Cranberry Crossing Vacations from $883
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Your Cranberry Crossing Vacation
When it's time for your next getaway, lock in a Cranberry Crossing vacation package. From its golfing to a whole lot more, there are so many tempting reasons to stay in this neighborhood. Some nearby attractions to check out during your trip to Cranberry Crossing include Naples Outlet Center, Eagle Lakes Golf Club and Boyne South Golf Course. Stop dreaming and start doing. When you're ready to book your ideal vacation to Cranberry Crossing, Expedia will help get you there.
The Latest Cranberry Crossing Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Bellasera Resort
Old Naples
Save 100% on your flight
Price was $1,373, price is now $883 per person
$883
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (2,219 reviews)
Joyful, relax and exceptional place in the center of the town. People at reception thanks to Tesse and her coworker was pleasant and welcoming , menu at Claw Bar and the London Club superbly delicious , service above and beyond accommodating , dream team of the cleaning crew (spotless clean, but invisible) , valet people friendly and entertaining . Whole experience during our stay was just perfect . Thank you , Bellasera , we will be back
Reviewed on Sep 29, 2025
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $2,719, price is now $1,712 per person
$1,712
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (1,002 reviews)
Our experience at La Playa was exceptional, everything was what we wanted and expected it to be
Reviewed on Sep 29, 2025
South Seas Resort
Save 100% on your flight
Price was $2,137, price is now $1,428 per person
$1,428
per person
Dec 24 - Dec 29
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.4/10 Very Good! (1,003 reviews)
The room was spotless, and the check-in staff was incredibly friendly. The trolley driver was very accommodating, and the team at the ice cream shop was also warm and welcoming. The beach was absolutely stunning—I keep thinking about how much I want to go back. Swimming with fish all around me was such a memorable experience. Overall, it was an amazing trip for both kids and adults. Thank you!
Reviewed on Oct 10, 2025
The Perry Hotel Naples
Save 100% on your flight
Price was $1,996, price is now $1,339 per person
$1,339
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (417 reviews)
This property was very relaxing. The room was spotless and nicely decorated. Beds and pillows were soft and comfortable. I loved the different amenities the property offers. You can spend all day onsite. They offer free sunset cruises and transportation to Barefoot Beach. The have an awesome roof top bar and restaurant with gorgeous sunset views. I loved the option of two pools One is adult only. The other has a pool par and floatable devices that make for a fun pool experience. Pool furniture was clean and comfortable. The hotel has a fresh clean aroma throughout. I highly recommend this place for a relaxing getaway.
Reviewed on Oct 13, 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
East Naples
4/5(171 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.
Cranberry Crossing Hotel Deals
Naples Grande Beach Resort
475 Seagate Drive, Naples, FL
$270 nightly
The price is $300 total per night from Oct 27 to Oct 28
$300 total
Oct 27 - Oct 28
Total with taxes and fees
9/10 Wonderful! (1,856 reviews)
"This is a beautiful resort and the staff is obviously very dedicated to making your staff a pleasant one because everyone from the valet attendants to the front desk to the restaurant and bar staff were attentive, professional and pleasant. The shuttle to the beach where the great guys providing ..."
Reviewed on Oct 12, 2025
Inn on Fifth
699 5th Ave S, Naples, FL
Fully refundable
$241 nightly
The price is $268 total per night from Nov 3 to Nov 4
$268 total
Nov 3 - Nov 4
Total with taxes and fees
9.2/10 Wonderful! (1,005 reviews)
"The only downside was that the balcony was small. Everything else was excellent!"
Reviewed on Oct 12, 2025
Hilton Marco Island Beach Resort and Spa
560 S Collier Blvd, Marco Island, FL
Fully refundableReserve now, pay when you stay
$252 nightly
The price is $280 total per night from Oct 29 to Oct 30
$280 total
Oct 29 - Oct 30
Total with taxes and fees
8.8/10 Excellent! (1,599 reviews)
"I truly enjoyed my stay here with my boyfriend for my birthday i will definitely be back!! They upgraded my room as well which was super nice!! The bar service and service is outstanding!!"
Reviewed on Oct 10, 2025
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.
Discover the most popular places to visit in Cranberry Crossing
Naples Beach
4.5/5(1,407 reviews)
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.
Fifth Avenue South
4.5/5(45 reviews)
Enjoy many happy hours exploring the variety of shops, dining options and cultural attractions of this popular shopping district in Naples, Florida.
Naples Pier
4.5/5(1,161 reviews)
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.
Things to do
Sunset Tour in Naples Bay on a New Godfrey- All included
$100
per adult
100% of travellers recommend
Naples, FL: Manatee, Dolphin, 10,000 Islands Beach Eco Tour
$127
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.