the nearby outdoor mall, The Mercato, for a delightful experience.
Vanderbilt Beach
1 out of top 10 points of interest in this area
While visiting Vanderbilt Beach, you might make a stop by sights like Vanderbilt Beach and Delnor-Wiggins Pass State Park.
Cranberry Crossing Hotel Deals
Hilton Marco Island Beach Resort and Spa
560 S Collier Blvd Marco Island FL
Fully refundableReserve now, pay when you stay
CA $271
CA $378 total
Sep 14 - Sep 15
includes taxes & fees
La Quinta Inn & Suites by Wyndham Naples Downtown
1555 5th Ave S Naples FL
Fully refundableReserve now, pay when you stay
CA $95
CA $106 total
Sep 20 - Sep 21
includes taxes & fees
8.2/10 Very good! (2,115 reviews)
"I will say just the parking"
Reviewed on Sep 7, 2026
Hyatt House Naples/5th Avenue
1345 5th Avenue South Naples FL
Fully refundableReserve now, pay when you stay
CA $199
CA $221 total
Sep 27 - Sep 28
includes taxes & fees
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.
Frequently asked questions
How much does a Cranberry Crossing vacation package cost?
Be ready to book, because a getaway to Cranberry Crossing starts from an affordable CA $849. When you combine your flights, hotels and car rentals into a vacation package, you'll walk away with the best bargains.
How do I get a cheap travel package to Cranberry Crossing?
Booking a Cranberry Crossing vacation package with Expedia is the easiest way to save. We have over 550 airlines and 1,000,000 hotels spread across the globe. With such a wonderful range to pick from, you'll have no worries pulling together your next dream escape.
Where should I stay in Cranberry Crossing?
Travelers come from all over to see Naples Pier and Barefoot Beach in Cranberry Crossing. Book yourself a room within a stone's throw of these top attractions to make sightseeing easy.
How far in advance should I book my Cranberry Crossing vacation?
It can be hard to know exactly when is the ideal time to book your trip to Cranberry Crossing. But typically the earlier you book, the lower the prices. Sometimes, you can reserve your flights and hotels up to a year before your departure date. If you're considering a last-minute getaway, no need to stress! There are great bargains featured on Expedia every single day.
What does an Expedia Cranberry Crossing travel package include?
With Expedia, you can choose a combination of hotels, flights and car rentals to create your perfect Cranberry Crossing package. Once you've made your booking, you can add on all the fun stuff like activities and tours. Remember — the more you bundle, the more cash you'll save!
What should I know before booking a Cranberry Crossing travel package?
A travel package can be tailored to your budget and is a terrific way to stretch your dollars further. What you include is your call. Rental cars, hotels and flights — decide on a combination that suits your style.
Can I choose my airline with a Cranberry Crossing Expedia vacation package?
Yes, you're in control. Expedia has access to more than 550 airlines around the world, so you can design your Cranberry Crossing trip according to your budget and needs.
If I'm not able to travel, can I cancel my Cranberry Crossing vacation package?
We totally understand that life can throw you the odd curveball. If you've booked a Cranberry Crossing vacation package and need to cancel or change it, we're here to help. We recommend having a look at our Customer Service Portal first for information. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel and rebook free of charge. If it's more than 24 hours, your airline, hotel or car rental company may impose a charge.
Things to do
Gulf of Mexico Sunset Cruise from Naples
CA $102
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.