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.
Hilton Marco Island Beach Resort and Spa

Hilton Marco Island Beach Resort and Spa

4 out of 5
South End
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.8/10 Excellent! (1,425 reviews)
It was no my first time at the property and I like it. However, I noticed more clients and I had an issue with my invoice when leaving.

Reviewed on Jul. 25, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.8/10 Excellent! (1,002 reviews)
The beach is beautiful! The staff is excellent! The rooms are always cleaned nicely! It’s our favorite place to stay! ❤️

Reviewed on Jul. 21, 2025

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (1,000 reviews)
Perfect stay , in the middle of amazing restaurants and close to beach . Pool is also perfect for relaxing

Reviewed on Jul. 22, 2025

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
Park Shore
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9/10 Wonderful! (1,583 reviews)
Perfect location and stay!

Reviewed on Jul. 25, 2025

Edison Beach House

Edison Beach House

3.5 out of 5
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Myers (RSW)
9.4/10 Exceptional! (1,405 reviews)
Employees were amazing ! So helpful. Property was the perfect spot with beautiful views. Will definitely stay again in the future.

Reviewed on Jul. 24, 2025

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
Naples Botanical Garden which includes a pond and a garden

East Naples

4/5(11 area reviews)

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.

Find hotels in East Naples

Cranberry Crossing Hotel Deals

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
Fully refundable
The price is CA $194 per night from Aug 26 to Aug 27
CA $194
CA $276 total
Aug 26 - Aug 27
includes taxes & fees
9/10 Wonderful! (1,609 reviews)
"Excellent"

Reviewed on Jul. 23, 2025

Naples Grande Beach 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
The price is CA $174 per night from Aug 3 to Aug 4
CA $174
CA $193 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (1,358 reviews)
"Pool"

Reviewed on Jul. 23, 2025

Hyatt House Naples/5th Avenue
Hilton Marco Island Beach Resort and Spa

Hilton Marco Island Beach Resort and Spa

4 out of 5
560 S Collier Blvd, Marco Island, FL
Fully refundableReserve now, pay when you stay
The price is CA $300 per night from Aug 26 to Aug 27
CA $300
CA $394 total
Aug 26 - Aug 27
includes taxes & fees
8.8/10 Excellent! (1,472 reviews)
"It was no my first time at the property and I like it. However, I noticed more clients and I had an issue with my invoice when leaving."

Reviewed on Jul. 25, 2025

Hilton Marco Island Beach Resort and Spa
See all 8,565 properties in Cranberry Crossing
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
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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 $586. 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.

Discover the most popular places to visit in Cranberry Crossing

Naples Beach

Naples Beach

Why not spend a carefree afternoon at Naples Beach during your travels in Naples? Stroll along the seaside or visit the shops while you're in the area.

Naples Beach
5th Avenue Shopping District which includes markets, street scenes and a city

Fifth Avenue South

Enjoy many happy hours exploring the variety of shops, dining options and cultural attractions of this popular shopping district in Naples, Florida.

Fifth Avenue South
Naples Pier featuring landscape views and a beach as well as a large group of people

Naples Pier

Visit this beloved Naples destination to experience the simple charms of the beachfront on a dock that has served the city for more than 100 years.

Naples Pier

Things to do

SEAS The Day with Pure Florida

Naples Sightseeing Boat Tour

CA $87
per adult
98% of travellers recommend
Naples Sightseeing Boat Tour
Cute Manatee

Manatee Sightseeing and Wildlife Boat Tour

CA $96
per adult
90% of travellers recommend
Manatee Sightseeing and Wildlife Boat Tour
Naples Florida: Downtown Electric Moped Tour

Naples Florida: Downtown Electric Moped Tour

CA $81
per adult
100% of travellers recommend
Naples Florida: Downtown Electric Moped Tour
See all activities in Naples
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.